Siena
Siena Wine Journey: Tuscan Tastings & Local Delights
Local Food & Drink Tastings • 2 hours
5
(69)
Siena Wine Journey: Tuscan Tastings & Local Delights
Discover Siena's authentic wine scene, sampling Tuscan wines with delightful local bites, personalized to your preferences and curiosity.
What makes this experience special
Enjoy a personalized tasting experience in Siena's favorite local wine bars, savoring expertly paired wines and authentic bites while exploring stories and traditions of Tuscan viticulture
Key highlights
- Taste a curated selection of celebrated Tuscan wines
- Enjoy pairings with artisanal cheeses, charcuterie, and bruschetta
- Explore Siena’s hidden wine bars beloved by locals
- Receive personalized wine selections based on your interests
- Learn the history and character of regional wine varieties
- Immerse in intimate, authentic atmospheres
- Conclude with an optional scenic stroll through historic Siena
What to know before you go
Here’s everything you need to know before your day unfolds.
2 hours
This experience is designed for guests aged 18 and over
English Other languages may be requested
Walking experience may use public transport for long distances
What’s included
Tailored itinerary based on your preferences
A knowledgeable host who knows the hidden gems
Flexible start times to fit your day
What’s not included
Food and drinks additional to the ones included in the experience
Transport fares or attraction entry fees
Meeting point
Piazza del Campo, Il Campo, 53100 Siena SI, ItalyCancellation
Free cancellation up to 24 hours before the experienceWhat to bring
How your day could unfold
A flexible, unscripted experience designed entirely around your interests. Your host will adapt the day based on what excites you mostHere’s what your experience could look like
These are just suggestions from our hosts to inspire your day. Your host will tailor the experience to suit your interests and tastes
Meeting point
Piazza del Campo, Il Campo, 53100 Siena SI, Italy
1. Select a date
2. Select start time
3. Tailor your experience
Answer a few quick questions to help your host craft the perfect day tailored to you.
1. What’s your preferred hosting style?
2. How would you like the pace of your day?
3. What’s your walking comfort level?
4. Are you celebrating something special?
Real Stories, Real Connections
See our hosts and guests creating memories
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Sipping Local Charm: A Sun-Drenched Wine Break with Friends in Italy
Cheers to Tradition: Toasting with Aperitivo and Cured Meats
Rustic Plates, Regional Wines: An Evening of Flavorful Connections
A Toast to Timeless Streets and Local Wines: Soaking Up the Spirit of Italy Over a Shared Table
17,500+ 5-Star Reviews and Counting
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recommended by 99% of travelers on google
recommended by 99% of travelers on tripadvisor
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What travelers think of our Italy experiences
Holland
Jun 2025
Our guide was excellent! She was very kind and answered all of our questions and was willing to personalize our tour.
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Carol
Jun 2025
Our first time visiting Naples and Serena did a fantastic job sharing her enthusiasm and love of her city while explaining and guiding us through the colorful chaos that makes Naples! Serena answered our questions and discussed various topic points brought up during our tour. We are ALREADY sharing her info with friends traveling to Naples this fall!
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Michael
Jun 2025
Our host was awesome!
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Deborah
Jun 2025
Our tour in Naples was fabulous. My husband and I met Roberto, our tour guide, and we had a walking tour through the heart of Naples, through Piazza’s, Parks, and Government buildings, the beautiful Theatre, centuries old buildings, neighborhoods and side streets, as well as learning the History of Naples as we went along. It was fascinating! Roberto Introduced us to vendors and provided the opportunity to see how the local residents live, where they gather, shop and eat. We would have never seen what we did or learn so much about Naples - Napoli on our own. Roberto was a wonderful Host, we were sad to leave him. We felt so lucky. I heartily recommend this tour and Roberto for anyone who wants a really fabulous enriched experience. MORE THAN 5 STARS!!
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Stuart
Jun 2025
The walking tour was great. Learned a lot about the history of Bologna and the present as well. Andrea was informative, funny and introduced us to some cured meats that we had not tried before. A nice way to spend the morning.
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Casandra
Jun 2025
Great tour. Very flexible and customized for your group. I highly recommended to anyone in Napoli. Enya is the best guide.
Show moreFAQs
Your questions, answered
Is this a traditional tour?
No. Our experiences are unscripted and designed around you. Instead of following a rigid itinerary, your host will plan a personalized journey that feels natural, immersive, and unique.
How does personalization work?
After booking, you’ll complete a short questionnaire about your interests and travel style. We’ll match you with the best host who will tailor the experience to you. You'll have the opportunity to chat with them before the experience and agree on a plan.
Will I know my itinerary in advance?
Yes, you will have the opportunity to chat with your host directly and agree on a plan for the day. However, there’s always room for spontaneity and local surprises!
Can I request specific places to visit?
Yes! After booking, you will receive a questionnaire where you can highlight must-visit spots and anything else you’d like to include, and your host will craft your experience around them.
Can my experience accommodate dietary restrictions?
Yes! You'll receive a questionnaire right after booking where you can note any dietary requirements, and your host will tailor the experience accordingly.
Can my host meet me at my accommodation?
Hotel meet-ups are available upon request in central areas. If you're staying outside the city, your host will recommend the best meeting spot and guide you with directions.
Can I change the meeting place?
Yes, you will be in touch with your host before your experience, and you can agree on a different meeting point with them. Your host can meet you anywhere central that’s convenient.