7 Day Tuscany Itinerary: The Perfect Tuscany Roadtrip
If you're planning a Tuscany road trip, this 7-night Tuscany itinerary covers Renaissance cities, rolling countryside, hilltop towns, and unforgettable luxury stays.
From Florence's Renaissance streets to the rolling hills of the Tuscan countryside, this route is ideal for travelers who want to experience Tuscany at a relaxed, immersive pace. Starting in Florence and continuing by car, this Tuscany itinerary balances scenic drives, historic towns, wine country, and truly special stays.
Jump to:
Day 1: Arrive in Florence
Morning / Afternoon:
- Fly into Florence Airport (FLR) and check into your hotel for 2 nights.
- Spend your first afternoon wandering the city's iconic streets, soaking in the Renaissance atmosphere.
Evening:
- Enjoy dinner at a traditional trattoria near Piazza della Signoria. Try classic Tuscan dishes like ribollita (vegetable soup) or bistecca alla Fiorentina (Florentine steak).
- Check out my Florence Restaurant Guide here.
Where to Stay in Florence:
- Four Seasons Hotel Firenze - A grand 5-star hotel set within a historic palace and Florence's largest private garden, offering serene grounds, an elegant spa, and refined dining just minutes from the historic center.
- The St. Regis Florence - A timeless luxury hotel overlooking the Arno River, known for its opulent interiors, impeccable service, and prime location near Florence's most iconic sights.
- Hotel Savoy (Rocco Forte Hotels) - A stylish luxury hotel in the heart of Piazza della Repubblica, blending contemporary design with classic Florentine elegance and walk-everywhere convenience.
Check out my complete Florence Hotel Guide here.
Day 2: Florence - Art & Culture
Morning:
- Start at the Uffizi Gallery, home to masterpieces by Botticelli, Michelangelo, and Leonardo da Vinci.
- Walk across the Ponte Vecchio and explore the artisan shops.
Afternoon:
- Visit the Duomo, climb the dome for a panoramic view of the city, and explore the Baptistery.
- Stop for lunch at a café in Oltrarno, the artisan quarter.
Evening:
- Optional wine tasting at a local enoteca (wine bar) to start your Tuscan wine adventure.
- Sunset from Piazzale Michelangelo - breathtaking views of Florence.
Tip: Book your museum tickets online well in advance for Florence's major sights to avoid long lines.
Day 3: Florence → Siena (via Chianti region)
Morning:
- Pick up your rental car and start your drive through the Chianti wine region, famous for vineyards and cypress-lined roads.
- Stop in Greve in Chianti (~45 minute drive from Florence), a charming town with wine shops and a lively piazza.
Afternoon:
- Continue to Siena (~1 hour drive from Greve), a medieval city famous for its Piazza del Campo.
- Check into your hotel in Siena for 2 nights and enjoy wandering its cobblestone streets.
Evening:
- Dinner at a trattoria in Siena's historic center. Try pici pasta with a rich meat sauce.
Where to Stay in Siena:
- Castel Monastero - A refined 5-star countryside retreat set in a restored medieval monastery just outside Siena, featuring a luxury spa, Michelin-starred dining, and sweeping views over the Tuscan hills.
- Grand Hotel Continental Siena - Siena's only 5-star hotel within the historic center, offering elegant, palace-style interiors, frescoed rooms, and a prime location steps from Piazza del Campo.
- Castello di Casole, A Belmond Hotel - A legendary luxury estate surrounded by rolling countryside, known for its exceptional service, panoramic views, spa experiences, and immersive Tuscan atmosphere.
- Borgo San Felice - A beautifully restored medieval village turned luxury hotel in the Chianti countryside, featuring Michelin-star dining, vineyards, and a serene, authentic Tuscan setting.
Day 4: Siena & San Gimignano
Morning:
- Explore Siena's Piazza del Campo and Siena Cathedral.
- Optional: climb the Torre del Mangia for city views.
Afternoon:
- Drive to San Gimignano (~45 minutes from Siena), the town of towers, famous for its medieval architecture and Vernaccia wine.
- Stroll the streets, visit local gelaterias, and admire the skyline of towers.
Evening:
- Return to Siena for a relaxing evening.
Day 5: Val d'Orcia - Pienza & Montalcino
Morning:
- Drive south toward the Val d'Orcia (~45 minutes from Siena), one of Tuscany's most picturesque regions.
- Stop in Pienza, known for its pecorino cheese and Renaissance architecture.
Afternoon:
- Continue to Montalcino (~30 minutes from Pienza), home of Brunello di Montalcino, one of Italy's finest wines.
- Check into your hotel for 1 night.
- Visit a winery for a tasting and vineyard tour.
Evening:
- Have a relaxing dinner at your hotel and enjoy the views of the Tuscan countryside.
Where to Stay in Montalcino:
- Castiglion del Bosco, A Rosewood Hotel - A legendary 5-star estate in the heart of Brunello wine country, offering elegant villas, Michelin-starred dining, a private winery, and stunning vineyard views.
- Il Castello di Velona Resort, Thermal Spa & Winery - A luxury hilltop retreat with thermal spa pools, wine tastings, and panoramic views over Montalcino's rolling countryside.
- Relais Sant'Elena - A boutique 5-star estate offering private villas, infinity pools, and a tranquil setting among Montalcino's famed Brunello vineyards.
- La Locanda di San Francesco - A charming luxury property in central Montalcino with elegantly restored rooms, refined dining, and easy access to the town's historic sights.
Day 6: Montepulciano & Cortona
Morning:
- Drive to Montepulciano (~45 minute drive from Val D'Orcia), a hilltop town known for Vino Nobile di Montepulciano. Explore its charming piazzas and wine cellars.
Afternoon:
- Head to Cortona (~1 hour drive from Montepulciano), a small town made famous by Under the Tuscan Sun.
- Check into your hotel for 1 night and relax at the poolside before heading into town.
Evening:
- Wander the narrow streets, visit art galleries, and enjoy panoramic views of the Val di Chiana.
- Enjoy a farm-to-table dinner at a local osteria.
Where to Stay in Cortona:
- Il Falconiere & Spa, Relais & Châteaux - A luxurious estate with a Michelin-starred restaurant, world-class spa, and panoramic vineyards, perfect for a relaxing and indulgent Tuscan stay.
- Villa di Piazzano - A small luxury hotel with refined suites, private terraces, and a tranquil setting amidst olive groves and rolling Tuscan hills.
- Relais La Corte dei Papi - A boutique 5-star hotel set in the heart of Cortona's historic center, blending Renaissance charm with modern luxury, spacious suites, and stunning hilltop views.
- Monastero di Cortona Hotel & Spa - A beautifully restored monastery offering elegant rooms, a serene spa, and sweeping views of the Val di Chiana.
Day 7: Return to Florence & Departure
Morning:
- Leisurely drive back to Florence (~90 minute drive from Cortona), stopping at scenic viewpoints or small towns along the way.
Afternoon:
- Drop off your rental car and spend any remaining time in Florence shopping for souvenirs or enjoying a final gelato.
Evening:
- Head to Florence Airport for your departure or continue onward to your next Italian destination.
Ready to Book Your Luxury Trip?
Want me to design a trip like this for you? Contact me today to start planning your bespoke Italian journey.
From private transfers and exclusive tours to handpicked hotels, I'll ensure every detail is perfectly tailored to your travel style.
More Travel Guides
Looking for other posts like this? Check these out:
