8 Day Tuscany Fly & Drive with Rome

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Duration

Tour Type

Daily Tour

Group Size

15 people

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8-Day Tuscany & Umbria Independent Road Trip: Montecatini, Florence & Rome

DAY 1 – Monday: Depart for Italy

Start your dream Italian adventure! Board your flight to Italy and get ready for a journey through Tuscan hills, medieval towns, and Renaissance treasures.


DAY 2 – Tuesday: Arrive in Rome and Drive to Montecatini

Arrive in Rome and pick up your rental vehicle. Drive north to Montecatini, a charming spa town in the heart of Tuscany. Spend the evening at leisure—stroll through the town, enjoy local cuisine, or relax in your hotel.

Drive Time: 4 hours | Distance: 210 miles
Overnight: Montecatini


DAY 3 – Wednesday: Day Trip to Lucca and Pisa

Spend a day exploring Lucca and Pisa, or enjoy Montecatini at your own pace:

  • In Lucca, walk the narrow streets of the historic Roman grid to San Michele Square, built on the site of the ancient Roman Forum.

  • In Pisa, explore the medieval streets of the Borgo Pio, visit the famous university, and admire the Piazza dei Miracoli, home to the Leaning Tower, Baptistery, and Duomo.

Return to Montecatini for the evening.

Drive Time: 2 hours | Distance: 70 miles
Overnight: Montecatini
Meals: Breakfast


DAY 4 – Thursday: Florence Excursion

Take a day trip to Florence, the birthplace of the Renaissance:

  • Marvel at the Duomo and Baptistery, including Ghiberti’s Gates of Paradise.

  • Explore Signoria Square, with Palazzo Vecchio and its collection of statues.

  • Stroll across the Ponte Vecchio, Florence’s historic “Old Bridge.”

Return to Montecatini in the evening. Train travel is suggested if staying late.

Drive Time: 2 hours | Distance: 65 miles
Overnight: Montecatini
Meals: Breakfast


DAY 5 – Friday: Chianti & Greve Wine Country

Drive into the Chianti countryside, the heart of Tuscany’s wine region:

  • Admire rolling hills, olive groves, cypress trees, and vineyards.

  • Stop in Greve, a medieval market town considered the gateway to Chianti.

  • Visit Montefioralle, a hilltop fortified village, and enjoy wine tastings and local specialties at a winery.

Return to Montecatini for the evening.

Drive Time: 2.5 hours | Distance: 90 miles
Overnight: Montecatini
Meals: Breakfast


DAY 6 – Saturday: Siena & San Gimignano

Explore Siena and San Gimignano, two of Tuscany’s gems:

  • In Siena, admire the Duomo, elegant palaces, and Piazza del Campo, famous for the Palio horse race.

  • In San Gimignano, wander narrow medieval streets and squares, and marvel at 14 remaining stone towers dominating the skyline.

Return to Montecatini for the evening.

Drive Time: 4 hours | Distance: 160 miles
Overnight: Montecatini
Meals: Breakfast


DAY 7 – Sunday: Orvieto En Route to Rome

Drive south toward Rome with an optional stop in Orvieto, a stunning hilltop town:

  • Take the funicular from the train station to the historic old town.

  • Visit the Duomo di Orvieto, Pozzo di San Patrizio, and Orvieto Underground, a network of tunnels and caves.

  • Relax in Piazza del Popolo and sample Orvieto Classico wine and Umbrian cuisine.

Continue your drive to Rome for your overnight stay.

Drive Time: 4 hours | Distance: 210 miles
Overnight: Rome
Meals: Breakfast


DAY 8 – Monday: Depart Italy

Drive to Rome Airport, return your rental car, and board your departure flight home.

Drive Time: 10 minutes | Distance: 4 miles
Meals: Breakfast


Package Includes

  • Round-trip flights: New York – Rome / Rome – New York (other departure cities available)

  • 6 nights accommodations: 5 nights Montecatini, 1 night Rome

  • 7-day car rental: Economy Manual (Fiat Panda or similar)

    • Unlimited mileage, RCA insurance, SCDW & STP coverage, airport charges, local taxes (VAT)

  • Daily breakfast

Optional Upgrades: Higher-category vehicles available
Not Included: Italian city taxes, optional excursions, and gratuities


Why Choose This Trip?

  • Explore Tuscany’s scenic countryside and iconic towns: Montecatini, Florence, Lucca, Pisa, Chianti, Siena, San Gimignano, and Orvieto.

  • Enjoy freedom and flexibility with your own rental car.

  • Perfect for travelers seeking art, culture, wine, and authentic Italian experiences.

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Owner

Aetekno

Member Since 2026

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