I realize it’s been almost 3 weeks since we have been back from the most magical place on Earth = and no, move over Disney, because Italy takes the cake on that rating for this fam. If you followed our slice of social media life, you may know we took the girls to Italy for the first time two years ago… we hit up Rome for the first week of fun and then ventured over to Venice for 4 more days of adventure. Safe to say we all enjoyed that trip so much we started planning another one almost instantly.
We’ve been hard at work on this specific itinerary for more than 18 months = yes, we are big about planning in advance. That way you can nail down the exact accommodations and experiences you want and then take your time honing in on all the extras [restaurant reservations, special hot spots not to miss, etc]. I have to give it up to my hubby and Mimi because they dominate the planning and we utilized the travel services of Laura Tuley Travel and the IDI Travel team who have done most of our European adventures [tell them I sent you and they will take great care of you]!
My apologies for just now getting this post live… honestly I needed a bit of time to decompress from all the travel, catch up on sleep, relive the moments and memories over again and then of course put pen to paper to make sure I highlighted all the magic for you in the hopes it can help you on your next trip to Italy!
Before we get into the nitty gritty details of our actual trip, I do want to mention our flights there. Months ago, we stumbled upon an incredible deal with American Airlines to fly on one of their flagship airplanes in the business class pod seats. Not something we would ordinarily do, but we went all in and said GO BIG OR GO HOME and had an absolute ball! The luxe seating really helped us relax and rest up for our first day in Europe and I can’t lie = the food was incredible, the service was beyond over the top and it was a highlight everyone in our family will always remember… so if you can find some extra funds in your vacation to splurge on these seats just once, do it!
Now, let’s get down to business… first stop FLORENCE = safe to say this city stole all our hearts all over again. It has THE perfect mix of history, beauty and so much good food. From admiring Michelangelo’s David in person [always a highlight to see!] to sipping cappuccinos in charming piazzas and watching the girls soak up every moment = Florence was the perfect way to kick off our summer travels.
Keep reading for all the details—where we stayed, what we loved, what we’d do differently and everything in between!
We flew into Rome [easier itinerary for our long travel day] and then we kicked things off with a private transfer headed north—but not without the dreamiest detour first! We made a pit stop in Orvieto, one of Tuscany’s most charming hidden gems. Perched high above the countryside, it’s a super quaint, hilltop town that was made famous by its stunning duomo (seriously, the façade is a showstopper) and picture-perfect streets filled with shops, cafés and great artisan finds. We stretched our legs, browsed handmade ceramics and olive wood souvenirs, and grabbed a casual but delicious lunch at La Pergola—a family favorite we were thrilled to revisit. After soaking up the views, we hit the road again made another quick, but fun stop in San Gimignano = it’s a tiny medieval town with tons of towers made for touring and hiking [the kids, Pappy and Jeff did that while Mimi + I shopped for art].
PRO TIP | In between larger, more metropolitan cities, try to visit 2-3 towns along your route… great for visiting smaller villages with gorgeous sights and such but not overwhelmed with people = also a fantastic way to taste out local faire and shop adorable shops without the high markup! Our personal favorites in Tuscany include Moltalcino, Cortona and Montepulciano.
From there, we arrived in Florence, where we checked into the most incredible AIRBNB apartment in the Bargello Luxury Apartment Building, perfectly nestled in the heart of the city and ready to be our home base for the week. Super spacious with everything we needed [and more], it was the absolute perfect away from home… and yes, I’d highly recommend staying here if you get the chance and have at least 6 people in your party.
That afternoon, we hit up the local grocery store for some essentials to have on hand, explored around our neighborhood and then finished our first night in Italy with dinner at Osteria Antica Casa Torre, a cozy spot with warm hospitality and hearty Florentine fare that hit the spot after a long day of travel [when in doubt ALWAYS order steak florentine]. Jet lagged but giddy, we were ready for a full week of exploring Firenze but tried to stay up as late as possible to avoid that dreaded next day fatigue and it definitely paid off!
