Top Siena Day Trips

From Siena Best of Tuscany Wines and Lunch in Montepulciano

9 hoursFree Cancellation

4.0

(14)

from $116

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

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.

4.9

(199)

from $224

Small-Group Montepulciano and Pienza Day Trip from Siena

San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting

4.9

(319)

from $224

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. Please note that from November to April, and in case of bad weather, lunch will take place indoors. For tours departing on Mondays, lunch is always served in an indoor restaurant. 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.

(181)

from $93

Val D’Orcia Tour From Siena Montalcino Pienza and Montepulciano

Val D’Orcia Tour From Siena Montalcino Pienza and Montepulciano

10 to 11 hoursFree Cancellation

4.6

(5)

from $270

Hidden Castles & Chianti Wine Experience– Small Group

5 hoursFree Cancellation

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.

(179)

from $58

Special Offer

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

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

10 to 11 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

(769)

from $47

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

San Gimignano, Chianti and Montalcino Tour through Tuscan wine

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.

(8)

from $165

Chianti Half Day Wine Tasting Tour from Siena

Chianti Half Day Wine Tasting Tour from Siena

5 hoursFree Cancellation

(11)

from $58

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

San Gimignano, Chianti, and Montalcino Day Trip from Siena

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.

4.3

(151)

from $165

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

9 hoursFree Cancellation

4.9

(1,012)

from $224

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

Siena: A Wine Tour and Tasting Experience

(82)

from $224

3 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.

(391)

from $100

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

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

4 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.

(352)

from $153

Chianti and Castles Tour from Siena Small Group

Chianti and Castles Tour from Siena Small Group

5 hoursFree Cancellation

3.6

(7)

from $100

Spend a memorable day exploring Tuscany’s most famous landmarks and landscapes on a relaxed and well-balanced itinerary from Siena. Your journey begins with a comfortable transfer by air-conditioned coach through the rolling hills of the Tuscan countryside. Reach Pisa, where you will have free time to explore the stunning Piazza dei Miracoli, a UNESCO World Heritage Site. Admire the world-famous Leaning Tower, the Cathedral, and the Baptistery from the outside, and take your time capturing unforgettable photos. Continue your experience with a stop in the heart of Chianti, where you will enjoy a traditional Tuscan lunch paired with a guided wine tasting at a local winery. In the afternoon, arrive in San Gimignano, one of Tuscany’s best-preserved medieval towns. On the way back from Pisa, you’ll pass through Florence before returning to Siena. This allows for a smooth and well-organized route across Tuscany.

From Siena: Pisa and San Gimignano Day Trip

From Siena: Pisa and San Gimignano Day Trip

Explore Chianti’s backroads and beautiful vistas while traveling in a private 4WD on this tour with hotel pickup. Soak up the scenery while a driver handles the country roads, stopping at off-the-beaten-track cellars and cantinas to taste several Chianti Classico wines along with Tuscan olive oil, honey, and other specialty products. Balance out all that wine with a traditional Tuscan lunch at a scenic family estate.

4.0

(1)

from $93

Private Off Road Wine Tour in Chianti from Siena

Private Off Road Wine Tour in Chianti from Siena

6 hoursFree Cancellation

Price varies by group size

(2)

from $472

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

(261)

from $182

Splendid Classic Siena Tour with guaranteed departure from Via di Città at 11am in English and at 12.15pm in Italian. An expert local Guide will introduce you, in an interesting and pleasant way, to the history of Siena, the Duomo, Piazza del Campo and other monuments of the city. We will talk about the Palio, the districts and visit the lesser known and quieter corners of the city. Including entrance ticket to the Duomo. In case of religious celebrations or extraordinary closures (such as Sunday morning for Mass), the visit will be moved to the Antico Ospedale di Santa Maria della Scala, still guaranteeing a complete experience.

Siena : Siena Guided Tour with Duomo or Museum

1 hourFree Cancellation

4.3

(45)

from $41

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

(64)

from $224

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

Pienza and Montalcino are top foodie destinations, but getting there by train and bus can eat hours out of your day. Experience the area's top cheese and wine with ease on this private tour from Siena. Admire the Val d’Orcia scenery, learn about cheese making during an organic dairy farm tour, visit the World Heritage–listed town of Pienza, and enjoy tastings of the region’s renowned Brunello wine at a Montalcino winery.

(6)

from $93

Private Tour: Pienza and Montalcino Organic Cheese and Wine Tour

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

(38)

from $824

Per group

8 hours

Price varies by group size

(36)

from $647

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Top Attractions in Siena

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

Attractions

What are people saying about Siena

San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting

Zoe_N, Jul 2026

Wonderful Surprise!

