Italy

Winter itinerary, in detail

In-depth details about our stays, food and activities on a winter trip through Italy, from the Dolomites to Puglia.

All Italy guides
In Detail
By Riddhi
  • kids
  • Europe
  • Italy

Italy in winter

Duration
12 days
Season
Winter
Who travelled
2 adultsChild
Route schematic · Italy in winter12 stops · not to scale
  1. 1Milan
  2. 2Cortina & Tre Cime
  3. 3Seceda
  4. 4Bolzano
  5. 5Pisa & Siena
  6. 6Florence
  7. 7Bari & Puglia
  8. 8Trulli & Beaches
  9. 9Rome
  10. 10More Rome
  11. 11Lago di Garda
  12. 12Home

Day 1 Milan to Bolzano

We arrived in Milan via Newark. The weather had held up for us this late in December, and we landed as scheduled at around 9 am. We took the Malpensa Express to Milano Centrale. From here we walked the short distance to a hotel we had booked for just a few hours during the day, chosen for how close it was to Milano Centrale. Once checked in, we showered and slept for a few hours.

Around lunchtime, we walked about 15 minutes to Pizzium. This restaurant offered incredibly delicious pizza, bruschetta and coffee. The well-designed restaurant was full of locals. We were stuffed after our first Italian lunch in Italy.

Two Neapolitan pizzas on patterned plates at Pizzium

Food at Pizzium.

Next we headed to Terra Gelato, just a short walk away. This gelato shop was modern, fancy and contemporary. We tried the salted pistachio and the chocolate hazelnut. The gelato was phenomenal, and we were excited for more amazing food on the rest of the trip.

Ordering at the counter of a modern gelato shop

At Terra Gelato.

After the meal, we stopped by a bookshop on the way back to the hotel. We rested a bit more before heading back to the train station for our evening train to Bolzano. We grabbed sandwiches and coffee from a cafe at the station to eat on the train. We had booked business class tickets for a more comfortable ride, and the almost four-hour journey passed quickly. The only drawback was that it was completely dark outside, so we could not enjoy any views.

Boy writing at a table in a business class train carriage

On the train.

Old town Bolzano is close to the train station. We took a short taxi ride from the station to our wonderful hotel, ideally located in old town Bolzano with lots of food and shopping nearby. We especially loved its modern design and spacious interior. Once settled in, we went to bed to prepare for an early start.

Day 2 Lago di Braies, Cortina & Tre Cime

We began the morning early by walking to the train station. We picked up coffee and breakfast from the Panella cafe while we collected our rental car. From here we headed to Lago di Braies, about an hour and a half away. The drive was gorgeous, through numerous small towns. The roads got windier as the snow-covered mountains began to appear.

Once we made it to the parking area, we were in awe of the beauty all around us. We walked the short path to the lake. The entire lake was frozen over, with ice thick enough to walk on, covered in a few inches of snow. We thoroughly enjoyed walking around the lake, admiring the mountains and taking lots of photos. We spent over an hour here. There are paid restrooms in one of the buildings near the parking lot, and parking is paid as well. It was not difficult to find a space after 10 am, though that is probably not the case in summer.

A wooden boathouse on the snow-covered, frozen lake below rocky peaks

The most photographed boat dock in the Dolomites, at Lago di Braies.

People walking across the frozen, snowy lake between steep mountains

Frozen Lago di Braies.

We left Lago di Braies and drove toward Cortina d’Ampezzo. Again, the hour-long drive was beautiful, with snowcapped mountains in and out of view. We had a very hard time finding parking in this town. Our plan was to have lunch and see the town center, but every one of the ten or so public parking lots we tried was full. We drove around for about an hour. Finally we found a little lot just outside the main town, across a bridge and down a hill, and walked about 10 minutes back to the center to find lunch. The food in Cortina mixes German and Italian influences. We got pizza, salad and dessert, and were lucky to get a table, as the town was so busy.

Busy pedestrian street in Cortina d’Ampezzo with mountains behind

Cortina d’Ampezzo town center.

After lunch, we wanted to reach Tre Cime before sunset, so we had no time to explore the town at all. We were sorry to leave this spectacular place so soon. We wound our way through the incredible Dolomites toward Tre Cime. About 20 minutes from the parking lot (according to Google Maps), we came to a road closure outside a lodge and restaurant. The road beyond was closed due to snow. They do run snowmobile shuttles to the Tre Cime area, but the last one leaves at 3 pm. We missed it by 30 minutes.

A snowy clearing with a picnic table and jagged peaks behind, near the road closure

A frozen lake near the Tre Cime road closure.

We were disappointed not to see the famous viewpoint, so we made the most of it by walking up the road toward Tre Cime. After about 20 minutes of snowball fights and gorgeous views of the Dolomites, we turned back. The Tre Cime parking lot was still a long way off, sunset was at 4:30 pm, and we wanted to be back at the car before dark. More snowball fights, falls and crunching around in the snow followed at a frozen lake just in front of the car. The part of the Dolomites we could see behind the lake glowed in the sunset. We still felt grateful to enjoy such an amazing view.

A single peak glowing in the last sun beyond a snowy frozen lake

The view of a frozen lake from the car park.

From here we drove back to Bolzano, just under two hours away. Driving in this part of Italy is challenging during the day, and more so in the dark. We were lucky to make it through the web of highways and small roads to our hotel.

Shoppers on a lit-up street in Bolzano’s old town at night

Bolzano old town in the evening.

Once we had parked in the hotel’s garage, we walked around old town Bolzano. We picked up falafel wraps from Kebz, just down the road, and ate them in our room. We had another early start the next day to make the most of the daylight, so we called it a night.

