8-Day Tuscany Vacation

Flights & Transportation:

• Round-trip airfare from:
  • New York City (NYC)
  • Boston (BOS)
  • Orlando (MCO)
  • San Francisco (SFO)
  • Los Angeles (LAX)
  • Washington, DC (IAD)
  • Miami (MIA)
  • Denver (DEN)
  • Houston (IAH)
  • Dallas (DFW)
  • Chicago (ORD)
  • Atlanta (ATL)
• Transportation between cities via Car
• Airline taxes & fuel surcharges
• Airline & flight times are determined at the time of booking.
• Return car hire from Milan Airport included for 6 nights

8-Day Tuscany Vacation – Hotels (6 nights + 1 overnight flight)

• 5 nights of accommodations in a Standard Double Twin Room at Hotel Savoia & Campana Montecatini OR Hotel Nuovo Savi OR Similar in Montecatini

• 1 night of accommodations in a Standard Double Twin Room at B&B Hotel Milano Ornato OR B&B Hotel Milano – Sesto OR Similar in Milan

Ideas for Your Vacation

An 8-day Tuscany vacation invites you into the heart of Italy’s most romantic and historic region, blending medieval cities, rolling vineyards, artistic treasures, and rustic countryside charm. Your journey typically begins in Florence, the cradle of the Renaissance, where you can explore masterpieces at the Uffizi Gallery, marvel at the Florence Cathedral’s iconic dome, stroll across the Ponte Vecchio, and wander through picturesque piazzas lined with cafés and boutiques.

From there, the trip often continues into the Chianti countryside, offering wine tastings at traditional vineyards, scenic drives through olive groves, and leisurely meals featuring regional Tuscan cuisine. Next, you may visit Siena, known for its striking Gothic architecture and the famous Piazza del Campo, followed by a stop in San Gimignano, with its distinctive medieval towers and charming hilltop ambience.

The journey usually includes time in Pisa, where you’ll see the world-renowned Leaning Tower and the Piazza dei Miracoli, along with optional coastal visits to spots like Viareggio or Lucca for relaxed strolls along ancient walls and vibrant local markets. Throughout your stay, you’ll enjoy the region’s slow pace, warm hospitality, and stunning landscapes before wrapping up your Tuscan escape and returning home refreshed and inspired.

Here is a polished, enriched, and travel-ready version of your 8 Days / 7 Nights Montecatini & Tuscany Self-Drive Adventure—written in the same style and tone as your Delhi–Jaipur itinerary.

Itinerary

• Day 1: Overnight Flight to Milan Begin your Italian escape with an overnight flight from US airports to Milan, the gateway to Northern Italy and the starting point of your Tuscan adventure.

• Day 2: Arrive Milan → Drive to Montecatini Arrive at Milan Airport, complete immigration formalities, collect your baggage, and pick up your rental car. Begin your picturesque drive into the heart of Tuscany. Montecatini welcomes you with its historic charm, elegant promenades, and renowned thermal spas. After checking in, the rest of the day is at leisure to unwind or take a relaxed stroll around town. Drive Time: Approx. 3.5 hours Overnight at the hotel – Montecatini

• Day 3: Lucca & Pisa Buffet breakfast at the hotel. Today, explore two of Tuscany’s most iconic cities. Start with Lucca, a beautifully preserved walled town filled with cobblestone lanes, scenic ramparts, and medieval towers. Continue onward to Pisa to admire the architectural masterpieces of the Piazza dei Miracoli, including the Leaning Tower, the Baptistery, and the Cathedral. Return to Montecatini in the evening after a day rich in history and culture. Drive Time: Approx. 2 hours total Overnight at the hotel – Montecatini

• Day 4: Florence Buffet breakfast at the hotel. This morning, travel to Florence—the crown jewel of the Renaissance. Visit the city’s legendary sites such as the Duomo and its iconic dome, the Baptistery with its bronze doors, the medieval Palazzo Vecchio, and the postcard-perfect Ponte Vecchio. To avoid city traffic and parking, we recommend taking a train from Montecatini; the last trains typically return around 9:30 PM. Travel Time: Approx. 2 hours return (train or car) Overnight at the hotel – Montecatini

• Day 5: Chianti & Greve Buffet breakfast at the hotel. Embark on a scenic self-drive through the Chianti countryside, known for its rolling vineyards, stone farmhouses, and world-famous wine. Stop in Greve—the gateway to Chianti—and continue to the medieval hamlet of Montefioralle for wine tastings, panoramic views, and authentic Tuscan flavors. Drive Time: Approx. 2.5 hours total Overnight at the hotel – Montecatini

• Day 6: Siena & San Gimignano Buffet breakfast at the hotel. Proceed to Siena, a Gothic treasure renowned for its stunning cathedral and the fan-shaped Piazza del Campo. Later, continue to the enchanting medieval town of San Gimignano, celebrated for its ancient tower-studded skyline and charming streets. After sightseeing, drive back to Montecatini. Drive Time: Approx. 4 hours total Overnight at the hotel – Montecatini

• Day 7: Parma → Milan Buffet breakfast at the hotel. Today, begin your journey north toward Milan, pausing en route in Parma. Walk through its elegant streets, visit the magnificent Parma Cathedral, and indulge in the region’s famed culinary delights—prosciutto di Parma and Parmigiano Reggiano. Later, continue to the Milan Malpensa area for your final night. Drive Time: Approx. 4 hours total Overnight at the hotel – Milan Malpensa Area

• Day 8: Depart Italy After breakfast, drive to Milan Airport, return your rental car, and board your flight back to the US, taking with you the unforgettable memories of Tuscany’s towns, vineyards, and timeless beauty. Drive Time: Approx. 10 minutes

Optional Tours & Excursions

• Optional Tours in Montecatini

  • Relaxing visit to the Montecatini Terme Thermal Pools
  • Tuscan wine experience with guided vineyard tour & wine tasting

• Optional Tours in Milan

  • Entry to the renowned Science and Technology Leonardo da Vinci Museum
  • Scenic cruise along the charming Navigli Canals

Contact Weekender Breaks at 1-929-207-0129 for Questions About:

• Flying from any airport not listed here
• Extending your trip or traveling on dates not listed here
• The availability of your desired travel dates
• Traveling with kids; all travelers age 2 and over are required to purchase a voucher
• Booking optional tours and upgrades