8 Day Tuscany Fly & Drive with Milan

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

DAY 1 – Monday: Depart for Italy

Begin your Italian adventure! Board your flight to Italy and prepare for an exploration of Tuscan landscapes, Renaissance art, and culinary delights.

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

Arrive in Milan, pick up your rental car, and drive to Montecatini, a charming spa town nestled in the heart of Tuscany. Spend the evening at leisure, strolling through the quaint streets or enjoying a local trattoria.

Drive Time: 3.5 hours | Distance: 220 miles
Overnight: Montecatini

DAY 3 – Wednesday: Explore Lucca and Pisa

Enjoy a full day at leisure, or drive to Lucca and Pisa:

• In Lucca, wander narrow streets and visit San Michele Square, built on the ancient Roman Forum.

• In Pisa, explore the medieval streets of the Borgo Pio, admire the historic university, and visit the iconic 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: Discover Florence

Spend the day exploring Florence, the cradle of the Renaissance:

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

• Visit Signoria Square and admire Palazzo Vecchio and the statues lining the open-air museum.

• Walk across the Ponte Vecchio, the historic “Old Bridge” over the Arno River.

Return to Montecatini in the evening; trains are recommended if staying late.

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

DAY 5 – Friday: Chianti & Greve Wine Country

Take a scenic drive into the heart of Tuscany to explore the Chianti wine region:

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

• Visit Greve, the historic market town at the gateway to Chianti.

• Stop in Montefioralle, a charming fortified village, and enjoy wine tastings of Chianti’s famous reds and local specialties.

Return to Montecatini for the evening.

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

DAY 6 – Saturday: Siena & San Gimignano

Spend a full day exploring Siena and San Gimignano:

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

• Discover San Gimignano, a medieval walled town known for its 14 remaining stone towers, narrow lanes, and charming squares.

Return to Montecatini in the evening.

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

DAY 7 – Sunday: Drive to Parma en Route to Milan

On your journey back north, stop in Parma, famous for Prosciutto di Parma and Parmigiano Reggiano:

• Explore the elegant historic center, including the Parma Cathedral Baptistery.

• Walk across the River Parma and enjoy Parco Ducale.

• Savor a local cheese and ham plate before continuing to the Milan area.

Drive Time: 4 hours | Distance: 220 miles
Overnight: Milan Malpensa Area
Meals: Breakfast

DAY 8 – Monday: Depart Italy

Drive to Milan Malpensa Airport, return your vehicle, and board your departure flight home.

Drive Time: 10 minutes | Distance: 1 mile
Meals: Breakfast

Package Includes

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

• 6 nights accommodations: 5 nights Montecatini, 1 night Milan Malpensa

• 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?

• Discover Tuscan treasures: Montecatini, Florence, Lucca, Pisa, Chianti, Siena, and San Gimignano.

• Enjoy flexible independent travel with a rental car and scenic drives.