Top Siena Day Trips

Explore southern Tuscany on a full-day tour from Siena through the scenic Val d’Orcia, combining food, wine and history. In the Montepulciano area, enjoy lunch at Vecchia Cantina di Montepulciano, outside the historic town centre. Savour a Tuscan appetizer, pasta with ragù or lasagna, and cantucci with Vin Santo. A vegetarian menu is available. Taste three wines from Cantina del Redi: Riccio Toscana Bianco IGT or Nobile di Montepulciano, Briareo Nobile di Montepulciano Riserva, and Vin Santo. Continue to Pienza, the Renaissance town known for its panoramic views and artisan shops, with free time to explore. Finally, visit Montalcino, home of the famous Brunello di Montalcino, before returning to Siena through the Tuscan countryside.

From Siena Best of Tuscany Wines and Lunch in Montepulciano

9 hoursFree Cancellation

Discover Tuscany's stunning landscape, culinary delights, and UNESCO-listed sites on a day trip to Montepulciano and Pienza from Siena. Avoid the hassle of driving yourself and be led by a local guide. Admire the architectural gems of the Val d'Orcia region and stop at a dairy farm for lunch and samples of salty Pecorino cheese. Conclude your trip in the scenic hill town of Montepulciano, with a visit to a winery.

Small-Group Montepulciano and Pienza Day Trip from Siena

8 hoursFree Cancellation

Special Offer

Avoid the hassle of planning routes between scattered wine towns and booking separate tastings on your own with a guided day trip from Siena. This experience connects the flavors of Montepulciano and Pienza with the scenic landscapes of Val d'Orcia, letting you move easily between villages without logistics stress. Spend your time enjoying wine, local food, and countryside views at a relaxed pace.

Siena: Val d’Orcia Wine Tour with Lunch & Brunello

10 to 11 hoursFree Cancellation

Pisa, San Gimignano & Chianti Day Trip with Lunch & Wine Tasting

Enjoy a day trip to three of Tuscany’s most iconic destinations: Montalcino, home of the famous Brunello wine; Pienza, renowned for its Pecorino cheese; and Montepulciano, known for its prestigious Nobile wine. Travel through the UNESCO-listed Val d’Orcia aboard a premium air-conditioned minivan with an English-speaking driver and complimentary water. Small group experience, maximum 8 participants. Why choose us? • Guaranteed departures • Secure booking • 24-hour cancellation policy • Best rates guaranteed For operational reasons, the itinerary order may vary between Montepulciano and Montalcino.

Val D’Orcia Tour From Siena Montalcino Pienza and Montepulciano

10 to 11 hoursFree Cancellation

Visit San Gimignano and Volterra the easy way from Siena, on an intimate small-grop tour. Head to the hilltop town of Monteriggioni, then stop for a while in UNESCO World Heritage–listed San Gimignano, with its medieval towers and views over the Tuscan countryside. Drop into an alabaster workshop in Volterra, then indulge in a rustic lunch at a Tuscan farm. Learn about local history and culture along the way.

Small-Group San Gimignano and Volterra Day Trip from Siena

8 hoursFree Cancellation

If you've only got limited time in Siena, make sure you maximize your experience of the Tuscan hot spot on a sightseeing tour that includes skip-the-line entry. An expert guide gives you an insider's view of this UNESCO World Heritage-listed town. Linger for a while in Piazza del Campo and stroll the streets with your guide, learning about the history of the place and leaving the navigating to someone else. Visit the Duomo, Siena's stunning cathedral, and stroll right in thanks to your skip-the-line ticket.

Skip the Line: Siena Duomo and City Walking Tour

2 hoursFree Cancellation

Hidden Castles & Chianti Wine Experience– Small Group

5 hoursFree Cancellation

Siena: A Wine Tour and Tasting Experience

3 hoursFree Cancellation

Take a day excursion to San Gimignano, Chianti, and Montalcino to experience the charm of the Tuscan countryside. Savor the best local blends during a wine tasting at a renowned Chianti winery. Optional lunch for an authentic gastronomic experience. Begin your full-day journey by seeing San Gimignano, well known as the City of Fine Towers. With your tour guide's insights, take advantage of your free time to explore the historical center and its artisan stores. Explore the birthplace of Vernaccia, the renowned white wine that is regarded as Italy's first DOCG wine, after that. Enjoy a sample of Chianti and you can choose to buy the optional lunch at a nearby winery. Discover the UNESCO World Heritage Site of Val d'Orcia before continuing on to Montalcino, which is famous for its panoramic vistas of Brunello grapes. Finish your tour by visiting a local wine cellar to experience the renowned Brunello di Montalcino.

