List of vacation packages
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Customer feedback (5)Florence - San Gimignano - Rome (Self Drive)
9 to 13+ nights from$1,329*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 Self Drive Vacation to some of our most popular destinations in Italy!. Spend a few days in artistic Florence (capital of Italy’s Tuscany region, is home to Renaissance art and architecture), then pick up your Rental Car and drive for a visit to San Gimignano (famous for its medieval architecture and towers). Finish with a stay in monum ...
Florence - San Gimignano - Rome (Self Drive)
9 to 13+ nights from $1,329 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on August 12, 2026. Choose your own departure city and dates.
This 9 night sample itinerary includes:
- Flight into Florence and out of Rome
- Hotel for 3 nights in Florence
- Rental Car for 4 days
- Hotel for 3 nights in San Gimignano
- Hotel for 3 nights in Rome
Driving Time
Florence - San Gimignano: 1 hr. 10 mins. approx.
San Gimignano - Rome: 3 hrs. 20 mins. approx.
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Customer feedback (5)Rail to Road: Tuscan Journey (Pisa - San Gimignano - Siena - Florence - Rome)
10 to 15+ nights from$1,727*This packages is recommended for 10 to 15+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
Delight yourself in the charming Tuscany Region, during your vacations in Italy!. From Pisa (world-renowned Leaning Tower of Pisa), drive along the Tuscany visiting San Gimignano (medieval architecture, unique in the preservation of about a dozen of its tower houses) after that, Siena (medieval cityscape and the Palio, a horse race held i ...
Rail to Road: Tuscan Journey (Pisa - San Gimignano - Siena - Florence - Rome)
10 to 15+ nights from $1,727 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on August 12, 2026. Choose your own departure city and dates.
This 10 night sample itinerary includes:
- Flight into Pisa and out of Rome
- Rental Car for 9 days
- Hotel for 2 nights in Pisa
- Hotel for 2 nights in San Gimignano
- Hotel for 2 nights in Siena
- Hotel for 2 nights in Florence
- Train from Florence to Rome
- Hotel for 2 nights in Rome
Driving Time
Pisa- San Gimignano: 1 hr. 25 mins. approx.
San Gimignano - Siena: 50 mins. approx.
Siena - Florence: 1 hr. 45 mins. approx.
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Customer feedback (4)Florence and San Gimignano (Self Drive)
7 to 11+ nights from$1,529*This 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 $1,529 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on August 8, 2026. 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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Customer feedback (3)Rome - Florence - Venice: Chauffeured Collection
7 to 11+ nights from$1,879*This packages is recommended for 7 to 11+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
Explore our favorite Italian cities and hidden gems, including Montepulciano and UNESCO-listed cities Ferrara and San Gimignano, with private transfers. Begin this twist on our classic Italy getaway in historic Rome (the Eternal City) where the Colosseum looms large and the Vatican's treasures await discovery, and after that, travel to Fl ...
Rome - Florence - Venice: Chauffeured Collection
7 to 11+ nights from $1,879 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on November 25, 2026. Choose your own departure city and dates.
This 7 night sample itinerary includes:
- Flight into Rome and out of Venice
- Hotel for 3 nights in Rome
- Transfer from Hotel in Rome to Hotel in Florence via Montepulciano and San Gimignano
- Hotel for 2 nights in Florence
- Transfer from Hotel in Florence to Hotel in Venice (Piazzale Roma Terminal) via Ferrara
- Boat transfer from Venice port to closest hotel dock not included; guests must book it independently
- Hotel for 2 nights in Venice
Easily upgrade your vacation to a Luxury Private Guided Experience, featuring upgraded hotels, private transportation between cities, and private activities including a Colosseum tour, Florence city tour, Venice food tour, and more!
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Customer feedback (2)Tuscan Highlights Self Drive (Florence - Siena - San Gimignano)
7 to 11+ nights from$1,548*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 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 Self Drive (Florence - Siena - San Gimignano)
7 to 11+ nights from $1,548 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on September 14, 2026. 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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Customer feedback (1)UNESCO Heritage Highlights of Italy from Rome - Florence - Venice - Milan
10 to 15+ nights from$3,029*This packages is recommended for 10 to 15+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
Perhaps it is no surprise that Italy tops the list for UNESCO World Heritage Sites, with its wealth or history, culture, art ... etc. Discover the best of the best, from the beauty Amalfi Coast plus Pompeii Ruins to breathtaking Cinque Terre Villages, to the romantic canals of Venice and the inspiring Last Supper at the Santa Maria delle ...
UNESCO Heritage Highlights of Italy from Rome - Florence - Venice - Milan
10 to 15+ nights from $3,029 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on July 7, 2026. Choose your own departure city and dates.
This 10 night sample itinerary includes:
- Flight into Rome and out of Milan
- Hotel for 3 nights in Rome
- Train from Rome to Florence
- Hotel for 3 nights in Florence
- Train from Florence to Venice
- Hotel for 2 nights in Venice
- Train from Venice to Milan
- Hotel for 2 nights in Milan
Sample of Included Tours: - Colosseum Tour in Rome
- Day Trip to Pompeii UNESCO Heritage Site and the Amalfi Coast
- Day Trip to Cinque Terre from Florence
- Canal Cruise around Venice
- Guided City Tour plus The Last Supper by Da Vinci in Milan
Your price will only include confirmed available tours; some tours may collect for entrance fees or attraction tickets on site. If an included tour becomes unavailable, alternate options may be available at an additional cost.
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The Best of Florence plus Tuscany
8 to 12+ nights from$2,109*This packages is recommended for 8 to 12+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
Under the Tuscany Sun in Italy!. Combine a stay in Florence (capital of Italy`s Tuscany region and home to many masterpieces of Renaissance Art and Architecture) with Day Trips to the dreamy Tuscan Countryside (from glorious landscapes, vast history, delicious cuisines and wines, to even artistic legacy along cities and small villages sca ...