The arched shopfront of Kebz, a kebab and veggie takeaway

Kebz in Bolzano.

Day 3 Seceda & Santa Maddalena

The day began early again; we left our hotel at around 8 am after a quick breakfast from the cafe under the hotel. We headed for Seceda, about 45 minutes away. Seceda is the name of the mountain, but the cable car up to it leaves from the town of Ortisei. Parking here was challenging again. We were lucky to get a spot at the very end of the lot, just barely approved by the parking attendant. We paid for parking and bought cable car tickets (around $40 round trip). We got on the first cable car without a wait, and the ride is simply gorgeous. The second cable car took about an hour of waiting, as the line of skiers going up the mountain was incredibly long.

Boy and man smiling inside a cable car cabin, with snowy forest outside

The first Seceda cable car.

Once we reached the top, the views took our breath away. It is hard to believe what you are looking at is real, with views in every direction for miles. We took the path around the corner and walked up toward a viewing area, where the views were even more amazing. Next, we walked toward the Seceda peak. The path was covered in snow but walkable. We walked as far as a viewpoint to take some photos. The path beyond was steep, and we worried about slipping on the climb back up, so we turned back from there.

Looking down a snowy slope into a deep valley with mountains beyond

The view of the valley.

A person at a railing looking at the sharp, snow-dusted Seceda ridge

Looking at Seceda.

A wide ski slope with skiers, and a range of Dolomite peaks on the horizon

The view from the path back down to the restaurant.

We made it back to the restaurant area. The restaurant had spectacular views of the mountains and standard food options. We were hungry from all the exploring, so we had pizza and soup. We found the soups in these mountain towns fabulous in the cold weather. After lunch, it was back down the cable car to our car.

After round two of the beautiful views on the way down, we drove toward the village of Santa Maddalena, about 45 minutes away. The day before, we had saved the addresses of some public parking lots in town, so we entered one into Google Maps. We wanted to see the famous view of the jagged gray Dolomites behind a quaint church. Once we parked, we followed Google Maps to the panoramic Santa Maddalena viewpoint: toward the edge of town past the farmland, up a road toward some farmhouses, and finally a rough hiking path to the viewpoint. The walk was easy and enjoyable.

A narrow road with snow banks leading out of the village toward the hills

The path up to the viewpoint.

A hiker on a grassy path above the village and its church, with the jagged Odle peaks behind

The view close to the top of the Santa Maddalena panoramic trail.

Some things to note about this area. We saw signs asking visitors to stay off the grass and keep to the road or the hiking path. Cars may not drive up this road unless they live in the area. As it is a residential area, it is important to respect the rules so it stays open to everyone. Even though we took tons of photos, it was impossible to do justice to this fairytale scene. We spent around an hour just taking in the views. For photography, we recommend coming early in the morning. We came in the hour or so before sunset, which worked well for photographing the scenery, but not as well for portraits.

Wooden trail signposts beside the road near Santa Maddalena

Signs for the Santa Maddalena panoramic trail.

A quiet road through the village of Santa Maddalena at dusk

Dusk in the village of Santa Maddalena.

We walked back into town and to our car as the sun was about to set. Our rental car was due back in Bolzano that day, and we wanted to get there with some daylight left. The mountain roads are harder to drive at night, with few street lights and narrow, winding roads. Unfortunately, we missed one turn and then another, adding about thirty minutes and a ton of traffic to the drive.

The roads close to Bolzano are complicated, with small side streets going in every direction. We were relieved, after returning the car, not to have to drive in Bolzano for the rest of our stay.

Boy standing by a carved stone fountain in Bolzano’s old town at night

Walking around Bolzano old town.

We walked through the Christmas markets near the train station. They were lit up with sparkly lights, selling an assortment of handmade goods and food. For dinner, we walked to Indian Tandoori Grill. The food was delicious and homey, and the naan was cooked fresh in their own tandoor oven. The food was great, but it was a long wait after ordering. After dinner, we went back to our hotel, did a bit of packing and got ready for bed.

The warmly lit entrance of an Indian restaurant in Bolzano

The Indian Tandoori restaurant in Bolzano.

Day 4 Bolzano, the Ritten cable car & on to Florence

We woke up ready to check out. Our hotel had no room to hold luggage, but the Bolzano train station offers a luggage storage service, so we took our bags there. We waited a few minutes for the person working there to open up.

Our next stop was the famous Loacker cafe. We love these wafers, which we buy from World Market at home, and were excited to learn the brand started in Bolzano. The cafe offers breakfast, desserts and specialty coffee. We enjoyed all the sugary treats.

A Loacker menu on the table, with the cathedral blurred through the window

The Loacker cafe, across the street from the cathedral.

Next we walked to the Ritten cable car station (also called the Renon cable car), about 10 minutes from the main square. The station is outside the old town, closer to the mountains. We bought a combined family ticket for the cable car and the train at the top. The ride was comfortable, with stunning views of the snow-covered, iconic peaks of the region.

Looking down past the cable car’s wheels to the rooftops of Bolzano

Riding the Ritten cable car.

Vineyards and a valley seen through the cable car window

The view from the cable car.

At the top, we took a beautiful train ride to a small fairytale village. It looked like something out of a Disney movie, and we felt like we were in Austria rather than Italy. We walked around for about an hour, past a churchyard, a park and some beautiful homes. It felt like a peaceful side to the busy town of Bolzano. We could not explore the village or the hiking trails further, as the weather was cold and rainy.

A wide view over forest to a long line of Dolomite peaks under cloud

The view from the train.

A boy walking along a village street of white houses with green shutters

The village from the train ride.