San Gimignano, Chianti and Montalcino Tour through Tuscan wine

Spend a day sipping one of Italy’s top wines, Brunello di Montalcino, on this trip from Siena to Montalcino. Travel first to a small winery to explore the vineyards and cellars and taste the famous Rosso and Brunello di Montalcino wine. Then, visit a family-run winery in Montalcino, where you tour the grounds and sit down for a classic Tuscan meal with more wine. Visit the Abbey of Sant'Antimo before tasting even more wine at your third and final winery of the day.

Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena

9 hoursFree Cancellation

Explore the enchanting Chianti wine region on a half-day tour from Siena, where rolling hills and lush vineyards create an idyllic backdrop. Visit Castellina in Chianti and enjoy exclusive wine tastings at renowned estates. This tour is tailored for wine lovers and nature enthusiasts, offering a rich cultural experience through Tuscany's famous landscapes. With expert multilingual guides, savor the essence of Chianti’s rich heritage and take in the stunning scenery that has inspired countless artists and wine aficionados.

Chianti Half Day Wine Tasting Tour from Siena

5 hoursFree Cancellation

Discover the picturesque wine region of Chianti on a half-day excursion from Siena. Enjoy the Tuscan scenery of gently undulating hills and vineyards while tasting Chianti wines. A day journey from Siena to the Chianti region allows you to experience the gorgeous Tuscan landscape. Begin with a visit to Castellina in Chianti, followed by a wine tasting at a nearby vineyard. Immerse yourself in the bright colors of the rolling hills, where the views, smells, and flavors of the region will captivate your senses. Enjoy a stroll in Monteriggioni, a medieval village where time seems to stop. Proceed to another winery in the heart of the Chianti Classico region, where you can have a second wine tasting and sample extra virgin olive oil. A return trip to Siena marks the end of the excursion.

Chianti and Castles Tour from Siena Small Group

5 hoursFree Cancellation

Learn to cook traditional Italian dishes during this Tuscan cooking class in Siena. From homemade pastas to juicy cuts of meat, a professional chef leads you through a combination of family-favorite recipes and time-tested dishes, culminating with a shared meal and excellent wine. This class is held in a professional kitchen and limited to a small group of 15 people or fewer for a more intimate experience.

Tuscan Cooking Class in Siena with Handmade Pasta, Wine & Dinner

4 hoursFree Cancellation

Explore Tuscany outside Siena on this small-group day trip, visiting San Gimignano and Montalcino. Don't worry about hiring a car, as all transportation is arranged. Take a break from the city as you discover medieval architecture and scenic views of Tuscany, with ample free time in each of the hill towns. The tour also includes a visit to a Montalcino winery, with the opportunity to sample Chianti and Brunello di Montalcino.

San Gimignano, Chianti, and Montalcino Day Trip from Siena

Italian Opera in Siena Experience

1 hour 20 minutesFree Cancellation

See the top sights in Siena without the hassle of a guidebook or map with this small-group walking tour through the medieval old town. Join your local guide for a stroll along picturesque historic lanes to take in landmarks like the Piazza del Campo, Basilica of San Domenico, and Sanctuary of St. Catherine of Siena. Opt to add on a visit to the city’s magnificent Cathedral, rich in artworks by Renaissance masters.

Discover the Medieval Charm of Siena on a Private Walking Tour

2 to 3 hoursFree Cancellation

Price varies by group size

Embark on an adventure that will take you through the fascinating hills of the Chianti, crossing the iconic gravel roads of the Eroica, revealing, in a slow and contemplative way, an area rich in food and wine traditions, cradle of the famous Chianti Classico wine (tasting included) and proud of its tradition and culture linked to the long rivalry between Siena and Florence. In addition, the experience includes a guided tour of one of Chianti's most characteristic castles, the castle of Brolio, from which you can take in magnificent panoramic views to the vineyards and the city of Siena. To experience the most out of the territory, we'll book lunch at a local family owned restaurant (or in the Eroica Caffeteria) where you, in addition to enjoying its tranquility and warm welcome, can savour the dishes of the Tuscan tradition. The way back is mainly descending and the guide will stop in magnificent sightseeing spots before getting back to the starting point.

