Tuscany And Hill Towns Vacation Packages
Tuscany is one of the most popular travel destinations in the world, offering beautiful Renaissance cities like Florence and Pisa as well as small medieval towns like Siena, San Gimignano, and Lucca scattered throughout the countryside. Visitors come to this region for many reasons - be it the art, the architecture, the food or the wine, there is no shortage of things to see and do. The only question is where to begin.
Best Vacation Packages
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Exclusive Florence - Southern Tuscany - Cinque Terre (Chauffeured Collection)
Your private chauffeur navigates the sun-drenched Tuscan Countryside, seamlessly connecting the Renaissance splendor of Florence with the medieval majesty of Siena and the scenic Cinque Terre Villages in ultimate luxury and comfort! Enjoy door-to-door service between these destinations and discover medieval cities (and a few UNESCO World Heritage Sites) including: Monteriggioni, San Gimignano, Lucca, Colle Val dElsa, Pisa, and Montecatini Alto.
Essential Highlights and Recommended Experiences:
- Climb Brunelleschi's Dome for breathtaking Florence city views
- Visit the Uffizi Gallery, Michelangelo's David at the Accademia Gallery, and walk along the Ponte Vecchio Bridge
- Explore the shell-shaped Piazza del Campo, Torre del Mangia, and admire the striped Gothic architecture of the Duomo in Siena
- Walk the Via dell'Amore in La Spezia, Hike the Sentiero Azzurro (Blue Trail) connecting the five colorful villages or take a Ferry/Boat Trip along the coast for stunning views of the cliffside towns of the Ligurian Sea
- Sample authentic Tuscan cuisine, award-winning Chianti wines, the freshest seafood, and other delectable aperitivi
This premier vacation package features thoughtfully curated services and is fully flexible. You can customize it to suit your needs and preferences by adjusting the number of nights in each city and browsing our hand-picked selection of hotels, transportation options, activities, and experiences.Includes:
- Flight into and out of Florence
- Private arrival and departure transfers in Florence
- 4-Star or better hotels for 4 nights in Florence and 2 nights each in Siena and La Spezia (Cinque Terre Area)
- Private driver from Florence to Siena via Monteriggioni and San Gimignano
- Private driver from Siena to Cinque Terre via Lucca and Colle Val dElsa
- Private driver from La Spezia to Florence via Pisa and Montecatini Alto
- Live phone and chat support
8 nights from $2,569*
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Experience Florence plus Tuscany Villages
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 scattered about the lush greenery like: Pisa and Lucca, to experience the best of this world-famous Italian region!.
Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city while enjoying included, curated activities that enhance your experience!Includes:
- Flight into and out of Florence
- Hotel for 8 nights in Florence
Curated Experiences Based on Availability: - Guided City Tour, visiting iconic sites and popular neighborhoods
- Visit Uffizi and Accademia Museums
- Tuscan Cheese and Wine Tastings
- Day Trip to Lucca and Pisa
- Chianti Wine Tour (a Protected Designation of Origin)
Your price will only include confirmed activities; some tours may collect for entrance fees or attraction tickets on site.
8 nights from $2,089*
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Tuscan Scenery Self Drive (Florence - Siena - Pisa - Lucca)
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 medieval city walls and its cobblestone streets). Drive back to Florence to drop off the car and finisht this trip with one last night stay.
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.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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Florence and The Chianti Wine Region (Self Drive)
Discover Italy's most famous Wine Region by car!. Visit Florence (capital of Italy’s Tuscany region, home to Renaissance art and architecture). From there, with a Rental Car, leap up to the charming Chianti Wine Region (green, gentle hills covered with wide fields of vineyards and olive groves, small stone villages, characteristic parishes and countryside homes in stone and of course, its worldwide Chianti Wine, made primarily with Sangiovese grapes). Drive back to Florence to drop off the car and finisht this trip with one last night stay.
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.Includes:
- Flight into and out of Florence
- Hotel for 3 nights in Florence
- Rental Car for 5 days
- Hotel for 3 nights in Chianti Wine Region
- Hotel for 1 night in Florence
Driving Time
Florence - Chianti Wine Region: 50 mins. / 1 hr. 10 mins. approx.
Chianti Wine Region - Florence: 50 mins. / 1 hr. 10 mins. approx. approx.
Areas of Tuscany
Suggested Itineraries
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Tuscan Adventure Self Drive (Florence - Montecatini - Lucca)
Tuscany Road Trip in Italy!. Visit the magnificent Florence (capital of Italy’s Tuscany region, home to Renaissance art and architecture), and from there, with a Rental Car, leap up to Tuscany Region, visiting Montecatini Terme (known for the art nouveau architecture, the Parco delle Terme Spa Complex) and Lucca (fantastic medieval city walls that still encircle most of the historic old town and its cobblestone streets). Drive back to Florence to drop off the car and finisht this trip with one last night stay.
