About 4 years ago, a couple of years before Chris turned 40, we both decided that for our 40th birthdays, we would go on trips. It would be up to the milestone birthday holder to decide where and with whom–but we’d go all out and that’s how we would celebrate. For Chris’s 40th, we got a villa in Mexico and brought a couple of his brothers and their wives, and we spent a week relaxing in the sun. For mine, we brought our girls (they’re really at the perfect ages for traveling–15, 11, and 7–and my parents to Italy! My birthday isn’t until the end of the year (November 27), but our travel agent, Eli at Wagner Bespoke, told us June would be pretty great in Italy, and that worked best for our schedules as well.
Last year, as we were mapping out the details of the trip I suggested we take my parents as well. A couple years ago, my dad was going through pretty serious cancer treatments. It was incredibly scary and difficult and while my sisters and I took turns flying out and helping, my mom took care of him day and night endlessly for months. Feeding him through a feeding tube. Taking him to chemo appointments. Many nights in the ER. It was a dark time. My dad, recognizing her love through service and sacrifice, said, “When we get through this, I’m going to take you to Italy.” With that promise and my mom turning 70 this summer, I couldn’t imagine going without her and my dad.
Here’s everything we did on our 12 day trip to Italy with 3 kids!
To celebrate my 40th birthday, we planned the most unforgettable 12-day adventure through Italy — filled with food, design, history, and plenty of family memories. From the ancient ruins of Rome to the rolling hills of Tuscany and the Renaissance beauty of Florence, every day was thoughtful and full of meaning (and let’s be honest, gelato). Here’s exactly what we did, where we stayed, and a few favorite highlights.
🇮🇹 Rome
Hotel: Bulgari Hotel Roma
Modern luxury meets Roman history — we couldn’t have asked for a more elegant start. (There’s a documentary about it on Prime we watched before our arrival which made us even more in awe of the rooms) and luckily some of the rooms were available when we arrived so we could get a quick power nap in before we set off to our first tour!
- Day 1: Panoramic golf cart tour of Rome — Colosseum, Trevi Fountain, Spanish Steps, Piazza Navona, The Pantheon.
- Polly was having a very bad PFAPA flare up and she couldn’t even walk when we landed in Italy. It makes her joints very stiff, but it had never been this bad. Chris carried her through the airport, until we spotted an open wheelchair. So the golf cart was a total blessing. We also stopped for our first gelato at Venchi and “one of the best pizzas in Rome” according to our guide at Forno Campo de Fiori. He wasn’t lying. The artichoke pizza (his recommendation) was divine.
- Polly was having a very bad PFAPA flare up and she couldn’t even walk when we landed in Italy. It makes her joints very stiff, but it had never been this bad. Chris carried her through the airport, until we spotted an open wheelchair. So the golf cart was a total blessing. We also stopped for our first gelato at Venchi and “one of the best pizzas in Rome” according to our guide at Forno Campo de Fiori. He wasn’t lying. The artichoke pizza (his recommendation) was divine.
- Day 2: Private guided tour of the Colosseum and Roman Forum in the morning.
- Polly was still not doing well, and our hotel provided us a wheelchair for her. Our tour guide, Daniel, (booked by our travel agent) was so fantastic. We all wore headsets and he wore a mic so we could hear him well no matter where we were. He knew stories about everything and presented all of this history in a really engaging way that my girls grasped onto. It was incredibly hot in the colosseum but the girls had their neck fans that helped and I wrongfully assumed there would be a place to get water. (Water is not really a “thing” there. I never see anyone drinking water and I don’t understand how! haha!) After the colosseum we walked over to the roman forum but Polly was getting a fever again so we stopped for gelato and went back to the hotel so she could rest.
- After a nap, we went to the LDS Rome Temple and Visitor’s center. It was incredible.
- Before dinner, we went for a swim in the hotel pool that had incredible marble columns in it. So beautiful!
- Day 3: Morning tour of the Vatican Museums, Sistine Chapel, and St. Peter’s Basilica. (My favorite day!!)
- Afternoon: Self-led Gelato tour (Giolitti and La Strega Nocciola were standouts!), Lunch at Matricianella (get a reservation! Our concierge called ahead for us. One of the best meals we had.)
- Dinner at Mama Eat — A restaurant with a focus on food sensitivities (but I’d skip this one!)
- After dinner, we went up to the rooftop of the Bulgari to see the city lights and have a little bite and some mocktails–perfect ending to our stay in Rome.
🌿 Tuscany
Villa: Rosewood Castiglion del Bosco
Set in the hills of Montalcino, this villa stay was the heart of our trip — warm, restorative, and full of once-in-a-lifetime experiences. It couldn’t have come at a better time. My dad described this place as “where the world goes to rest.” We all felt so rejuvenated here.
- Day 1: Drove from Rome to Tuscany with a stop in charming Orvieto for lunch and a stroll through the old streets and most amazing church.
- Kicked off our villa stay with a private Pizza Party dinner.
- Kicked off our villa stay with a private Pizza Party dinner.
- Day 2: Truffle hunting through the forest (with the cutest truffle dog, Rose.) followed by a rustic outdoor lunch made with truffles!.
- Dinner at Campo Del Drago on property — farm-to-table and wildly beautiful. (While Chris and I loved this chef’s tasting experience, this was a little too fancy and long for our girls.)
