Portugal & Italy Itinerary for Families

Where do you like to travel over the holidays? My husband, João, my kids and I took a 18-day trip to Italy and Portugal over our Winter Break. It ended up being one of the best family travel experiences we could imagine. Here’s our Portugal and Italy itinerary, a great trip for families.

We left on Christmas Day and returned on January 12. It was a family affair: my mother-in-law and sister-in-law came from Brazil to join us.

First, the flights to Italy for Winter Break:

We’d been talking about doing this trip with my in-laws for a while, but when I saw round-trip tickets to Rome for just $440 (!) per person, I knew it was the right time.

Since then people have asked me how we found such cheap tickets. Here’s the basic strategy: try Google Flights, which shows fares for every day of the year. Simply enter the origin and destination, maybe alternative airports, and then start scrolling through the calendar. I just tried it out and found the same flights (SFO – Rome) for $523 this fall.

Why Southern Europe in winter?

First, Italy is one of the best places to visit in Europe with kids, and Portugal is a safe and affordable destination. Second, as a teacher, I can take big trips either in summer or winter, never in the shoulder seasons of spring and fall.

But I’ve always loved traveling in Europe in winter. The week between Christmas and New Year is a busy travel time for everyone, so expect crowds then. But overall winter is less crowded and more affordable. With both thinner crowds and lower prices, it’s easier to see how the local people really live and get more travel bang for your buck.

Fortunately, Italy and Portugal are warm places in Europe in December so they don’t get as cold as much of Europe. We were especially lucky with many sunny days and no rain! In southern Europe, the weather can be quite nice in winter!

Read more: How much does a trip to Italy cost?

And because Catholics celebrate Christmas through Epiphany on January 6, it’s very festive. One of the reasons I love Italy in winter is the Christmas decorations. Besides the streets filled with lights and colorful balls that reach from one side of the street to the other, the nativity scenes are a delight! This is a tiny nativity scene outside Santo Spirito in Florence, but we saw some very elaborate ones with moving characters in Rome.

Italy in winter: Sample schedule

We left on Christmas Day and returned on January 12 with this itinerary: 3 days in Florence, 4 days in Rome, 2 days in Venice, 6 days in Lisbon (plus a couple of day trips), and 1 more day near Rome before flying home. We were with my mother- and sister-in-law from Brazil for all of it except the first part in Florence.

The trip was mostly planned around my mother-in-law’s wish list. She’d never been to Europe and wanted to visit Rome, Venice, and Lisbon (Portugal is a popular choice for Brazilians because of their heritage). This trip was at a much faster pace than I normally like, and there was too much time traveling from one place to another, especially because we had to fly to Lisbon and back.

But despite the fact that we didn’t travel slowly, we had a wonderful time and ended up feeling grateful that we packed in as much as we did. The faster pace in Italy didn’t bother me too much because I know we’ll be back. One thing that helped was that we slowed way down in the second half with six days in Lisbon.

Our Italy Itinerary for 10 days with kids

Day 1: Overnight in Rome

We left the U.S. on December 25 and landed in Italy in the early evening of December 26. We needed to be in Rome just one night before taking the train to Florence the very next morning. (As it turns out, there’s now a new direct train from the airport to Florence!)

After taking the train from the airport to Rome, we walked just a few blocks to our accommodations for the night, the Beehive.

Run by Americans Linda and Steve, the Beehive is a welcoming hostel with unique perks like homemade dinners, storyteller evenings, and an all-organic, made-to-order breakfast (delicious!). We stayed in the annex and had two rooms each with two beds. This fit our needs perfectly because we needed a quiet place near the station to get a good night’s rest before hopping on the train again the next morning.

Read more: Italy Travel Tips

That night we were tired but hungry so asked Steve where we could get a quick dinner before bed. On his recommendation, we walked about 10 minutes to the Mercato Centrale, Rome’s trendy indoor food market (if you’re in or near Rome’s main train station, Termini, I highly recommend visiting this market).

After happily getting our first taste of local cuisine with arancini, local craft beer and wine, and plates of gnocchi and pasta, we went back to our rooms and got a full night’s sleep.

The next morning we nourished our jet-lagged bodies with a homemade, organic breakfast at The Beehive before catching the train to Florence.

Days 2-4: Florence

I love Florence so much that my family teases me about my unusual obsession with this city (which I had visited 5 times before and where I studied Italian Renaissance art history in 1995). I was so excited to take my three guys there so they could finally experience it for themselves and, I hoped, understand a bit why I feel so connected to it.

