List of vacation packages
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Rome - Florence - Southern Tuscany and Venice
11 to 17+ nights fromThis packages is recommended for 11 to 17+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
Enchanting landscapes, magical hilltop hamlets and vineyars in The Southern Tuscany, in addition to cities with rich history in Italy. Start in Rome (the Eternal City, with the Colosseum, Roman Forum and delicious food), after that, catch a train to Florence (Italy’s Tuscany region, is home to Renaissance art and architecture). From there ...
Rome - Florence - Southern Tuscany and Venice
11 to 17+ nights from $1,835 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2026-03-03T00:00:00. Choose your own departure city and dates.
This 11 night sample itinerary includes:
- Flight into Rome and out of Venice
- Hotel for 3 nights in Rome
- Train from Rome to Florence
- Hotel for 2 nights in Florence
- Rental Car for 4 nights
- Hotel for 3 nights in Southern Tuscany
- Hotel for 1 night in Florence
- Train from Florence to Venice
- Hotel for 2 nights in Venice
Driving Time
Florence - Southern Tuscany: 1 hr./ 1 hr. 20 mins. approx.
Southern Tuscany - Florence: 1 hr. /1 hr. 20 mins. approx.
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Florence and San Gimignano (Self Drive)
7 to 11+ nights fromThis packages is recommended for 7 to 11+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
Explore the beautiful cities in Italy by car!. 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, continue with your Rental Car and spend a few days at your leisure in San Gimignano (famous for its medieval architecture, unique in the ...
Florence and San Gimignano (Self Drive)
7 to 11+ nights from $1,538 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2025-09-15T00:00:00. Choose your own departure city and dates.
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 San Gimignano
- Hotel for 1 night in Florence
Driving Time
Florence - San Gimignano : 1 hr. approx.
San Gimignano - Florence: 1 hr. approx.
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Tuscany and Lake Como (Self Drive)
10 to 15+ nights fromThis packages is recommended for 10 to 15+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
Pinturesques landscapes of Italy, tavelling by car!. Start with a visit to Florence (capital of Italy’s Tuscany region, home to Renaissance art and architecture). From there, with a Rental Car, leap up to Southern Tuscany (boasting the most captivating countryside and vineyards that produce Tuscany's mightiest red wines in cities like: ...
Tuscany and Lake Como (Self Drive)
10 to 15+ nights from $1,081 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2025-11-11T00:00:00. Choose your own departure city and dates.
This 10 night sample itinerary includes:
- Flight into Florence and out of Milan
- Hotel for 3 nights in Florence
- Rental Car for 8 days
- Hotel for 3 nights in Southern Tuscany
- Hotel for 3 nights in Lake Como
- Hotel for 1 night in Milan
Driving Time
Florence - Southern Tuscany: 1 hr./ 1 hr. 20 mins. approx.
Southern Tuscany - Lake Como: 5 hrs./ 5 hrs. 20 mins. approx.
Lake Como - Milan: 1 hr. 35 mins. approx.
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Florence - Southern Tuscany and Positano (Self Drive)
10 to 15+ nights fromThis packages is recommended for 10 to 15+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
Visit Italy`s charming regions, with this holiday package!. From Florence (capital of Italy’s Tuscany region, home to many masterpieces of Renaissance art and architecture); pick up the Rental Car and drive along the beautiful Southern Tuscany (renowned as one of the world's best wine regions, like Chianti, with its hilltop towns and lush ...
Florence - Southern Tuscany and Positano (Self Drive)
10 to 15+ nights from $1,486 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2025-11-18T00:00:00. Choose your own departure city and dates.
This 10 night sample itinerary includes:
- Flight into Florence and out of Naples
- Hotel for 3 nights in Florence
- Rental Car for 8 days
- Hotel for 3 nights in Southern Tuscany
- Hotel for 3 nights in Positano
- Hotel for 1 night in Naples
Driving Time
Florence - Southern Tuscany Area: 1 hr. 10 - 50 mins. approx.
Southern Tuscany - Positano: 5 hrs. 10 - 55 mins. approx.
Positano - Naples: 1 hr. 20 mins. approx.
