Local Food & Drink Tastings

5 (69)

Siena Wine Journey: Tuscan Tastings & Local Delights

2 hours English

5 (69) 100% Personalized

Discover Siena's authentic wine scene, sampling Tuscan wines with delightful local bites, personalized to your preferences and curiosity.

Filippo

Lillo

Match with one of our local hosts

Be matched with a host based on your interests and preferences, to tailor your perfect day.

100% Flexible: Adapt in real time

Your host will fine-tune the experience in real time to match your mood.

Experience Overview

Time:

2 hours

Age restriction:

This experience is designed for guests aged 18 and over

Language:

Hosted in English (Other languages may be requested)

Transport Mode:

Walking experience (may use public transport for long distances)

Meeting point:

Piazza del Campo, Il Campo, 53100 Siena SI, Italy

Cancellation:

Free cancellation up to 24 hours before the experience

What’s Included:

Tailored itinerary based on your preferences

A knowledgeable host who knows the hidden gems

Flexible start times to fit your day

5 glasses of Tuscan wine and 2 food pairings

What’s Excluded:

Food and drinks additional to the ones included in the experience

Transport fares or attraction entry fees

What makes it 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 travelers think of our Italy experiences

Holland 1 June 2025

Our guide was excellent! She was very kind and answered all of our questions and was willing to personalize our tour.

Carol 1 June 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!

Michael 1 June 2025

Our host was awesome!

Deborah 1 June 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!!

Stuart 1 June 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.

Casandra 1 June 2025

Great tour. Very flexible and customized for your group. I highly recommended to anyone in Napoli. Enya is the best guide.

Here’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

Enoteca I Terzi

Start your tasting in an atmospheric, local favorite

Siena Wine Journey: Tuscan Tastings & Local Delights

Begin at Enoteca I Terzi, a renowned spot cherished by locals for its diverse selection of Tuscan wines. Enjoy sampling classic Chianti, crisp Vernaccia di San Gimignano, or the refined Brunello di Montalcino, thoughtfully paired with regional cheeses and charcuterie, guided by passionate hosts.

Liberamente Osteria Wine Bar

Relax at a lively and cozy local wine bar

Continue your journey at Liberamente Osteria Wine Bar, an inviting locale frequented by Siena's residents and delight in distinctive glasses of regional wines.

Optional Close: Via di Città Scenic Walk

Enjoy a charming stroll through historic Siena.

Optionally conclude your experience with a gentle walk along Via di Città, appreciating elegant architecture and tranquil courtyards, providing the perfect reflective finale to your Tuscan wine adventure.

Real Stories, Real Connections

Heritage on the Table: Family-Style Meal with Local Wine in a Hidden Trattoria

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

FAQs

Your questions, answered

Is this a traditional tour or something different?

This isn’t a traditional tour with a fixed script. It’s a fully personalized day shaped around your interests, whether it’s culture, history, neighborhoods, or hidden local spots. Your host is a knowledgeable local, more like a friend showing you their city. It’s flexible, one-on-one, and tailored entirely to you.

How does personalization work?

After booking, you’ll receive a short questionnaire where you can share your interests, travel style, and any must-see spots. Based on that, we’ll match you with a local host who’ll reach out to plan your personalized itinerary..

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 or types of stops?

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.

See what a personalized experience feels like!

Start Booking with us

★★★★★

Nina

Dec 2025

Esper was very pleasant, knowledgeable, and took us to places we would never have discovered on our own. The 300 steps up the tower were challenging, but we were rewarded with spectacular views at the top. Highly recommend this tour.

Melanie

Dennis is a top rate guide! He showed us exactly what we asked for and we had a great time.

Dwight

Mark was an excellent guide. He had a tremendous knowledge of Berlin and was able to answer questions and show me really interesting aspects of the city. Very professional, friendly, and willing to adjust the tour for my specific requests. Highly recommend Mark. 5 Stars!!