Despite kind of ugly weather (chilly and lots of clouds except for the last afternoon), we had a fantastic time. In fact, Florence was Noah’s and Gabe’s favorite part of the trip!

We stayed in the San Niccolò district of the Oltrarno, my favorite part of Florence where crowded artisans’ workshops and stylish cafes are nestled into small streets between the river and the hills.

I knew we’d just be able skim the surface of Florence with only three days, but we packed a lot in. I decided to buy the Firenze Card, which allows for skipping the long lines at about 90 of the city’s attractions. While we didn’t have time for even close to all 90 sights, for us the convenience was worth it, and we visited enough places that the card paid for itself.

What did we do in Florence?

The art in Florence can be hard to grasp because there’s just so much. I tried to give João, Noah and Gabe a crash course in the Italian Renaissance by taking them to a few places in chronological order so they could see, in a very basic way, the progression from Medieval to Early Renaissance to High Renaissance and beyond.

I might have been too ambitious! Late on the third day, while at the Uffizi, I gave Noah a tiny quiz to see if he could recognize Renaissance style painting, and he totally failed…but that’s okay. He actually loved seeing the art, and I know that all the imagery and architecture in Florence really are overwhelming, especially for a first-time visitor.

On our first day, we walked in the Oltrarno, had lunch at a trattoria, walked up to Piazzale Michelangelo and visited the 1000-year-old church of San Miniato al Monte at dusk. We witnessed part of a service in this old, old church, watched the sunset from the cemetery, and perused the shop where the monks sell their wares.

Read more: How to spend 3 days in Florence

At dusk we returned to town and walked through the center at night, stopping for persimmon gelato at Perché No, a bottle of Chianti Classico at a tiny wine shop, our Firenze Cards at the Palazzo Vecchio, and views of the sculptures in the Piazza della Signoria.

When I first visited Florence at age 16, my dad took me to this piazza at night, and I was so overwhelmed by its beauty that I can still picture turning the corner and seeing it for the first time. I don’t know if my kids will remember it this way, but I wanted them to see it at night just like I did all those years ago.

On day two, we spent most of the time in the historic center. We began at Santa Croce to see what the very beginnings of the Renaissance looked like with Giotto’s frescoes and how Renaissance proportions create harmony in the Pazzi Chapel, but my guys were especially impressed with stories of the 1966 flood and the tomb of Michelangelo.

While walking through the center and stopping at the Duomo, we noticed what I foolishly hadn’t expected: Florence during the week between Christmas and New Year is PACKED. I knew it would be busy, but I didn’t expect so many people everywhere!

We stopped to make reservations at the only sight that requires them, the climb to the top of the Duomo, only to find out that the next opening was five days out! With this new reality of visiting Florence, we headed for a place I knew would be less crowded, Palazzo Medici-Ricardi, the Renaissance palace of the Medici family.

After that, it was time for lunch, and we took the short walk over to the Mercato Centrale, one of my favorite stops in Florence, but ugh, there were so many people! After finding no seats in the big open dining hall upstairs, we gave up and walked back toward the Duomo to eat at Eataly. I doubt my Italian friends would approve, but the friendly service and delicious food hit the spot. After that, it was 3:00, a good time to walk to the nearby Accademia and see David.

Sadly, with so much access to information nowadays, we’re so saturated with images of the world’s most incredible sights that they lose their power. That makes visiting with kids especially refreshing because they don’t know what to expect and therefore are able to have a truly authentic experience.

They raved about the David then and for days to come (and warmed the heart of this former art history major). Even now, Gabe says that he loved seeing the David “because it’s huge! And it’s amazing that someone could make that with their own hands….and he made the veins and the shape of the feet really well. And his hair looks really good.” 🙂

That evening my friend Alexandra of the blog Arttrav and her husband, Tommaso, had us over for dinner. A long meal that started with lasagna and wine ended with a splendid array of beautiful things that I could eat every single day — fresh mozzarella, local prosciutto, a salad of orange and fennel, a cheese board with jam I couldn’t stop eating, all accompanied by Dievole wine from Tuscany.

The conversation was just as fantastic as the food, and I wished we lived closer so I could treat them to a lovely meal.

The next day continued with a late morning visit to the Boboli Gardens, which are beautiful and fun for kids but almost too big.