Back in Bolzano, we were hungry. We found Oberon, a traditional South Tyrolean restaurant used mostly by locals. We enjoyed the most perfectly cooked aglio e olio (spaghetti with olive oil and garlic) and spinach ravioli.

A plate of pizza topped with fries and a bowl of spaghetti on a checked tablecloth

Food at Oberon restaurant.

We had a couple more hours before our train to Florence. We wandered around the Christmas markets (there are two in Bolzano) in the rain, sampling snacks. Just before heading to the station, we picked up falafel wraps to eat on the train.

Handmade ceramic pieces on display at a Christmas market stall

Handmade items at the Christmas market.

We collected our luggage and got on the train to Florence, about four hours away. Florence welcomed us with a full New Year’s Eve atmosphere, with young people gathered around the station ready to celebrate. We walked about 10 minutes to our Airbnb in the narrow streets of the old town. Once settled in, we could not pass up seeing Florence in its New Year party mood. We walked around the different piazzas, with light shows, art and live music. After some mediocre gelato, we walked back to our apartment ready to settle in. Unfortunately, we were not aware how seriously Italians take New Year’s Eve. The fireworks went on well beyond midnight. We heard bottles breaking, police sirens and fireworks until we got up at 5:30 am. It was a sleepless, but memorable night.

Palazzo Vecchio lit up with colored lights for New Year’s Eve

Piazza della Signoria decorated for the New Year.

Woman and boy hugging on a crowded, lit-up street in Florence at night

The busy streets of Florence.

Day 5 Pisa, Siena & San Gimignano

We started New Year’s Day early with a full-day tour of Tuscany. Since many of the things we wanted to do in Florence were closed that day, we chose a tour to take in the sights of Tuscany instead. All the similar tours leave from a bus terminal outside town. The day before, we had worked out the best way to get there for 6:30 am. Our Airbnb host told us a taxi would cost around 50 euros! The best and easiest way turned out to be walking about 10 minutes back to the train station and taking the 25-minute tram to the bus terminal, the last stop on the line. It costs only around 1.50 euros each, one way.

The white marble cathedral of Pisa with the Leaning Tower beside it

The cathedral and the Leaning Tower of Pisa.

Once we checked in with our guides, we got some breakfast at the cafe. The guides split up the groups and we got on our bus. Our first stop was Pisa. We got our first glimpse of the Tuscan landscape, rolling hills and pale-colored buildings, through the big bus windows. In Pisa, we walked from the bus parking to the main square with the baptistery, the Leaning Tower and the cathedral. The white marble buildings against the deep green grass were striking. The tour gave us about an hour here. We chose not to climb the tower, and spent our time walking around and taking in the gorgeous architecture. Taking silly photos with the Leaning Tower was super fun. The baptistery was free to enter, so we had a quick look inside. The cathedral needs a ticket from the ticket booth, and we didn’t want to spend time in line, so we skipped it. Restrooms are available here for a fee. Street vendors line the street outside, selling leather goods, souvenirs, sports jerseys and more, but the tour left no time for shopping.

Boy posing as if holding up the Leaning Tower of Pisa

The typical pose at the Leaning Tower of Pisa.

Our next stop was lunch at a gorgeous vineyard. As we left Pisa, the scenery became quintessential Tuscany: hills dotted with cypress trees and olive groves, with beautiful estates perched on each hilltop. Lunch was a simple pasta meal with wine and cheese tastings. The location and views were spectacular. We don’t drink, so we would not usually visit a winery, but we enjoyed it as part of the tour.

Bruschetta with tomato and arugula on a wooden board at the vineyard

The first course of the vineyard lunch.

Man smiling in front of racks of wine barrels

Barrels at the vineyard.

After lunch we headed further into the heart of Tuscany to Siena. The bus parked outside the city walls, and we enjoyed the 15-minute walk along the tall, beautifully built walls. In the historic center, we had free time to explore on our own.

A narrow street of tall stone buildings in Siena’s old town

Siena old town.

Man and boy with arms out in front of the striped bell tower of Siena Cathedral

Outside the Siena Cathedral.

The first thing we wanted to see was the Siena Cathedral. This gorgeous striped cathedral of white and dark green marble is unique among the many cathedrals in the region. We waited in line about 15 minutes for tickets, which were free since it was New Year’s Day. Inside, the cathedral was even more impressive. Stunning art and artifacts lined the walls, and the stripes continued inside too. The ceiling looked like an evening sky dotted with stars. The carvings all around the building and the stained glass windows were incredibly beautiful.

Inside Siena Cathedral, with striped marble columns and frescoed walls

Inside the Siena Cathedral.

The streets of the old town were full of shops, restaurants and places to people-watch. We did some shopping for local goods like soap, kitchen towels and perfume. We enjoyed a pizza almost as long as my arm. Soon our time was up and we met back up with our tour group.

Long rectangular pizzas in a glass counter at a Siena pizzeria

Huge pizzas in Siena.

The last stop on the tour was the gorgeous village of San Gimignano. I was looking forward to this true medieval Tuscan gem the most. However, we arrived at around 5:45 pm, after the sun had set, and it was completely dark. The village was still lit up from Christmas in all the alleys and the main square, but we could not see any of the Tuscan countryside views we had been looking forward to, or the medieval towers. We spent our hour walking around the shops along the main street, selling ceramics, chocolate, olive oil, leather goods and more. We found the prices a bit higher than we wanted to spend, but walking the medieval cobblestone streets was incredible. There is a paid restroom in the alley near the main square (exact change in coins required).

A ceramic dog statue among painted pottery in a souvenir shop

A ceramics souvenir store in San Gimignano.

People walking a stone street strung with lights in San Gimignano at night

The streets of old town San Gimignano.

