An A+ company rated by BBB
Book with Tripmasters.com to enjoy mobile app during your trip.

Call US 7 days a week

from 8AM to Midnight ET

1-800-430-0484
Chat
Home Manage Bookings Top Deals Reviews Recently Viewed0
Destinations

⚠ Announcement

Europeandestinations.com is Tripmasters.com now.
Ownership, management, and activity remain the same. All existing bookings will be serviced as always.

Florence and South East Tuscany (Self Drive)
7 to 10+ Nigths from $1,163*
This sample price: priced within the past 7 days for arrival on 9/10/2025, departure from New York City NYC (All Airports) (NY), US. Choose your own departure city, cabin type and dates.
Overview
Itinerary
Hotels
Tours
Map
Country Info
Feedbacks
Price Guidance
Click for larger image or other views
See all the images
This is a suggested independent itinerary that you customize. Please select the best flights, hotels, trains, activities, transportation and number of nights in each destination to fit your needs.
Explore the beautiful Italian South East Tuscanywith a Rental Car!. Visit the magnificent city of Florence (capital of Italy’s Tuscany region, is home to Renaissance art and architecture) and from there, with your Rental Car, leap up to South East Tuscany Area (a land of castle-dominated hill towns, misty blue mountains, and the remnants of Apennine forests with Arezzo and Cortona as main cities). 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
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 South East Tuscany
  • Hotel for 1 night in Florence

  • Driving Time
    Florence - South East Tuscany: 1 hr. 20 mins. approx.
    South East Tuscany - Florence: 1 hr. 20 mins. approx.

Price history for this itinerary (past 7 days):
From New York City NYC (All Airports) (NY), US for 7 nights
1162.51 * incl.tax
Related Itineraries:
Related Cities:
Florence (230)     South East Tuscany (7)    
Customize and Book
With Int'l Flight     Without Int'l Flight
From:
Cabin:
Destination
Arrival date
Stay
1. Florence
  286 hotels
2. South East Tuscany
   (30 hotels)
3. Florence
   (286 hotels)
Guest:
Please contact us for any special arrangements such as more than three rooms and partial stays.
View Price
Trip Summary
3 nights in 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.



3 nights in South East Tuscany

South East Tuscany is a land of castle-dominated hill towns, misty blue mountains, and the remnants of Apennine forests. Snowy white cattle graze in the wide Chiana Valley, while light industry toils at the edges of medieval centers. There are splendid landscapes where you can find famous monastic settlements, completely surrounded by trees and Romanesque parishes. This is the area where the humanist Renaissance of Tuscany melds with the intangible, hazy spirituality of Umbria's green hills.

Visit and explore the nearby Arezzo, Cortona, Anghiari, Monterchi , Sansepolcro and the beautiful castle of Poppi, and so much more.



1 nights in 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.



Book This Package
Flexible Itinerary
Florence
Day 1
Arrive to Florence
Overnight in Florence   286 hotels offered
Optional   1338 Things to do
Day 2
Overnight in Florence   286 hotels offered
Optional   1338 Things to do
Day 3
Overnight in Florence   286 hotels offered
Optional   1338 Things to do
Day 4
Departing from Florence
Transportation to next city by: Regional Air
South East Tuscany
Day 4
Arrive to South East Tuscany
Overnight in South East Tuscany   30 hotels offered
Day 5
Overnight in South East Tuscany   30 hotels offered
Day 6
Overnight in South East Tuscany   30 hotels offered
Day 7
Departing from South East Tuscany
Transportation to next city by: Regional Air
Florence
Day 7
Arrive to Florence
Overnight in Florence   286 hotels offered
Optional   1338 Things to do
Day 8
Departing from Florence
Book This Package

Loading ...
Florence Hotels (286 total)
›
South East Tuscany Hotels (30 total)
›


Loading ..
Tours in Florence (1338 total)
›


Loading ...
Package Map Picture
Italy

For centuries <b>Italy</b> has drawn foreign visitors - mostly for its architectural, artistic, and scenic splendors. Italy can truly be all things to all people. From the passion and excitement of noisy urban crowds to the quiet, rural idyll where the traditional life can be experienced, Italy's great cities are replete with rich attractions and culture alongside some of the most pristine beaches and spectacular mountains in the world.
Italy
20166 Customer Feedbacks
Customer Reviews
Share your thoughts with other travelers
Write a Review
Share your thoughts with other travelersWrite a Review
Price Guidance

The package rates displayed are your total price per person based on Double Occupancy and your Arrival Date and Number of Nights selected. You can change details after selecting your travel date.

Price history for this itinerary (past 7 days):

Your Preferred Major Airport:

*Sample prices on display include ALL taxes & fuel surcharges... read more
Close [x]
Photo
Florence and South East Tuscany (Self Drive)
Photos
Map
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.
South East Tuscany
South East Tuscany is a land of castle-dominated hill towns, misty blue mountains, and the remnants of Apennine forests. Snowy white cattle graze in the wide Chiana Valley, while light industry toils at the edges of medieval centers. There are splendid landscapes where you can find famous monastic settlements, completely surrounded by trees and Romanesque parishes. This is the area where the humanist Renaissance of Tuscany melds with the intangible, hazy spirituality of Umbria's green hills.

Visit and explore the nearby Arezzo, Cortona, Anghiari, Monterchi , Sansepolcro and the beautiful castle of Poppi, and so much more.
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.

close [X]

close [X]

close [X]