phone_icon

Destinations

Main Menu

My Booking

Main Menu

About Us

Main Menu

Florence and Radda in Chianti (Self Drive)

5.0 out of 5 stars
1 Customer Feedbacks 1 Customer Feedbacks
7 to 10+ Nights from $1,306*
* Sample price: priced within the past 7 days for a 9/10/2025 arrival, departing New York City NYC (All Airports) (NY), US. Choose departure city, cabin and dates.

Customize and Book

Add Outbound & Return Flights

This 7 night sample itinerary includes:

  • Flight into and out of Florence
  • Hotel for 3 nights in Florence
  • Rental Car for 5 days
  • Hotel for 3 nights in Radda in Chianti
  • Hotel for 1 night in Florence
  • Driving Time
    Florence - Radda in Chianti : 1 hr. 10 mins. approx.
    Radda in Chianti - Florence: 1 hr. 10 mins. approx.

Charming trip to Italian Central Tuscany!. Visit the magnificent city of Florence (capital of Italy’s Tuscany region, is home to many masterpieces of Renaissance art and architecture) and after that, rent a car and spend a few days at your leisure along Radda in Chianti (a comune in the Province of Siena in the Italian Tuscany, a beautiful medieval town enclosed in large defensive walls). Drive back to Florence to drop off the car and finisht this trip with one last night stay.

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
Live phone and chat support

Flexible Itinerary

  • Florence

    about
  • Radda in Chianti

    about
  • Florence

    about
Italy

Customer Reviews

5.0 out of 5 stars

Trip Summary

  • Florence
    Florence

    The city of Florence sits nestled among the rolling Tuscan hills, with an unmistakable skyline dominated by the fabulous Duomo. With so much Renaissance art and culture, shopping opportunities, and incredible culinary delights, you will be spoiled for choices in what to do and see in this exciting capital city of Tuscany. Florence's museums, palaces, and churches house some of the greatest artistic treasures in the world.

    Visit The Duomo Complex, Church of Santa Croce, The Cathedral, The Uffizi Gallery, Galleria dell'Accademia, Ponte Vecchio, Palazzo Vecchio, Pitti Palace, Boboli Gardens and so much more.

  • Radda in Chianti
    Radda in Chianti

    Located on a hilltop, covered with woods and extensive vineyards, between the valleys of Arbia and Pesa, Radda in Chianti is a beautiful medieval town enclosed in large defensive walls. The town retains its narrow medieval streets that meet in the main square where you'll find the Church of San Niccolo, from the 14th century, and the Palazzo Pretorio, built about 1415. The town has been the head of the League of Chianti since 1415. Just outside the village, in the Vignale farm, are the headquarters of the Chianti Classico consortium and the Centro di Studi Chiantigiani (Centre for Chianti Studies), founded in 1984, with a small library and an archive devoted to the history of Chianti and its agriculture.

    Discover and explore the Castelo di Volpaia Winery, Fattoria di Montemaggio, Brancaia Winery, Castello di Radda, Cantina Castelvecchi in Chianti and so much more.

  • Florence
    Florence

    The city of Florence sits nestled among the rolling Tuscan hills, with an unmistakable skyline dominated by the fabulous Duomo. With so much Renaissance art and culture, shopping opportunities, and incredible culinary delights, you will be spoiled for choices in what to do and see in this exciting capital city of Tuscany. Florence's museums, palaces, and churches house some of the greatest artistic treasures in the world.

    Visit The Duomo Complex, Church of Santa Croce, The Cathedral, The Uffizi Gallery, Galleria dell'Accademia, Ponte Vecchio, Palazzo Vecchio, Pitti Palace, Boboli Gardens and so much more.

  • You can now

    Stagger

    your payment!

.