List of vacation packages
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Customer feedback (8)Florence - Siena - Pisa - Lucca by Train
6 to 9+ nights from$1,788*This packages is recommended for 6 to 9+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
Explore the absolute best of Tuscany Italian Region!. Visit Florence (capital of Italy’s Tuscany region, is home to Renaissance art and architecture), then Siena (famous for its cuisine, art, museums, medieval cityscape and Piazza del Campo), continue to Pisa (home to the world-renowned Leaning Tower of Pisa and many other architectural w ...
Florence - Siena - Pisa - Lucca by Train
6 to 9+ nights from $1,788 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on August 13, 2026. Choose your own departure city and dates.
This 6 night sample itinerary includes:
- Flight into and out of Florence
- Hotel for 2 nights in Florence
- Train from Florence and Siena
- Hotel for 1 night in Siena
- Train from Siena and Pisa (via Empoli)
- Hotel for 1 night in Pisa
- Train from Pisa and Lucca
- Hotel for 1 night in Lucca
- Train from Lucca and Florence
- Hotel for 1 night in Florence
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Customer feedback (7)Tuscan Scenery Self Drive (Florence - Siena - Pisa - Lucca)
6 to 9+ nights from$1,662*This packages is recommended for 6 to 9+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
A perfect introduction to Italy`s Tuscany Region by Car!. Visit Florence (home to Renaissance art and architecture) and after that, drive along these charming cities in the Tucany Region, like: Siena (famous for its horse race held twice a year in Piazza del Campo), Pisa (world-renowned Leaning Tower of Pisa) and Lucca (fantastic mediev ...
Tuscan Scenery Self Drive (Florence - Siena - Pisa - Lucca)
6 to 9+ nights from $1,662 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on July 1, 2026. Choose your own departure city and dates.
This 6 night sample itinerary includes:
- Flight into and out of Florence
- Hotel for 2 nights in Florence
- Rental Car for 5 days
- Hotel for 1 night in Siena
- Hotel for 1 night in Pisa
- Hotel for 1 night in Lucca
- Hotel for 1 night in Florence
Driving Time
Florence -Siena: 1 hr. 15 mins. approx.
Siena - Pisa: 1 hr. 40 mins. approx.
Pisa - Lucca: 40 mins. approx.
Lucca - Florence: 1 hr. 20 mins. approx.
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Customer feedback (6)Rome - Siena - Florence - Bologna - Milan - Verona - Padua - Venice (Self Drive)
12 to 18+ nights from$2,437*This packages is recommended for 12 to 18+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
A fantastic chance to visit main cities of Italy in a Car!. Begin with a stay in Rome (the Eternal City, with the Colosseum and the Roman Forum and delicious food) and after that, with your Rental Car, drive along the country visiting: Siena (famous for its cuisine, art, museums, medieval cityscape and the Palio), Florence (home to many ...
Rome - Siena - Florence - Bologna - Milan - Verona - Padua - Venice (Self Drive)
12 to 18+ nights from $2,437 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on December 19, 2026. Choose your own departure city and dates.
This 12 night sample itinerary includes:
- Flight into Rome and out of Venice
- Hotel for 3 nights in Rome
- Rental Car for 10 days
- Hotel for 1 night in Siena
- Hotel for 2 nights in Florence
- Hotel for 1 night in Bologna
- Hotel for 1 night in Milan
- Hotel for 1 night in Verona
- Hotel for 1 night in Padua (Padova)
- Hotel for 2 nights in Venice
Driving Time
Rome - Siena: 2 hrs. 50 mins. approx.
Siena - Florence: 2 hrs. approx.
Florence - Bologna: 1 hr. 45 mins. approx.
Bologna - Milan: 2 hrs. 30 mins. approx.
Milan - Verona: 2 hrs. 15 mins. approx.
Verona - Padua: 1 hr. 55 mins. approx.
Padua - Venice: 45 mins. approx.
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Customer feedback (5)Rome - Siena - Pisa - Florence - Verona - Venice by Train
9 to 13+ nights from$2,007*This packages is recommended for 9 to 13+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
A fantastic highlights of Italy travelling by train!. Discover Rome (the Eternal City) then, travel to Siena (representing a quaint medieval time with gothic palaces and altarpieces, tasty pastry shops) and next, to Pisa (world-renowned Leaning Tower of Pisa and many other architectural wonders). Continue to Florence (home to Renaissance ...
