A Perfect 10-Night Italy Itinerary: Rome, Florence & The Tuscan Countryside

Planning a dream trip to Italy? Our 10-night journey through Rome, Florence, and Tuscany was nothing short of magical. From historic landmarks to breathtaking countryside views, incredible food, and, of course, amazing wine—this itinerary is packed with recommendations to make your trip unforgettable.

Rome: 2 Nights in the Eternal City

We started our adventure in Rome, a city steeped in history and charm. Even if you’re not a history buff, a guided tour of the Vatican and Colosseum is an absolute must. We booked through HEADOUT, and it was worth every penny.

Travel Tip: Skip the hassle and book a fast-track tour to avoid long lines!
After soaking in the history, we indulged in Rome’s vibrant food scene before catching a fast train to Florence—the best and easiest way to travel between these two iconic cities.

Florence: 4 Nights of Art, Culture & Cuisine

Florence is a walkable city filled with Renaissance art, stunning architecture, and fantastic food. We spent our days strolling the charming streets, indulging in delicious cuisine, and sipping on wine.

Tourist Trap Alert! Be mindful of overpriced, low-quality restaurants in heavily trafficked areas. Researching ahead of time or asking locals for recommendations can help you find authentic spots.

From Florence, we arranged a private driver to take us into the Tuscan countryside. Highly recommend Alessandro Demi for transportation! (email: [email protected])
On the way, Alessandro made a stop at Il Cellese Winery, where we enjoyed spectacular views and even better wine.

Tuscany Countryside: 3 Nights of Relaxation & Wine

We spent three dreamy nights in the Tuscan countryside, fully immersing ourselves in the region’s beauty and flavors. Some highlights:

Winery Visits:
Poggio Amorelli – A fantastic winery with incredible wines.
Casal Piano– A perfect stop on our way back to Rome for one last wine tasting.

Day Trips:
Siena & San Gimignano – While beautiful, these towns were actually closer to Florence. In hindsight, we would have visited them while staying there.

Cooking Class: We took a pizza-making class at our resort—an absolute must for food lovers!

Where We Stayed

Tuscany: @BorgoSantoPietro A breathtaking luxury resort in a restored medieval village. Our villa was a 12th-century bakery, and everything from the hospitality to the farm-to-table dining was five-star. Activities include cooking classes, wine tastings, hiking, and more. Truly a dream destination!
Florence: @fsflorence (Four Seasons Florence)This restored Renaissance palace and convent is beyond stunning. The lush garden was the perfect place to sip an Aperol Spritz, and their vintage Negroni is unforgettable. Located just outside the city center, it’s a peaceful retreat while still being close to everything.
Rome: @hotelvilon A small, luxury boutique hotel in a historic 16th-century mansion. The location was perfect, tucked away in a quiet area but still close to all the must-see spots. The breakfast? Simply divine.