Discover family-owned wineries, exclusive tastings, and stunning landscapes on a boutique, small-group wine and food tour.
Learn MoreTuscany has a way of seducing you quietly. It's not always the postcard moments, though there are plenty of those. It's the way the late afternoon light spills across a vineyard. The sound of footsteps on centuries-old cobblestones. A conversation with winemakers who have been perfecting Tuscan wine-making for generations.
This 8-day, 7-night wine vacation in Tuscany doesn't stick to the usual routes. Instead, it takes you off the beaten path to family-owned wineries and experiences you didn't know you were missing. You'll sip Brunello di Montalcino in medieval castles, learn the wine-making process from local experts, and walk the backstreets of Florence, Siena, and Lucca.
From the rolling hills of the Chianti region to the stunning landscapes of Pienza, there are no checklists here — just great wine, authentic food, and the warm hospitality of the Tuscany region. Savor it all on our small group wine tours! Whether you are visiting Tuscany in spring or fall, the beautiful landscape never fails to impress.
Embark on an amazing trip in Italy, where we offer the perfect blend of exclusive access and local charm. Our Tuscan tour curated to showcase one of Italy’s world-renowned wine regions while surrounding you with the warm hospitality of passionate winemakers. From sun-dappled vineyards to private tastings in a castle, every detail of this tour is designed to immerse you in the culture and traditions of the region. Here’s what’s included:
Over the next eight days, we will travel through the heart of Tuscany to explore its most iconic wine regions. From the rolling hills of the Chianti Classico area to the breathtaking landscapes of the Val d'Orcia, this itinerary is designed for those who want to taste wines at family-run wineries and experience the warm hospitality of the Tuscan countryside.
Book A Call with usArrive at Florence airport to meet your small group and travel to Pienza. After checking into the four-star Hotel Corsignano, enjoy an orientation walk and a three-course welcome dinner featuring excellent wines.
Accommodation Hotel Corsignano Included Meals DinnerExplore Val d'Orcia, home to some of the world's most delicious wines. You'll take a guided stroll in Montalcino and have the option to add a visit to its medieval fortress. Next, enjoy a winery tour and wine tasting paired with lunch at Castello Trecerchi, followed by free time to explore the ancient abbey of Sant’Antimo.
Accommodation Hotel Corsignano Included Meals Breakfast, LunchVisit Podere Il Casale, one of the region's premier organic wineries, for an immersive orchard and cheese tour. After enjoying a farm-to-table seasonal lunch, we’ll continue to Montepulciano to take in the breathtaking landscapes and discover hidden gems in the local wine shops.
Accommodation Hotel Corsignano Included Meals Breakfast, LunchWe check out of the Pienza accommodations and take a scenic one-hour drive to Siena, where a local city guide provides an orientation of the city's rich history. We'll visit a Contrada museum to explore the Palio horse race traditions. After lunch on your own, you'll enjoy some free time, and then the group drives to Agriturismo Il Piastrino in Vinci for a two-night stay. The day concludes with an optional stroll through Vinci, Leonardo da Vinci's birthplace, followed by a group dinner featuring a three-course meal with wine.
Accommodation Agriturismo il Piastrino Included Meals Breakfast, DinnerStart your leisurely morning with an optional countryside hike or a visit to the Leonardo da Vinci Museum. Later, join a hands-on cooking class at the Agriturismo, followed by a lunch — crafted from our class — with wine. In the afternoon, we travel to Lucca, where a local city guide joins us for a walking tour of the region's most popular and beloved ancient town. In the evening, enjoy free time and dinner on your own before returning to the hotel
Accommodation Agriturismo il Piastrino Included Meals Breakfast, LunchWe head off on a day trip to the Chianti Classico wine region with scenic photo stops, a visit to Poggio Amorelli's cellar, and a traditional Tuscan lunch paired with wine tasting. Afterward, we'll drive to Florence, check in at the four-star Horto Convento Hotel, and have an orientation walk to the cathedral, followed by dinner at your leisure.
