Siena
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From Siena Best of Tuscany Wines and Lunch in Montepulciano
Experience the highlights of southern Tuscany on a full-day tour from Siena through the rolling landscapes of the Val d’Orcia. Travel in comfort and enjoy a perfect blend of food, wine, history, and scenery. Your first stop is Montepulciano, where you’ll enjoy an authentic Tuscan lunch featuring local cured meats and cheeses, followed by handmade Pici pasta with ragù, or tomato sauce for vegetarian guests. During lunch, take part in a guided tasting of Rosso di Montepulciano and the renowned Nobile di Montepulciano, perfectly paired with the regional cuisine. Continue to Pienza, the “ideal Renaissance city,” and enjoy free time to stroll its picturesque streets, admire panoramic countryside views, and browse artisan food shops. In the afternoon, reach Montalcino, home of the prestigious Brunello di Montalcino. Visit a local winery for a guided tasting and learn about the traditions and aging process behind one of Italy’s most celebrated wines.
4.2(6)
9 Hours
Siena
- Free cancellation
- New
From
$153
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Viator
Signature Brunello di Montalcino Wine Tour from Siena
Brunello di Montalcino, widely celebrated as one of the finest wines in the world, is the ultimate expression of a centuries-old winemaking heritage rooted in the passion, dedication, and traditions of the people of Montalcino. Passed down through generations, this remarkable legacy has transformed Brunello into a true icon of Italian excellence. Nestled atop a picturesque hill in the heart of Tuscany, the enchanting town of Montalcino is the birthplace and sanctuary of this extraordinary wine, crafted exclusively from carefully selected Sangiovese grapes. Surrounded by rolling vineyards, medieval charm, and breathtaking landscapes, Montalcino offers an authentic taste of Tuscany’s timeless beauty. During this unforgettable experience, you will explore the historic town, admire its majestic centuries-old fortress, and visit some of the region’s most renowned wineries, celebrated by prestigious international wine publications. .
4.0(66)
5h 30m
Siena
- Free cancellation
- Likely to sell out
From
$141
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Viator
Private Montalcino and Pienza Tour from Siena
Travelling through the Val d’Orcia is an unforgettable experience. Your eyes will be dazzled by the colours and harmony of this landscape, unsurprisingly listed as a UNESCO World Heritage Site. This tour is designed to let you discover the most iconic and photographed corner of Tuscany, with its enchanted scenery and tree-lined avenues. We will explore the legendary road that stretches from Montalcino to Pienza, considered one of the most beautiful routes in Italy. Guests will enjoy one hour of free time in Montalcino to stroll, shop, or simply soak in the atmosphere, and one hour of free time in Pienza, the “ideal Renaissance city.” Here, you will also enjoy a cheese tasting in a traditional local shop, discovering the flavours of the famous Pecorino di Pienza. Pick-up and drop-off from your hotel or apartment in Siena are included.
4.0(3)
6 Hours
Siena
- Free cancellation
- Private tour
From
$555
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Viator
Private E-bike tour in Chianti from Siena
Unsurprisingly, Tuscany is a favorite destination for cyclists: the views, the scent of the trees along the avenues, and the typical colors of the hills make this region unique for both tourists and locals. We will pick you up and return you to your hotel or apartment in Siena and guide you along a variety of cycling routes, from easy rides to challenging climbs for cycling enthusiasts. During the ride, you can stop freely to rest or admire the stunning landscapes of the Tuscan hills. At the end of the tour, a well-deserved full lunch awaits, featuring traditional Tuscan dishes paired with three selected wines. Your only task is to relax and savor the flavors while surrounded by one of the most beautiful areas in the world.
4.0(1)
6 Hours
Siena
- Free cancellation
- Private tour
From
$453
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Viator
Siena: Val d’Orcia Wine Tour with Lunch & Brunello
Discover the enchanting allure of Tuscany's most renowned winery region, where every step through the picturesque landscapes of Pienza and Montepulciano is a delightful fusion of rich history and flourishing countryside. Allow yourself to be mesmerized by the sensational beauty that surrounds you, as you savor the exquisite, locally produced wines, each sip a proof of the unforgettable memories you'll create during your trip.
