THE ULTIMATE TUSCANY TOUR: Florence & Countryside
Days: 5D/4N Group Size: 2 - 8 Start: Florence Ends: Florence
Immerse yourself in the heart of Italy with our carefully curated Florence & Tuscany Countryside Tour. From the historic streets of Florence to the rolling hills of Chianti, this tour offers the perfect blend of art, culture, and indulgence. Explore the medieval towns of San Gimignano, Siena, and Cortona, savor world-class wines during two exclusive Chianti wine tastings, and uncover the secrets of Tuscan cuisine with a hands-on cooking class.
Whether you're strolling through Florence’s vibrant piazzas, enjoying a sunset aperitivo, or sipping wine overlooking Tuscany’s vineyards, this journey is designed to create lasting memories
Perfect for small groups and solo travelers, this tour blends guided experiences with flexibility to explore at your own pace.
Ideal For:
Places You'll See
San Gimignano
Florence
Val d'Orcia
Chianti
Highlights:
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A Perfect Blend of Guided Experiences and Free Time: Enjoy expertly guided tours while also having the freedom to explore at your own pace.
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Convenience and Comfort: With seamless transportation, comfortable accommodations in Florence and Chianti, and a carefully planned itinerary, all the details are taken care of so you can relax and enjoy your trip.
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Sample Local Wines and Flavors: Indulge in authentic wine tastings and savor traditional Tuscan cuisine.
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Medieval Towns & Scenic Landscapes: Explore the most Tuscany's most beautiful medieval towns, filled with charm, history, and stunning architecture.
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Small-Group Experience: Travel with like-minded adventurers in an intimate setting, ensuring personalized attention and the chance to make meaningful connections along the way.
Itinerary
Day 1
Arrival
Arrive in Florence and check in to your accommodation from 2:00 PM. After check-in, join your guide for a welcome walk through the historic center. Admire landmarks such as the Duomo, Piazza della Signoria, and the Ponte Vecchio as Florence’s timeless beauty unfolds before you.
Spend the evening discovering Florence at your own pace. Whether it’s dining in a traditional trattoria, sipping wine in a cozy café, or exploring hidden corners of the city, Florence offers endless charm.
Day 2
Free Day to discover Florence at your pace
Spend the day exploring Florence’s treasures on your own. Marvel at world-famous art in the Uffizi Gallery or the Accademia Gallery, home to Michelangelo’s David. Climb Giotto’s Bell Tower or visit Piazzale Michelangelo for breathtaking views of the city. Wander the Ponte Vecchio and enjoy Florence’s vibrant culinary and shopping scenes, from local trattorias to artisan workshops.
Day 3
Tuscany & San Gimignano
Head into Tuscany’s Chianti region, where rolling vineyards and olive groves define the landscape. Begin with an immersive visit to a wine tasting school, sampling four premium wines like Chianti Classico and Brunello di Montalcino, along with truffle olive oil and aged balsamic vinegar. Continue to a local winery, where you’ll tour the vineyards and cellars before tasting more regional wines. Spend the evening exploring the medieval town of San Gimignano, known as the "Town of Fine Towers," before retiring to your accommodation in Chianti.
Day 4
Explore Siena, Cortona & Montepulciano
Delve into Tuscany’s history with a guided tour of its most enchanting towns:
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Siena: Visit the stunning Piazza del Campo and admire the Gothic architecture of the Siena Cathedral.
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Cortona: Roam this charming hilltop town, famous for its breathtaking views and connections to Under the Tuscan Sun.
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Montepulciano: Discover the medieval streets of this wine-lover’s paradise, where you can taste the renowned Vino Nobile di Montepulciano.
Return to your Chianti accommodation for a relaxing evening.
Day 5
Tuscan Cooking Class & Return to Florence
Wrap up your Tuscan adventure with a hands-on Tuscan cooking class led by a local chef. Master traditional recipes using fresh, regional ingredients, then enjoy the fruits of your labor with a glass of local wine. Return to Florence by 5:00 PM, filled with memories of Tuscany’s rich flavors, landscapes, and culture.
What's Included
Accommodation: 2-night stay in Florence & 2-night stay in a carefully selected Tuscan hotel in San Gimignano.
Transportation: Comfortable travel between Florence & the Chianti region
Meals: Daily breakfasts
Local tour leader with information about the area and places visited
Wine Tasting: Visits to two esteemed wineries with guided tastings of wines, balsamic vinegar, and olive oil.
Activities: Orientation walk of Florence, Share Group tour to Siena, Cortona, Montepulciano and Val d'Orcia by minivan. Share Hands on Cooking class.
Additional info
Accommodation
3* Hotel in Florence and San Gimignano, in the heart of the Tuscan Countryside.
Room Type:
Double Room for 2 people complete with an en-suite bathroom—ideal for couples or friends seeking extra comfort.
Single Rooms available on request
Optional Upgrade: For a more countryside experience, choose a rustic agriturismo surrounded by vineyards and olive groves. Enjoy fresh local cuisine, tranquil scenery, and authentic Tuscan charm.
Transport
Minivan
Tour Leader
We choose tour leaders who are deeply connected to the areas they serve, ensuring you get the most authentic and knowledgeable experience.