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Florence and Southern Tuscany: Chauffeured Collection

7 Nights from $2,273*
* Sample price: priced within the past 7 days for a 5/16/2026 arrival, departing New York City NYC (All Airports) (NY), US. Choose departure city, cabin and dates.

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This 7 night sample itinerary includes:

  • Flight into and out of Florence
  • Hotel for 3 nights in Florence
  • Transfer from Hotel in Florence to Hotel in Siena via Monteriggioni and San Gimignano
  • Hotel for 2 nights in Siena
  • Transfer from Hotel in Siena to Hotel in Cortona via Montepulciano
  • Hotel for 1 night in Cortona
  • Transfer from Hotel in Cortona to Hotel in Florence via Lucignano
  • Hotel for 1 night in Florence

Southern Tuscany Getaway!. From Florence (capital of Tuscany; home to Renaissance Art and Architecture), travel Southern Tuscany and visit Siena (famous for its cuisine, art, museums, medieval cityscape, horse races in Piazza del Campo). After that, have a pleasant stay at Cortona (famous for its traditions, history, culture and its magnificent landscapes as well as its artisan industries). Finally, get back for one last night stay in Florence. Along your way, by door-to-door service between these destinations discover: medievals Monteriggioni and San Gimignano (famous towers and wine); Montepulciano and Lucignano.

What Makes Tripmasters Vacation Packages Different?
Unique, fully custom approach to vacation planning
Choose your preferred flight cabin class
Select up to 14 nights in each city during your stay
Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more)
Add transfers, activities and experiences, and more services to enhance your vacation
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