The Best of Florence plus Tuscany
8 to 12+ nights from $2,109 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on November 6, 2026. Choose your own departure city and dates.
This 8 night sample itinerary includes:
- Flight into and out of Florence
- Hotel for 8 nights in Florence
Sample of Included Tours: - Guided City Tour
- Visit Uffizi and Accademia Museums
- Tuscan Cheese and Wine Tastings
- Day Trip to Lucca and Pisa
- Day Trip to Siena and San Gimignano
- Chianti Wine Tour (a Protected Designation of Origin)
Your price will only include confirmed available tours; some tours may collect for entrance fees or attraction tickets on site. If an included tour becomes unavailable, alternate options may be available at an additional cost.
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Florence and Southern Tuscany: Chauffeured Collection
7 to 11+ nights from$2,157*This packages is recommended for 7 to 11+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
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 magni ...
Florence and Southern Tuscany: Chauffeured Collection
7 to 11+ nights from $2,157 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on August 12, 2026. 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
- 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
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The Best of Tuscany and Umbria
8 to 12+ nights from$2,518*This packages is recommended for 8 to 12+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
If you are trying to see the best of these two popular Italian Regions, we recommend basing yourself in Florence and exploring from there. You will find it easy and accessible, especially because Day Trips are already included!. All you need to do is enjoy!. You`ll get to walk around Florence, visit Uffizi Museum and Accademia Museum. Yo ...
The Best of Tuscany and Umbria
8 to 12+ nights from $2,518 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on August 18, 2026. Choose your own departure city and dates.
This 8 night sample itinerary includes:
- Flight into and out of Florence
- Hotel for 8 nights in Florence
Sample of Included Tours: - Guided City Tour in Florence
- Day Trip to Siena and San Gimignano from Florence
- Day Trip to Umbria from Florence
- Visit Uffizi and Accademia Museums in Florence
- Day Trip to Lucca and Pisa from Florence
- Chianti Wine Tour (a Protected Designation of Origin) from Florence
Your price will only include confirmed available tours; some tours may collect for entrance fees or attraction tickets on site. If an included tour becomes unavailable, alternate options may be available at an additional cost.
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Florence - Southern Tuscany - Cinque Terre: Chauffeured Collection
7 to 11+ nights from$2,689*This packages is recommended for 7 to 11+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
Experience Southern Tuscany and Cinque Terre in depth. From Florence (the capital of Tuscany and birthplace of the Renaissance), travel through Southern Tuscany and visit Siena (famous for its cuisine, art, museums, medieval cityscape, and horse races in Piazza del Campo). After that, have a pleasant stay at La Spezia (a Ligurian seaside ...
Florence - Southern Tuscany - Cinque Terre: Chauffeured Collection
7 to 11+ nights from $2,689 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on August 12, 2026. 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
- Transfer from Hotel in Florence to Hotel in Siena via Monteriggioni and San Gimignano
- Hotel for 1 night in Siena
- Transfer from Hotel in Siena to Hotel in Cinque Terre Area via Lucca and Colle Val dElsa
- Hotel for 2 nights in La Spezia
- Transfer from Hotel in Cinque Terre Area to Hotel in Florence via Pisa and Montecatini Alto
- Hotel for 1 night in Florence
Easily upgrade your vacation to include guided activities with our Luxury Private Guided package, featuring upgraded hotels, private activities, and more!
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Florence and Umbria: Chauffeured Collection
8 to 12+ nights from$2,865*This packages is recommended for 8 to 12+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
Visit Florence and Umbria!. Visit artistic Florence (capital of Italy’s Tuscany region, home to Renaissance art and architecture), continue to Assisi (best known as the birthplace of St. Francis, Italy's patron saint, in Umbria's rolling hills) with a stop in Loro Ciuffenna and Perugia. After that, visit Orvieto (a small city perched on a ...
Florence and Umbria: Chauffeured Collection
8 to 12+ nights from $2,865 w/air, hotel & air taxes*This sample price includes ALL air taxes & fuel surcharges: priced within the past 7 days for arrival on July 28, 2026. Choose your own departure city and dates.
This 8 night sample itinerary includes:
- Flight into and out of Florence
- Hotel for 3 nights in Florence
- Transfer from Hotel in Florence to Hotel in Assisi via Loro Ciuffenna and Perugia
- Hotel for 2 nights in Assisi
- Transfer from Hotel in Assisi to Hotel in Orvieto Via Todi
- Hotel for 1 night in Orvieto
- Transfer from Hotel in Orvieto to Hotel in Siena via Montepulciano and Lucignano
- Hotel for 1 night in Siena
- Transfer from Hotel in Siena to Hotel in Florence via Monteriggioni and San Gimignano
- Hotel for 1 night in Florence
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Beautiful Tuscany Self Drive (Florence - Lucca - San Gimignano - Siena)
9 to 13+ nightsThis packages is recommended for 9 to 13+ nights.
Customize it by selecting dates, No. of nights in each city and your departure city.
Focus your visit to Italy in wonderful Tuscany!. Visit artistic Florence, then pick up your car and spend some leisurely days staying in Lucca, San Gimignano and Siena to be able to experience all the different aspects of this charming region. Return to Florence for one last stay. What Makes Tripmasters Vacation Packages Different?Uniqu ...
Beautiful Tuscany Self Drive (Florence - Lucca - San Gimignano - Siena)
9 to 13+ nightsThis 9 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 Lucca
- Hotel for 2 nights in San Gimignano
- Hotel for 2 nights in Siena
- Hotel for 1 night in Florence
