Nearly two and a half years later, we finally made it on our multi-generational trip to Italy! After COVID completely changed our plans for our original scheduled trip in May of 2020, we put our plans on hold and decided to start a family. With no end in sight as far as the virus and travel restrictions, we continued to push back our Italy travel dates further and further into 2022.
Our original itinerary was on-the-go from the northern part of the country to the south. We were planning to hop from Venice to the Tuscan countryside and finish off our trip on the Amalfi Coast. Fast forward to September of 2022 and our travel crew looked a whole lot different than the 6 adults going previously. We now had not one but TWO little ones joining us on the international adventure.
Although travel (especially international travel) looks a lot different with babies and toddlers involved; I would not change our experience for the world. I have to thank my friend Carey with Jetset Travel for planning out all the wonderful details for our baby-friendly European itinerary.
My hope is that this blog can provide some inspiration, encouragement and helpful ideas for families looking to keep traveling once they have a little one. If you go into it with the right mindset and expectations, it can truly be a trip of a lifetime and provide unbelievable memories along the way.
The Planning Process
Let’s just start with the fact that we started planning this family trip to Italy back in mid-2019. It was supposed to be a trip for my dad’s 70th birthday; 6 adults and consisted of stops in Venice, Tuscany and Amalfi Coast. Fast forward to our originally scheduled itinerary dates in May of 2020 and a global pandemic put a two and a half year delay on our trip. Luckily, we worked with a travel agent turned mom friend, Carey Dreyer at Jetset World Travel who made the planning process seamless.
Between navigating world-wide travel restrictions in place due to the pandemic, the addition of two babies, and a completely altered Italy travel itinerary; I don’t know how we would have gotten through the planning without her.
From start to finish, Carey put together the PERFECT family-friendly 11-day Italian adventure for 5 adults and 2 little ones under 2. While she worked with her local partners in Italy, she gave me autonomy in hand-picking our final accommodations, destinations and excursions.
Although I typically enjoy planning out all the details of my travels, working with Carey opened the door to hotel perks, private tours, and helpful baby travel tips. She curated an itinerary complete with a private winery tour in Siena, a private market and cooking class in Florence, a day-trip to Venice with a private tour guide, a rooftop cocktail class and special occasion dining reservations.
10/10 would recommend going this route if you’re looking for a seamless planning process and a LOT less stress.
Where We Stayed:
Antica Torre Tornabuoni:
All I can say is WOW. We absolutely LOVED our stay at Antica Torre in Florence located right on the Arno River. We stayed in their 3-bedroom suite which was 3X larger than any of us could have ever imagined. Typical European accommodations typically are smaller and cramped which was a concern traveling with 2 toddlers and all the baby gear. However, this apartment-style setup was anything but cramped.. We were on our own floor of the hotel; complete with 3 gathering/living room spaces, 3 king bedrooms, 2 kitchens, and 3 bathrooms…! Needless to say, we never wanted to leave.
To top it all off, the Panoramic Bar at the top of Antica Torre had the most breathtaking views of Florence rooftops, an amazing breakfast buffet and the kindest bartender who whipped up amazing cocktails for us nightly!
What To Do:
Private Cooking Class:
This was our main ‘excursion’ chosen during our stay in Florence and it was by far one of our biggest highlights of our entire trip. We got set up with the amazing Chef Ilaria Ricci who took us to the local food market, helped us to handpick exactly what we wanted to cook, and then finished off cooking at her beautiful home.
After preparing mouthwatering food for several hours, we got to sit down and enjoy our hand-made gnocchi with pesto sauce, tomato sauce and Cavatelli and extra creamy parmesan sauce with thick-cut bacon. Nothing tastes better than SUPER fresh pasta dishes with a cold refreshing sparkling Prosecco in hand after a few hours of hard work. Oh, and we finished off with freshly homemade lemon gelato. Mmmmm mmm. We would love to be back@
10/10 recommend this experience if you find yourself in Florence ! (will update this post soon with the direct website of our chef once I can locate)
If traveling to Venice for the day with 2 toddlers makes us crazy… then we are most definitely crazy! Would I recommend doing this to others? Honestly, I would only do this day trip if you are okay with a little chaos 😉 It is a LONG day of travel consisting of 2 train rides approximately 2 hours each way and a non-stroller friendly city with lots of tourists and water taxis, etc.
All that being said, we were happy we did the trip especially since I was the only one who had been to Venice and it’s an extremely unique city for anyone who has not experienced it!
While you are there, I would highly recommend a private tour of the city. This allows you to see the city from a local’s point of view and takes you away from the overcrowded touristy attractions. We got to see backstreets and view points that I would never have known without our guide!
Also don’t forget to take a gondola ride! It’s overpriced, yes but how often will you be in a Venetian gondola floating through the waterways? It’s worth a one-time experience in my opinion.
