Top Siena Private Sightseeing Tours - page 3

Tour with a certified sommelier guide expert on Brunello. Discover Tuscany with local expert out of beaten path. learn the history of Brunello wine making and visit historical wineries.

Become a pilgrim of sorts and take a scenic hike on the historic Via Francigena, an old pilgrimage route that stretched from Canterbury in England to Rome. The rural route takes you through villages, vineyards, and some of the most scenic countryside in Tuscany. Best of all, once you get to the medieval village of Monteriggioni you're rewarded with a wine tasting. At the end, head back to Siena via train.

Our Polaguides will allow you to discover the most hidden, but no less fascinating places than Siena and instant photography will allow you to appreciate the beauties of the city from a unique and unrepeatable point of view. Each shot will capture your favorite moments in photos immediately ready to be touched, waved and attached in the guide-albums created to be customized, to be browsed whenever you want. Transform your visit to Siena into unique memories to share with the whole family, young and old, and with friends. N.B. In the days of the Palio (29 June-2 July and 13-16 August) the normal route of the Top 10 in Siena is not feasible and is replaced with that of the Top 10 dedicated to the places of the Palio, of which we will provide a dedicated guide and map.

Take a break from the crowds in Siena, and spend an afternoon in the wine town of Montalcino on this group tour. Don't worry about hiring a car to get there, with transportation all sorted. Learn about Brunello di Montalcino wine and its production, along with wine tastings paired with local snacks. Admire views of the Tuscan countryside from this hill town as you discover the region’s generations-old winemaking traditions.

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.

The perfectly intact medieval center of Siena is stuffed with important historic sights, and it’s hard to know where to begin. Get your bearings and touch on the top attractions in just a few hours with this private walking tour. Stroll through the cobblestone streets with a guide so you can focus on the architecture rather than a map and marvel at highlights like the Piazza del Campo and cathedral.

Begin your day in the magical city of Florence, the Renaissance jewel. Marvel at the panoramic masterpiece from Piazzale Michelangelo, capturing the essence of this timeless city. Stroll through the historic center, a living canvas adorned with Palazzo Pitti, Ponte Vecchio, and Piazza della Signoria. Embark on a scenic drive through Chianti, where postcard-worthy landscapes of rolling hills and cypress-lined roads unfold. Trace the paths of ancient pilgrims, venturing through vineyards that breathe life into the iconic Chianti region. Farm Lunch: Indulge in a flavorful Tuscan feast at a charming farm, where Lasagna, Pecorino, and savory Ham are paired with the finest regional wines. Let the tastes of Tuscany enchant your palate. Afternoon Charms of San Gimignano: Discover the medieval enchantment of San Gimignano, a town adorned with towering structures that echo tales of history. Sample the world's best gelato as you explore the charming streets and absorb the town's timeless allure.

Siena is one of Italy’s most captivating medieval cityscapes, but its mazelike historic center is a challenge to navigate. With this private tour, explore with a local guide to cover the highlights in a few hours. Marvel at the Piazza del Campo, stroll the historic center, and take in the Basilica of St. Francis and Medici Fortress while you learn about the local history and architecture.

Avoid the hassle of navigating the rural roads and trying to locate the small cellars in Tuscany’s wine country with this wine tour that includes round-trip transportation. Stop for a tour and tasting at one or two scenic wineries near Siena before a lunch break. In the afternoon, visit cellars in Montalcino or the Val d’Arno to sample some of Tuscany’s most historic labels.

Many of Italy’s most charming hill towns are a challenge to reach with public transport. This private day trip offers seamless round-trip transport, giving you time to explore Volterra and San Gimignano at your own pace. Enjoy free time in both towns, with lunch at a Chianti cellar accompanied by a tasting of five different wines.

Savor the flavors of Siena on this delightful food tour, where you’ll explore the culinary treasures of Tuscany. A local guide will lead you through the charming streets, sharing fascinating insights about the region’s food and wine culture. Enjoy tastings of sparkling wine, red wine, gelato, pecorino cheese, cured meats, pizza and traditional sweets like cantucci and panforte. This small group experience ensures an intimate atmosphere, perfect for food lovers looking to immerse themselves in authentic Tuscan cuisine. - 2 - hour walking food tour through Siena’s enchanting streets - Taste a variety of local Tuscan products - Learn about the history and culture of Siena’s culinary scene - Enjoy a small group setting for personalized attention from your guide

Surround yourself with the unrivaled scenery of Valle de Orcia while trying some of its epicurean delights on a private tour from Siena. Begin in the hill town of Montalcino, where you'll sip on locally produced wine at a popular winery. Later, head to the historic center of UNESCO-listed Pienza, where you'll enjoy free time to explore independently. A typical Tuscan lunch, cheese tasting, and hotel pickup are included.

Leave the planning and driving to someone else on this daylong winery tour specializing in Brunello di Montalcino—a wine produced in the vineyards around the town of Montalcino. Visit 2 historic wine cellars in Montalcino and vineyards, have lunch in Montalcino a winery in the hill town of Montalcino itself.

The hills south of Siena are home to some of Tuscany’s most prestigious wines, but navigating the country roads can be a challenge. This private tour includes visits to three historic wineries in Montepulciano and Montalcino for tours, tastings, and lunch. Break up your cellar visits with a stop in Pienza for a pecorino cheese experience.

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.

Siena Historic Center (Siena Centro Storico) is a UNESCO World Heritage Site for its glorious Gothic architecture and rich culture. Join an official, licensed guide who specializes in the city and understands it deeply on this in-depth tour. You'll see the signatures: Piazza del Campo, home of the annual horse race, and Siena Cathedral, with its marble stripes. But you'll also delve further into Siena's medieval neighborhoods and local lifestyles.

Experience the culinary delights of the Chianti region on a half-day tour from Florence to a Tuscan farmhouse. Go in search of truffles with an expert guide and his trained dog during a 1-hour forest walk, then enjoy a traditional lunch that features the fresh truffles accompanied by extra virgin olive oil and Chianti Classico wine. Includes tastings of wine, olive oil, and honey, and a 3-course lunch.

Explore the landscape of Tuscany on a private, full-day cycling tour from Siena. With the full attention of your guide, follow a route along the Via Francigena, an ancient pilgrimage route that once linked Canterbury to Rome and a popular destination for photographers. Rest and refuel after a day of activity with a three-course lunch and wine pairings at a Tuscan vineyard. Hotel pickup and drop-off is included.

Participate in the Tuscan tradition of grape stomping on a private four-hour tour in the Chianti hills. Explore a local vineyard with your private guide and discover the winemaking process. In addition to living out your Italian dreams of crushing grapes with your bare feet, you’ll also enjoy a wine tasting, along with a homemade lunch.

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.

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.

Meet with a local chef-instructor at their home and watch a cooking presentation during this half-day culinary experience in Siena. Learn to prepare a 4-course Italian meal, then enjoy the lunch or dinner that you helped to make with your host. You’ll also sample a selection of red and white wines from Tuscany.

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.

Travel between destinations and visit sights along the way. Stop to visit the medieval fortress of Monteriggioni before spending leisure time in the hill-town of San Gimignano browsing the many stores or savouring the rich cuisine in one of its many restaurants (not included). In the afternoon visit the Chianti town of Greve in Chianti and the picturesque hamlet of  Montefioralle before having your Private driver drop you off at your Florence destination.