We walked a few minutes back to the bus with our guide and returned to the bus terminal near Florence. At the final stop, we went to the tram station to buy our return tickets. The tram machine is easy to use, with an English option, and our credit card worked without any issues. Since nearly everybody was taking the tram back into the city, it was pretty full. We made it back to Florence right in time for dinner.

After our traditional Italian lunch and a busy day of walking, we craved something different. We chose an Indian restaurant called Indian Palace. We waited a few minutes for a table. The food was incredibly satisfying, just what we needed after our tour of Tuscany.

Man at a restaurant table with plates of Indian food

Dinner at Indian Palace.

Day 6 Florence, markets & a pasta class

After our tour of Tuscany, we were ready to see Florence. We had an early morning reservation at the Uffizi Gallery, booked about a month in advance. We stood in a short line at the box office to collect our tickets. Bring your passports, as they may ask to see them to check identities. We didn’t have to show ours, but had them just in case.

We entered the museum on the first floor and went through the displays of ancient Greek and Roman sculpture and some interesting art. Next we headed upstairs, where the walls and ceilings themselves are works of art. Each room is arranged by theme or artist, and we walked through several rooms of the most stunning masterpieces. We didn’t run into any crowds, so we could get close and look at the art for as long as we liked without blocking anyone. We saw all the collections on the top floor. By then it had been about two hours. We hadn’t had breakfast in order to make our entry time, and our son was starting to complain. We had seen some stunning pieces and decided to get him some food, so we may have skipped some rooms on another level.

A long gallery hallway lined with statues under a painted ceiling

A hallway on the second level of the Uffizi Gallery.

An ornately painted ceiling in the Uffizi

The ceilings of the Uffizi Gallery.

When we left, we walked toward the Ponte Vecchio, our next stop. The restaurants open along the river were quite expensive, so we backtracked a bit to a cafe further from the bridge. We enjoyed fresh chocolate croissants and coffee. Happy with breakfast, we walked back to the Ponte Vecchio. The bridge is beautifully painted in shades of Tuscan color. For the best photos of the bridge itself, walk along the riverbank toward the next bridge for a little way. There is also a great viewpoint on the Ponte Vecchio itself for photos of the riverbanks and the Arno.

Boy leaning on the wall of the Ponte Vecchio, looking along the Arno at the colorful riverside houses

Looking out from the Ponte Vecchio.

The Ponte Vecchio’s arches and shops reflected in the Arno

The Ponte Vecchio.

The bridge is lined with jewelry shops, and we did some shopping at a few of them. From here we walked toward the Duomo, the Cathedral of Santa Maria del Fiore. We stopped at a smaller leather market on the way. We enjoyed all the markets and Italian goods. We love bringing things back from our trips to remember the places by.

Woman looking into a lit jewelry shop window on the Ponte Vecchio

Jewelry stores on the Ponte Vecchio.

Colorful leather bags and backpacks hanging at a market stall

Leather goods at a roadside market.

The line to go inside the cathedral wrapped all the way around the building and further back. My husband stood in line while my son and I explored the area. We used the time to buy postcards and bookmarks, eat some tiramisu, and visit a candy shop and various souvenir shops. The wait took about an hour and a half in total. The cathedral doesn’t need an entry ticket; the line is mostly for the security check at the gate, but it can be very long at peak times. We were lucky to have dry, cool weather, so the outdoor wait was easy.

The marble facade of Florence’s Duomo against a gray sky

The Cathedral of Santa Maria del Fiore in Florence.

Inside, the Cathedral of Santa Maria del Fiore has a few beautiful pieces of art and a magnificent, multi-level central dome. It is impossible to stop staring at all the details. The outside of this cathedral is much more detailed and grand than the inside. We found Siena Cathedral more intricate and full of stunning art; here the walls are simpler, and the dome is the focal point. We spent about 20 minutes walking around admiring it.

The frescoed inside of the Duomo’s dome, seen from below

The ceiling of the Santa Maria del Fiore Cathedral.

Next we headed to Aroma of India for lunch. The food was homey, comforting and delicious. After our meal, we went to the San Lorenzo leather market to buy leather goods for family. We had a few hours before our cooking class at 4:30 pm, so after some time at the market, we went back to our Airbnb to drop off the shopping and rest briefly.

We made it to our cooking class at Pasta Mania, about 10 minutes from our Airbnb, in a historic building on the other side of the river. This class was one of our favorite family experiences ever. We watched a short video about pasta before getting started. We were in the class with another family group without kids. Our son is a chef in training. Using his hands to measure, knead the dough and fold ravioli, and finally eating the pasta made from scratch, was unforgettable. We learned invaluable skills about recognizing good ingredients and their effect on our diets. We highly recommend this cooking class in Florence.

Boy and man kneading pasta dough at a marble counter in aprons

Making pasta at the Pasta Mania cooking class.

Boy in an apron smiling over a tray of handmade ravioli

Making ravioli.

After the class, we got gelato at Venchi on the way back to our Airbnb. Venchi is arguably the best gelato and chocolate shop we tried on the whole trip.

Boy and woman at the counter of the Venchi gelato shop

Getting gelato at Venchi in Florence.

Day 7 Florence to Bari

We left early in the morning with all our luggage for the long train journey to Bari. Breakfast was coffee and croissants from one of the cafes at the station. We had booked business class seats for most of our train trips, so we got a bottle of water and some snacks on each one. The trip was about six hours. We spent it reading, snacking, chatting, sleeping and planning the next few days. The time went by surprisingly fast.

Boy and woman relaxing in business class train seats

On the train to Bari.

