Day Trip from Florence to Tuscany with Wine Tasting

Walking Tour

Full-Day

Florence

Embark on a transcendent day trip from Florence to Tuscany with a wine tasting through the Val d'Orcia, a Tuscan tapestry of emerald hills, cypress groves, and medieval charm, renowned for its exquisite wines and cheeses. Under the azure Tuscan sky, your senses will awaken as you wind through the picturesque countryside, marveling at the rolling hills, ancient villages, and iconic cypress trees that grace this idyllic valley.

You will travel by car to Pienza, a stunning Renaissance town overlooking the countryside. With your local expert guide, you'll explore its elegant Duomo and picturesque streets before indulging in the region’s flavors, sampling artisanal Pecorino and other specialties at charming boutique shops.

Next, you'll visit Montalcino, a world-renowned wine town, where you'll enjoy a light lunch at a traditional winery. Savor local cheeses, salami, and the famous Brunello wine, while learning about its rich history and production.

As the sun casts its golden glow over the Tuscan hills, you will be driven back to your accommodation, sated by both appreciation for the region's culinary traditions and the tastings.

Choose this tour if...

You're a photography enthusiast seeking picturesque landscapes and photo-worthy moments without an overnight stay
You like to indulge your passion for food and wine, embarking on a culinary journey through tantalizing local delights
You want to sit back, relax, and allow our team to handle all the transportation details – ensuring you reach your destination hassle-free and return with ease

Sites Visited

Pienza – hill town known for its Renaissance architecture in the Val d'Orcia.
Local trattoria in Montalcino – casual restaurant serving authentic Tuscan cuisine.
Montalcino winery – Tuscan winery specializing in the red wine production made exclusively from Sangiovese grapes.

Logistics

Transportation

This tour includes a private car service that will pick you up at your accommodation in Florence, drive you to the different sites visited in Val D'Orcia, and drop you off at your accommodation in Florence at the end of the tour.

Lunch

The tour will take time for a lunch break at a local trattoria, but you are responsible for the cost of your own lunch.

Tastings

You are prepaid for the cost of the wine tastings; however, please keep in mind that you are responsible for the cost of the Pecorino cheese tastings, as the cost may vary depending on your taste.

Accessibility

Itinerary

The itinerary is adaptable for clients with mobility issues.

Wheelchair accessibility

Most of the sites are wheelchair accessible.
If you have mobility concerns, please contact us to discuss the best tour option for you

Frequently Asked Questions

For more information about Context Tours, please visit our FAQs.

What if I am not staying in Florence?

The tour is exclusively for departure from Florence. If you’re staying in Siena, please take a look at our Full-Day Tuscany Day Trip from Siena with Wine Tasting.

Cancellation Policy

Book with confidence — see Context's flexible cancellation policy here.

day trip from florence to tuscany wine tasting

From iconic landmarks to tucked-away local favorites, these are the places you’ll explore and experience firsthand with your Expert.

Pienza
Montalcino
Abbey of Sant'Antimo
Local Winery

Here’s a look at what your tour covers, plus anything you’ll want to consider arranging separately, so you can plan with confidence.

Included

English-speaking expert guide
Tours led in English, offering you unbroken understanding throughout.
Intentionally sized groups
A smaller group means more time for conversations and questions.
Tickets and entrance fees
All entry tickets included (unless clearly stated otherwise).
Headsets
Headsets are included on tours that need them, so every word can be heard.

Not Included

Food and drink

Unless booking a Food & Drink tour or tasting experience, refreshments are not included.
Transportation to and from the meeting point

Unless noted, pre- and post-tour transport isn’t included - this service can be added by request.
Gratuities

Tips aren’t included, but we encourage tipping as a way to thank your guide after your experience.
Hotel pickup or drop-off

Unless noted, travel to or from accommodation isn’t included - this service can be added by request.

Some helpful advice for getting the most from your experience, from practical prep to small on-the-day tips.

Dos:

Wear comfortable footwear
Check the weather and dress appropriately
Bring a bottle of water (no glass)
Feel free to ask your Expert anything

Don'ts:

Bring firearms or weapons
Bring sharp objects (e.g. knives, swiss army knives, switchblades, hiking sticks)
Dress inappropriately to enter religious sites or sacred monuments

Any questions? You can always contact us.

24 Reviews

Wonderful day...Stella was excellent and Stephon was so cordial. Had a great day, beautiful weather was an added plus!

Richard Apr 27, 2026

Stella and Stefano were wonderful guides for our day trip to Tuscany. Stella had great recommendations for all the best shops to stop at in Pienza and Montalcino and the wine tasting was phenomenal. A great way to spend the day!

Sara Apr 22, 2026

The best tour due to the laid back nature, great scenery, facts and food. Alessandra gave great recommendations and felt like part of the family. For our last day in Italy, it really was enjoyable

Nicole Apr 30, 2025

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