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24 results
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Kick off your day with a comfortable ride through the stunning Tuscan countryside. First, we’ll arrive in Siena, one of Tuscany’s most beautiful towns. Explore Piazza del Campo, famous for the Palio di Siena horse race, admire the breathtaking Duomo (Cathedral), and wander through the charming, narrow streets of the historic center. Wine Tasting & Light Lunch Next, we’ll head to a renowned winery for a light lunch paired with an amazing wine tasting experience. A sommelier will guide you through five exceptional wines, plus an olive oil tasting. After lunch, we’ll continue our journey with a spectacular drive through the rolling Vernaccia di San Gimignano vineyards, home to Tuscany’s most famous white wine. Stop in San Gimignano you’ll have free time to explore this medieval gem, known for its 14 towers dating back to the 13th century. The town’s atmosphere will transport you back to the Middle Ages! And of course, you can’t miss the world’s best gelato at Gelateria Dondoli.
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Private Tour Siena San Gimignano and Chianti from Cortona
8 to 9 hours
Free Cancellation
5.0
(4)
from
$482
Price varies by group size
Likely to Sell Out
Tuscany produces one of Italy’s flagship wines: Brunello di Montalcino. Exploring the countryside where these wines are produced, however, means navigating confusing rural roads and searching for remote wineries. With this wine tour, leave the hassle of driving to the experts and instead enjoy a stress-free day of wine tasting and sightseeing. Visit two winereis and a cellar.
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Brunello and Montepulciano Wine Tour from Cortona
6 to 8 hours
Free Cancellation
4.6
(24)
from
$587
Price varies by group size
Likely to Sell Out
When you’re in Arezzo, treat yourself to an immersive culinary experience, learning to create authentic pasta with a local. Taking place in your host’s personal home, this small-group cooking class covers the preparation of two pasta dishes as well as a classic tiramisu. As you cook, you’ll hear about Tuscan cuisine from your host, a member of the Cesarine community of passionate Italian home cooks.
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Share your Pasta Love: Small group Pasta and Tiramisu class in Arezzo
3 hours
Free Cancellation
5.0
(11)
from
$159
Discover the secrets to creating the perfect pizza and tiramisu during a private cooking class in Siena. Set in a local's home, your host will teach you their special techniques passed on from previous generations. No culinary experience is necessary, and families with children are welcome. After the class, you’re ready to wow your friends and family back home or just prepare an extra large portion for yourself.
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Authentic Wood-Fired Pizza Class near Siena
3 hours
Free Cancellation
5.0
(57 Operators)
from
$175
Likely to Sell Out
Spend a full day visiting the family-run wineries and olive oil producers that surround Cortona—hidden gems that are tricky to find without a local connection. A guide drives you and your group between estates where you taste wines and extra-virgin olive oil, tour vineyards and aging rooms, and speak directly with the people who make them.
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Wine and olive oil tastings with the locals
8 hours
Free Cancellation
5.0
(64)
from
$247
Likely to Sell Out
Take a break in the countryside with a private tour that includes visits to boutique wineries and a sustainable, family run cheese farm. Enjoy a full day dedicated to wine and cheese, exploring the heart of Tuscany. Drive through the Val d'Orcia, a UNESCO World Heritage Site, and savor some of the region’s finest red wines, including Vino Nobile di Montepulciano and Brunello di Montalcino. Stroll through the medieval squares of Pienza and sample authentic Tuscan cheeses at a historic estate, featuring one of the most breathtaking terraces overlooking the Orcia Valley.
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Private tour Wine and cheese a perfect combinations val 'Orcia
8 to 9 hours
Free Cancellation
4.5
(6)
from
$541
Price varies by group size
Likely to Sell Out
Rent a car with driver and face your journey with serenity, whatever the destination. Tuscany Luxury Tours NCC offers a rental service with driver able to satisfy any transfer need. Whether it's work or holidays, Tuscany Luxury Tours NCC offers its customers a modern and comfortable fleet of vehicles with expert and professional drivers able to satisfy any type of request.
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Rent with driver
1 hour to 1 day
Free Cancellation
5.0
(27)
from
$118
Price varies by group size
Likely to Sell Out
Swap the cobbled streets of Cortona for its surrounding countryside on this small-group e-bike tour—and cover plenty of ground with ease. Follow the winding Tuscan roads through the Val di Chiana with views of vineyards and cypress-lined hills. A local guide leads the way and adjusts the route based on the group, stopping at a boutique winery where an optional wine tasting and lunch are available.
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Cortona - eBike tour and wine tasting in the Val di Chiana [+40€]
5 to 6 hours
Free Cancellation
4.9
(42)
from
$220
Likely to Sell Out
You can't visit Italy without trying at least one pasta dish... So, we'll teach you two! Learn how to roll 'sfoglia' (fresh pasta) by hand and how to prepare 2 simple different kinds of pasta from scratch with your local host. As the icing on the cake, you will learn to prepare also the iconic Tiramisu. Share your passion for the Italian cuisine as you make new friends in this hands-on cooking class. It's a great way to truly experience Italian culture. This experience is held by Cesarine, the oldest Italy’s network of home cooks available in more than 500 cities all over the country. Cesarine stands for "home cook", they are passionate and welcoming local hosts that open the doors of their own homes to curious travellers for immersive culinary experiences. The Cesarine serve only local specialties from their family cookbooks to tell the great story of their traditional regional cuisine.
