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Venice - Florence - Southern Tuscany and Coast

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11 to 16+ Nights from $1,994*
* Sample price: priced within the past 7 days for a 8/25/2025 arrival, departing New York City NYC (All Airports) (NY), US. Choose departure city, cabin and dates.

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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

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 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
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Flexible Itinerary

  • Venice

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  • Florence

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  • Southern Tuscany

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  • Tuscany Coast

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Italy

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Trip Summary

  • Venice
    Venice

    With sumptuous palaces and romantic waterways, Venice is straight out of an 18th-century Canaletto masterpiece. No matter how many times you have seen it in movies or on TV, the real thing is more surreal and dreamlike than you ever imagined. Its landmarks, the Basilica di San Marco and the Palazzo Ducale are exotic melanges of Byzantine, Gothic, and Renaissance styles. It is full of secrets, ineffably romantic, and - at times - given over entirely to pleasure. You must walk everywhere in Venice; and where you cannot walk, you go by water.

    Explore Piazza San Marco, stroll across the Rialto Bridge, get lost in the endless canals, admire the Basilica Santa Maria della Salute, visit the San Giorgio dei Greci, walk around the Jewish Ghetto, learn about Venice's musical history, tour Venice's unique architecture at Campo Santa Maria Formosa, celebrate one of Venice's many festivals, go window shopping, and so much more!

  • Florence
    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.

  • Southern Tuscany
    Southern Tuscany

    The hill towns and valleys south of Siena comprise what is perhaps Tuscany's most captivating and picturesque region. Much of the area is filled with the expansive and beautiful Val d'Orcia (most people's idealized picture of Tuscany). It is a land of medieval castles guarding narrow passes, isolated farm houses sitting atop long, eroded limestone ridges, clusters of cypress and ribbons of plane trees against a rural setting, and thermal spas dating from times long ago. Most of the region has been landscaped over thousands of years, turning the low, rolling hills into farmlands and vineyards that produce Tuscany's mightiest red wines.

    Visit and discover Montepulciano, Pienza, Chianciano Terme, Terme di Petriolo, and Bagno Vignoni, the necropolis near Sovana, thermal spas, and vineyards that produce two of Italy's top red wines.

  • Tuscany Coast
    Tuscany Coast

    Tuscany's Coastline is made up of fine sandy beaches with clean water (certified blue flag beaches), sheer cliffs, and hidden coves surrounded by fresh pinewoods against the backdrop of the Apuan Alps, known for their famous marble production. It's also home to picturesque villages rich in art and culture where time seems to pass slowly. Small squares enchant visitors with their pleasant views, flowering windows, and ancient stores. This immortal charm has bewitched many artists and authors in the past, and even today makes this stretch of Tuscany one of the most beautiful to experience.

    Discover and relax on Blue Flag beaches at Cecina, Marina di Bibbona, Castagneto Carducci, and San Vincenzo as well as the Nature Park of Sterpaia (Piombino), with its sandy dunes in the very heart of nature, complete with pine woods and so much more.

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