Summary of Key Tours in Siena
- Siena 2-Hour Walking Tour with Skip-the-Line Duomo Tickets
- Educational Wine Tour and Tasting
- Siena 4-Hour Tuscan Cooking Class
- Half-day Guided Hike from Siena to Monteriggioni
- Small Group E-Bike Tour with Winery Lunch
- Guided Walking Tour with Optional Cathedral Visit
- Vintage Fiat 500 Tour and Chianti Roads from Siena
- Horseback Riding from Siena
- Pienza and Montepulciano Small Group Tour from Siena
- Medieval Legends Exploration Game and Tour
- 5-Hour Chianti and San Gimignano Tour from Siena
- The Life of St. Catherine Tour
- Vespa Tour of Chianti and Tuscan Hills
- Siena Street Food Tour with Local Guide
- Historic Siena Guided Walking Tour
Located in central Italy’s Tuscany region and just a short journey south of Florence, Siena is a medieval city renowned for its remarkable architecture and copious historical landmarks, as well as the renowned horse race conducted in the central piazza twice a year.
The city is often described as a vast open-air gallery that houses a plethora of priceless art collections. For individuals interested in uncovering its history and culture, numerous tour options are available, ranging from a few hours to full-day experiences.
Below are 15 notable tours in Siena that cover diverse themes, including cuisine, natural attractions, archaeology, and medieval history.
1. Siena 2-Hour Walking Tour with Skip-the-Line Duomo Tickets
Siena’s Piazza del Campo serves as the central square from which many of its most iconic sites are accessible.
During this two-hour walking tour, participants and their guide will visit the UNESCO World Heritage Site, explore other significant historical structures like Palazzo Tolomei and Basilica San Domenico, and benefit from skip-the-line access to the Duomo.
Many attractions in the city date back over 1,000 years, showcasing impressive architecture, intricate histories, and cultural perspectives that visitors on self-guided tours may overlook.
These tours typically last around two hours and involve considerable walking, hence participants are advised to dress appropriately and wear suitable footwear.
2. Educational Wine Tour and Tasting
Italy is among the top wine-producing countries globally, and regardless of which region you choose to visit, vineyards and wineries are typically nearby.
Unlike many wine-focused tours that primarily concentrate on tasting, this experience examines the historical and cultural significance of wine, including the cultivation of grapes in the favorable climate and their transformation into cherished beverages.
Alongside their guide and host, participants will tour an organic winery just outside Siena, culminating in a wine tasting and a light, traditional Tuscan lunch in a scenic countryside setting.
3. Siena 4-Hour Tuscan Cooking Class
Many visitors to Italy indulge in local cuisine just as much as they explore the nation’s remarkable attractions.
While this is certainly understandable, for food enthusiasts and budding chefs, cooking classes with local residents offer enriching experiences that enhance traditional tours with hands-on activities.
This four-hour, mid-morning cooking class encompasses both culinary and cultural elements. Participants will learn fundamental Tuscan cooking techniques and how to select optimal ingredients before applying their newfound skills.
Attendees will enjoy the dishes they prepare and have the remainder of the afternoon and evening free for further exploration.
4. Half-day Guided Hike from Siena to Monteriggioni
After extensive hours spent on international flights or crowded transfer buses, outdoor activity tours provide excellent opportunities to rejuvenate and experience the local landscape through unfiltered perspectives.
This half-day tour commences in Siena and includes the services of a local guide, who will escort fit and enthusiastic participants to an array of attractions, including picturesque vineyards, sprawling olive groves, and a medieval fortress in a fortified city.
In Monteriggioni, guests will delve into historical sites and engage in a tasting of local, organic wines, while also having time to unwind or explore independently.
5. Small Group E-Bike Tour with Winery Lunch
E-bike tours represent an ideal option for those who prefer to explore the outdoors without excessive physical exertion.
In this small-group tour, participants, accompanied by experienced bikers and local guides, will traverse scenic roads in Chianti, gain insights into the region’s history and culture, while keeping a comfortable distance from the crowds often found at more urban attractions.
Tours include a visit to a local monastery and a family-owned winery, where guests will partake in a wine tasting and a full lunch prior to returning to Siena via a comfortable air-conditioned van.
6. Guided Walking Tour with Optional Cathedral Visit
Characterized by narrow streets, stunning architecture, and significant historical charm, Siena serves as a pedestrian-friendly destination favored by active travelers who prefer exploring on foot rather than relying on air-conditioned transport or buses.
Despite its brief duration of just two hours, the tour covers considerable ground, including multiple landmark attractions such as Piazza del Campo, Palazzo Publico, and the Museum of the Contrada.
The museum offers a wealth of knowledge regarding the city’s history, traditions, and distinctive neighborhoods, along with art and archaeological artifacts.
Participants may also opt to visit Libreria Piccolomini if time allows.
7. Vintage Fiat 500 Tour and Chianti Roads from Siena
While markedly different from the Ferraris and Lamborghinis that frequently capture the attention of automotive enthusiasts, Fiat 500s are iconic Italian vehicles that locals and tour operators commonly utilize.
