Wine and Bliss in Tuscany
SMALL GROUP TOURS
Dates: Oct 2 - Oct 9, 2027 • Destination: Italy • Duration: 8 days / 7 nights • Dates: Oct 2 - Oct 9, 2027 • Destination: Italy • Duration: 8 days / 7 nights
Destination: Italy
Dates: Oct 2 - Oct 9, 2027
Duration: 8 days / 7 nights
Experience the True Rhythm of Tuscany – Slow, Authentic, and Deeply Local
Returning for its 5th consecutive edition, this signature 8-day journey is one of our most beloved small group experiences.
Designed for travelers who crave authentic connection over tourist checklists, this signature 8-day journey bypasses the crowded tour bus routes to reveal the genuine soul of Tuscany.
Instead of rushing between sights, you’ll travel in slow-paced comfort: checking into upscale 4-star accommodations, savoring prestigious vintages in private cellars, learning generational pasta secrets at a countryside farmhouse, and soaking in the golden light of the Renaissance.
From the peaceful rolling vineyards and medieval stone towers of San Gimignano to the vibrant artistic heart and rooftop sunsets of Florence, this is Tuscany as it was meant to be experienced.
Trip Highlights & High-Value Inclusions
We believe the true luxury of travel lies in ease, private access, and authentic encounters. Unlike conventional tours, your journey includes premium experiences that elevate every moment:
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Two Distinct 4-Star Base Stays: Unpack and truly relax with multi-night stays at premier properties—3 nights in the countryside near San Gimignano at Capuccina Country Resort 4* (spa & indoor pools), and 4 nights in the historic heart of Florence at Hotel Degli Orafi 4*.
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Exclusive Food & Wine Encounters:
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Welcome multi-course dinner and tasting at a historic 300-year-old family winery in San Gimignano.
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Sienese lunch paired with regional Chianti wines in Siena
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Guided Brunello wine tasting and lunch at a boutique estate in Montalcino.
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Guided Vino Nobile tasting with dinner at an ancient underground wine cellar in Montepulciano.
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Vineyard lunch and wine tasting at a boutique estate nestled in the Lucca hills.
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Hands-on 3-course pasta cooking masterclass with 2 expert chefs and flowing wine at a private farmhouse outside Florence.
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Grand farewell dinner featuring authentic Bistecca alla Fiorentina and fine estate Chianti wines in the Florentine hills.
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Golden Hour from Above: An exclusive rooftop sunset tour of Florence with classic Italian aperitivi and Tuscan wines overlooking Brunelleschi's Dome.
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Iconic & Seamless Transport: Customized private arrival and departure transfers timed to your flight or train, private AC mini coach touring throughout the countryside, and scenic local rail.
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Licensed Private Local Guides & VIP Access: Priority entrance and expert guided walking tours of Siena, Pisa's Campo dei Miracoli (with optional Leaning Tower climb), and Florence's Accademia Gallery to marvel at Michelangelo’s David.
Hosted by Alida (@alidalifetravel)
“Tuscany was the second itinerary I ever designed for Vagabonda Travel, and it has been a beloved bestseller running in its original, perfected form since 2024.
As a dedicated wine lover, this journey is pure joy for me. My favorite part of leading this tour is introducing my travelers to the passionate local winemakers and families behind these historic estates. Supporting these small producers while sharing their world with our guests is deeply rewarding.
Together, we get to go beyond the typical tourist spots to taste remarkable wines, enjoy unforgettable meals, and discover the art of pairing food and wine - an art the Tuscan people have brought to absolute perfection.”
Traveling alongside you from arrival to departure, Alida handles every logistical detail, bridges language barriers, and opens private cellar doors so you can relax, immerse yourself, and enjoy every single moment.
Pricing & Room Configurations
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Double Occupancy (Sharing with a partner/travel companion): $5600 per person
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Solo Traveler (Private Room / Double room for single use): $6780 flat total
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Deposit required to reserve your spot: $500 per person
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Space is strictly capped at 14 guests.
How to Reserve Your Spot & Access the Full Itinerary
To ensure a seamless, secure experience, all bookings, live spot availability, payment schedules, and complete PDF itinerary downloads are hosted on our dedicated, bank-level secure booking platform, WeTravel.
There, you can:
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Download the complete, printable PDF brochure with the detailed day-by-day program, hotel descriptions, and full terms.
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Select your room preference (Double or Private Single).
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Secure your spot directly with your initial deposit.
(Clicking above will securely redirect you to our official WeTravel booking page)
Happy Clients
- The Coscia-Mancuso Family, White Plains, NY
We cannot thank Vagabonda Travel enough for custom-designing our family trip to Italy. Memories to last a lifetime. Every detail of our trip was perfectly curated and exceptional. We would have never been able to plan this adventure on our own. Communication with the staff is excellent and we felt secure knowing we had contact number while we were traveling. Cannot wait to book our next trip with you soon!
Trip of a lifetime.
Happy Clients
- Megan and Jerry, Los Angeles, California
We have never used a travel service before, and Vagabonda absolutely blew us away! From their hotel bookings, to the day-by-day itinerary, to hidden gems we definitely would have never found on our own, we can't thank their team enough! Highly recommend for anyone who wants an authentic experience in Europe!
BEST TRIP EVER! We'll remember this for the rest of our lives!
Happy Clients
- Pete and Paula, Lindenhurst, New York
When my husband and I started planning our 30th Anniversary trip to Italy we had no idea where to even begin. That’s when I stumbled across Alida’s TikTok videos. I absolutely LOVED her content. To be honest, at first I was skeptical about planning a trip like this off of someone I saw in a TikTok video, but after meeting with her we knew we picked the right travel agency. Our 17-day trip was absolutely incredible. Alida and Vagabonda Travel made our lifetime dream of touring Italy one we will never forget!
Happy 30th Anniversary to Us! A TRIP OF A LIFETIME!
Explore More Small Group Tours
Vagabonda's European small group tours are led by our professional hosts. We're dedicated to making sure that every moment of your trip counts. We believe in taking it slow and connecting with locals as we uncover amazing experiences in unforgettable destinations. Travel should be more than just a vacation - it should be an experience that touches your heart and deepens your relationship with the world.
