3-Day Tuscany Luxury Wine & Culinary Experience near San Gimignano

Delight in Tuscan wine, farm-fresh cuisine, and luxury at a historic countryside estate

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3-Day Tuscany Luxury Wine & Culinary Experience near San Gimignano 5 / 5 See All 5 Reviews
· 8.00h · Tuscany, Italy

Finding a true taste of Tuscany’s wine country without overpriced tourist traps or generic hotels is harder than it seems. Our three-day retreat at Villa Sabolini includes a romantic farmhouse stay, private wine tasting, and candlelit dinners surrounded by rolling vineyards. Slow down, sip fine Chianti, and experience Tuscany’s timeless beauty the way it was meant to be savored.

  • Meeting Point at Poggibonsi Train Station​
  • Private transfer to Villa Sabolini​
  • Sweet welcome​
  • Dinner
  • Breakfast
  • Wine tasting and vineyard tour​
  • Dinner
  • Breakfast​
  • Check-out​

Your three-day, two-night retreat begins at Poggibonsi station, where a private transfer brings you to Villa Sabolini in the heart of Chianti. Settle into your romantic room and enjoy a sweet welcome with Chianti wine. Over three days, indulge in farm-fresh breakfasts, candlelit dinners, and a private vineyard tasting. Stroll the estate’s gardens, swim in the pool, and soak in Tuscany’s charm before returning to Poggibonsi station.

3-Day Tuscany Luxury Wine & Culinary Experience near San Gimignano Description

Your 3-day/2-night tour includes

  • Roundtrip transfer from Poggibonsi station

  • 2 night stay in a romantic Tuscan estate

  • Pool access

  • 2 three-course dinners included (drinks not included)

  • Welcome kit with Chianti wine

  • Wine & olive oil tasting in a local vineyard

Day 1 - Arrival at Villa Sabolini and Romantic Welcome

Your Tuscan escape begins as you arrive at Poggibonsi train station, 1-hour from Firenze station, where a private transfer will be waiting to take you on a scenic drive through the rolling hills of Chianti and Val d’Elsa.

As you approach Villa Sabolini, you’ll be captivated by its timeless elegance—a historic noble estate dating back to the 18th century, now transformed into a refined countryside retreat. Nestled in the heart of Tuscany, Villa Sabolini combines the charm of its aristocratic past with modern comforts, offering panoramic views of vineyards, a serene garden, and an inviting outdoor pool where you can unwind. Upon arrival, you’ll check into your romantic room, a beautifully decorated space with classic Tuscan touches, wooden beams, and warm, inviting colors. To welcome you, a special romantic kit awaits—featuring a bottle of fine Chianti wine and a sweet treat to set the mood for your indulgent retreat.

Day 1 – Free time and dinner à la carte

After settling in, take some time to explore the villa’s stunning surroundings. Stroll through the manicured gardens, admire the views of the rolling Tuscan countryside, or simply relax and soak in the tranquility of this enchanting location. As evening falls, prepare for an unforgettable three-course à la carte dinner at the villa’s renowned restaurant, where you’ll savor authentic Tuscan flavors prepared with fresh, local ingredients. From handmade pasta and succulent meats to vegetarian delights and decadent desserts, each dish is crafted to highlight the best of Tuscan cuisine. Although drinks are not included, the villa’s extensive wine list offers the perfect pairing to enhance your meal.

Day 2 - Wine Tasting & Culinary Delights

Wake up to the gentle sounds of nature and start your day with a delightful breakfast: enjoy your meal while taking in the breathtaking countryside views, a perfect way to energize for the day ahead. Next, embark on an exclusive wine-tasting experience at a prestigious nearby winery. Your experience begins with a guided tour of the vineyard, where you’ll learn about the unique terroir and winemaking traditions that make this region’s wines world-famous. Next, visit the wine cellar, where barrels of aging Chianti and Super Tuscan wines fill the air with rich aromas. Here, you’ll uncover the secrets of the fermentation and aging process, gaining insight into how each bottle captures the essence of Tuscany.

Then, it's time to indulge in a curated tasting of the estate’s finest wines and olive oil, accompanied by typical Tuscan products. This sensory experience will deepen your appreciation for Tuscany’s rich culinary heritage.After an afternoon of wine appreciation, return to Villa Sabolini for a relaxing evening. Take a dip in the outdoor pool, enjoy a peaceful walk through the estate’s gardens, or simply unwind with a book while sipping a glass of wine.

