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35 results
Best Seller
Discover Cortona, the town made famous by the novel Under the Tuscan Sun, during a prvate walking tour. With a local guide, you’ll hear fun facts about the book and the film as you stroll through the Roman square of Piazza della Repubblica and see landmarks such as Teatro Signorelli and the Palazzo Comunale. Choose between a morning or afternoon tour when you book.
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Cortona Private Guided Tour
2 hours
Free Cancellation
4.8
(25)
from
$306
Per group
If you're looking for a fun and curious way to visit Arezzo, you've come to the right place! With this digital guide created with the support of a local, you will be able to visit all the most important monuments at your own pace. You'll get to know the stories and curiosities of Arezzo! But also you will discover everything about local foods, Italian Aperitivo in authentic local restaurants, and much more!
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Arezzo Walking Tour with Audio and Written Guide by a Local
3 to 4 hours
Free Cancellation
4.5
(12)
from
$7
Price varies by group size
A large theme park dedicated to oil in the heart of Tuscany: this is SuprEvo! Come and discover a completely new, interactive, sensorial, immersive and multimedia museum suitable for all ages. Let yourself be taken on a real journey into the world of extra virgin olive oil from the plant to the table. Discover the ancient tools of the past and be amazed by the engaging interactive installations and the most modern processing technologies. Be inebriated by the aromas and taste of our extra virgin olive oils during the final tasting. Explore our shop full of local excellences, niche products, gastronomy and cosmetic specialties, all based on our extra virgin olive oil. Relax in our garden area among the Tuscan olive trees. We are waiting for you at the foot of the historic village of Monte San Savino, a stone's throw from the exit of the A1 motorway and the E78 highway which connects Arezzo-Siena-Grosseto. Convenient parking adjacent to the museum.
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Oil museum and oil mill in Tuscany: tour and tasting
1 to 2 hours
Free Cancellation
4.8
(17)
from
$24
This e-bike tour around Cortona offers a unique and engaging way to explore Tuscany's stunning landscapes and rich history, featuring stops at Villa Bramasole, Fortezza del Girifalco, and the Basilica of Santa Margherita. The tour provides an immersive cultural experience, with insider insights from a knowledgeable local guide who shares fascinating stories about the area. Perfect for adventure seekers and families with children, the e-bike allows you to navigate Cortona's charming streets and hilly terrain effortlessly, ensuring you experience the best of the region’s natural beauty and architectural wonders. This tour promises memorable encounters with local traditions, offering a deeper connection to the enchanting town of Cortona.
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Half Day Tour by Ebike Around Cortona
2 to 4 hours
Free Cancellation
5.0
(17)
from
$176
Tuscany is one of the most beautiful areas in Italy, with lots of spots to take magical photographs. I will create magical memories through the photos for you to keep forever. Exploring the famous and hidden gems together will be great!
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Tuscany Private Photoshoot Experience
2 hours
Free Cancellation
5.0
(215 Operators)
from
$906
Per group
In the cellar, in Mugliano, we offer the opportunity to taste our organic products combined with cutting boards made with local products in the different locations present, from the "Garden" to the "Barricaia", to the "Wine Rooms". The wine cellar and the garden atmosphere will guarantee the wine enthusiast a special experience.
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Private Tasting of Organic Wines in the Cellar in Mugliano
2 hours
Free Cancellation
4.7
(11)
from
$35
We are going to do a walking tour of the city visiting the most attractive places and views from the city to the valley around. Starting from the beginning of Cortona, we are going to discover the main street, the most important Churches of the town and the Etruscan walls hidden in Cortona. Walking around 3000 years of History together.
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Walking Tour in Cortona
1 hour 30 minutes to 2 hours
Free Cancellation
4.6
(20)
from
$59
Tasting with the senses: a sensory experience that will accompany enthusiasts to the cellar to learn about how our Syrah is born and to savor its peculiarities. An all-round gustatory embrace that leads us to welcome, by reservation, small groups of enthusiasts, from two up to a maximum of eight people.