We hit the ground running on our first full day in Florence with a private half-day walking tour that gave us the perfect lay of the land. Our guide met us right outside our apartment [talk about door-to-door service!] and we set off to see some of the city’s most iconic sights—the Duomo, Santa Maria del Fiore, Giotto’s Campanile, the Opera del Duomo Museum [a newly created museum dedicated to showing the workmanship of the actual duomo = it is EXCELLENT!!] and of course, the Accademia Gallery to see Michelangelo’s David in all his glory = and no, even seeing this for the second time you can’t imagine the and scale and the intricate details! It was the best way to dive into the rich history of Firenze while keeping things relaxed and fun for everyone = highly recommend asking for a tour guide that’s great with kids… it makes all the difference, especially when touring historic monuments/museums/galleries, etc.
After our tour, we grabbed authentic Tuscan inspired paninis from the famous Retrobottega—quick, delicious and exactly what we needed to refuel before a bit of afternoon wandering and window shopping. We ended the day with a dinner to remember at Antico Ristoro Di Cambi, a classic spot known for traditional Florentine dishes like pasta and againm my personal favorite, the famous Florentine steak. Full hearts, full bellies and already falling in love with this magical city.
Day three took us beyond Florence for a Tuscan day trip that checked all the boxes—views, villages, and vino vibes. We hit the road early and made our first stop in San Gimignano, a picture-perfect medieval town known for its skyline of ancient towers. We spent the morning wandering the cobblestone streets, popping into little shops, and of course grabbing a scoop [or two] of famous Italian gelato while soaking in the sweeping countryside views.
From there, we headed to Siena [MY FAVORITE TOWN IN TUSCANY!!] where we sat down for lunch at Antica Trattoria Papei—rustic, delicious and tucked right near the heart of the city. Afterward, we met up with our guide for a three-hour walking tour, covering the stunning Piazza del Campo, the intricate Siena Cathedral, the breathtaking Piccolomini Library, and Santa Maria della Scala—an unexpected highlight full of history and hidden gems. We were visiting the town at the PERFECT time, as the city was in preparations for their annual Palio di Siena = the most famous attribute of the town and a HUGE highlight where visitors come from all over to witness the race in the middle of the city! It was truly remarkable and one day I hope we can actually attend. We wrapped up the day back in Florence with a casual dinner near the apartment, grabbing pizza and sandwiches before calling it a night. Trust me, after this day we needed a relaxing night in! A long but totally worth-it day exploring more of Tuscany…
PRO TIP | Set up your home base in Florence because you can take day trips to SO many close towns and cities all within a 1-2 hour drive = renting a driver with a private car makes for easy transport, too!
After a few jam-packed days of sightseeing and road-tripping through Tuscany, Day 4 was all about slowing down and soaking up the charm of Florence at our own pace… and yes, that was a morning we decided it was absolutely necessary to sleep in a bit! We spent the day wandering the cobblestone streets, popping into boutiques, artisan shops for some art and local markets, with plenty of time for window shopping and people-watching.
We had originally planned to hit up the Uffizi Gallery for a dose of culture, but made a gemtime decision to pause and just enjoy the city. For lunch, we braved the line at All’Antico Vinaio—arguably the most famous sandwich shop in Italy—and let’s just say, it lived up to the hype. We wrapped up the evening at Trattoria del Pennello, a cozy neighborhood favorite with all the classic Tuscan comfort food we were craving. A slower day, but one of our favorites—sometimes the best memories are made without a plan, right?!?! And with the hustle and bustle of so many other days, I was thrilled that we took a day to savor the sights without a set to-do list.
PRO TIP | If you have extra time in your itinerary, try to build in rest and recovery days… after exploring museums, taking tours of old ruins and such you’ll need some downtime to recover before you do it all over again! We like to build in one of these in between two busier days = your feet will thank you for it!