3.9(101)
10 Hours - 11 Hours
Siena
- Free cancellation
From
$153
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Viator
Best Of Tuscany In 1 Day From Livorno: Siena, Monteriggioni, San Gimignano
IF YOU ONLY HAVE ONE DAY IN LIVORNO, THAT'S THE BEST TOUR YOU CAN DO, OUR VEHICLES REACH ANY RESTRICTED PLACE AND WE TAKE OUR CUSTOMERS INSIDE THE HISTORICAL CITY CENTER
7 Hours - 9 Hours
Siena
- Free cancellation
- Private tour
From
$309
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Viator
Full-Day Private Montalcino & Montepulciano Wine Tour from Siena
Embark on this Full-Day Private Montalcino and Montepulciano Wine Tour and indulge your senses in the heart of Italy's renowned wine country! Your day begins with a personalized, chauffeur-driven journey through the stunning Tuscan countryside, setting the scene for an unforgettable adventure. As you traverse the picturesque landscape, you will visit two prestigious wineries - in Montalcino and Montepulciano - each with its own unique charm and distinctive wines. Expert sommeliers and winemakers will guide you through tastings of exceptional Tuscan varietals, sharing their deep knowledge and passion for winemaking. Enjoy a delightful Tuscan lunch at a selected vineyard, paired with local specialties, perfectly complementing the wines you've tasted throughout the day. Don't miss this opportunity to create lasting memories on this Private Montalcino and Montepulciano Wine Tour, escaping the hustle of Siena for a day of indulgence and appreciation of Italy's vinicultural heritage.
7 Hours
Siena
- Free cancellation
- Private tour
From
$1,010
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Viator
Private Taste of Tuscany Tour
Tour with a passionate Toscana lover, sommelier guide expert on Brunello. Discover Tuscany with local expert out of beaten path.
9 Hours
Siena
- Free cancellation
- Private tour
From
$392
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Viator
Highlights of Florence Day Tour from Siena
Explore Florence’s artistic heritage on this comprehensive 11-hour tour from Siena. Visit the iconic Accademia Gallery to see Michelangelo's "David," followed by a guided walking tour through the historical city center, showcasing the magnificent Florence Cathedral and the famous Ponte Vecchio. Conclude your journey at the Uffizi Gallery, home to masterpieces by Botticelli and da Vinci. With expert guidance and insights into the Renaissance, this tour offers a rich cultural experience filled with history and art appreciation. - Full-day guided tour from Siena to Florence, lasting 11 hours - Includes entry to Accademia Gallery, Cathedral, and Uffizi Gallery - Small group size with a maximum of 14 participants - Comfortable walking required; headphones provided for larger groups
11 Hours
Siena
From
$231
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Viator
Private Hiking in Chianti
Chianti and its ancient roads reconnect with the spiritual, archaeological, and rural traditions of this land. There are few places in the world like Chianti, where the natural landscape merges with millenary history. Several footpaths lead you along routes dating back to the Middle Ages, which left deep and well-preserved traces among these hills. Together with a local hiking guide, you will have the chance to walk along these age-old paths, once considered strategic routes that, for centuries, attracted pilgrims to this sublime territory. This experience is one of the best ways to enjoy Tuscany’s landscape in full harmony with nature. Simply slow down and immerse yourself in it. Different hiking levels and routes are available, making this outdoor activity suitable for everyone. To complete the experience, you will enjoy a typical Tuscan lunch paired with wine. The meeting point is at our office in Castellina in Chianti.
5 Hours
Siena
- Free cancellation
- Private tour
From
$292
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Viator
Private Tuscan tour with Love
Being able to visit Tuscany with a local person, your tour will be even more unique, passionate and full of stories and anecdotes. Furthermore, being also an expert sommelier each of your questions will be an exchange of ideas and insights.
7 Hours
Siena
- Free cancellation
- Private tour
From
$238
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Viator
Chianti Classico Ebike Experience Tour and Wine Tasting
The journey takes place mainly along white gravel country / dirt roads and as much as possible away from traffic. During the tour, travelers will be accompanied by an outdoor environmental guide who will indicate the route, presenting the visited area. A tour that explores the magnificent hills of Chianti Classico, among history, nature, and postcard-perfect landscapes. Cycling along old country roads, we’ll have the chance to visit some of the most famous and suggestive castles and villages in the area. And obviously, we couldn’t miss a Tuscan lunch accompanied by a tasting of Chianti Classico.