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Genoa - Cinque Terre - Tuscany - Amalfi Coast
10 to 15+ nights fromThis packages is recommended for 10 to 15+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
Start in with a visit to Genoa (a city in and the capital of the Italian region of Liguria, and the sixth-largest city in Italy), then continue to beautiful Cinque Terre (a string of centuries-old seaside villages on the rugged Italian Riviera coastline), then visit artistic Florence (Old town recognized for the Oregon Dunes and is nestle ...
Genoa - Cinque Terre - Tuscany - Amalfi Coast
10 to 15+ nights from $1,751 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2025-11-30T00:00:00. Choose your own departure city and dates.
This 10 night sample itinerary includes:
- Flight into Genoa and out of Naples
- Hotel for 2 night in Genoa
- Train: Genoa to La Spezia (Cinque Terre)
- Hotel for 2 nights in Cinque Terre
- Train: La Spezia (Cinque Terre) to Florence
- Hotel for 2 nights in Florence
- Rental car for 5 days
- Hotel for 2 nights in Southern Tuscany
- Hotel for 2 nights in the Amalfi Coast
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Tuscan Highlights (Florence - Siena - San Gimignano - Self Drive)
7 to 11+ nights fromThis packages is recommended for 7 to 11+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
A unique trip to Italy's Tuscany Region by car! . Discover Florence (capital of Italy’s Tuscany region, home to Renaissance art and architecture) and from there, with Rental Car, main cities in Tuscany, like Siena (famous for its cuisine, art, museums, medieval cityscape and the Palio horse race in Piazza del Campo) and San Gimignano (fa ...
Tuscan Highlights (Florence - Siena - San Gimignano - Self Drive)
7 to 11+ nights from $1,765 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2026-04-03T00:00:00. Choose your own departure city and dates.
This 7 night sample itinerary includes:
- Flight into and out of Florence
- Hotel for 2 nights in Florence
- Rental Car for 6 days
- Hotel for 2 nights in Siena
- Hotel for 2 nights in San Gimignano
- Hotel for 1 night in Florence
Driving Time
Florence - Siena: 1 hr. 10 mins. approx.
Siena - San Gimignano: 1 hr. approx.
San Gimignano - Florence: 1 hr. 15 mins. approx.
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Venice - Florence - Southern Tuscany and Coast
11 to 17+ nights fromThis packages is recommended for 11 to 17+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
An enchanting vacation package, visiting some destinations in Italy!Start with a visit to romantic Venice, then catch a train to artistic Florence. Continue with a rent a car to explore beautiful Southern Tuscany and end with a relaxing stay in the Tuscany Coast.What Makes Tripmasters Vacation Packages Different?Unique, fully custom appr ...
Venice - Florence - Southern Tuscany and Coast
11 to 17+ nights from $1,926 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2025-11-10T00:00:00. Choose your own departure city and dates.
This 11 night sample itinerary includes:
- Flight into Venice and out of Pisa
- Hotel for 2 nights in Venice
- Train: Venice to Florence
- Hotel for 3 nights in Florence
- Rent a car for 6 days
- Hotel for 3 nights in Southern Tuscany
- Hotel for 3 nights in Tuscany Coast
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Southern Tuscany Getaway
7 to 11+ nights fromThis packages is recommended for 7 to 11+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
Italy! Spend a relaxing vacation in Southern Tuscany and Florence (Michelangelo`s David, Botticelli`s Birth of Venus, and Raphael`s La Velata). Make your home base one of the charming properties in this area and use your rent a car to visit the whole area at your own pace. What Makes Tripmasters Vacation Packages Different?Unique, fully c ...
Southern Tuscany Getaway
7 to 11+ nights from $1,208 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2026-02-14T00:00:00. Choose your own departure city and dates.
This 7 night sample itinerary includes:
- Flight into and out of Florence
- Rent a car for 8 days
- Hotel for 6 nights in Southern Tuscany
- Hotel for 1 night in Florence
- Daily breakfast (if stated in hotel description)
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Rome - Florence and Southern Tuscany
9 to 13+ nights fromThis packages is recommended for 9 to 13+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
Main cities and the pinturesque Tuscany in Italy!. Start in Rome (the Eternal City, with the Colosseum, Roman Forum and delicious food), after that, continue by train to Florence (capital of Italy’s Tuscany region, is home to Renaissance art and architecture). From there, with a Rental Car, leap up to Southern Tuscany (boasting the most c ...
Rome - Florence and Southern Tuscany
9 to 13+ nights from $1,956 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2026-05-02T00:00:00. Choose your own departure city and dates.