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Wine Tasting: a SYRAH that makes you fall in love
2 hours
Free Cancellation
from
$35
This is not simply an e-bike tour — it is a curated private experience for travelers who value authenticity, comfort, and true local elegance. Set among the timeless landscapes of the Val di Chiana and Cortona, the journey unfolds at a relaxed pace, allowing you to connect deeply with the territory rather than simply pass through it. Carefully selected panoramic routes avoid crowds, offering breathtaking views, silence, and the true rhythm of Tuscany. Effortless riding is ensured by premium-quality e-bikes with all modern comforts, while your **certified local guide** shares authentic insights, history, and storytelling, offering a genuine perspective of the region with refined attention to detail. Designed for couples, families, and discerning travelers seeking privacy and quality, this is an intimate and elevated way to discover Cortona — immersive, seamless, far removed from ordinary group tours, and tailored for each guest
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Cortona E-Bike Scenic Ride - Private Medieval Countryside tour
3 to 4 hours
Free Cancellation
5.0
(10)
from
$328
Discover the iconic Tuscan town of Cortona (made famous in the book by Frances Mayes "Under The Tuscan Sun"). Located between Florence and Rome, Cortona is rich in Etruscan roots. Cortona is an easy city for everyone to really love. This is because of its atmosphere, its Etruscan past, its delightful medieval old town and also its splendid panoramas.
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Cortona private walking Tour
2 hours 30 minutes
Free Cancellation
5.0
(8)
from
$174
Price varies by group size
Discover Arezzo your way with Ciceru’s self-guided walking tour—audio and text in 7 languages, right on your phone. No app, no hassle—just press play and explore! Walking through the streets of Arezzo is like stepping back in time. Be enchanted by the frescoes of Piero della Francesca, the grandeur and splendour of the Duomo and the wonder of Piazza Grande. Arezzo is the ideal destination for a short trip between nature, art and good food!
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Arezzo Interactive City Tour
2 hours
Free Cancellation
from
$8
Discover the most popular landmarks and best kept secrets of Arezzo on a 2-hour private walking tour. The short jaunt around the historic center is the perfect way to orient yourself to the Tuscan city for future exploring. Highlights include the Parish Church, Piazza Grande, Antique Market, and more. Be sure to ask for recommendations for things to see, do, and eat during the rest of your vacation.
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Arezzo Private Tour with Official Guide
2 hours
Free Cancellation
4.8
(13)
from
$341
Per group
During this 2-hour private tour, your expert guide will lead you through the most important and interesting sites of the beautiful city of Arezzo. You will be able to admire the medieval city and visit its historic shops.
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Arezzo Private walking tour
2 hours
Free Cancellation
5.0
(7)
from
$153
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
I was Born and raised in this magical region od Tuscany, I have key villagers that I have known for many years and you know in Italy is all about relationships...I go above and beyond to take care of my clients. One thing that makes me unique is that I have lived abroad for several years and my spoken English is excellent, this is very important for you to maximize your tour and investment, I comunicate well and I know how to relate to the culture overseas. One other thing is I can sure teach you history but what my clients love about me is the stories and secret I tell them and one thing is for sure...you will laugh and not be the usual boring tour!!!!!
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Val D'Orcia Dreaming!!
4 hours
Free Cancellation
5.0
(19)
from
$231
This is not a classic tour, but an immersive outdoor photography experience led by a professional photographer. We focus on light, composition, and observation, adapting locations and pace to conditions, for a relaxed and authentic way to experience the landscape.
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Private Tuscany Photo session Tour with a Local Photographer
4 hours
Free Cancellation
5.0
(2 Operators)
from
$377
Per group
Discover the rich flavors of Tuscany on this immersive food and wine tour. Begin your day at a family farm in Pienza, renowned for its pecorino cheese, where you'll explore the grounds and enjoy a cheese tasting featuring six varieties, along with homemade accompaniments. Next, savor a delightful three-course lunch paired with Brunello wine in Montalcino, and take a guided tour of the vineyard and aging room. Conclude your adventure in Pienza, heritage UNESCO with a breathtaking view from the town - Explore a family farm in Pienza, the heart of pecorino cheese - Enjoy a tasting of six cheeses with local products and wines - Indulge in a three-course lunch paired with Brunello in Montalcino - Visit the medieval underground city of Montepulciano with a wine tasting
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Pecorino Cheese and Brunello Tasting Tour in Tuscany
9 hours
Free Cancellation
5.0
(277 Operators)
from
$388
Get to know an Italian family by dining with them in their home. Take the stress out of finding a restaurant by booking this private dinner for an intimate experience of Italian cuisine and culture. You and your group will enjoy a delicious three-course meal paired with local wine. Sample delicacies like tiramisu and pasta dishes made using fresh ingredients from their garden.
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Typical Tuscan family dinner in a Villa near Cortona
3 hours 30 minutes
Free Cancellation
3.7
(3)
from
$80
Born from a "dream of love and an idea of beauty", Pienza, the ideal city of the Italian Renaissance, is still today an intact testimony of an illustrious architectural project, commissioned by Pope Pius II Piccolomini and made concrete by the great Florentine architect Bernardo Rossellino. Built in a very limited period of time (1459-1462), the city of Pio is the result of a single master plan marked, by the will of the great humanist pope who gave it the name, by design criteria of harmony and aesthetic perfection still today. clearly visible in the small urban center that was Corsignano in the Middle Ages.