That afternoon there was finally a bit of sun. After a slow but lovely lunch at the tiny Sott’arno in the Oltrarno, we stopped at Santo Spirito (one of Brunelleschi’s churches), visited the Baptistery, and went to the Uffizi for a quick evening visit.

Because Florence was so crowded, we had to wait until late in the day to visit the Uffizi (even though we got to skip the regular line with our Firenze Card, the fast line was still very long!). I wish I could gush about seeing the art in the Uffizi, but it was hard to even get close to most of the works, and the pressure of trying to explain things to the kids left me feeling tired.

We did have a few moments of wonder, like at the flowers in Botticelli’s Primavera, the babies’ feet in Raphael’s Madonna of the Goldfinch, and the emotion of Botticelli’s Annunciation, one of my personal favorites.

There were many other special moments in Florence, often in response to the “little things” that make travel so special…those perfect morning cappuccinos, the surprising nightime light show on the Ponte Vecchio, the insanely good gelato, the details of the sculptures like Cellini’s Perseus. But the next morning it was time to head back to the train station.

Days 5-8: Rome

Next it was time to meet my in-laws in Rome. We took a morning train from Florence to Rome and then the metro from Termini to the Borgo Pio neighborhood near the Vatican. When we arrived at our rented apartment, my mother- and sister-in-law had just stepped out of the taxi from the airport, and we happily settled in together.

I’m not one to waste any time while traveling, so João and I left the kids with their grandma and aunt so we could get acquainted with the city at night. We walked from our apartment to Castel Sant’Angelo, crossed the Tiber River and explored the small streets around the Pantheon and Piazza Navona.

After getting some mulled wine, admiring the shops and sculptures, and feeling emotional at the beauty and history that are Rome, we stopped in a small bar for beer, wine, panini and cheese platters.

The next day we spent showing the boys and my in-laws what we’d done the night before: we visited the Christmas market at Piazza Navona, ate gelato at Grom, visited the Pantheon, and walked the small streets of the historic center. Fortunately, the neighborhood we chose to stay in has many good options for food, and we were able to get a big lunch of panini and salads before the shop closed for the New Year.

We happened to be in Rome for New Year’s Eve, which we spent out on the town. We started at Piazza del Popolo and walked to the nearby Il Brillo for our dinner reservation. After a long dinner, we made our own walking tour to the Spanish Steps and Trevi Fountain before finally getting the subway just before midnight.

When we emerged from the subway station, fireworks were going off all around us (even flying off balconies!). We were ecstatic to celebrate the New Year together in beautiful place so full of life.

The next morning was New Year’s Day. My mother-in-law strolled just a couple of blocks to the Vatican to see the Pope greet the crowd. If it’s something that’s important to you (as it is to her), it’s surprisingly easy to participate. You just need to get yourself to the Vatican — the earlier the better so you can be closer — and viola, the Pope appears.

One challenge for our time in Rome was that it fell over the New Year, meaning that most attractions were closed on January 1. To complicate it even more, the Colosseum tickets were sold out on December 31. So we went to the Colosseum on New Year’s Day when it was closed.

We could still walk up Palatine Hill, see the Arch of Constantine and Arch of Titus, visit the old church of San Sebastiano al Palatino, and walk around the Colosseum to see it from the outside. It wasn’t the full experience, yet it was still wonderful, and it was the best we could do.

That evening we got take out from a nearby restaurant in Borgo Pio, which solidified our trust in Italian cuisine. We couldn’t believe how tasty, and affordable, a “simple” gnocchi alla sorrentina and cacio e pepe could be.

Our last full day in Rome was blocked off for an afternoon at the Vatican Museums. In the morning, Joao and I walked across the Tiber and visited the market at Campo dei Fiori. We drank fresh-squeezed pomegranate juice while viewing the array of local products for sale, but I have to admit, the market lacked a certain something for me. I fear it’s become less local in flavor over the years and sadly geared toward tourists like us.

The streets around the Campo are a sight in themselves, so we enjoyed the walking, viewing churches and admiring the colorful corners that are so characteristic of Rome. We also came upon I Colori di Dentro, the shop where painter Maria Grazia Luffarelli sells her work. It’s perfect for souvenirs and centrally located at Via dei Banchi Vecchi 29 near Campo dei Fiori.

And then the Vatican…

I spent hours upon hours trying to figure out how to visit the Vatican Museums with my kids and mother-in-law (who doesn’t speak any English). After much thought, I decided to try a guided tour and reached out to Livitaly Tours for help. They graciously set us up with their three-hour guided tour with the knowledgeable and friendly Jade.