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.Includes:
- Flight into and out of Florence
- Hotel for 2 nights in Florence
- Rental Car for 6 days
- Hotel for 2 nights in Montecatini
- Hotel for 2 night in Lucca
- Hotel for 1 night in Florence
Driving Time
Florence - Montecatini: 1 hr. 10 mins. approx.
Montecatini - Lucca: 40 mins. approx.
Lucca - Florence: 1 hr. 30 mins. approx.
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Florence and Southern Tuscany: Chauffeured Collection
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 magnificent landscapes as well as its artisan industries). Finally, get back for one last night stay in Florence. Along your way, by door-to-door service between these destinations discover: medievals Monteriggioni and San Gimignano (famous towers and wine); Montepulciano and Lucignano.
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.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
7 nights from $1,880*
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Beautiful Tuscany Self Drive (Florence - Lucca - San Gimignano - Siena)
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.
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.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
9 nights from $1,439*
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Florence - Tuscany - Italian Riviera: Chauffeured Collection
Dreamy Italian Tuscany and Riviera!. Combine unforgettable stays at these Tuscany cities: Florence (capital of Tuscany; home to Renaissance Art and Architecture) and Lucca (fantastic medieval city walls that still encircle most of the historic old town); with Santa Margherita Ligure (a charming fishing village) and port city of Genoa (rich cultural heritage encompassing art, music, and culinary traditions) in Italy's Riviera Coast. By private door to door service stops along your way, visit Pisa (world-renowned Leaning Tower), Prato (textil industry, traditional cuisine and wines) and at the Genoese Coast, Castello di Lerici (medieval prison and fortress with spectacular views).
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.Includes:
- Flight into Florence and out of Genoa
- Hotel for 3 nights in Florence
- Transfer from Hotel in Florence to Hotel in Lucca via Pisa and Prato
- Hotel for 2 nights in Lucca
- Transfer from Hotel in Lucca to Hotel in Santa Margherita Ligure via Castello di Lerici
- Hotel for 2 nights in Santa Margherita Ligure
- Transfer from Hotel in Santa Margherita Ligure to Hotel in Genoa
- Hotel for 1 night in Genoa
8 nights from $1,957*
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Florence - Siena - Pisa - Lucca by Train
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 wonders) and Lucca (fantastic medieval city walls that still encircle most of the historic old town). Finally enjoy a last night stay in Florence before returning home. All these destinations are connected by train rides.
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.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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Florence - Umbria - Tuscany: Chauffeured Collection
Explore Italy!. 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 Cortona (famous for its traditions, history, culture and its magnificent landscapes as well as its artisan industries) with a stop in Castiglio Fiorentino. Lastly, Lucca (it is known throughout Italy for its fantastic medieval city walls that still encircle most of the historic old town) with a stop in Pisa and Montecatini Alto. Before heading back home, return to Florence with a stop in Prato.
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.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 Cortona via Castiglio Fiorentino
- Hotel for 1 night in Cortona
- Transfer from Hotel in Cortona to Hotel in Lucca via Pisa and Montecatini Alto
- Hotel for 1 night in Lucca
- Transfer from Hotel in Lucca to Hotel in Florence via Prato
- Hotel for 1 night in Florence
8 nights from $2,357*
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Pisa and the Coast of Tuscany (Self Drive)
Enjoy three beautiful and exciting destinations across Italy with a unique vacation package! Fly in to Pisa International airport (a city in Italy's Tuscany region best known for its iconic Leaning Tower), pick up your car and enjoy a stay in the Coast of Tuscany.
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.Includes:
- Flight into and out of Pisa
- Rent a car for 7 days
- Hotel for 6 nights in Tuscany Coast
- Daily breakfast (if stated in hotel description)
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Florence and Arezzo (Self Drive)
Explore the beautiful Tuscany cities during your trip along Italy!. Visit 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 to Arezzo (rich in monuments, parks, archaeological remains, churches, and historic squares as well as s a place for art lovers and shopping fans). Drive back to Florence for one last stay, before returning home.
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.Includes:
- Flight into and out of Florence
- Hotel for 3 nights in Florence
- Rental Car for 5 days
- Hotel for 3 nights in Arezzo
- Hotel for 1 night in Florence
Driving Time
Florence - Arezzo : 1 hr. approx.
Arezzo - Florence: 1 hr. approx.
7 nights from $1,251*
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Rail to Road: Tuscan Journey (Pisa - San Gimignano - Siena - Florence - Rome)
10 nights from $1,757*
Rail to Road: Tuscan Journey (Pisa - San Gimignano - Siena - Florence - Rome)
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 in Piazza del Campo) and up to Florence (capital of Italy’s Tuscany region, home to Renaissance art and architecture). From there, catch a train to the fabulous Rome (the Eternal City, with the Colosseum, Roman Forum and delicious food).
Fully Flexible Itinerary: Personalize your hotels, transportation, and length of stay in each city. Easily add curated experiences to complete your journey.Includes:
- Flight into Florence 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.