Experiencing a long table for lunch with new found friends while tasting several wines & eating authentic Italian food was much more than expected. I even bought Biscotti & Pasta! Discovering Siena on foot, seeing the Cathedral & revisiting the history & learning the culture of the city is priceless!

Skip the Line: Siena Duomo and City Walking Tour

Irene_E, Jul 2026

Great tour

Great time walking around the city & learning about the history of Siena! We were here during the Palio di Siena! To learn about the horse race and all the neighborhoods. The Duomo was beautiful! Sylvia, our guide, did a fantastic job of explaining everything!

Siena: A Wine Tour and Tasting Experience

Robert_B, Jun 2026

If you love wine, food, and Tuscany, DO THIS TOUR!

This was one of the highlights of our trip to Italy. Lorenzo was an outstanding guide—enthusiastic, knowledgeable, and entertaining from start to finish. The winery tour was informative without feeling rushed, the wines were excellent, and the food was delicious. To top it off, Lorenzo even helped us arrange a taxi back to Siena at the end of the tour. One tip: don’t try to walk to the winery. It looks possible on mapping apps, but it’s much farther and more difficult than it appears. You’ll definitely want to take a taxi. Since taxis can be hard to find in Siena, I recommend messaging the winery in advance to see if they can arrange one for you. Thank you for such a wonderful experience. We hope to visit again someday!

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

Jennifer_B, Jun 2026

Traditional Tuscan Treat

This was the best cooking class I have experienced - based on other experiences in France, China, and the United States. Francesco, who is now the owner, and Julie , who also helped translate from Italian to English, both gave each of us (7 participants) individual attention on techniques, tips along the way, and patiently answered questions in between demonstrations. The food we created from all fresh and local ingredients was delicious and based on traditional local Tuscan cuisine! When any friends and family visit Siena, I will be recommending this experience! And for the reader here, you will enjoy every step of the process!

Small-Group Montepulciano and Pienza Day Trip from Siena

Catherine_D, Jun 2026

Tutto benissimo

10/10 would recommend. Keko was a knowledgeable and charismatic tour guide. While we drove through the Tuscan countryside, he provided engaging commentary about the history, the landscape, and the local food traditions of the region. If you want to see the Tuscan country, this is the way to do it. I particularly enjoyed the lunch at the farm and tasting the local recipes with ingredients made right there. The time in Pienza and Montepulciano flew by. I would definitely take this tour again.

Small-Group San Gimignano and Volterra Day Trip from Siena

Barbara_J, Jun 2026

A Wonderful Experience

This tour was the highlight of my trip! Our guide, Guglielmo / William was very knowledgeable, courteous and gave us plenty of time to explore San Gimignano and Volterra. My favourite parts of the day were actually the side trips. At the artisanal farmlandfwe had an incredibly delicious lunch.. I also loved meeting and watching the alabaster craftman work. He is truly gifted and I will treasure two of his pieces I am taking home. I had such a wonderful day that I could not stop smiling.

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: Secret Siena Walking Tour

Susan_Y, Apr 2026

The absolute best! Must do!

This was probably one of the best tours we've been on. Georgia, our guide, was so much a great guide. She was very in tune with us too, knowing when she had to slow down her talking for my older mother who was not understanding and when to speed it up. She customized our tour with us and gave us so much history and lore, we fell instantly with Siena because of her. 10/10 best thing to do in Siena. Highly recommended!

Private Tour: Pienza and Montalcino Organic Cheese and Wine Tour

Kevin_L, Feb 2026

The Perfect Tuscan experience!

Exactly what we were looking for! A unique experience-. Mattea was a colorful guide, fun and knowledgeable of the area and wines. A small self sustaining cheese farm with olive oil and wine. Pienza is a must see and finally a private wine tasting in montalcino.! Thanks Mattea for a great day!

Hidden Castles & Chianti Wine Experience– Small Group

Christina_P, Nov 2025

Great guided experience with Luca

Our guide Luca was very knowledgeable and gave great information all day throughout the tour. He had good recommendations for restaurants in the cities we visited, and explained the different wines and products very well. The tour itself was nice, with visits to two wineries and some cities with impressive views over the hillside in Tuscany.

Small-Group Chianti Trip with Wine Tasting from Siena

Janice_K, Sep 2025

Excellent wine tour

If you are looking for an all-day wine tour that visits more than one winery this is a great option. The tour stops at three wineries. The first two were my favorite. The second tour included an excellent lunch. Our driver/host was knowledgeable and explained the pyramid of wines and we traveled. He was very courteous and gave the group options on how long we wanted to stay.