Milan, Venice and Florence in 10 Days: A Family Itinerary

You’ll likely arrive in Milan mid-morning. I recommend early check-in if at all possible (let me know if this perk appeals to you!) for a 1-2 hour power nap. If you’re the type to keep sleeping, leave your bags at the hotel, skip the nap altogether, and hit the pavement with comfortable walking shoes! Take the afternoon to browse the city center. The Galleria Vittorio Emanuele II is the perfect location to eat Gelato, shop luxury brands, people watch, and power through the jet lag. Take this opportunity to twirl on the mosaic Turin bull in the center of the arcade. This traveler’s tradition is not only accepted, it’s encouraged because lore says if you do this while making a wish, your wish will come true and it will bring you back to Milan! Picky eaters will love that there’s a McDonald’s 1 block from the Galleria.

Take a private or small-group tour of the 3rd largest church in the world - The Duomo di Milano. Plan to tour the rooftop as well and learn why the magnificent spires differ so much in thematic concept from the church’s conception in 1386 to its final craftsman’s touch in 1965. A “must do” tour for the architecture enthusiasts in your family.

Allow me to book an authentic Italian pizza-making experience for your family. Learn the secret formula for the perfect crust from an Italian chef and get knead-deep in dough! Enjoy wine, pizza, and getting to know classmates from all over the world. Bonus - take the recipes home with you!

Ok. So…St. Moritz is not in Italy, so consider this day trip a unique opportunity to visit a second country for the price of one! Take a private tour bus from Milan to Lake Como. Here you will board a boat tour of the lakeside town with beautiful views of the pre-Alp region for a hint of what’s to come. After the lake tour, hop on the Bernina Express. Listen to your guide’s expert account of the train’s history as you journey into the Swiss Alps. Once in St. Moritz, deboard the train for time to explore, shop, wine, and dine in town. Trust me, you’ll never forget this beautiful experience.

Travel like an executive on board one of a few Italian train lines straight from Milan to Venice. Enjoy the Italian rail’s luxurious transportation for less than the price of a U.S. city bus pass. Snacks, wine, sodas, leather seats, free wi-fi, and huge windows for spectacular countryside viewing. The kids will love this experience as it offers instant food and media gratification from the comfort of a reclining seat!

If you don’t mind getting to Venice after 8pm local time, consider hopping off the train in Verona for a fine glass of regional wine. Take a look at Shakespeare’s most famous balcony at La Casa di Guiletta.

Take advantage of local historians leading you through the city of Venice on a private or small-group history tour. Go inside the incredible St. Mark’s Basilica and Doge’s Palace, including the prisons (kids love this part!). If you travel during Carnivale (late January to mid-February), you’ll experience locals dressed in elaborate costumes and masks. It’s an awesome feast for the eyes and a dive into the abundant Venetian culture.

Allow me to make an early dinner reservation (early by Italian standards!) for your family at TEN Restaurant Venezia. Here you’ll enjoy amazing house wine and local live music before you walk a short 5 minutes to experience a unique performance. Vivaldi’s Four Seasons performance in the historical and beautiful Scuola Grande di San Teodoro, where the performers are dressed in 18th-century fashion. My 12-year-old son and 16-year-old daughter loved this experience!

In the morning, visit Murano island to learn the why and how of Italy’s famous glass art. In the afternoon, shop Venice’s quaint boutiques for authentic Italian handbags, shoes, ornaments, linens, and on and on. Eat Italian pastries, gelato, and keep the espresso flowing until it’s time to wine and dine at Rossopomodoro.

Take your seat aboard one of Italy’s premium rail lines for a relaxing trip to Florence. This is about the time in your itinerary when you’ll appreciate a “free” day. I recommend staying at the Riva Lofts, within walking distance to most major sightseeing opportunities. Also providing family rooms with separation space and experiences for well being, fitness and fun!

Enjoy a “culture-rich must do” activity on my list at the Uffizi Gallery. Perfect for families, the Uffizi displays and educates on ancient paintings and sculptures. Fun for the entire family, the Uffizi Gallery offers two unique kids’ tours with a scavenger hunt-type activity to keep them engaged. Don’t miss the works of Botticelli, Caravaggio, and of course, Michelangelo. Speaking of Michelangelo, head over to the Galleria dell'Accademia di Firenze to see the original statue of David. All the while on your private or small-group museum tour, you’ll learn about the history and influence of the fascinating Medici family.

On the last full day of your Northern Italian Cities Tour, relax and walk slowly through Florence. Take a walking tour of the city center or a food tour. Stop and browse the artisan fair and leather market. Alternatively, consider a day trip into Tuscany for wine tasting or to see the Leaning Tower of Pisa. Do not miss dinner at Trattoria Marione - voted one of the best restaurants in Florence, and I can attest to that. Allow me to make a reservation to ensure your family gets a table. Walk-ins are welcome, but the line to get in stretches around the block!

Enjoy a buffet breakfast and lots of water to hydrate and protein up for your trip home. Be sure to check and double-check your hotel room for misplaced souvenirs and travel essentials. Did you leave a shoe in the hotel safe on purpose? Double check - you might find something valuable in there too, like passports or jewelry. Allow me to book a private car or van for your safe, relaxing, no-fuss airport transfer.