Trip Overview November 21 - 28, 2026
Get ready for a journey filled with culture, history, gastronomy, wine and underscored in luxury! From the canals of Venice to making your own Venetian mask then whisking past the beautiful Italian villages you've only seen in film, you have now arrived to Florence in all its splendor. You will marvel at Italian masterpieces, test your cooking skills and indulge in the flavors of Italy. Did someone say wine tasting? Gain exclusive access to the best cellars of the region and be blown away by the beauty of the Tuscan countryside.
- Day 1: Arrive in Venice and check into the L'Orologio Venezia Hotel for 2 nights
- Day 2: Venice exploration
- Day 3: Hotel checkout then scenic high speed train to Tuscany / Afternoon arrival in Tuscany and check into the Castel Monastero Hotel for 4 nights
- Day 4: Wine & Gastronomy experience
- Day 5: Medieval Towns exploration
- Day 6: Thanksgiving Celebration Feast
- Day 7: Hotel checkout and private transfer to the Brunelleschi Hotel for your final night in Florence, Italy
- Day 8: Hotel checkout and airport transfer for journey home
Create beautiful memories as you linger in La Dolce Vida and fully capture the romantic allure of Venice and the dramatic beauty and artistic splendor of Tuscany. Escape into a world and truly give thanks as you gasp, dance, laugh and make memories on this unforgettable Italian Thanksgiving adventure which offers a unique glimpse into the country's rich history, culture and exquisite food & wine paired with intimate encounters with artisans devoted to timeless romantic traditions.
DAY 1: WELCOME TO VENICE!
Meet your guide for your boat transfer to your hotel.
After settling in, be prepared to be swept off your feet by a dazzling sunset gondola ride and serenade followed by our signature welcome cocktails!
DAY 2 - VENICE LIKE A PRO
Explore sites featured in famous films, such as Indiana Jones, The Last Crusade, The Italian Job and others in addition to visiting St. Mark's Square; St. Mark's Basilica, beholding its mosaics; and the Doge's Palace. But no visit to Venice would be complete without learning from a master and making your own Venetian Mask - Explore Venice’s Carnival tradition on a family-friendly private tour that balances hands-on learning with light adventure.
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DAY 3 - ONWARDS TO TUSCANY
Ride in luxury on the high speed train from Venice to Florence after your morning checkout from your luxury hotel. Meet your driver at the train station for your private transfer to your hotel. Remain the rest of day at leisure to explore your new accommodations and surrounds. Did someone say spa?
DAY 4 - UNDER THE TUSCAN SKIES
Pisa, San Gimignano and Siena. Discover the region's highlights with the help of a local guide. Explore the medieval city of Siena and its cathedral before heading to the hills of Chianti for a Tuscan lunch and wine tasting. Roam the streets of San Gimignano, and travel to Pisa to admire the architectural drama of Cathedral Square—home to the UNESCO-listed Leaning Tower of Pisa.
DAY 5 - FOR THE LOVE OF WINE & FOOD
Embark on a delightful day trip through Tuscany's iconic Val d'Orcia, a UNESCO World Heritage Site. Visit Montalcino, home of Brunello wine, Pienza, famed for Pecorino cheese, and Montepulciano, celebrated for Nobile wine. Enjoy breathtaking views, rich culture, and mouthwatering food.
Feel like you're part of a Florentine family as you meet your hosts to embark on a private afternoon cooking class guided by expert chefs. This immersive experience goes beyond simply following recipes; it invites you to embrace the Italian philosophy of food as an expression of love and tradition. After the class, enjoy the fruits of your labor in a tasteful, inviting setting, savoring the dishes you’ve crafted alongside a paired glasses of wine.
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DAY 6 - THANKSGIVING FEAST ITALIAN STYLE
Enjoy the day at leisure. Or visit the famous Mall Firenze for some retail therapy. (Optional$)
Or soar above the patchwork landscapes of Chianti at sunrise on a private hot air balloon flight, then touch down for a countryside picnic breakfast with regional delicacies and chilled Prosecco. (Optional$)
This Thanksgiving Day, enjoy a deliciously prepared, private Italian Thanksgiving meal. Bask in the gastronomic splendor of Tuscany while you celebrate a new and splendid Thanksgiving tradition with your friends and family.
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DAY 7 - FANTASTIC FLORENCE
Enjoy your scenic drive to Florence after your morning checkout from your luxury hotel. Meet your driver in the hotel lobby for your private transfer to the Brunelleschi hotel.
Enjoy a 3 hour introductory walk through the lively streets of Florence with your local guide, who accompanies you to fascinating sites, including the Accademia, where you behold striking masterworks such as Michelangelo's incomparable David.
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DAY 8 - ARRIVEDERCI
Check out from your hotel for your airport transfer to catch your return flight home.
Credits:
Created with images by f11photo - "Downtown Siena skyline in Italy" • ValentinValkov - "View from gondola during the ride through the canals of Venice i" • mickael - "The Grand Canal of Venice at nightfall" • Tomas Marek - "Colorful carnival masks at a traditional festival in Venice, Italy" • barmalini - "Typical vineyards hills of Tuscany, as seen from Montepulciano," • LianeM - "Tuscany vineyard 04" • banepetkovic - "Roses at balcony in San Gimignano, Tuscany landscape background" • sabino.parente - "Siena" • spyrakot - "Middle-Aged Friends in Cooking Class Making Homemade Pasta with Chef Guidance" • Kakabe - "A vibrant Italian cooking scene with fresh tomatoes, greens, pasta, wine, and a person's hands preparing the meal, suitable for culinary blogs, cooking classes, or restaurant promotions," • muratart - "Ponte Vecchio Bridge over Arno river - Florence, Italy" • Mariia Petrakova - "plane flies over the city at sunset, flies away"