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Traditional Tuscan Pasta & Tiramisu Masterclass in Arezzo
3 hours
Free Cancellation
4.8
(6)
from
$175
Likely to Sell Out
Put a professional touch on your Tuscany vacation photos, and book a day-long photo tour with an award-winning photographer at your side. Created and led by the talented Marco Bulgarelli, the tour takes you to impressive vantage points around Val d'Orcia and the Siena province where gorgeous shots are guaranteed every time.
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Private Tuscany Photo Tours
8 hours
Free Cancellation
4.9
(18)
from
$353
Price varies by group size
Likely to Sell Out
Cortona's cobblestone streets and hilltop position make it a rewarding place to explore—but the elevation can make getting around on a traditional bike exhausting. This small-group tour covers the town's most scenic routes and historic stops with the help of a powerful, pedal assisted eBike. Hop off to explore the Basilica of Santa Margherita and the Villa Bramasole, famously featured in the film Under the Tuscan Sun.
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Cortona - Easy guided eBike tour around the Etruscan City.
2 to 3 hours
Free Cancellation
5.0
(63)
from
$174
Likely to Sell Out
Explore the exquisite wines of Tuscany with the Brunello di Montalcino Wine Tour from Cortona. This half-day adventure takes you to the renowned Wine Resort Colsereno, where you’ll enjoy wine tastings and a delicious lunch featuring local flavors. Relax on a comfortable ride in an air-conditioned vehicle while learning about the rich history and craftsmanship of Brunello wines from expert guides. Perfect for wine lovers, this small-group tour ensures a personalized experience and can accommodate dietary preferences.
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From Cortona Brunello di Montalcino Wine Tour with Lunch
4 hours
Free Cancellation
5.0
(1)
from
$215
Likely to Sell Out
This Cortona cooking experience is perfect for food lovers, curious travelers, and anyone looking to connect with authentic Italian food and culture. Join a local in her charming Tuscan farmhouse for a 1.5-hour hands-on cooking class featuring traditional Italian recipes. Begin your experience with a welcome aperitif and a scenic stroll around her beautiful countryside home. Learn to make classic dishes like handmade pasta or pizza, and beloved desserts such as tiramisu or cantucci. Learn family recipes and expert tips passed down through generations of Italian cooks. An immersive culinary journey through Tuscany, filled with local ingredients, heartfelt tradition, and authentic flavors.
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Cortona Cooking Class: Make Fresh Pasta or Pizza with Giada
2 hours
Free Cancellation
5.0
(2)
from
$179
Price varies by group size
Likely to Sell Out
During our visit we will discover everything about the past of this wonderful town, known as the "ideal city". We will talk about its origins and the way it was turned into a beautiful Renaissance city, mostly thanks to the efforts of the Pope Pius II. Not only will we discover every secret (Is the shape of the main square trying to send a hidden message? What happens twice a year?), but we will also go and look for the best corners and panoramic spots where to take great pictures. Last but not least, we won't leave Pienza without tasting its typical and super tasty Pecorino cheese! IMPORTANT: the tour schedule in the system is 10am and 15pm, but the tour times can be arranged directly with the guide upon request.
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Private Walking Tour of Pienza with Licensed Tour Guide
2 hours
Free Cancellation
5.0
(4)
from
$146
Price varies by group size
Likely to Sell Out
Don’t just head out for aperitivo in Arezzo, learn to create the classic pre-dinner drink and snack yourself with this private aperitivo experience. Taking place in your local host’s private home, the experience gives you a bite-size taste of local Arezzo culture, with an aperitivo prepared with regional delicacies, local wine, and warm Italian hospitality.
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Pasta and Tiramisu Cooking Class in Tuscany near Arezzo
3 hours
Free Cancellation
5.0
(1)
from
$175
Likely to Sell Out
Immerse yourself in Italian culinary traditions with a hands-on pasta and tiramisu cooking class. Learn how to roll fresh pasta ('sfoglia') by hand and prepare two iconic pasta dishes from scratch. Plus, master the art of making Italy’s beloved dessert, tiramisu. Join a small group and share your love for Italian cuisine while connecting with fellow food enthusiasts. The experience begins with an Italian Aperitivo to kickstart your cooking adventure. Hosted by Cesarine, Italy's oldest network of home cooks, this class offers a unique opportunity to learn from passionate local hosts who share authentic regional specialties passed down through generations. A perfect way to experience the heart of Italian culture!
