Our 15-day Two Week Italy Itinerary for family vacation took us from Rome to Florence, through Tuscany’s rolling hills, and the colorful seaside villages of Cinque Terre.
We mixed famous landmarks with some cute hidden gems, of course pasta with gelato, and adventure for the kids with some relaxation built in for us!
I am sharing exactly what we did, and I hope tips to make your own Italy trip unforgettable.
Hope you’re ready to eat a lot of gelato though, we loved every bit of it! When we got home, we immediately bought this gelato machine and wow… it churns out the creamiest, dreamiest gelato that tastes exactly like what we devoured in Italy. It is truly the sweetest souvenir!
Last December in Paris HERE, I casually asked, “Where should we go next?” My daughter didn’t hesitate — “ITALY!” Her enthusiasm was contagious, and within a week, I had flights booked into and out of Rome. Tuscany was my first thought, but our plan quickly expanded to include Florence and Cinque Terre – because how could we visit Italy and not see the sea?
Two Week Italy Itinerary (15-Day) Family Itinerary Overview
- Days 1–4: Rome – Ancient history, Vatican City, and the best gelato and tiramisu spots.
- Days 5–6: Florence – Renaissance art, Tuscan steak, wine windows and affogato.
- Days 7–9: Tuscany – Montepulciano villa stay, wine tasting, cooking class, truffle hunting, and e-biking.
- Days 10–13: Cinque Terre – Coastal villages, beach clubs, and ferry rides.
- Days 14–15: Back to Rome – Relaxation and farewell dinner.
Days 1–4: Exploring Rome with Kids
Day 1: Arrival in Rome
We landed in Rome after flight delays, missing our private driver, and surviving the taxi line. Our home base: A.Roma Lifestyle Hotel — luxurious, family-friendly, and with a pool (this was essential in the summer heat).
Day 2: Trastevere & Rome by Night Tour
After a little nap, we explored Trastevere, a charming neighborhood with cobblestone streets. Dinner at La Tavernetta 29 was a win, but the highlight was a Rome by Night golf cart tour — Pantheon, Trevi Fountain, Spanish Steps — with fewer crowds and cooler temperatures.
Day 3: Vatican City & St. Peter’s Basilica
We booked a private tour with Maria Claudia’s team through the Vatican Museums, Sistine Chapel, and St. Peter’s Basilica. Pro tip: dress code enforcement is relaxed in summer, but inside the Sistine Chapel — silence and no photos.
Day 4: Colosseum & Roman Forum
With our guide from Maria Claudia Tours we explored the Roman Forum and Colosseum before cooling down with lunch at Ristoro Della Salute (misting fans = lifesaver). And later, dinner at Bistrot Luce gave us a taste of local Rome away from the tourist crowds.
Find our 4 Days in Rome Itinerary HERE.
Days 5–6: Florence — Art, Food & Gelato
Day 5: Arrival & Gelato-Making
A train ride from Rome brought us to Arte Boutique Hotel in Florence. After a gelato-making class, we had dinner at Ristorante Il Latini for a massive Tuscan steak.
Day 5: Michelangelo’s David & Ponte Vecchio
We visited the Accademia Gallery and took this tour HERE to see David in person — stunning. Lunch by Ponte Vecchio, Aperol spritzes on Rinascente Firenze’s rooftop, and the best meal of the trip at La Bruschetta capped off the day. Make a plan to go to La Bruschetta.
Find our Florence in Two Days Itinerary HERE.
Find our Florence in Two Days Itinerary HERE.
Day 6: Montepulciano Villa Arrival
We picked up an Alfa Romeo rental car (it was an Avis upgrade – thanks to Avis!) and drove to La Vittoria10, a dreamy villa surrounded by olive trees and sweeping Tuscan views. Dinner at Dopolavoro La Foce was perfection. Truly perfection with the most gorgeous sunset!
Day 7: Villa Sant’Anna Wine Tasting
Private tour and tasting at Villa Sant’Anna with owner Simona — so good we shipped cases home.
Day 8: Truffle Hunting & Pasta-Making
Morning truffle hunt with the cutest dogs, followed by a pasta-making class at the villa with Chef Asia — fettuccine, ravioli, spaghetti, plus tiramisu. So much food we are still in a food coma.
Day 9: e-Bike Tour of Tuscany
Beautiful tour of Tuscany via e-bikes did not disappoint. We required much needed relaxation after 10 miles through Tuscany.
Days 10–13: Cinque Terre — Beach Town Bliss
Day 10: Pisa Stop & Monterosso Arrival
On the drive from Tuscany to Cinque Terre, we stopped at the Leaning Tower of Pisa before checking into Hotel Pasquale in Monterosso. This hotel is a top pick in Cinque Terre so book early and email them directly.
Day 11: Riomaggiore & Manarola
Ferry to Riomaggiore, lunch in Manarola, and a beach afternoon back in Monterosso. Dinner at Pizzeria La Smorfia hit the spot.
Day 12: Beach Club Day
Stella Marina Beach Club with iconic orange and green umbrellas (the ones you see in all the photos of Italy) — Aperol spritz, pizza, family meet-up, and swimming (jellyfish drama included).
Day 13: Vernazza Girls’ Day
Train to Vernazza (one of the five Cinque Terre villages) for shopping, seafood, and village charm before a cozy dinner at Lapo’s.
Find our Cinque Terre Itinerary HERE.
Days 14–15: Back to Rome & Farewell
Day 14: Return by Train
From Monterosso to Rome with lunch at Mino near Termini Station. Our final stay, La Gaura Guest House, had a pool for one last afternoon of sun. Dinner at Le Terrazze was a Google Translate adventure worth every bite. They did not speak any English (which was quite alright, but it really put us to the test on our last night, and we were thankful for that – testing our skills!)
Day 15: Departure Day
Espresso, breakfast, and an easy trip to the airport — carry-on bags only made travel smooth.
Top Italy Family Travel Tips
- One major activity per day to enjoy some downtime (and relaxation at the pool!).
- Eat gelato daily, multiple times a day (no regrets).
- Carry-on only — skip checked luggage hassles. Trains and large luggage do not mix!
- Book trains in advance for popular routes.
- Stay flexible in this beautiful country — leave room for spontaneous moments.
Final Thoughts: La Dolce Vita
Pasta, piazzas, wine, wobbly cobblestones, sweaty uphill climbs, breathtaking views, hilarious fails, unforgettable meals, and so many laughs.
This was the family adventure of a lifetime. Check out our trip details to Rome HERE, and Florence HERE, and Tuscany HERE, and Cinque Terre HERE.
If you love exploring the world’s most amazing city stays, don’t miss our guide to the 10 Best Family Hotels in NYC after your Italian adventure.