Beginning at 9:30 AM, this eight-hour driving tour is capped in size, offering participants breathtaking views of the city and surrounding countryside while benefiting from personalized service by their driver and guide.
The tour includes a light, traditional lunch at a Chianti winery and stops at several picturesque viewpoints, historic sites, and medieval villages that appear untouched by time.
8. Horseback Riding from Siena
From Fiat cars and e-bikes to horseback riding, various methods exist to immerse oneself in the beauty of Siena and the surrounding region.
While equines may seem daunting for some, this horseback excursion from Siena includes all the necessary training and safety gear, with each participant paired with a gentle horse experienced in accommodating novice riders.
The pace of the tour can vary based on the abilities and ages of participants; throughout the journey, everyone will encounter idyllic landscapes, ancient vineyards, and magnificent views of the countryside.
This experience lasts approximately 90 minutes and includes round-trip transportation to and from Siena.
9. Pienza and Montepulciano Small Group Tour from Siena
Tours that provide substantial value in affordably priced, small-group formats are becoming increasingly popular among discerning travelers.
If this resonates with you, consider this eight-hour, multi-stop tour departing from Siena.
As guests receive insights into the region’s history and culture from their knowledgeable driver-guide, they will leave the city behind to explore the villages of Pienza and Montepulciano.
Tour highlights include an opulent palace, a family-owned dairy, and an award-winning winery.
Participants will savor a traditional lunch alongside several food and wine tastings throughout the journey.
10. Medieval Legends Exploration Game and Tour
Self-guided exploration games are increasingly favored as a tour option by individuals who appreciate mental engagement, physical activity, and the flexibility to discover at their own pace.
Utilizing a mobile application as their guide, participants will embark on an enjoyable and informative tour of Siena, solving riddles and clues that guide them from one landmark to another.
This activity is particularly suitable for small groups and families with children, as the tour encompasses significant spots like the stunning fountain of Gaia, Piazza del Duomo, and Palazzo Tolomei.
These exploration games typically last under two hours, allowing participants to uncover intriguing aspects they may wish to explore more deeply afterwards.
11. 5-Hour Chianti and San Gimignano Tour from Siena
During hot summer months, air-conditioned coach tours provide efficient means to visit numerous attractions quickly while remaining comfortable.
This five-hour tour from Siena includes assistance from a local guide who will narrate the journey as they venture out to explore Chianti and San Gimignano.
The landscape is characterized by undulating hills, charming hamlets, and plentiful wineries renowned for their legendary red wines.
Guests will discover the grape-growing process and the intricacies of winemaking, while sampling an array of wines paired with local fare, including cheese, cured meats, and bruschetta.
12. The Life of St. Catherine Tour
Siena is the birthplace of St. Catherine, a significant figure who lived over 500 years ago. The sanctuary established in the mid-15th century post her canonization represents one of the city’s most iconic sites.
During this three-hour guided tour, participants will gain insights into her life and explore this sacred sanctuary, featuring three distinct oratories from various periods that narrate her life’s journey in detail.
The tour also includes visits to the Basilica of San Domenico and the Baptistery. Depending on available time, guests may opt to explore additional attractions for a moderate extra charge if they are inclined to leave no stone unturned.
13. Vespa Tour of Chianti and Tuscan Hills
The Tuscan hills present visitors with some of the country’s most breathtaking scenery and attractions. For those comfortable spending their day on two wheels, Vespas offer an exhilarating mode of touring.
From Siena, participants will be transported to Chianti by bus, where they will meet their guide and receive their Vespas.
These stylish scooters are enjoyable, safe, and user-friendly, with a comprehensive orientation conducted before proceeding on the open road.
Tours extend for approximately 7.5 hours, encompassing a wine tasting and traditional Tuscan lunch, while those who prefer not to drive can opt to ride behind a guide.
14. Siena Street Food Tour with Local Guide
Though it may seem like a well-worn expression, there are few better methods of achieving cultural immersion than engaging with locals while avoiding tourist traps.
In this 2.5-hour tour, culinary enthusiasts will do just that. They will visit some of Siena’s notable attractions while gaining valuable cultural insights along the way.
The tour traverses multiple neighborhoods within the city, each of which boasts unique culinary traditions.
Participants will visit four different eateries, mingle with local residents, and sample a delightful range of items, including soup, homemade pasta, cured meats, and traditional Tuscan gelato.
15. Historic Siena Guided Walking Tour
Siena is a wealth of artistic, historical, religious, and cultural attractions. Many of these sites are closely situated, allowing visitors to experience a multitude in just a few hours.
This efficiency means minimal time wasted in transit. On this tour, participants will spend the majority of their time walking and learning from a knowledgeable local guide.
Highlights include the centrally located Piazza del Campo, Palazzo Communale, and the magnificent Basilica of San Domenico.
Depending on the available time and guest interests, there may also be an opportunity to visit the Cathedral.