This 9 night sample itinerary includes:
- Flight into Rome and out of Florence
- Hotel for 3 nights in Rome
- Train from Rome to Florence
- Hotel for 2 nights in Florence
- Rental Car for 4 days
- Hotel for 3 nights in Southern Tuscany
- Hotel for 1 night in Florence
Driving Time
Florence - Southern Tuscany: 1 hr./ 1 hr. 20 mins. approx.
Southern Tuscany - Florence: 1 hr. /1 hr. 20 mins. approx.
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Florence - Southern Tuscany and Tuscany Coast (Self Drive)
9 to 13+ nights fromThis packages is recommended for 9 to 13+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
A tuscany holiday in Italy!. From Florence (capital of Italy’s Tuscany region, home to many masterpieces of Renaissance art and architecture); pick up the Rental Car and drive along the beautiful Southern Tuscany (renowned as one of the world's best wine regions, like Chianti, with its hilltop towns and lush landscapes, delicious dishes ...
Florence - Southern Tuscany and Tuscany Coast (Self Drive)
9 to 13+ nights from $1,926 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on 2025-11-21T00:00:00. Choose your own departure city and dates.
This 9 night sample itinerary includes:
- Flight into Florence and out of Pisa
- Hotel for 3 nights in Florence
- Rental Car for 7 days
- Hotel for 3 nights in Southern Tuscany
- Hotel for 3 nights in Tuscany Coast
Driving Time
Florence - Southern Tuscany: 1 hr. 10 mins. approx.
Southern Tuscany - Tuscany Coast: 1 hr. 30 mins. approx.
Tuscany Coast - Pisa Airport: 40 mins. approx.
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Florence - Southern Tuscany and Sorrento (Self Drive)
10 to 15+ nightsThis packages is recommended for 10 to 15+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
Visit two of Italy`s most charming regions with a Rental Car!. Start in Florence (capital of Italy’s Tuscany region, is home to Renaissance art and architecture). From there, with a Rental Car, leap up to Southern Tuscany (boasting the most captivating countryside and vineyards that produce Tuscany's mightiest red wines in cities like: Mo ...
Florence - Southern Tuscany and Sorrento (Self Drive)
10 to 15+ nightsThis 10 night sample itinerary includes:
- Flight into Florence and out of Naples
- Hotel for 3 nights in Florence
- Rental Car for 8 days
- Hotel for 3 nights in Southern Tuscany
- Hotel for 3 nights in Sorrento
- Hotel for 1 night in Naples
Driving Time
Florence - Southern Tuscany: 1 hr./ 1 hr. 20 mins. approx.
Southern Tuscany - Sorrento: 5 hrs. 30 mins. approx.
Sorrento - Naples: 1 hr. 10 mins. approx.
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Florence and Southern Tuscany (Self Drive)
7 to 11+ nightsThis packages is recommended for 7 to 11+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
Enjoy the wonderful Italian Southern Tuscany Region!. Delight yourself in Florence (capital of Italy’s Tuscany region, is home to many masterpieces of Renaissance art and architecture). From there, with a Rental Car, leap up to Southern Tuscany (boasting the most captivating countryside and vineyards that produce Tuscany's mightiest red ...
Florence and Southern Tuscany (Self Drive)
7 to 11+ nightsThis 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 Southern Tuscany
- Hotel for 1 night in Florence
Driving Time
Florence - Southern Tuscany: 1 hr./ 1 hr. 20 mins. approx.
Southern Tuscany - Florence: 1 hr. /1 hr. 20 mins. approx.
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Florence and Chianciano Terme (Self Drive)
7 to 11+ nightsThis packages is recommended for 7 to 11+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
Tuscany`s treasures in Italy!. Visit Florence (capital of Italy’s Tuscany region, home to Renaissance art and architecture) and after that, continue with your Rental Car to Chianciano Terme (one of the best known spa resorts in Tuscany and Italy). Drive back to Florence for one last stay, before returning home. What Makes Tripmasters Vaca ...
Florence and Chianciano Terme (Self Drive)
7 to 11+ nightsThis 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 Chianciano Terme
- Hotel for 1 night in Florence
Driving Time
Florence - Chianciano Terme : 1 hr. 40 mins. approx.
Chianciano Terme- Florence: 1 hr. 40 mins. approx.