Top Siena Tours by Duration - page 3

See Tuscany in classic Italian style by exploring the bucolic region in a vintage Fiat 500. Take the wheel of the classic Italian automobile then ride to the stunning hilltop town of Monteriggioni, cruise through the rolling hills of Chianti, and stop at a local vineyard for a hearty lunch of local fare.

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.

Avoid the challenge of navigating Tuscany’s rural roads and finding hidden countryside trails on your own with a guided horseback ride from Siena. This gentle journey carries you through rolling hills, vineyards, and olive groves, reaching quiet landscapes that cars can’t access. Ride at a relaxed pace while taking in the region’s natural beauty and rural charm without any planning or navigation stress.

Explore Tuscany beyond Florence or Siena with a full-day wine tour. Get picked up at your hotel for a small-group tour to visit local wineries and relax over lunch in the town of Montepulciano. Learn about how wine is made and taste regional specialties including Nobile. Meet the people behind the wine without the hassle of a rental car or navigating between wineries.

Home to medieval hilltop towns and fertile vineyards, Tuscany is widely considered the jewel in Italy’s crown. On this tour, visit the beautiful Tuscan towns of Pienza and Montepulciano, and enjoy a complete immersion in authentic Italian culture and cuisine. With travel from your Chianti or Siena hotel, sample local wines in historic cellars and savor a delicious lunch in a traditional Montepulciano winery.

Siena is one of Tuscany’s most picturesque medieval towns and this private walking tour is ideal for first-time visitors or those short on time. Take in the highlights of the UNESCO-listed center, stroll around lively Piazza Del Campo, and admire landmarks such as San Domenico Basilica, Palazzo Tolomei, and Cathedral of Siena.

Optimize your travel time with this private transfer that breaks up the trip from Siena to Rome with stops in Orvieto and Civita di Bagnoregio to sightsee, shop, and dine. Enjoy hassle-free pickup at your hotel or other accommodation in Siena and enjoy views of the Tuscan countryside as you head south. Stop for free time to explore Orvieto and Civita before drop-off at your final destination in Rome.

Discover the history of the Chianti region, visit Montalcino's medieval fortress, and enjoy a scenic drive through Val d'Orcia on this small-group tour from Siena. Taste Chianti Classico and Brunello wines paired with Pecorino cheese, bruschetta, salame, and extra virgin olive oil. Explore the historic cellar and learn about the wine production process in a boutique family-owned winery.

Enjoy a private tour of two of Montalcino’s most exclusive wineries, taste their award winning wines and visit their winemaking facilities. Our native English speaking guide will be with you throughout your unforgettable experience and will take you to lunch at one of the regions top restaurants.

Brunello di Montalcino is one of Italy's most prestigious wines, but navigating to the rural wineries outside of Montalcino on your own can be stressful. On this private wine tour, let your driver take the wheel and focus on vineyard views as you make your way to the top wine estates and cellars for exclusive tasting experiences. Explore stunning vineyards, learn about traditional winemaking techniques, and savor the rich flavors of Tuscany with guided tastings and a traditional lunch.

Visit two of Tuscany's beautiful hilltop towns, plus enjoy tours and tastings at boutique wineries in Chianti and Montalcino on this small-group tour from Siena. All transport is included for a hassle-free experience, with free time to explore Pienza. Sample top Chianti, Brunello, and Super Tuscan wines, and relax over a Tuscan lunch featuring local specialties.

Discover the architecture, art, and culture of Tuscany's medieval era on this private tour from Florence. Journey to the city of Siena and visit its most-important landmarks, including the 13th-century cathedral. Afterward, travel to San Gimignano to understand why the small city is known as the "Manhattan of the Medieval Ages."

Make pizza and gelato like a pro during a 3-hour cooking class in Florence, with optional round-trip transport from Lucca. With the help of a local chef, you’ll create a pizza from scratch: kneading the dough, making the sauce, and baking it to crisp perfection. Learn about the art of gelato making and the importance of quality ingredients, then sit down to eat your creations with drinks. The full experience, with transport from Lucca, lasts five hours.