Bari train station was less than 10 minutes by taxi from our Airbnb in old town Bari. It was perfectly located near local shops, and just one street over from the famous street where the nonnas make handmade pasta. We settled in quickly. It was only about 3:30 pm, so we spent the afternoon exploring. We walked for about 20 minutes in and out of the narrow, winding streets. None of the focaccia or gelato shops were open; the whole city seemed to be taking a siesta. After making it all the way to the main piazza by the sea, we headed back to our Airbnb to wait a couple of hours until the shops opened (around 5:30 pm). On the way back, we walked through the newer part of Bari, full of shopping, mostly big brand stores. Wandering without following any directions, we found the street where the nonnas make pasta in their own kitchens to sell, mostly to tourists. We bought a big bag of colorful orecchiette (the ear-shaped pasta of Puglia) to take home.

The pale stone facade of Bari Cathedral under a deep blue sky

The Cathedral of Bari.

Woman walking down a narrow, stone-paved alley in old town Bari

Walking around the old town of Bari.

We left at around 5 pm to walk to Panificio Fiore, one of the most popular focaccia bakeries in all of Bari, and for good reason. Focaccia is a specialty of Puglia, and this bakery has won awards for it. When we arrived at 5:15 pm, about 20 people were already in line waiting for it to open. Everyone in line was local, buying enough focaccia and bread to feed a neighborhood. We knew we were in the right spot. When our turn came, the person at the counter and some people in line behind us helped us get just the right amount of piping hot tomato focaccia, right out of the oven.

A line of people outside the Panificio Fiore bakery in an old town street

The Panificio Fiore bakery in Bari.

Man holding a slice of tomato focaccia wrapped in paper

Enjoying delicious focaccia.

This was the crunchiest, chewiest, most delicious focaccia we had ever tried. The bakery makes only one kind, perfected over generations. We ate it while wandering the streets. Next, we walked to the restaurant we had picked for dinner. We tried eggplant parmigiana, aglio e olio and spinach ravioli, and they brought salad and bruschetta first. The main courses were too large for us to finish. The food was homey and comforting.

The entrance of Cantina dello Zio, decorated for Christmas

Dinner in Bari old town.

From here we headed to the street with the nonnas (grandmothers) making pasta. It was lit up with Christmas lights and decorations, perfect for photos. We bought croissants for the next morning’s breakfast and a pastry for dessert before heading back to our Airbnb.

Tables of drying handmade pasta along a narrow street, with a woman and boy browsing

The street where nonnas sell homemade pasta.

Day 8 Alberobello, Monopoli & Polignano a Mare

After breakfast bright and early, a taxi took us to the rental car agency. We arrived around 8:30 am, but it was still closed, though it was supposed to open at 8 am. This kind of thing is common in Italy: opening and closing times are not taken as seriously as in the US. We waited 20 to 25 minutes before the person who works there showed up. We were nervous, as we had planned an early start to fit everything in, but the delay didn’t set us back much.

Once the paperwork was done, we were on our way. Renting a car here was more expensive than we expected, so we kept it for just a day. We began our road trip with Alberobello. This town is famous for its conical houses, with white walls and gray stone roofs, called trulli. Trulli are found all around Puglia, but the most are in the picturesque town of Alberobello. We parked in a public lot (really an olive grove) for 5 euros.

A whitewashed trullo with a conical stone roof, decorated with garlands

A trullo in Alberobello.

A white street of trulli strung with Christmas decorations

The trulli-lined streets of Alberobello.

The parking was a short walk from the trulli. The houses are now used as souvenir shops, restaurants, homes and museums. The town was incredibly well kept, and we felt like we had stepped into a different place and time. The streets were lined with conical buildings of all sizes for quite a distance. We checked out some souvenir shops, bought some small trinkets, visited a terrace for a panoramic view, and walked all the streets taking many photos. The section before the main square is more commercial (shops and restaurants). The area behind the church, uphill from the main square, is more residential. We found a viewpoint tucked between some houses with a great view over the area. Some locals let people into their homes, but we didn’t feel comfortable going into someone’s house. There is a museum that preserves the inside of a trullo for visitors. We walked most of the trulli-lined streets in just under two hours. The only paid restroom is in the main square.

Man and boy at a gate in a stone wall, with the trulli rooftops behind

A viewpoint over the trulli.

We had an early lunch at Focacceria La Lira in the main square. We tried the puccia sandwich, something of a local specialty. The friendly chef made ours special with roasted vegetables. The sandwich was made with fresh, puffy pizza-dough bread, layered with roasted vegetables, mozzarella and a pesto-like sauce. We tried some focaccia too, a must in Puglia. This lunch really hit the spot. We took a different street of trulli back to the olive grove parking lot. Overall we spent about two hours in Alberobello. With so much more to see, we were happy we stuck to a schedule.

The whitewashed front of Focacceria La Lira

Focacceria La Lira.

Our next stop was the Calette di Torre Cintola (the coves of Torre Cintola), gorgeous ruins of an ancient port on the beach, about 30 minutes from Alberobello. Google Maps took us to a free parking lot for the area. The drive cuts through hills, olive groves, orchards and farms of the Puglian countryside. This part of the coast was amazing, and the ruins made the beach more interesting. Even in winter, we had a great time climbing the rocks and ruins for different views. By the time we arrived, the noon sun was directly overhead. We recommend coming at sunset for better photos without harsh shadows among the ruins. We could have explored for a few more hours, but we had to move on to Monopoli, about 10 minutes away.

Pale limestone ruins cut into the rocks beside the blue sea

The ruins at the coves of Torre Cintola.

Rocky limestone blocks with the sea washing between them

Waves among the rocks at Torre Cintola.

