Top Siena Private Sightseeing Tours - page 2

Discover the medieval landmarks of Siena and learn about their significance on this private walking tour. During this half-day tour, walk with your guide to highlight attractions around Siena’s historical center, including the Piazza del Campo, Siena Cathedral, and the Basilica di San Domenico. There is a limit of eight travelers on the tour and admission fees to attractions are not included.

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. With this day trip, round-trip transport takes the stress out of visiting Volterra and San Gimignano and gives you time to explore both in a single day. Enjoy seamless pickup and free time in both towns, breaking up your visits with lunch at a Chianti cellar accompanied by a tasting of five different wines.

IMPORTANT: For those who booked in the mixed group mode (and not private group) contact me before you book: at least 5 people booked to go. This tour will take you through the fascinating world of the Palio, the renowned horse race that showcases the Sienese people's pride in their Contrada and their city. We'll stroll along picturesque medieval streets, immersing ourselves in the authenticity and charm that earned Siena a spot on the Unesco World Heritage list. Along the way, we'll encounter significant figures who hail from this city, like Santa Caterina. We'll also delve into secular institutions such as the medieval hospital, Santa Maria della Scala, one of the oldest in Europe, the stunning Cathedral (exterior), and the civic powerhouse, Palazzo Pubblico with the magnificent Piazza del Campo. These iconic Sienese landmarks will grant you a genuine insider's perspective, allowing you to truly know the city and see it through the eyes of a local.

Participate in the Tuscan tradition of grape stomping on a private four-hour tour in the Chianti hills.  Explore a local vinyard with your private guide and discover the wine making 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.

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.

Explore the enchanting Chianti region during your trip from Siena to Florence with our expert local driver, aboard a comfortable Minivan with a large trunk. Immerse yourself in the picturesque Tuscan landscape adorned with rolling hills, vineyards, cypresses, olive trees, and sunflowers. Itinerary: • Private collection at the indicated address. • 1st stop at the Monteriggioni Castle, an invincible castle and ancient outpost built by the Republic of Siena, serving as a strategic control point along the historic Via Francigena (the medieval road once traveled by Crusader soldiers and pilgrims). • 2nd stop in San Gimignano, a true open-air museum, famous worldwide for its valuable medieval towers and typical shops managed by expert craftsmen. If you wish, you can ask our driver to make an additional stop in the cellar to enjoy a typical lunch or a fine wine tasting, with an additional cost based on the extended time. This is our beautiful Tuscany for you !

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.

Experience the best of Tuscany—cheese and wine, of course!—on this private tour from Siena. You’ll admire fabulous scenery in the Val d’Orcia, learn about cheese making during a tour at an organic dairy farm, visit the World Heritage–listed town of Pienza, and enjoy tastings of the region’s renowned Brunello wine during a cellar tour at a winery in the hilltop town of Montalcino. With a privately guided tour, enjoy a more personalized experience.

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.

Opt for a personalized experience of Siena’s top attraction on a private tour of Siena Cathedral (Il Duomo). With just your private guide and party, you’ll discover easy-to-miss details in the cathedral’s interior and benefit from commentary integral to understanding the statues of Michelangelo and the art inside the Chapel of St. John the Baptist. Plus, booking in advance means you’ll save hours of waiting in line with a skip-the-line admission ticket.

Drench yourself in the fabled Tuscan countryside on this private, day-long hiking tour from Siena. Meet your expert guide in Siena and then drive in a comfortable minivan to the trail where you perambulate through verdant vineyards, rustic villages, and over the classic rolling hills of Tuscany. Stop halfway along the hike to indulge in a classic lunch of Tuscan treats and then travel via minivan to the town of San Gimignano, known as the ‘medieval Manhattan’ for its many gothic towers that form a medieval skyline in the 21st century. 

A two hours enchanting walk, discovering Siena most beloved places. Start in front of the Basilica San Domenico, where the relics of St. Catherine are kept, then continues towards her ancient house. Stroll in the characteristic streets and reach the Cathedral. Decide with your guide if you want to enter shortly to see the unique marble floor and artworks by Donatello, Bernini and Michelangelo. Arrive at the famous Piazza del Campo, the main square, where the Palio (horse race), takes place twice a year. Discover this medieval tradtion and understand why it is so important for the Sienese. The Town Hall is an example of Italian architecture, which houses the important city museum. Admire also the Joyfull Fountain and listen to funny anecdotes about the mysterious river called "Diana". At the end of the tour visit our location in an historic palace, Palazzo Scotti, where you can take amazing pictures from our exclusive windows overlooking Piazza del Campo. Relax and enjoy your time!

One of the best wine region of the world with a local driving-guide and wine connoisseur, born and raise in the area.Private tour in a boutique wineries , driving through the most scenic road of Val d'Orcia with chance to stop for the best Tuscan countryside pictures. Day trip in a fully licensed Mercedes van

Capture your memories of Siena on camera during this private photo shoot in the heart of the city. Bookable for a group of up to five people, the experience is led by a professional photographer with knowledge of the best backdrops around the beautiful city of Siena. Bring any additional clothing, shoes, or accessories to make the most of your photo shoot. After the shoot, take home a collection of quality digital images to impress friends and family back home.

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, includes hotel pickup and drop-off, and finishes with a lunch of Tuscan dishes and wine.

Surround yourself with the unrivaled scenery of Valle de Orcia while trying some of its epicurean delights on a private day 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 and cheese tasting also accompany the immersive experience.

On this private walking tour you will explore a city declared a UNESCO World Heritage Site. You will visit its most important places, such as the Siena Cathedral, Piazza del Campo, Torre del Mangi, Fonte Gaia, Market Square. The beautiful city of Siena is famous not only for its beautiful, historic buildings and the picturesque landscape that surrounds it, but also for its cuisine, art, museums, medieval cityscape and, of course, the Palio, the famous horse race held in the city twice a year.

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 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.

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 Mercedes vehicle with a private guide who shares the best of the region.

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.

Immerse yourself in Florentine culinary culture with this private food-focused tour. Spend two hours with your private group—this tour is a great option for families—tasting the top Tuscan treats, such as pastries, snacks, espresso, and more. Visit several local food markets to see where the freshest meat and produce are sold; you can even purchase some with the expert haggling help of your guide.