Where to Eat & Drink:
La Giostra –
The PERFECT date night spot! I cannot recommend La Giostra highly enough and definitely suggest making reservations. Get their warm and creamy burrata appetizer and their pear and pecorino ravioli. It is to die for! Enjoy the romantic setting and on-the-house Prosecco upon arrival.
Another gem in Florence. If you studied abroad in Italy, chances are you already know and love this spot. If not, treat yourself to one of their pizzas and you won’t regret it!
Ristorante Lorenzo de’ Medici–
ALL of my gluten-free friends out there, this is your spot! We were shocked in general how gluten-free friendly Italy was and this place went above and beyond. If you are celiac or know someone who deals with these restrictions, check it out. **Even if you are NOT seeking gluten-free; they have non-GF options and their food is amazing. (try the truffle ravioli and their Florentine steak!)
Thousands and thousands of amazing reviews! We made the mistake of not making reservations at Trattoria ZaZa and when we showed up for dinner the line was wrapped around the restaurant way out in the street. Needless to say we did not get to try this out for ourselves but I trust the hype! Make reservations !!! (or get there super early)
Panoramic Rooftop Bar at Antica Torre
Mike and James enjoyed a father-son buffet breakfast overlooking the Arno River and had nothing but rave reviews to share. We also enjoyed nightly cocktails on the Panoramic Rooftop Bar, listening to live music from below and watching the sunset over the river. The views overlooking the rooftops of Florence is a hard one to beat and we LOVED the bartender! Try out their spin on the Aperol Spritz or the house-made passionfruit infused cocktail!
I would have went here every single day if it was up to me. Don’t get me wrong, I LOVE Italian food (too much!) but I also crave greens and fresh fruit, smoothies, etc. especially when I don’t have regular access. If you’re anything like me, check this spot out for some overnight oats, smoothie bowls, almond-milk lattes, avocado toast, chia seed pudding and more.
Where to Stay:
Working through a travel agent opened the door to homes/villa rentals that we would have never known about or had access to without. Carey booked us in a beautiful Villa Venere, a 3 bedroom, 2 bathroom villa overlooking the harbor of Portovenere. We were situated a convenient 5-minute walk outside of the main square where all the shops and restaurants are; and where the ferry departs from. It was quiet and tucked away yet easily accessible to everywhere we wanted to go by foot.
The villa came with two pack-and-play cribs for the babies, a full kitchen, main gathering space, outdoor dining patio space and a private pool/lawn on property.
Spending time relaxing at our villa on the front lawn with a bottle of rose, local pesto, parmesan, and freshly baked focaccia bread with the family is one of the biggest trip highlights. We had the space all to ourselves and the freedom to play music, swim, and take in the breathtaking Italian coastline views.
What to Do:
Day trip to Cinque Terre:
Typically you can take the ferry from Portovenere to 4 of the 5 Cinque Terre towns. However, during our visit the waters were too rough and the ferry was canceled every single day. This was definitely a bummer given how convenient it would have been to hop on the ferry just steps outside of our villa and pulling up to the first of the five towns in roughly 30 minutes. Therefore, the trip went from super simple to a rather long day of taxi rides and train rides but it was worth it for the adventure (sans-babies).
We ended up taking a taxi from the town square of Portovenere to La Spezia train station. From there, we took the regional train (you’ll need the Cinque Terre Pass) from La Spezia to the Cinque Terre villages. We skipped the first stop due to a shortage of time and hopped off at Manarola. These towns are definitely much more touristy than our home base town of Portovenere but beautiful and charming nonetheless.
Given our limited time, we took straight to the hiking trail which takes approximately 2.5 hours to complete. It’s considered a moderate hike but I wouldn’t recommend if you have a serious fear of heights or issues with balance as it’s a pretty straight-up path and several cliffside pathways. That being said, the views were worth every drop of sweat and the winery stop at at the top of the mountain didn’t hurt either!
After we made it to Corniglia, we hopped on the train to Vernazza where we enjoyed some refreshing gelato, hard earned pizza and took a dip in the turquoise blue waters.
TIP – Be prepared for lots of train delays as you make your way back to the starting point. Luckily once you get on a train that is heading towards La Spezia, it is a quick and easy trip. Once you arrive back at La Spezia station, there are a ton of taxis available to get back to Portovenere.
**Logistics** Mike and I decided to take the adventure by train (sans-babies) to scope it out for the entire group. We had to call a taxi who picked us up in the town center of Portovenere and took us to the La Spezia train station (~20-25 min drive). From the La Spezia train station; it’s a 10-15 minute train ride to the first village, Riomaggiore. Each town there on out is roughly 5 minute train rides apart.
Note – you will need to purchase a Cinque Terre pass which works for both hiking and the train from town to town. I can’t speak to the process because our travel agent did all of this work behind-the-scenes but I would recommend buying them before you get to the La Spezia train station to avoid the headache of waiting in a loooong line upon arrival. **You will also need your passport!!