As night falls, delight in another three-course à la carte dinner at the villa’s restaurant. With a variety of dishes to choose from, you can savor another taste of Tuscany’s finest cuisine. Whether you opt for a classic Florentine steak, fresh handmade pasta, or a light and flavorful vegetarian dish, your meal promises to be a gastronomic highlight of the trip.

Day 3 - Farewell Breakfast & Departure

On your final morning at Villa Sabolini, wake up to another delicious breakfast featuring a variety of fresh, locally sourced ingredients. Take your time to enjoy the peaceful atmosphere, sipping on a steaming cappuccino or a glass of freshly squeezed juice, while reflecting on the unforgettable experiences of the past days. Before departure, you may want to take one last walk through the villa’s gardens, breathing in the fresh Tuscan air and capturing a few more memories of this picturesque retreat.

When it’s time to leave, your private transfer will take you back to the nearest train station, ensuring a smooth and stress-free journey. Though your three-day escape has come to an end, the flavors, aromas, and landscapes of Tuscany will stay with you long after you return home.

What you get with this tour

  • Roundtrip transfer from Poggibonsi station
  • 2-night stay in a romantic room
  • 2 farm-fresh breakfasts
  • 2 three-course dinners (drinks not included)
  • Welcome package with Chianti wine
  • Wine and olive oil tasting at a local vineyard
  • Pool access
  • Free time in the countryside
  • Charming villa gardens
  • Beverages during dinners
  • Train tickets
  • Gratuity

See what people are saying

5 total reviews

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5.0/5 (based on 5 reviews)
5 stars
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3 stars
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1 stars
Tuscan charm
09 July 2025
L
Reviewed by
Lisa Nicholson

Set among rolling hills and historic towers, we indulged in top-tier wines, exquisite food, and impeccable service. A luxurious yet authentic Tuscan experience — simply perfect.

Chill stay with amazing food and wine
04 July 2025
T
Reviewed by
THOMAS JOHNSON

We stayed 2 nights just outside San Gimignano—beautiful countryside, super peaceful. The villa was elegant but still cozy, and the views were unreal. Highly recommended!

An elegant taste of Tuscany’s finest
03 July 2025
R
Reviewed by
Ricky Lynn Weirich

This experience perfectly combines luxury and authenticity. The stunning views and attentive service made it an unforgettable escape. Ideal for anyone looking to savor Tuscany in style.

show more reviews

Frequently Asked Questions

What to bring?

Please bring a valid passport or ID document matching the name provided at the time of the booking. We also recommend comfortable walking shoes and swimwear if you plan to use the pool.

What to bring?

Please bring a valid passport or ID document matching the name provided at the time of the booking. We also recommend comfortable walking shoes and swimwear if you plan to use the pool.

Is this tour run by The Tour Guy?

No, this experience is operated by one of our trusted and vetted partners in Tuscany.

What if I have concerns about my mobility on this tour?

If you have any doubts about your mobility, please let us know beforehand. Portions of this experience include walking on uneven terrain and through vineyards.

Can I expect to walk a lot during this tour?

This tour is relaxed with minimal walking, but you will explore vineyards and the villa’s surroundings at your own pace.

Is lunch or dinner included in the price of the experience?

Yes, 1 sweet welcome, 2 dinners (beverages excluded), a wine and food tasting and two breakfasts are included in the price of this tour.

What if I have food allergies, intolerances, or other dietary requirements?

Please contact us in advance so we can do our best to accommodate your needs. We will work with our tour partners to provide you with an alternative when possible.

Are drinks included in the price of the tour?

Yes! A bottle of Chianti wine is included in your welcome kit, and wine is served during your wine tasting experience in the nearby vineyard.

Can I bring my kids, and do I have to pay for them?

Of course! Please keep in mind that there will be an extra charge per child, or additional participants and wine tastings are only available for guests 18 and older with a valid ID. Reach out to us directly to find out the price.

Does this tour include pickup?

Pick up from Poggibonsi train station is included.

What time is check-in?

Check-in is from 3:00 pm to 11.30 pm. Please contact us in advance so we can do our best to accommodate your needs.

What time is check-out?

Check-out is at 11.00 am.

Start From: $657.58

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Free cancellation up to 7 days in advance!

Reserve Now $657.58 / per person
$657.58 / per person

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