Rome - Siena - Pisa - Florence - Verona - Venice by Train
9 to 13+ nights from $2,007 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on September 1, 2026. Choose your own departure city and dates.
This 9 night sample itinerary includes:
- Flight into Rome and out of Venice
- Hotel for 2 nights in Rome
- Train from Rome to Siena
- Hotel for 1 night in Siena
- Train from Siena to Pisa
- Hotel for 1 night in Pisa
- Train from Pisa to Florence
- Hotel for 2 nights in Florence
- Train from Florence to Verona
- Hotel for 1 night in Verona
- Train from Verona to Venice
- Hotel for 2 nights in Venice
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Customer feedback (4)Milan - Montecatini Terme - Venice by Train
7 to 11+ nights from$1,526*This packages is recommended for 7 to 11+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
Create an unforgettable vacation in Italy!. Combine cosmopolitan Milan (one of the fashion capitals of the world; a thriving high-tech metropolis), Montecatini Terme (a town in Tuscany, known for the art nouveau architecture, the Parco delle Terme Spa Complex, its elegant buildings and leafy parks) and Venice (set on gorgeous canals, in ...
Milan - Montecatini Terme - Venice by Train
7 to 11+ nights from $1,526 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on July 10, 2026. Choose your own departure city and dates.
This 7 night sample itinerary includes:
- Flight into Milan and out of Venice
- Hotel for 2 nights in Milan
- Train from Milan to Montecatini Terme
- Hotel for 3 nights in Montecatini Terme
- Train from Montecatini Terme to Venice
- Hotel for 2 nights in Venice
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Customer feedback (4)Journey through Tuscany and Umbria Self Drive(Rome - Siena - Pisa - Florence - Assisi)
8 to 12+ nights from$1,810*This packages is recommended for 8 to 12+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
Combine several of the most popular cities in Italy! Rome (Italy`s treasure with two millennia of artistic achievement), Siena, Pisa (a city in Italy's Tuscany region best known for its iconic Leaning Tower), Florence (Michelangelo`s David, Botticelli`s Birth of Venus, and Raphael`s La Velata) and Assisi with a rent a car. What Makes Trip ...
Journey through Tuscany and Umbria Self Drive(Rome - Siena - Pisa - Florence - Assisi)
8 to 12+ nights from $1,810 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on July 13, 2026. Choose your own departure city and dates.
This 8 night sample itinerary includes:
- Flight into and out of Rome
- Hotel for 2 nights in Rome
- Rent a car for 7 days
- Hotel for 1 nights in Siena
- Hotel for 1 night in Pisa
- Hotel for 2 nights in Florence
- Hotel for 1 night in Assisi
- Hotel for 1 night in Rome
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Customer feedback (2)Montecatini Terme Getaway
7 to 11+ nights from$1,495*This packages is recommended for 7 to 11+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
A perfect introduction to Italy! Base yourself in Montecatini Terme (a town in Tuscany, Italy, known for the art nouveau Parco delle Terme spa complex) and Florence (Michelangelo`s David, Botticelli`s Birth of Venus, and Raphael`s La Velata) with a rent a car for exploring the area on your own. What Makes Tripmasters Vacation Packages Dif ...
Montecatini Terme Getaway
7 to 11+ nights from $1,495 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on July 12, 2026. Choose your own departure city and dates.
This 7 night sample itinerary includes:
- Flight into and out of Florence
- Hotel for 6 nights in Montecatini Terme
- Hotel for 1 night in Florence
- Car rental for 7 days (Florence pick-up/ drop-off)
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Customer feedback (2)Rome - Spoleto - Perugia - Florence by Train
7 to 11+ nights from$1,916*This packages is recommended for 7 to 11+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
Hidden treasures in cities in Italy!. From Rome (the Eternal City, with its Colosseum, Roman Forum and delicious food), travel to Spoleto (ancient city on the foothill of the Apennines, famous for its historical Festival dei Due Mondi) after that, to Perugia (Umbria`s capital, famous for its preserved historic centre, architecture and c ...
Rome - Spoleto - Perugia - Florence by Train
7 to 11+ nights from $1,916 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on June 1, 2026. Choose your own departure city and dates.