Here too we parked in a public lot close to the center, free in the winter. From the parking lot, we walked to a small cove beach (perhaps called Porto Bianco). The weather was perfect for a winter beach walk: not too cold, with a gentle sea breeze. Local families were playing on the shore and walking along the beach path. In this part of Italy, we felt surrounded by more locals than anywhere else on the trip. We passed some smaller beaches on our way to the harbor. The walkway was well maintained, new even, and we saw local kids enjoying new basketball courts and a skate park. We walked toward the old town, got some gelato, and walked back down some stairs near the old port walls to the car. From here we drove to Polignano a Mare, 15 minutes away, the final stop of the road trip.

The rocky coast near Monopoli with a sea arch and blue water

The coast at Monopoli.

Man and boy standing on the rocks looking out to sea

On the rocks at Monopoli.

Boy at a railing looking across the water to Monopoli’s white old town

Looking across to Monopoli’s old town.

We timed our arrival in Polignano a Mare for about an hour before sunset, to enjoy the golden hour for photos. We parked in a public lot and paid a few euros for a couple of hours. It was about a 10-minute walk to the main rocky beach under the bridge. First we took in the view from the bridge above the beach, then backtracked a bit to find the path down. The path is a bit rocky, with some incline, but an easy walk. The sun was still a bit harsh for photos on the beach, but we got some good shots. The water is too cold and rough for swimming in winter, though we saw one brave man go in for a quick two-minute swim. The houses jutting out of the cliffs above the sea, seen from the rugged, rocky beach, were simply spectacular.

Boy sitting on the pebble beach below the tall cliffs of Polignano a Mare

The pebble beach at Polignano a Mare.

Back up at the main bridge, we walked through the town to the viewpoint over the beach. This balcony-style viewpoint, behind some restaurants, has a glorious view of the sheer rocky cliffs, the houses, the sunset and the sparkling sea below. It was a busy spot, as everyone wanted that unforgettable picture. We waited just a couple of minutes to get close to the best spot and took some great pictures ourselves. After taking in the beauty for several minutes, we headed back to the old town for some snacks.

Man and boy at a balcony railing looking down at the beach between the cliffs at sunset

The balcony viewpoint over the beach.

We had coffee and pastries at a small coffee shop. The light was just perfect by then, so we walked toward the cliffs to the left of the beach for a different view. This view was certainly our favorite. The limestone cliffs run all the way into the sea. We found the stairs, almost at the end of town, that lead onto the cliffs. From here we walked over the rocks to see the crashing waves, the houses jutting out of the cliff faces and the rocky beach. This was the best sunset of our entire trip. We spent a long time taking pictures from every angle in the amazing golden dusk light. It was also an incredible spot to just sit and people-watch. We were sad to head back, but didn’t want to walk back to our car in the dark in a new town.

Woman sitting on the rocks facing the white town on the cliffs of Polignano a Mare

The cliffs of Polignano a Mare at sunset.

Man sitting on the rocks with the town and its cliffs behind him

The view from the rocks.

Back at the car, we drove about 35 minutes to Bari to return it. Renting and driving were easier here than in Bolzano. We had dinner at Frulez, as online reviews mentioned good vegetarian options. We had a vegetarian moussaka, a tofu stir-fry and some tacos. The moussaka and tacos were a bit different from what we expected, but still good. The stir-fry was the best.

The bright counter and logo inside Frulez restaurant

Dinner in Bari.

We enjoyed a pleasant 15-minute walk back to our Airbnb. After showering and packing, we reflected on how perfectly everything had worked out that day, with gorgeous weather and gorgeous places.

Day 9 Rome

We took the same taxi service back to the train station, picked up croissants and coffee at the little station cafe, and got on our train to Rome with plenty of time to spare. We used the four hours on the train to relax, read, snack, sleep and plan our time in Rome. We had only about 24 hours there. This was our second time in Rome, so we knew which outdoor sights we wanted our son to see. We didn’t have time for museums and all the monuments, but we spent our evening walking through the open-air museum that is ancient Rome.

Boy and woman with their bags outside Roma Termini station

Roma Termini station.

At Roma Termini, we worked out how to get to the metro. We had picked a hotel near the Colosseum, our main destination for the next day, just a couple of stops away. Finding the right station and the right track was challenging. After several flights of stairs up and down the underground station with our luggage, and about 15 minutes of walking, we reached the correct platform. We waited about 10 minutes for the train.

Getting onto the crowded metro with our son and all our luggage was hard. To add to the stress, we saw something interesting. Some young women were moving through the train, bumping into other passengers, including me. I thought nothing of it, assuming locals were just used to less personal space. About 30 seconds later, the women got off the train and into a confrontation with an older gentleman, who had taken a couple of wallets back from them. He started waving the wallets around the train, asking if they belonged to anyone. That’s when we realized the women had been picking pockets as they bumped into people. It was especially nerve-wracking since we had everything with us, including wallets, credit cards and passports. Off the metro, it was one more flight of stairs and a couple of minutes to reach our hotel.

We were able to check in a little early. We left our bags in the room, changed into rain gear, and headed out to see the five main monuments and squares on our list. We decided to stay off the metro and walk the whole route. That let us see more of the city we love and kept the pickpocketing risk low.

We stopped at a beautiful restaurant in one of the alleys for lunch. When in Rome, cacio e pepe is a must: fresh pasta with a creamy sheep’s milk cheese and black pepper. The mushroom pappardelle was amazing too, and we had delicious focaccia with roasted vegetables. This lunch was worthy of the splendid city. After this hearty meal, we walked about 30 minutes to the Spanish Steps (#1).

Plates of pasta and grilled vegetables on a restaurant table in Rome

Lunch in Rome.