- Dinner at Campo Del Drago on property — farm-to-table and wildly beautiful. (While Chris and I loved this chef’s tasting experience, this was a little too fancy and long for our girls.)
- Day 3: Italian BBQ in the villa with a private chef — think grilled vegetables, Chianina beef, local sausages, and buffalo mozzarella and fresh tomatoes under the stars.
- Day 4: The girls did a pastry-making class in the villa (Panna Cotta! Pavlova! Chocolate mousse! They were so proud!)
- Followed by another Tuscan BBQ night — we definitely didn’t go hungry here. We had all of their desserts afterward.
🎨 Florence
Hotel: Four Seasons Florence
History, gardens, frescoed ceilings — and just steps from the Duomo.
- Day 1: Arrived from Tuscany and jumped right into a city tour — Duomo, where we climbed all the way to the top and saw 360 views of Florence. It was so moving and emotional and rewarding. (It is quite the climb and can be tight if you have claustrophobia), Accademia (hello, Michelangelo’s David), and dinner at Vini e Vecchi Sapori.
- Day 2: Walked around the city in the morning and took the girls on the carousel right in the square. We went to the markets by Ponte Vecchio and walked along the Arno River.
- That evening, we did a sunset e-bike tour through Florence’s cobblestone streets and piazzas. (One of our absolute favorite activities! My parents stayed back with Polly, who was still not 100% and enjoyed the gardens at the hotel). We went up to the countryside and saw where Galileo lived and wild capers and olive trees in the countryside. We rode by bleachers where hundreds of people gathered to watch the sunset together, while musicians play. Our tour guide said it happens every night, organically.
- That evening, we did a sunset e-bike tour through Florence’s cobblestone streets and piazzas. (One of our absolute favorite activities! My parents stayed back with Polly, who was still not 100% and enjoyed the gardens at the hotel). We went up to the countryside and saw where Galileo lived and wild capers and olive trees in the countryside. We rode by bleachers where hundreds of people gathered to watch the sunset together, while musicians play. Our tour guide said it happens every night, organically.
- Day 3: We started our day vintage shopping at a local market (I think it was called Mercato delle Pulci) and I could have stayed all day. It was a very immersive experience. And although I loved everything, I ended up not buying anything. But feel very content with all the memories and photos.
- Later that day, we did a fresco painting class with a Florentine master at Studio Iguarnieri — it was such a creative, hands-on experience, that my whole family loved. (I was ready to do my own thing, but it was really geared toward beginners and a fun and memorable activity that you get to take home!)
- Later that day, we did a fresco painting class with a Florentine master at Studio Iguarnieri — it was such a creative, hands-on experience, that my whole family loved. (I was ready to do my own thing, but it was really geared toward beginners and a fun and memorable activity that you get to take home!)
- Day 4: A private cooking class with local chefs at “The Cooking Touch” on the Ponte Vecchio. This was a MUST DO! Everything was from scratch and we made gelato, chocolate lava cake, gnocchi, pasta with fresh tomato sauce and stuffed zucchini flowers. We learned so much and all sat down to eat everything we made afterward.
- Day 5: Early morning flight back home, full hearts and full memory cards.
I have gotten a lot of questions about how I handled the food in Italy. I have been very strictly gluten free/dairy free for 10 years (meaning I never ever have it and was diagnosed with celiac last year) and grain free and egg free for the past few years to help reduce my chronic inflammation so I was, naturally, very worried about how my body would react to the food in Italy.
Our travel agent made sure everywhere we went, there were options I could have, but I’ve also wanted to have pasta and pizza in Italy for…ever. I packed a bunch of digestive enzymes and tried a bite of anything I wanted to. I wanted the full experience, or as close I could get. Surprisingly, my gut did okay, (it is a completely different wheat than anything we have here. The way it is grown, the weather and the type making it much more digestible) but I did get pretty bad headaches when I ate the gluten there and my hands and knees are still stiff a week later from all the inflammation I packed on. It was still worth it. “When in Rome…” I’m gonna try everything. And I would do it allllllll again. (And Chris is already re-living the trip with a new Italy-inspired recipe!) Truly a trip of a lifetime.
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Long time follower here! My young daughter is celiac and will be visiting Rome and Florence next month. Could you please share the gluten free places you visited and would recommend?
Everyone knows that Italians know how to eat, but it’s fascinating that you were able to indulge without too many side effects – I think it has to be stated that the difference in eating whole foods, organic or not, is just a game changer in terms of how well our bodies can cope when we aren’t adding all of the “extras” into our food.
To this day I can recall the flavor of a caprese sandwich I are on Capri – appropriately enough. Just good hard wheat ciabatta, buffalo mozzarella, fresh basil and heirloom tomatoes, drizzled with bright green olive oil. ..each element bursting with flavor.
Your kids are lucky to have experienced this together with you.
We visited Sicily for our 30th anniversary, and although it was supposed to be a mommy/daddy trip, I couldn’t help but feel sorry for them for all that they were missing.
Wishing you many more family adventures!
Travel agent?
Wagner Bespoke Travel. Highly recommend!
Your trip with your family looked awesome, could not help but wonder how you pack all those beautiful clothes! Your outfits were perfection! Maybe a segment or post on packing?
Sounds magical. Thank you for sharing!