During the tour, there'll be lots of time to relax and to enjoy the good company while cycling in the famous Eroica Gravel roads of the Chianti.

E-Bike Tour: Explore the Chianti, its Enogastronomy and Castles

7 hours 15 minutesFree Cancellation

Price varies by group size

Private Tour: Secret Siena Walking Tour

3 hoursFree Cancellation

VIP Chianti, Brunello wine & Pienza with lunch From Siena

8 to 9 hoursFree Cancellation

With no train station and spotty bus service, San Gimignano can be a hassle to reach from Siena. On this small-group tour, sip world-class wine and watch the sunset over Chianti and San Gimignano with stress-free transportation. Led by an expert guide, explore the medieval town of Monteriggioni and visit Chianti wineries for tastings. Then, head to the UNESCO-listed San Gimignano to see the sunset as you savor a traditional Tuscan dinner in a farmhouse overlooking the hills.

Small-Group Chianti and San Gimignano Sunset Trip from Siena

8 to 9 hoursFree Cancellation

Avoid the stress of navigating winding country roads or unfamiliar public transit on your own and instead discover the fine wines and rich historical heritage of Chianti on this full-day trip from Siena. Travel through the Tuscan countryside to Castello di Brolio in the heart of the Chianti wine country for guided tasting sessions and a traditional Italian lunch. Enjoy the intimate atmosphere of a small group capped at only eight people.

Small-Group Chianti Trip with Wine Tasting from Siena

8 hoursFree Cancellation

Chianti Classico E-Bike Tour

5 to 6 hoursFree Cancellation

Price varies by group size

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Must-Dos in Siena

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The magnificent Gothic and Romanesque structure of Siena Cathedral (Duomo).

What are people saying about Siena

Chianti Half Day Wine Tasting Tour from Siena

Rob_H, Nov 2026

A great day touring the Val d'Orcia!

We reserved a half-day tour, but a few days before, received communication from My Tour in Italy (the tour provider)that our tour could not go because of unexpected technical issues. They apologized and offered an alternative of a full day Val d'Orcia Tour. We agreed with the alternative, and had a wonderful day touring Montepulciano, Pienza, and Montalcino with tour guide Lily and driver Massimo, along with a bus full of fellow tourists. Communication was clear and timely, and very helpful -- when we had a question about where to meet the group, My Tour in Italy responded with a photo to help us orient ourselves and get to the tour on time. This experience and the places we visited, the wine tastings and lunch included in the tour made this probably our favorite day or our time in Italy: highly recommend!

Siena: A Wine Tour and Tasting Experience

John_L, Oct 2026

We recently took a wine...

We recently took a wine tour here, and to say it exceeded our expectations is an understatement. From the moment we arrived, the atmosphere was incredibly welcoming, warm, and sophisticated yet entirely relaxed. The estate boasts stunning, panoramic views that are worth the visit alone—make sure your phone is charged because you will want to take a lot of photos! Our host, Lorenzo, was absolutely fantastic. He was incredibly thoughtful, attentive, and his deep knowledge of the winemaking process made the tour both insightful and engaging. He didn't just rattle off facts; he shared genuine insights that gave us a whole new appreciation for what goes into every bottle. The wine tasting itself was outstanding. Each pour was excellent, beautifully paired, and generously served. Lorenzo guided us through the notes of each wine in a way that was accessible but highly informative. Everything about this day was perfect, from the breathtaking scenery to the immaculate hospitality. If you are considering booking this tour, do not hesitate—it is a flawless experience!

Small-Group San Gimignano and Volterra Day Trip from Siena

Albert_M, Oct 2026

This was such an amazing...

This was such an amazing tour! Loved visiting and exploring Monteriggioni, San Gimignano and had the MOST amazing lunch on terrace overlooking the Tuscan landscape. Ended tour seeing a master craftsman creating works with alabaster. Truly amazing tour!