As expected, there was an enormous crowd here, especially at the bottom of the steps and at the fountain. We made the best of it and took some pictures. The crowds were lighter at the top, so we climbed up. There is a church at the top that would have been great to visit. We saw the obelisk and the fountain. The whole area was still decorated with huge Christmas trees and lights, which added to the atmosphere.

A tall stone column in the square by the Spanish Steps, under a cloudy sky

Near the Spanish Steps.

Man and boy on the Spanish Steps, with the church at the top behind them

Up the Spanish Steps.

From here we walked to the Trevi Fountain (#2). Again it was extremely crowded, as it was around 4 pm. We spent about 10 minutes waiting for a spot to take photos.

Crowds around the Trevi Fountain

The Trevi Fountain.

Next we headed to the Pantheon (#3). We only saw it from outside, as we didn’t have time to go in. Gunther’s Gelato was highly rated online, so it was on our list. It was great gelato, but apart from one place in Florence, we didn’t have any bad gelato in Italy.

The columned front of the Pantheon under a cloudy sky

The Pantheon.

The next stop was Piazza Navona (#4). We enjoyed walking around here. There was a fair or night market set up in the square, which, along with the holiday decorations, added to its beauty.

Man and boy sitting in front of the lit-up Fountain of the Four Rivers at dusk

The Fountain of the Four Rivers in Piazza Navona.

Our last stop was Piazza del Campidoglio (#5), close to the Roman Forum and the Colosseum. Being up on a rise, it had great views of the surrounding area. The walk here was a bit tiring, as we had been walking for what felt like three hours.

Piazza del Campidoglio lit up at night with a Christmas tree

Piazza del Campidoglio.

We tried Avocado Bar for dinner. Unfortunately, the food was a letdown. Nothing we ordered was what we expected, or even good, except the juice. Disappointed, we went back to our hotel. Our son was still hungry, so we tried our luck again at a touristy pizza restaurant across the street from the hotel. The pizza was really good, and we wished it had been our first choice.

Woman and boy at a table eating pizza

The restaurant near our hotel, with great pizza.

After dinner, we got ready for bed, as we had an early reservation for the Colosseum and the Roman Forum.

Day 10 Colosseum & Roman Forum, then Milan

Breakfast was included at our hotel, and it was one of the best of the whole trip: a lavish spread of eggs, pastries, fruit, coffee, tea, cereal and more. We left our luggage with the hotel to store until we returned from the Colosseum.

We had booked skip-the-line Colosseum tickets through GetYourGuide about a month ahead. When we tried to book directly on the official Colosseum website, it was already sold out. GetYourGuide and Viator both had skip-the-line tickets with various options, such as guided tours, a 3D movie or arena access. We got the basic skip-the-line admission without the arena, worried about being short on time. We were meant to pick up the tickets at the tour company’s office, about 20 minutes from the Colosseum, that morning. But on the way there, just passing the Colosseum, the company called to say they could send the tickets on WhatsApp. We couldn’t believe our luck and thanked them. Entry to the Colosseum is timed, and we had about an hour before our window began.

Boy standing beneath the Arch of Titus at the entrance to the Roman Forum

The entrance to the Roman Forum.

We used the time to see the Roman Forum. Something to know: kids’ tickets for the Roman Forum and the Colosseum can’t be bought through GetYourGuide or even the official website, but you need them at the entrance. The guard at the Roman Forum entrance showed us a QR code to scan for a free ticket for our son, which only works at the Forum. For the Colosseum, we had to go to window number 4 at the box office for a free kids’ ticket. It was all a bit confusing and set us back a few minutes.

Ruins and green lawns of the Roman Forum under a cloudy sky

The Roman Forum.

Even on a cold, rainy day, the Roman Forum was mesmerizing. We hadn’t visited on our first trip to Rome and couldn’t believe we had missed it. It is unbelievable to walk the same paths and see the same buildings as the ancient Romans. We especially enjoyed the view from Palatine Hill, over the whole ancient city below. Thrilled, we headed to the Colosseum right at the start of our entry window.

The ruins of the Roman Forum spread out below Palatine Hill

The view from Palatine Hill.

This was our second visit to the Colosseum, but sharing it with our son made it even more spectacular. We picked up his kids’ ticket at the box office before climbing the stairs to the viewing areas. There are viewing areas on the lower levels too, but the view from higher up adds to the grandeur of the ancient arena. We looked at the displays and models of how it was built. It was crowded even on a rainy weekend day. We walked the whole path past the various viewing areas, and saw people on the arena tours down on the lower levels. The Colosseum is a masterpiece of ancient architecture.

Boy looking out over the inside of the Colosseum

Inside the Colosseum.

With the crowds so heavy, our son often got a bit uncomfortable, and sometimes told us he was ready to leave. Since we had to finish the loop to get out, we found quiet corners away from the crowds to wait a few minutes and let groups pass. Then we would find a small gap and enjoy the views again. We did this several times. It gave us a chance to see the seating areas and some overlooked corners with great views.

The tiers and arena floor of the Colosseum

The Colosseum.

After finishing the circuit, we went to the gift shop, as our son wanted a model of the Colosseum. The shop had unique souvenirs and interesting books and art about ancient Rome. We got a bit lost looking for the exit. Once downstairs, we saw the lower level from two different viewing platforms. Then we went outside the gates to take photos from outside. Having taken a satisfying number of photos, we walked back toward our hotel.

The Colosseum’s outer arches against a cloudy sky

The Colosseum from outside.

We were hungry for lunch by now. Yala Yala, a Mediterranean restaurant, was the perfect choice after a cold morning at the ruins. The staff were friendly, and the place was right by our hotel and not too busy. We enjoyed fresh falafel wraps, hummus and warm pita. After lunch, we walked a bit more around the streets that run above and around the Roman Forum. We loved seeing it from a different perspective than that morning. After about 30 minutes, we went back to the hotel for our bags.