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Private Guided Tour of Pienza on Foot
3 hours
Free Cancellation
4.7
(6)
from
$247
Per group
Explore the enchanting landscapes of Pienza on our e-bike tour, featuring visits to iconic attractions such as the picturesque streets of Pienza and the rolling hills of Val d'Orcia. What makes this tour truly special is the immersive cultural experience it offers, including a cheese-tasting and lunch at one of the area's best cheese farms. Led by knowledgeable local guides, you’ll gain insider insights into the region’s rich history and traditions. Perfect for adventure seekers and families with children, this tour combines stunning scenery with a taste of Tuscany’s renowned culinary heritage, ensuring a memorable and enriching experience for all participants. Enjoy the perfect blend of adventure, culture, and gastronomy in the heart of Tuscany.
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Private Valdorcia Ebike Tour with Tuscan Pecorino Cheese Tasting
4 to 6 hours
Free Cancellation
5.0
(85 Operators)
from
$659
Price varies by group size
Ride through the rolling hills of Pienza’s countryside on a private e-bike experience, discovering charming landscapes and historic villages. After the ride, step by step, visit a working mill where your guide will show the journey from wheat to fresh pasta, sharing local stories, traditions, and insights into Tuscan culture, wine, gastronomy, and the region’s vineyards. Glide through vineyards and golden fields in the heart of UNESCO-listed Val d’Orcia, near Montalcino, enjoying cinematic views, iconic cypress-lined roads, and hidden gems beyond usual sights. With TREK e-bikes and carefully chosen routes, the journey unfolds at a relaxed pace, letting you explore far from crowds. The tour concludes with a light Tuscan lunch in a special setting beside a castle, offering a final gastronomic moment highlighting the region’s culture, flavors, beauty, and local craftsmanship — an immersive Tuscan journey for travelers seeking authenticity, refinement, and true Tuscan elegance.
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PIENZA Countryside E-Bike and Exclusive Mill Journey
4 to 5 hours
Free Cancellation
5.0
(31 Operators)
from
$441
Explore the enchanting city of Arezzo on our private kid-friendly tour designed to captivate the imagination of the whole family! Our adventure begins at the picturesque Piazza Grande, the heart of Arezzo, where you will be amazed by the medieval architecture and the lively atmosphere. Next, we will marvel at the imposing Medici Fortress and the Duomo from the outside. One of the highlights of our tour is the entrance to the Archaeological Museum of Gaius Mecenas and the adjacent Roman Amphitheater. Here, kids will have the chance to uncover the mysteries of ancient Rome through interactive exhibits. Additionally, fans of the beloved movie "La Vita è Bella" will delight in spotting the iconic filming locations throughout the city, adding a touch of cinematic magic to our journey. Join us for an unforgettable 2.5-hour adventure in Arezzo, where history, culture, and fun come together to create lasting memories for the entire family!
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Kid-Friendly Arezzo Private Guided Tour for Families
2 hours 30 minutes
from
$268
Price varies by group size
Tuscany is famed for its scenery and gastronomy, but navigating this rustic region isn’t easy—especially for first-time visitors. Enjoy a deluxe introduction to the rolling Tuscan landscape during this full-day tour of Cortona and Montepulciano. A heart Tuscan lunch is included, plus a guided tour of a historic wine cellar and five exclusive wine tastings.
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Private Art & Wine Tour in Cortona & Montepulciano, with lunch & 2 wine tastings
8 hours
Free Cancellation
5.0
(40 Operators)
from
$306
Price varies by group size
This tour of Pienza stands out by combining clear Renaissance urban design with authentic local culture and scenic landscapes in a compact and accessible format. The route covers key spaces, beginning at Porta al Prato, continuing along Corso Rossellino, and arriving at Piazza Pio II, where architecture, history, and civic identity come together. It then reveals panoramic views from Via dell'Amore, explores quieter backstreets such as Via del Bacio, and incorporates a culinary stop that highlights regional traditions. Throughout the experience, the tour connects built form with natural surroundings, balances major landmarks with intimate spaces, and allows a deeper understanding of how planning, culture, and landscape interact within a unified setting.
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Explore Pienza From Ideal Renaissance City to Tuscan Views
2 hours
from
$235
Price varies by group size
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