Explore the magic of Tuscany with a sommelier and an expert local guide. Visit Florence, Siena, Montalcino, Pienza, San Gimignano, and San Quirico d'Orcia. Discover the delights of the region over the course of a week.
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 someone who’s been making wine or artisanal food the same way for generations.
This 8-day, 7-night journey doesn’t stick to the usual routes. Instead, it takes you off the beaten path—to places you wouldn’t find on your own, and experiences you didn’t know you were missing. You’ll sip Brunello in a medieval castle. Learn to roll pasta with someone’s Nonna. And walk the backstreets of Florence, Siena, and Lucca with locals who make the history feel alive.
There are no checklists here—just great food, wine, and culture -- and the time to savor it all!
The group will start meeting at 2pm at Florence Airport. Once assembled, we'll transfer from there to the historic town of Pienza, arriving in about 1 hour and 40 minutes after a scenic drive. At 5pm, you'll check into the 4-star Hotel Corsignano; then an hour later, enjoy an early evening orientation walk with your tour leader. The day concludes as everyone gets further acquainted over a three-course Welcome Dinner with wine at the hotel restaurant.
Accommodation Hotel Corsignano Included Meals dinnerToday's journey takes you through the scenic Val d’Orcia in southern Tuscany, where the famous Brunello di Montalcino wine is produced. You'll take a guided stroll in Montalcino and have the option to add a visit to its medieval fortress. Next, enjoy a cellar tour and wine tasting paired with lunch at Castello Trecerchi, followed by free time to explore the ancient abbey of Sant’Antimo. The day concludes with a return to the hotel, where you can choose your own dinner spot in Pienza with your tour leader's restaurant suggestions within walking distance of the hotel.
Accommodation Hotel Corsignano Included Meals breakfast and lunchThe day starts with a visit to Podere il Casale, a historic organic farm in southern Tuscany founded over 300 years ago, for a scenic tour featuring olive orchards, friendly animals, and an inside look at their award-winning Pecorino di Pienza cheese. Enjoy the bucolic atmosphere and a generous tasting of the farm's products during a fresh, seasonal lunch. In the afternoon, we transfer to Montepulciano where you'll have free time to explore, relax, and dine – from your choice of provided restaurant recommendations before returning to our hotel in Pienza.
Accommodation Hotel Corsignano Included Meals breakfast and 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 and 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 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 and 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 4-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 and lunchThe day begins as we meet a Local City Guide for a mid-morning guided walking tour of Florence, 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 in the evening. Enjoy a dinner of your choosing, with recommended dining options.
Accommodation Horto Convento Hotel Included Meals breakfast and pre-dinner aperitif (glass of wine & food bites)Guests will have breakfast at the hotel prior to check out. We'll bid arrivederci and then you'll 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.
Florence, Siena, ancient villages, wine cellars, restaurants, farms and strolling amongst the rolling hills of the region.
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.
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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