This 7 night sample itinerary includes:
- Flight into Rome and out of Florence
- Hotel for 2 nights in Rome
- Train from Rome to Spoleto
- Hotel for 1 night in Spoleto
- Train from Spoleto to Perugia
- Hotel for 2 nights in Perugia
- Train from Perugia to Florence
- Hotel for 2 nights in Florence
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Customer feedback (2)Rome - Tuscany - The Veneto - Lake Como - Milan by Train
13 to 19+ nights from$2,491*This packages is recommended for 13 to 19+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
Sample Italy with this unique, customizable vacation package!. Begin in Rome (the eternal city). From there, the train will allow to admire the beautiful tuscany countryside and its main cities, like: Siena (medieval atmosphere, time has stood still in this quaint city), Pisa (famous for its Leaning Tower) and Florence (home to Renaissanc ...
Rome - Tuscany - The Veneto - Lake Como - Milan by Train
13 to 19+ nights from $2,491 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on June 1, 2026. Choose your own departure city and dates.
This 13 night sample itinerary includes:
- Flight into Rome and out of Milan
- Hotel for 2 nights in Rome
- Train from Rome to Siena
- Hotel for 1 night in Siena
- Train from Siena to Pisa
- Hotel for 1 night in Pisa
- Train from Pisa to Florence
- Hotel for 2 nights in Florence
- Train from Florence to Verona
- Hotel for 1 night in Verona
- Train from Verona to Venice
- Hotel for 2 nights in Venice
- Train from Venice to Lake Como
- Hotel for 2 nights in Lake Como
- Train from Lake Como to Milan
- Hotel for 2 nights in Milan
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Customer feedback (1)Siena Getaway (Self Drive)
7 to 11+ nights from$1,537*This packages is recommended for 7 to 11+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
Spend a relaxing vacation in the Italian Tuscany. Make Siena (a region halted in time, representing a quaint medieval time with gothic palaces and altarpieces, tasty pastry shops); your home base 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 ...
Siena Getaway (Self Drive)
7 to 11+ nights from $1,537 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on July 12, 2026. Choose your own departure city and dates.
This 7 night sample itinerary includes:
- Flight into and out of Florence
- Rental Car for 8 days
- Hotel for 6 nights in Siena
- Hotel for 1 night in Florence
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Customer feedback (1)Tuscany and Pisa (Self Drive)
6 to 9+ nights from$1,792*This packages is recommended for 6 to 9+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
Explore beautiful Tuscany cities in Italy by car!. Base yourself in Pisa (home to the world-renowned Leaning Tower of Pisa and many other architectural wonders) and with a Rental Car explore the sorrounding Tuscany Region (renowned for its stunning landscapes, rich history, and artistic legacy) on your own. What Makes Tripmasters Vacatio ...
Tuscany and Pisa (Self Drive)
6 to 9+ nights from $1,792 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on July 1, 2026. Choose your own departure city and dates.
This 6 night sample itinerary includes:
- Flight into and out of Florence
- Hotel for 6 nights in Pisa
- Rental Car for 7 days
- Pick Up/Drop Off: Florence Airport
Driving Time
Florence Aiport - Pisa : 1 hr. approx.
Pisa - Florence Aiport: 1 hr. approx.
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Assisi Getaway (Self Drive)
6 to 9+ nights from$1,551*This packages is recommended for 6 to 9+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
Base yourself in Italy with a rent a car for exploring the area on your own. Assisi (Birthplace of Saint Francis and a UNESCO World Heritage Site). What Makes Tripmasters Vacation Packages Different?Unique, fully custom approach to vacation planningChoose your preferred flight cabin classSelect up to 14 nights in each city during your sta ...
Assisi Getaway (Self Drive)
6 to 9+ nights from $1,551 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on July 12, 2026. Choose your own departure city and dates.
This 6 night sample itinerary includes:
- Flight into and out of Florence
- Hotel for 6 nights in Assisi
- Car rental for 7 days
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Customer feedback (1)Umbria and Perugia (Self Drive)
6 to 9+ nightsThis packages is recommended for 6 to 9+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
Here is a Italy you don`t often see on postcards (but that you should see)! Base yourself in Perugia (an Italian city and the capital of the Umbria region. It’s known for its defensive walls around the historic center. The medieval Priori Palace exhibits regional art from the 13th century onward. Looking onto Piazza IV Novembre, the Gothi ...
Umbria and Perugia (Self Drive)
6 to 9+ nightsThis 6 night sample itinerary includes:
- Flight into and out of Florence
- Hotel for 5 nights in Perugia
- Rental Car for 6 days
- Pick Up/Drop Off: Florence Airport