Experience the enchanting Tuscan countryside as if you've stepped into an old Italian movie, cruising in a vintage FIAT 500 across the rolling hills of Chianti. Let us transform this dream into reality for you on our scenic driving tour along the most captivating routes and stops at the most charming villages. These hidden gems offer a glimpse into the authentic essence of Tuscany, preserving their timeless beauty for centuries. Immerse yourself in the sights and sounds of the region as you drive through winding roads, bordered by vineyards and olive groves. Marvel at medieval village, each one a testament to Tuscany's rich history and culture. During your journey, take a break to join a wine tasting at a Chianti winery. Savor the flavors of the region as you sip on locally produced wines, surrounded by breathtaking scenery that seems straight out of a painting.

Explore southern Tuscany with your own private guide on a full-day wine and food tour from Siena. Visit Pienza, Val d'Orcia, Montalcino, and more as you take in small towns, a 14th-century monastery, and sample Brunello di Montalcino, the famous wine of the region. Ride in comfort in a luxury vehicle with a private guide who shares the best of the region.

Get an extra boost from your electric bike on a half-day bike tour of the Chianti region. Follow your guide through a picturesque landscape of gentle hills with vineyards, olive groves, and small villages, stopping at a 12th-century castle and a winery. Your tour includes a wine tasting, bottled water, and use of all necessary equipment.

The Tuscan countryside is a premier hiking destination, but navigating unfamiliar trails and country roads on your own can be daunting. On this private hiking tour, explore the rolling hills and vineyards stress-free with a guide leading the way. Meet in Siena and transfer to the trailhead by minivan, setting off through the verdant countryside and past rustic villages. Take a break to relax over a classic lunch of Tuscan treats and then travel via minivan to San Gimignano for a stroll through town and along a stretch of the Via Francigena before the return ride to Siena.

Navigate through the picturesque landscapes of Tuscany with the Tootbus Tuscany Multi-Day Pass. Enjoy unlimited travel across Florence, Pisa, Siena, Lucca, and San Gimignano, allowing you to explore at your own pace. This flexible pass eliminates the stress of rigid schedules, offering scenic routes through the stunning Chianti countryside. With Tootie, your AI-powered guide, receive personalized recommendations and real-time travel tips in over 50 languages, making your journey seamless and enriching. Start your adventure from any city at any time and immerse yourself in the beauty and culture of Tuscany.

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.

This customized day trip pairs the otherworldly landscapes of southern Tuscany with the region’s frozen-in-time villages and prized flavors. Relax and take in the views from a luxury vehicle while a private guide and driver handles the country roads. Taste famed Brunello wine in Montalcino and Pecorino cheese in lovely Pienza, visit a medieval monastery, and get hand-picked recommendations for an authentic Tuscan lunch.

Take off your shoes and - literally - immerse yourself into ancient Tuscan culture on a grape stomping excursion to the Chianti hills.  In addition to grinding grapes into juice with your bare feet, you’ll also get an up close look at life at a Tuscan winery. A visit to the wine cellar and tasting is also included. After you’ve stomped to your heart’s content, replenish your strength with a homemade lunch.

This private tour is designed to offer an authentic experience with maximum comfort and local insight. It starts directly from your hotel in a fully licensed Mercedes van with air conditioning for a smooth and relaxing ride. Accompanied by a professional driver-guide-certified sommelier, fluent in English and Italian born and raised in the Montalcino area. Travel through the stunning Val d’Orcia admired worldwide for its rolling hills and iconic landscapes. The highlight of the tour is an exclusive visit to a family-owned, organic Brunello winery, where you will walk through the vineyards, tour the cellars, and enjoy a guided tasting of selected red wines, including the celebrated Brunello di Montalcino, accompanied by a tasting extra virgin olive oil. The experience concludes with free time in the medieval town of Montalcino, the heart of the Brunello wine region, where you can explore historic streets, admire monuments, and browse charming local shops at your own pace.

Unlock the mysterious world of Tuscany's tasty truffles on this half-day private tour from Florence. Look for these black and white treasures using man and pup power as you learn all about these delicious delicacies from an expert hunter. Afterwards, enjoy a lunch featuring truffles and wine tasting (own expense) and experience nature with every bite while exploring this exquisite part of Italy.

Bus tours of Tuscany can feel out of touch with the beautiful, rolling countryside that travelers love. This tour allows you to get out of the bus and into the landscapes of the Tuscan countryside on a bike, following routes designed for casual cyclists or professionals. It’s a small-group affair and finishes with a lunch of Tuscan dishes and wine.