4 Hours - 6 Hours
Siena
- Free cancellation
- Private tour
From
$642
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Viator
"Ramble Through The Rolling Hills Of Chianti" with lunch and 2 wine tastings
A full day trip traveling through the rolling hills of Chianti, among avenues of cypress trees, medieval villages, fields of sunflowers and legends. Tasting of the best Chianti wines with a delicious lunch in a family-run farm. This is the best private tour for couples, families or small groups of friends: Itinerary: • In the morning meeting with the driver at your hotel or another place of your choice (B&B or private apartment) • We will cross the rolling hills of Chianti, among olive groves, cypresses and vineyards. • We will visit the magnificent Towers of San Gimignano and the historic center. • For lunch we will move to a real Tuscan farm, to understand the secrets of wine production and enjoy a lunch with typical Tuscan foods and 6 tastings of local wines. • After lunch we will visit the invincible Monteriggioni Castle • On the way back we will have a second wine tasting at a local winery, which produces its Chianti Classico wine following the old way. Check out "What to Expect"
8 Hours
Siena
- Free cancellation
- Private tour
From
$297
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Viator
Private Art & Wine Tour in Cortona & Montepulciano, with lunch & 2 wine tastings
Follow us inside the rolling Tuscan landscape, amidst wine, art, Middle Ages, Renaissance and history visiting Cortona and "the secret underground cellars" of Montepulciano. You will taste the best wines of our Region and meal with a typical tuscan lunch. The beautiful and untouched landscape is the absolute protagonist in Val d' Orcia. This area of Tuscany boasts of endless rolling hills covered with grain or sunflowers, a rich green valley which encompasses the Orcia river. First we will explore the South of Tuscany and visit the Medieval town of Cortona. Later we'll visit the "Underground Wonders" of Montepulciano (The Historic Cellars of the city) where you will find gigantic oak barrels, in which the famous Vino Nobile di Montepulciano DOCG “rest”. In Montepulciano we'll have also a first and a second wine tasting experience in two differerent cellars, with a delicious tuscan lunch. (Pecorino cheese, bruschettas, ham, cold cuts, always with the best wines of our Region).
8 Hours
Siena
- Free cancellation
- Private tour
From
$309
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Viator
Siena to Florence Uffizi Gallery Guided Tour
Explore Florence's artistic treasures with a guided tour of the Uffizi Gallery on this day trip from Siena. Travel through the picturesque Tuscan countryside by train and marvel at masterpieces by renowned artists like Botticelli, Leonardo da Vinci, and Michelangelo. Your expert guide will share captivating stories behind each artwork, enriching your understanding of the Renaissance. After the tour, enjoy free time to further explore the gallery or the enchanting city of Florence at your leisure. - Duration: 7 hours and 30 minutes, including train travel - Guided tour of Uffizi Gallery with skip-the-line entry - Free time in Florence to explore at your own pace - Includes round-trip train tickets; van pick-up available for groups of 6 or more for an additional 20€.
7h 30m
Siena
- Likely to sell out
From
$162
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Viator
Siena, San Gimignano and Monteriggioni Wine Tasting and Tour
Uncover the soul of Tuscany on this 8-hour private tour through three of its most iconic towns: Siena, San Gimignano, and Monteriggioni. Travel in style aboard a luxury NCC van, accompanied by a local guide who brings the history and culture to life. Siena: Stroll through the medieval streets of this UNESCO World Heritage city, marvel at the stunning Piazza del Campo, and visit the inspiring Cathedral. San Gimignano: This hilltop town will enchant you with its skyline of towers and artisan shops. Enjoy free time to explore the village. Monteriggioni: Step back in time in this perfectly preserved medieval village nestled among olive groves and vineyards. Its fortress walls and quiet charm will transport you to another era. No Tuscan journey is complete without indulging in its world-renowned flavors. You’ll be treated to an exclusive wine tasting experience at a local winery, sampling celebrated Chianti wines paired with regional delicacies like pecorino cheese, and cured meats.
8 Hours
Siena
- Free cancellation
- Private tour
From
$1,189
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Viator
Exclusive Saturnia and City of Tuff
This is an exclusive tour for you and your loved ones and, comfortably seated in the car you can enjoy the beauty of the places. In fact, we will see fascinating landscapes that are a little lost in time. In fact, the Maremma, in addition to being considered the new Eldorado for its powerful and elegant wines, offers wild and splendid landscapes. The typical local cuisine is Mediterranean. The people of Maremma are the most outspoken in Italy. Furthermore, the story I told will take us back in time to the Etruscans. As our ancestral ancestors did, you can, if you wish, take a thermal bath in the Saturnia waterfalls. New shower and toilet rooms available.
8 Hours
Siena
- Free cancellation
- Private tour
From
$457
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Viator
Brunello Harvest Experience in Tuscany
Our exclusive experience invites you to uncover the secrets of the wine harvest — from learning traditional picking techniques to tasting wines straight from the barrel. Conclude your day with a harvest lunch perfectly paired with estate wines, and finish on a sweet note with dessert accompanied by freshly pressed grape juice.