We kicked off Day 5 with a quick trip west to check off a true Italian icon—Pisa! It was my first time and I have to admit I was nervous because a lot of people had said it wasn’t that exciting but we LOVED visiting the leaning tower town. Our 2-hour guided tour gave us just enough time to learn about the city’s rich history while still snagging that classic Leaning Tower photo [yes, we fully leaned into the cheesy pose… pun intended]. We purchased tickets to walk to the top of the tower and we all did it together = definitely an adventure, but the views from the top were absolutely stunning and we would definitely recommend doing it!
Afterward, we continued on to the charming town of Lucca for a slow afternoon exploring this lesser-known gem. From the stunning S. Martino Cathedral and San Michele to the quirky, oval-shaped Piazza Anfiteatro, Lucca totally won us over with its relaxed pace and unique layout. We grabbed lunch at L’Angolo Tondo Trattoria, a simple local spot serving up fresh, flavorful bites + then we headed back to Florence and capped off the day at Ristorante Il Granaio with another dinner that hit just right after a full day of exploring. P.S. I have to give it up to Jeff for all of his restaurant recommendations… he worked for MONTHS on finding the right hidden gems and every single destination was a winner!
Day 6 gave us a whole new look at Tuscany with a day spent exploring Lari: a medieval village tucked away in the hills—a slower pace, fewer crowds, and SO much sweet charm. We toured the famous local pasta factory, Martelli, watched fresh pasta being made by hand, and enjoyed a homemade lunch right there at a local nearby restaurant, complete with wine, fresh bread and the dreamiest sauces. And got a behind-the-scenes look at the Busti Cheese Grotto!
The afternoon included a visit to a nearby castle and a stop at a local butcher shop, where we got a peek into the region’s culinary traditions [and yes, came home with a few goodies to nibble on, too]. On the way back to Florence, we paused at Piazzale Michelangelo to snap some family photos and take in the unreal panoramic views of the city at golden hour—it’s one of those postcard moments that sticks with you and a must-stop for sure! We kept dinner casual that night with a quick bite near the apartment and toasted to another unforgettable day in beautiful Italia.
Last but not least of course!!! We saved some of the best for our final day in Florence, kicking things off with a guided tour of the Pitti Palace and Boboli Gardens—a stunning combo of art, architecture and outdoor beauty all in one. Our guide made the history come alive as we wandered through royal apartments, admired the grand halls, and took in the sweeping views from the gardens. P.S. see if you can get VIP tour access tickets for the bedrooms and private spaces in Pitti Palace= they were GORG!
We grabbed a casual lunch in town [always something delicious around every corner in a place like Firenze]), then made our way to Vivoli for dessert—because no trip to Florence is complete without their famous affogato. The afternoon was slow and sweet, with a walk over to Santa Croce for one last glimpse of Florence’s rich history and of course to see the tombs of Michelangelo + Galileo Galilei. We had planned to take a private boat tour of the Arno River, but had to cancel last minute due to rain and lightning so we headed to a local wine enoteca/bar/market called Enoteca Alessi which was INCREDIBLE = so many ways to taste lots of tapas and bites and explore some of the best wines and liquors ever!!
We ended the night on the perfect note with dinner at Ristorante Buca Mario—classic Florentine dishes, incredible win, and a table full of happy hearts. Just be sure to snag reservations MONTHS in advance as they sell out completely… this was hands down one of our favorite nights as a family and would highly recommend moving this one to the top of your Florence list! Caroline and I had the lasagna and agreed it was THE best we had! The perfect way to say ciao for now to this unforgettable city.
Don’;’t fret… we have the second half of our Italian summer adventure to recap oh so soon so stay tuned!! Sweet Sorrento plus all the coastal cities you’re itching to know more about BUT until then, I’ve saved our master itinerary with daily breakdowns below so you can download:
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