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Pasta and Tiramisu Cooking Class in Tuscany near Siena
3 hours
Free Cancellation
5.0
(57 Operators)
from
$159
Likely to Sell Out
Savor the flavors of Arezzo. On a locally guided tour of the city's best food, you'll be led to the best artisan shops, tasting delicious fare along the way. Sightsee and get to know the city on foot while sampling fresh ingredients. This small group tour gives you the chance to experience authentic Italian gastronomy as you familiarize yourself with the charming town of Arezzo.
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Small-group Street food tour in Arezzo
3 hours
Free Cancellation
4.5
(17 Operators)
from
$105
Likely to Sell Out
Immerse yourself in a private dining experience at a local's home, enjoy an exclusive cooking demo and taste authentic recipes treasured in family cookbooks passed down by real Italian Mammas. Feel the warmth of Italian hospitality as you connect with local people. Enjoy a 4-course menu including starter, pasta, main course with side dish, dessert with drinks included (water, selection of red and white wines from regional cellars and coffee). This experience is held by Cesarine: Italy’s oldest network of 1000+ home cooks all over the country in more than 500 cities. They are passionate and welcoming hosts that open the doors of their own homes to curious travellers for immersive culinary experiences.
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Lunch or dinner and cooking demo at a local home in Pienza
2 hours 30 minutes
Free Cancellation
5.0
(134 Operators)
from
$100
Likely to Sell Out
Enjoy a private dining experience at a local's home in Passignano sul Trasimeno, along with a hands-on cooking class. Learn how to make a 4-course menu including a starter, pasta, a main course with side dish, and dessert, served along with a selection of red and white wines from regional cellars and coffee.
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Dining Experience at a local's Home in Passignano sul Trasimeno
2 hours 30 minutes
Free Cancellation
from
$100
Likely to Sell Out
This exclusive private wine tour takes you from Cortona to the heart of the Chianti Classico Black Rooster, an iconic wine area rarely reached from this part of Tuscany. Travel in comfort with a local professional driver and enjoy a personalized journey through one of Tuscany’s most celebrated wine landscapes. The experience includes visits to three carefully selected Chianti Classico DOCG wineries, where you will enjoy guided cellar tours and premium wine tastings. Each winery offers a different perspective on the Black Rooster tradition, allowing you to discover the diversity, history, and craftsmanship behind authentic Chianti Classico wines. A traditional Tuscan lunch is included, perfectly paired with local wines and seasonal products, for a complete and immersive Chianti experience. Designed for travelers seeking authenticity, privacy, and high-quality wine experiences, this tour combines culture, scenery, and exceptional flavors in a relaxed and exclusive setting.
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Chianti Classico Black Rooster Private Wine Tour from Cortona
8 to 9 hours
Free Cancellation
5.0
(43 Operators)
from
$553
Price varies by group size
Likely to Sell Out
Pick up e Drop off from Pienza .Join us for a hands-on cooking class where you’ll master the techniques of preparing authentic Tuscan pasta, all while enjoying a delightful meal paired with our exquisite wines, including Brunello di Montalcino.You’ll have the chance to explore our historic cellar and indulge in a feast featuring a selection of mixed Tuscan appetizers, homemade pasta, and dessert, all accompanied by three organic wines, including Brunello and Rosso di Montalcino.As part of the tasting experience, you’ll even have the opportunity to sample wine straight from the wooden barrel!Feel free to capture the moments and share your culinary adventure on your social media!
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From Pienza Pasta Class with Brunello Wine Tasting and Lunch
2 hours 30 minutes
Free Cancellation
5.0
(7 Operators)
from
$328
Likely to Sell Out
Explore Italy’s culinary heritage and immerse yourself in the vibrant local market of Pienza, then enjoy an authentic hands-on cooking class with a local cook. Your host will explain how to select the best ingredients based on the seasons while at the market. Following that, learn how to make a pasta dish that’s traditional to Pienza and classic tiramisu. Enjoy the meal with local wines.
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Small Group Market tour and Cooking class in Pienza
5 hours
Free Cancellation
5.0
(1)
from
$116
Likely to Sell Out
Enjoy a welcome aperitif in a Tuscan farmhouse garden, then get hands-on making iconic local pasta dishes, from stuffed tortelli to tagliatelle and pici, discovering authentic Tuscan flavors in the countryside
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Cook Pasta Like a Local in Val di Chiana
3 hours
Free Cancellation
5.0
(1)
from
$163
Likely to Sell Out
Explore the exquisite wines of Tuscany on the Brunello di Montalcino Wine Tour from Pienza. This half-day adventure takes you to the renowned Wine Resort Colsereno, where you’ll indulge in wine tastings and a delicious lunch featuring local flavors. Enjoy a comfortable ride in an air-conditioned vehicle while learning about the rich history and craftsmanship of Brunello wines from expert guides. Perfect for wine lovers, this small group tour ensures a personalized experience, accommodating dietary preferences.
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Brunello di Montalcino Wine Tour from Pienza with Lunch
4 hours
Free Cancellation
5.0
(7 Operators)
from
$175
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