8 Hours
Siena
- Free cancellation
From
$355
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Viator
From Siena: Pisa and San Gimignano Day Trip
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.
8 Hours
Siena
- Free cancellation
- New
From
$94
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Viator
At Your Own Pace: Discovering Siena & Tuscany
Discover Siena's perfectly preserved medieval splendor with our self-guided audio tour app, allowing you to explore this Tuscan jewel at your own pace. Begin at the magnificent Piazza del Campo, the shell-shaped square that hosts the legendary Palio horse race and remains the heart of Sienese civic life after seven centuries. Marvel at the soaring Torre del Mangia and the Gothic grandeur of the Palazzo Pubblico, then ascend to the heavenly Duomo where Pisano's pulpit and the Piccolomini Library showcase Renaissance mastery. Wander through the contrade neighborhoods where medieval rivalries still define local identity, their fountains, flags, and parish churches marking territories unchanged for centuries. Discover the Pinacoteca's golden altarpieces and the Basilica of San Domenico where St. Catherine's head is reverently preserved, then lose yourself in the winding vicoli that reveal unexpected piazzas and artisan workshops.
9h 30m
Siena
- Free cancellation
- Private tour
- Special offer
From
$1
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Viator
From Siena to Florence & San Gimignano - Private Tour by Minivan
The tour starts with a ride by air-conditioned minivan and an English-speaking driver from Siena to Florence, about 1 hoiur by Motorway . The first stop arriving in Florence is Piazzale Michelangelo to take in the beautiful view of the city. At 09,30 departure for a group walking tour of the City with a Tour Leader. In about 2,30 H you will walk in front of the principal Attractions: Duomo Square, Signoria Square and Uffizi Museum, Ponte Vecchio and Pitti Palace. At the end you will have an optional lunch or free time before departure to reach San Gimignano. Free time to walk around the Medieval streets of San Gimignano - about 1 hour, before leaving to come back to Siena
9 Hours
Siena
- Free cancellation
- Private tour
From
$416
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Viator
Florence Duomo Cathedral Guided Tour from Siena
Visit the iconic Santa Maria del Fiore Cathedral in Florence on this guided tour from Siena. With a licensed guide, explore the stunning architecture and rich history of one of Italy's most famous landmarks. Receive a 3-day valid ticket to visit the Baptistery, the Opera del Duomo Museum, and the ancient basilica of Santa Reparata independently. - 1-hour guided tour of the Florence Duomo Cathedral - Round-trip train tickets from Siena to Florence included - Free time to explore Florence after the tour
7h 40m
Siena
- Free cancellation
- Likely to sell out
From
$88
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Viator
Siena & San Gimignano Port Tour (Driver Only/Self Touring)
This private shore excursion has been designed for those who have already visited the famous cities of Florence and Pisa, and are interested in exploring other beautiful areas of Tuscany rich in charm, history, and culture. Siena’s history extends as far back as Ancient Rome as a Roman colony. For centuries since, Siena grew into a prosperous significant medieval town, a rightful rival to the neighboring Florence. One of the historic traditions that date back to ancient tribal systems retained in Siena, is the town’s 17 districts (contrade)- each with its own coat of arm and strong identity. Every July 2 and August 16 the Palio is held in Piazza del Campo. San Gimignano has a distinctive skyline which has earned it its nickname "Medieval Manhattan" of Tuscany. During the Middle Ages towers were a symbol of power, therefore prestigious families competed in building the tallest and greatest towers to establish their relevance in the community.
9h 30m
Siena
- Free cancellation
- Private tour
From
$1,664
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Viator
MONTERIGGIONI: Private Luxury E-Bike Tour with Lunch&Wine Pairing
Discover the medieval charm of Monteriggioni on a private luxury e-bike experience, ride scenic Tuscan roads, enjoy a curated lunch paired with fine wines, and end with an exclusive winery visit scheduled just for your group. More than a bike tour, this is a curated Tuscan experience for couples, families, and small groups seeking an authentic, relaxed, and elevated way to explore. Led by a professional local cycling guide, far from crowded routes, your ride is tailored to your pace, allowing you to fully enjoy the landscape and timeless atmosphere. Premium e-bikes ensure a smooth, accessible ride with minimal effort. The experience concludes with a refined lunch and wine pairing in a carefully selected winery, featuring a private dining room reserved for you and a private cellar visit without overlapping guests. A seamless Tuscan day blending cycling, culture, landscape, and fine wine — designed for comfort, privacy, and authenticity.
4 Hours - 5 Hours
Siena
- Free cancellation
- Private tour
- New
From
$531
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