The entrance of Yala Yala restaurant on a Rome street

The Lebanese restaurant near our hotel.

Bags in hand, we made the one-mile uphill walk to Roma Termini. After what we had seen on the metro, we didn’t want to take any risks, and the metro stations have many stairs, which makes the trip harder with luggage anyway.

Trapizzino sandwiches were one thing our son was desperate to try, and our research showed a trapizzino shop in Roma Termini station. It is in a (really crowded) food court at the back of the station, past the shops and all the platforms, about a 15-minute walk from the platforms. The eggplant parmigiana trapizzino we tried was exquisite, but we only recommend going to the food court if you have about an hour before your train.

We made it to the train a few minutes early and ate the sandwich on board. We rested on the three-hour high-speed train to Milan. In Milan, we walked the short distance to our hotel and checked in. We were hungry and wanted something hearty and comforting, so we found an Indian restaurant about 10 minutes’ walk away. After dinner we walked back to the station to find the Malpensa airport bus stop.

Something to note: the Malpensa Express train only starts running at 5:30 every morning. Our flight was at 7:30, so we needed to reach the airport at about 5 am. It was hard to find another way to get there, and a taxi from the hotel would have cost 100 euros. After a ton of research on the train to Milan, we found the Malpensa bus, which starts at 3 am and leaves from near the train station. Since the station is huge, we decided to check the bus stop’s location and timings the night before. Once we had confirmed it, we went back to the hotel and straight to bed.

Day 11 Lake Garda & Sirmione

On our last trip to Italy, we explored Lake Como and enjoyed the slower pace, incredible food and spectacular views. This time we wanted to see the Lake Garda area. We began the morning with the train from Milano Centrale to Desenzano del Garda, just over an hour away. It was close enough that we felt comfortable making this day trip the day before flying home.

A red Italo high-speed train at the platform in Milano Centrale

An Italo train at Milano Centrale.

Unfortunately, the weather was not on our side. It was rainy, cloudy, windy and quite possibly the coldest day of the whole trip. At the station, we stopped at the tourist information office. The nice lady there suggested we take the ferry to Sirmione, another town on the lake, to visit its castle, and gave us walking directions to the ferry terminal.

The yellow station building at Desenzano del Garda on a wet day

The train station.

The walk took us through the newer residential parts of town, where locals were going about their day, and then through the older, historic parts, with quaint cobblestone streets and winding alleys of homes and shops near the lake. The ferry terminal turned out to be closed because of high winds on this early January day. We wanted to see more of the lake and its towns, so we took a taxi to Sirmione instead. Luckily, there was one taxi waiting at the stand. The ride took about 20 minutes one way and cost about 50 euros total.

Boy in a hooded coat by the railing of Desenzano’s harbor, with boats behind

The ferry terminal.

We were dropped off at the gate of Sirmione Castle. The taxi driver showed us the taxi stand just outside the castle entrance for our trip back. Since it was the first Sunday of the month, entry to the castle was free. We were so glad we visited this unique, well-preserved castle. Built right on the shore, it has walkways and towers jutting out over the turquoise water. We climbed several flights of stairs for amazing views of the lake and the surrounding area from different windows and vantage points. Even in the rain and cold, we were thrilled to explore it.

Boy looking over a castle wall at the turquoise lake and rooftops

The view from Sirmione Castle toward Lake Garda.

A crenellated stone tower and gateway inside Sirmione Castle

Sirmione Castle.

After about an hour at the castle, we explored old town Sirmione, a beautiful maze of lakeside perfume shops, cafes, snack bars and local shops. We did some shopping and made our way back to the taxi stand for Desenzano del Garda. We had several hours before our train back to Milan, but with the rain, and our phones not always working to call a taxi, we decided to head back with plenty of time to spare.

A stone building covered in climbing plants on a street in Sirmione

A gorgeous building in Sirmione.

Back at the port, we went into the sheltered alleys to look at shops and find lunch. Even fewer shops were open in Desenzano del Garda than in Sirmione, and by noon they were all closing. We wished we had spent more time in Sirmione, as there wasn’t much to do in Desenzano. We found a restaurant for lunch. It was cozy, but that was the only positive; the food was mediocre, bland and basic for Italy. We had been staying away from the lakeshore because of the cold wind and rain. When the rain let up for a few minutes, we got hot chocolate and walked to the lake. The lakeshore is amazingly beautiful.

Woman and boy at a coin-operated viewer on the rocky lakeshore, with mountains across the water

The view of Lake Garda and the surrounding mountains.

The snow-covered mountains above the turquoise lake are a sight not to miss. The central boat dock in Desenzano del Garda has gorgeous warm-colored buildings, a bridge and orange trees. In most places we visited, we were the only people there. Lake Garda may be bustling in summer, but we got to meet more locals and see it completely empty of tourists.

Small boats moored in front of a row of pastel buildings at Desenzano’s old port

The Desenzano del Garda boat dock.

We walked back through the winding alleys and the newer parts of town to the station, in time for our train to Milan. Back in Milan, we stopped at a small grocery store for cookies and chocolates to take home, and picked up falafel wraps to eat in our room. After packing and showering, we tried to get to bed early.

The platform and station building at Desenzano del Garda

The Desenzano del Garda train station.

Day 12 Return

We woke up at 3 am to make it to the bus stop by 4 am. The bus ride took just under an hour. Since it was so early, the airport was not too busy. We checked our bags, went through security and got some breakfast. Finally we got on our flight, happy to be going home with the most wonderful memories.