I’ll write more about the Livitaly tour experience in an upcoming blog post, but if you go to Rome, I highly recommend this tour. It made us feel relaxed while learning so much more than we would have if it had just been us. She even catered it to our kids, which kept them engaged despite the enormity of the place.

I honestly didn’t expect to love Rome as much as I did. I had been there a few times before and never felt a connection to it, but this time, I didn’t want to leave. In fact, I still daydream about it! I hope to return soon to spend two weeks getting to know the city better because four days was just a tiny introduction to this amazing city.

Days 9-10: Venice

I’ve been to Venice a few times, though before this, the last time was in 1997! I’ve always loved it, but I was curious if I would feel differently this time. After all, the city has been changed under the crush of tourism and the newer threats of climate change.

My fears were unfounded. I loved it just as much if not more, and the local people were friendly, just as they had been in Florence and Rome. We visited after the New Year, so there were crowds. But it wasn’t bad at all! We very rarely saw the big tour groups that I’d been dreading.

Due to our tight schedule, we had just two nights here, but we made the most of it. João and I spent almost every waking hour outside. The kids were especially enchanted by the boats and the shops selling Venetian glass and masks, so we did a lot of strolling, allowing ourselves to get lost in hopes of seeing a bit of the real Venice.

The highlight for us was the Basilica of San Marco. Who cannot be moved by the shimmering effect of the walls and ceiling covered in thousands of tiny pieces of gold? (No photos allowed inside!) We took our time there, visiting the Pala D’Oro and the museum upstairs with the ancient bronze horses and up close views of the mosaics.

We opted to skip the other major sites in order to have time to wander the streets, eat cicchetti, pop into churches (like San Zaccharia above) and try to soak in as much of the feel of Venice as possible. This included a long walk to the beautiful Basilica di Santa Maria della Salute and around the Dosoduro area at sunset.

You’ll notice that we had clear blue skies in both Rome and Venice. This sunny weather was of course welcome (no rain!). But I missed the moody fog of Venice, too. Venice in winter was also quite cold, between 28 and 34 degrees F, which made for very brisk walks!

And when we got too cold, we’d stop in a cafe for a beer, coffee, or snack. We definitely did not feel ready to leave Italy, but on January 5, we took at boat to the Venice airport and then a plane to Lisbon.

Our Portugal Itinerary for 7 days with kids

Days 11-16: Lisbon (& Cascais, Belém & Fátima)

In Lisbon we stayed at a gorgeous apartment on Costa do Castelo, an ancient street that forms a circle around the castle overlooking the city. The place had non-stop views over the city from the front windows, but its quiet location on mostly pedestrian streets felt like old Europe. If you’re coming to Lisbon and need three bedrooms, I highly recommend this apartment.

Lisbon surprised us. At first, it felt unexpectedly underwhelming. This was in part because we’d just come from Italy (which is hard to beat) and because we’d heard so much about it — expectations were high! But the longer we were there, the more it grew on us.

Read more: How much does a trip to Lisbon cost?

To me, Lisbon feels like a modern European city because it blends old and new, often in striking contrast. The winding cobblestone streets that lead to the Medieval castle are filled with graffiti and murals. The narrow, historic streets near the river lead to the hipster-filled Time Out Market, and near the city center is the Parque das Nações area, a new part of the city where modern architecture and waterfront living show a new direction for the city.

And because Lisbon is just starting to gain a place as a top tourist destination, it still has a bit of grit to it. The city could use a little makeover — weeds can be pulled, garbage can be cleaned up, and buildings can be restored — but this gives the city more character.

The colorful city is also lively and diverse, a contrast to what we experienced in Italy where there seems to be less ethnic diversity, at least in the city centers. In Lisbon it’s easy to hear other languages being spoken, not by tourists but by residents, and to see businesses of all kinds run by its diverse population.

I imagine this is in part due to its long relationship with Northern Africa, but perhaps also the relatively low cost of living and high quality of life, a combination attracts migrants, including a large number of Brazilians.

You might have heard about all the tiles, called azulejos, in Portugal. They really are just about everywhere you turn — on the fronts of many of the buildings and houses we passed and especially on important public structures like churches and train stations. The most common tiles make decorative geometric patterns but others are elaborate scenes of Portuguese history.