Skip the Line: Siena Duomo and City Walking Tour

Mattea_K, Oct 2026

We loved our tour with...

We loved our tour with Giulia! She is a Siena local, she was very passionate and knowledgeable about local history and culture. We only had a few hours in Siena so it was nice to get some background about the city. The trip inside the Duomo was lovely as well, Giulia’s explanation of different parts of the church made it more interesting that we could understand the history and images.

Small-Group Montepulciano and Pienza Day Trip from Siena

Karyn_I, Oct 2026

Perfect Day in Tuscany!

Outstanding! Hands down, the best day trip/tour we took while in Italy! Our guide/driver Keko was fantastic…. Knowledgeable, interesting, friendly and warm! He took us to beautiful, charming locations and it ended up being our favorite day of the two weeks we spent in Italy. Perfect! Thank you Keko!

Small Group E-Bike Chianti Tour with farm lunch from Siena

Peggy_S, Oct 2026

Best day ever!

I cannot say enough about our day with our tour guide, Enrico. He went way beyond the call of duty with giving us the history, taking us to the most stunning views of Tuscany, and stopping at a vineyard for a wine tasting and lunch. He was patient with those new to e-bikes, and he was there immediately when someone needed assistance. The wine tour was interesting and the wine and lunch was fresh and delicious. Be sure to eat the lunch they serve while tasting. You are riding a bike on a country road. Oh, and at the end Enrico called all of us taxis snd even provided recommendations of eateries and sights. Thanks Enrico for a memorable day.

Tuscan Cooking Class in Siena with Handmade Pasta, Wine & Dinner

Concetta_F, Aug 2026

Great Tuscan Cook Class

A very fun cooking class - we made a full 4 course meal with soup, pasta, main course and dessert. I liked that it was around dinner time so we got to eat the yummy food we made for dinner. The class was a good pace, the instructions were clear and the food was fantastic - definitely recommend :)

Private Tour: Secret Siena Walking Tour

Robert_P, Jul 2026

Informative and Fun

This is a fabulous tour. We requested a guide Giulia for the second time because she is accommodating and adaptable and made the tour of Siena fun, relaxed and informative. She is extremely knowledgeable as we learned about the contrade and especially the famous Palio horse race. I highly recommend this guide and this tour.

Small-Group Chianti Trip with Wine Tasting from Siena

merleh799, Apr 2026

A very special event

The Chianti tour was a special experience and a highlight of our holiday. It offers a great insight into Italian wine culture and we have learned a lot about the production process. Tuscan Escapes has selected beautiful wineries with a special history. The day is beautifully designed and offers a very pleasant change between wine tasting and exploring the area. The typical Tuscan lunch was incredibly delicious and a pleasant rest. Our guide explained a lot about the region, the terrain and the importance for winemaking and was very warm. The many wines, the extensive lunch and the great impressions absolutely justify the price of the tour and are worth their money. We really enjoyed the day and can only recommend the Chianti tour!

Discover the Medieval Charm of Siena on a Private Walking Tour

Jeffrey_G, Apr 2026

Siena tour - Not to be Missed!

Highly recommend this tour! Barbara was a wonderful tour guide! Very knowledgeable about Siena, having grown up in the area. It’s a fabulous city not to be missed! And the surprise at the end made us all fall in love with Siena that much more! Spectacular view! Thank you, Barbara!!

Private Tour: Pienza and Montalcino Organic Cheese and Wine Tour

Madeleine_R, Apr 2026

So much fun! The farm was...

So much fun! The farm was a definite highlight -- gorgeous views and incredible snacks to kickstart the day! We loved getting to walk around Pienza, and the wine was incredible (though definitely pricey if you wanted to purchase bottles to ship home). All in all a perfect way to explore Tuscany. We also loved our guide Frederico! The perfect balance of informational and letting us relax without pressure.

Pienza, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA

Regan_F, Jan 2026

We had a wonderful...

We had a wonderful experience with Roberto. 2 wineries and a lunch at a sheep farm that was marvelous. Local meet and cheeses and we even got to see the sheep. Then a stop in Pienza for some sightseeing and a lovely drive back to our hotel. First class experience.