The biggest learning lesson we encountered with the entire process of getting to Cinque Terre was the unpredictability and unreliability of transportation. Between the ferry cancellation and the train delays, cancellations and labor strikes; we decided that trying to do this day trip with two babies would have been a headache. However, it’s great for a couple or friends day out! (If you do go with a baby / toddler, leave the stroller at home and instead bring a comfortable baby carrier!)
Hike from one Cinque Terre village to the next:
We hopped off in the second town of Manarola and immediately took off on the path towards Corniglia. Hiking this route was the highlight of our day and the views were unparalleled. **Tip – stop halfway for gorgeous cliffside views and a refreshing chilled glass of local white wine !! You will not regret it.
Hike Portovenere or Palmaria:
We didn’t get a chance to do this hike but had we had a longer stay in Portovenere, we heard great things! There are plenty of boats in front of the cafes and restaurants in the square that will take you over to Palmaria. Here we can explore a different landscape and see colorful Portovenere from the other side!
Go shopping in the colorful backstreets and watch the sunset!
Don’t forget to explore the backstreets of Portovenere through the city gates. There are several restaurants, cafes and shops along the waterfront but there are even more hidden gems on the backstreet of the city. We found our favorite local made pesto shop that we frequented almost daily (don’t remember the name – sorry!), beautiful linen shops, souvenirs, and more.
No matter what you do, don’t miss out on the insane sunsets from the cliffside viewpoint in town.
Get Gelato (daily!)
There is no shortage of gelato shops in Italy and Portovenere is not an exception. One of our favorite spots was Moon Gelateria, Gelateria Artigianale La Pitonetta.
Where to Eat & Drink:
- Moon Gelateria – great cappuccinos, paninis and gelato
- Locanda Lorena: Make reservations ahead of time. This was a fun spot for a special anniversary lunch or dinner. Enjoy a ride on a venetian style boat after getting picked up in the town of Portovenere and get dropped off right at the restaurant. Here you’ll find charm, fresh seafood and breathtaking views!
- Imbarcadero: Ahhh, I can taste my daily morning cappuccino while typing this out. We loved this local coffee shop that we frequented most mornings during our stay in Portovenere. This quaint shop was located right below our villa. Get a chocolate pastry and a cappuccino overlooking the harbor.
Our final night we stayed in Milan since we had early flights out the following day to return to the US. Although we barely had any time to explore the city; it was the perfect ending to our trip. We had just enough time to walk around, grab a good dinner and attempt to get one last good night of sleep before our 10 hour drive the next day.
We stayed at Sina de la Ville which was centrally located and walkable to all the top sites in Milan along with lots of shopping, restaurants and bars. On the following day, we got picked up by our private transfer and driven to the Milan airport about 35-40 minutes away.
- Pack as lightly as possible: if you can find a way to NOT bring a car seat, pack and play and/or heavy duty stroller; do it! Less is more on this type of trip with a toddler. You will already have your hands full. We were able to pack all of our luggage for 2 adults and 1 toddler in 1 large Away checked bag, 1 Away carry-on, 1 diaper backpack and 1 regular backpack. No travel crib or car seat. We brought our super light and compact Colugo stroller that folds up with one hand and fits in the overhead compartment of the airplane!
- Don’t have high expectations of car seat standards: Multiple times we were supposed to have car seats in our transfers and we either got a booster seat ( try getting a 16 month old to sit in a booster! ) or a car seat facing forward. Very different restrictions and regulations than the US. If you are uncomfortable with this, I’d recommend bringing your own car seat. (We love the lightweight and affordable
- Many hands makes light work 😉: This goes without saying but if you are able to travel with family or friends who are on the same page, you can create a much better ‘vacation’ experience. We traveled with my mom, and my brother and his wife and baby and we alternated childcare in the evenings. This allowed for date nights and day outings for all adults in the group! Win-win for all.
- Request a travel crib at all your accommodations: There is always a small chance that a hotel or AirBnB will confirm a travel crib and then not have one upon arrival but from our experience, all places were very reliable. We brought pack-and-play sheets but never had to use them as the places we stayed always had the best set ups.
- Invest in a Slumberpod: I’ve talked about this in my travel gear blog post here. However, I still live by this product recommendation. The Slumberpod is a game changer in terms of traveling and staying in the same room as your little one. It’s a huge help for day time naps and putting your kiddo down before you’re ready to go to bed.
- Pack MORE snacks than you think you need: I thought I packed plenty of pouches, puffs and miscellaneous snacks but by the end of the trip I wished I brought twice as many. Good snacks can make the world of a difference when it comes to long days on the train, stroller walks through the city and long international flights. (We LOVE our Serenity Kids pouches and I love that they provide a healthy dose of protein and fats especially when we are thrown of our typical meal schedule)
For more European travel inspiration, check out our Iceland and Spain blogs here! If you need encouragement to travel with your baby, check out our post in Turks and Caicos.
For more helpful blogs on traveling with a baby; check out our beach travel guide with a baby under 6 months here or Flying with a Baby tips and product recs.