We devoted our first full day in Lisbon to the Castelo de São Jorge (St. George’s Castle), the Moorish fortress that overlooks the city. Because we visited in winter, there wasn’t even a line to enter, and we were able to explore the castle at ease.

The castle dates from two periods, pre-12th century when the Moors were here, and the Royal Palace (13th to 14th century). Much of it is in ruins due in part to the 1755 earthquake, but the castle is huge and beautiful and has fantastic views over the city and to the water.

Read more: Best Things to Do in Lisbon

That same afternoon we walked down to the Baixa neighborhood, stopped in Bebedouro Wine Bar for lunch, where I got a introduction to Portuguese wine, and visited the Praça do Comércio, the huge square that opens onto the Tagus River.

Lisbon has a long waterfront for walking, biking, or relaxing at a cafe with a drink. The city also has a Golden Gate Bridge look-alike, which we could always see in the distance. With sunny days and temperatures in the high 60s, we had the perfect conditions to be outdoors most of the days.

Because the long walkways are separated from traffic, they make it easy to explore with kids. In fact, the miles of waterfront along the Tagus River make me wonder why we haven’t done the same in Sacramento.

One of the days was devoted entirely to my mother-in-law’s wish to visit the pilgrimage site of the Sanctuary of Fátima where believers claim the Virgin Mary appeared in 1917. I stayed behind with the boys, and we explored Alfama, the oldest part of Lisbon.

This hilly maze of small streets sits just a few blocks downhill from where we stayed; we enjoyed lunch at a coffee shop with the friendliest servers and then continued walking until we came to the waterfront and the boys could run around before climbing the hills back up to the apartment.

We spent one day in the pretty seaside town of Cascais, just a short train ride away from Lisbon. After walking through the historic center and admiring the black and white designs of the sidewalks, we split up with my kids staying on the beach with my in-laws while we walked to the fort and through some local parks and residential streets. Because we needed to get back to our kids, we didn’t have a chance to visit the citadel, the most impressive sight in Cascais.

We spent one day in Belém, a town that’s basically connected to Lisbon’s waterfront. The town is famous for pastel de Belém, the delicious custard pastry, but we went there for its two UNESCO World Heritage Sites.

After a quick taxi ride the 6 km from the center of Lisbon, we began at the Tower of Belém. Built in the early 1500s as a defense post to protect the port, the Tower stands on a tiny island at the edge of the river. We paid the entrance fee (about 6 Euros per person) and explored the interior, which includes several viewpoints from the various levels of the tower.

The architecture is beautiful but unlike anything I’d seen before — I later learned about the Manueline style, which is really on display at the neighboring monastery (below).

While walking down the waterfront from the Tower to the Monastery, we came to the Monument to the Discoveries. Overlooking the water, this huge 1960 monument honors the grand discoveries made by Portuguese explorers. Like so many of the places we visited, the decorative black and white cobblestones were reason to visit in themselves.

The next stop was one that I’d had on my wish list: the Jerónimos Monastery, another UNESCO World Heritage Sites. Built in the 16th century in the Portuguese Manueline style. I’d never heard of this architectural style! It blends the elements of Late Gothic with the extreme ornateness of Moorish architecture. The details on the columns of animals and plants made it hard for me to leave, but the rest of the afternoon was waiting.

On our last day in Lisbon, we decided to devote the day to our kids. They had been such great travelers the entire trip, never complaining (which is saying a lot after our challenges traveling with kids in Scotland). We’d heard that Lisbon’s aquarium is the nicest in Europe, so we headed to a modern waterfront neighborhood and the Oceanário de Lisboa.

Besides the aquarium, which really is a nice one, we took the funicular over the river and walked through almost deserted gardens along the water. If you come to Lisbon with kids, I highly recommend taking a day for this! The contemporary feel of this area is totally different from the historic center.

Day 17: Back to Rome

Because our cheap tickets were in and out of Rome, we had to fly back to Rome. We stayed there one more night before heading home to California. I had it planned to maximize our time: take a morning flight from Lisbon, arrive in Rome just after lunchtime, visit the ancient ruins at Ostia Antica before staying the night at the airport Hilton.

But when we arrived at the Lisbon airport. we found that our flight had been canceled. So we spent the day waiting for the next flight and arrived in Rome at night. Ostia Antica will have to wait until next time!

Day 18: Back home

We loved this trip and found it to be so fun as a family. If you haven’t been to Italy or have been thinking about visiting Portugal, I highly recommend both! Do you have questions about this Portugal & Italy itinerary for families? Ask away!