Accommodation Horto Convento Hotel Included Meals Breakfast, LunchThe day begins with a mid-morning guided walking tour of Florence, led by a local city guide. We will be covering major sites, including Piazza Signoria, Piazza Santa Croce, and the cathedral's exterior, plus delightful hidden gems. The group then enjoys lunch at a local restaurant in central Florence. Your leisurely afternoon is free for personal exploration, with your tour guide available for suggestions. The day concludes with a farewell glass of wine and light bites. Enjoy a dinner of your choosing, with recommended dining options.
Accommodation Horto Convento Hotel Included Meals Breakfast, AperitifGuests will have breakfast at the hotel prior to check out. Transfer on your own to the Florence train station or airport. We are happy to assist with transfer coordination and recommendations.
Included Meals Breakfast
At Crush Wine Experiences, our mission is to introduce you to your favorite craft winery or distillery.
Explore the capital of Tuscany, a city home to many masterpieces of Renaissance art. You will discover ancient architecture, sweeping piazzas, and soaring churches as we take a walking tour with an expert local guide. We will visit the exteriors of Piazza Signoria, Santa Croce Square, the Florence Cathedral, and the Baptistery — all while soaking in the stunning views of this historic city.
We included two wineries for visits and private tastings, along with 14 meals throughout the trip. These include multi-course wine dinners and delicious lunch experiences carefully paired with local wines to showcase the region’s best foods. You will luxuriate in historic villages and vineyard hillsides, watching stunning sunsets with a glass of delicious wine in hand.
The Chianti region stretches between Florence and Siena and includes 14 towns. While the area is small, Chianti Classico has been produced here for over 2,000 years. Our Chianti wine tour takes you into the cellar of Poggio Amorelli, an iconic family-owned local producer in the Chianti Classico area.
Brunello di Montalcino is a world-famous red wine produced in the vineyards surrounding the town of Montalcino. Made 100% from the Sangiovese grape varietal, it is a hallmark of Tuscan winemaking. Our visit includes a winery tour at a highly regarded producer located in one of the region’s most stunning medieval castles.
Experience the magic of Florence, Siena, and ancient villages, where you can explore historic wine cellars, dine at local restaurants, and visit charming farms while strolling amongst the rolling hills of the region. Every moment is a perfect blend of culture and taste.
Local food and wine
Ponte Vecchio
Castello Tricerchi
Province of Siena
Sam Kimball is not just a sommelier; he’s a storyteller. With years of experience and a deep passion for Italian wines, he’ll introduce you to the art and science of wine tasting. From the majestic Chianti Classico and Brunello di Montalcino to the delightful and crisp Vermentino and Vernaccia, you’ll taste the diversity of Tuscany’s wine heritage on this tour.
Talk with SamTuscany is a living museum where every wine bottle tells a story of the past. From medieval castles that have stood for centuries to the winding roads once traveled by Renaissance masters, the Tuscany region offers a perfect blend of cultural heritage and world-class viticulture.
From the Chianti region to the historic streets of San Gimignano, discover why travelers from around the world consider our small-group experiences excellent. Whether drawn by the wonderful wines or the stunning landscapes, guests praise the high quality of our experiences in their reviews.
John G. My wife and I had a great experience traveling to Italy on a wine tour with Crush Wine Experiences. The trip was well organized and we had a great sampling of Italys history, farms and vineyards. We had free time in each area we visited to check out the culture and shops.We had a great group and made some new friends.This intimate tour is definitely a highlight of our travel experience this year.
Laurene M. This was my 5th trip with Sam and Crush Wine Experiences. The small group size, knowledgeable tour and local guides; as well as itineraries that immerse you in the food, wine and culture of each destination makes every trip unique. Looking forward to the next adventure!
Bret F. Sam did an incredible job of organizing and leading this trip. We were able to experience fantastic food & wines from wonderful vineyards, farms, and restaurants. We visited multiple localities with knowledgeable guides that provided interesting insights. We learned so much about wines, art, the local culture and history. It was so much fun that we have already booked another trip next year.
Explore our collection of past tour photos and get inspired for your next adventure in Italy. Our gallery showcases some of the the unforgettable moments our guests share while visiting Tuscany.
Don't miss your chance to experience history, food, and great wines. We’re ready to welcome you with the warm hospitality the Tuscany region is famous for. Spots are limited, so secure yours today!
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