Arezzo
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Viator
Brunello Wine Tour and Val D'Orcia Landscape
I was born and raised here in Tuscany and I know the best wine maker but the key is small wineries with high quality where they will call you by name and not by number.... Private experience for real. My English is quite good which will maximize your experience and that is very important. Also this tour as all of my tour are fully CUSTOMIZABLE..... is your tour..
5.0(95)
4 Hours
Arezzo
- Free cancellation
- Private tour
From
$262
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Viator
Private Tour: Montalcino Wine Tasting Experience
Private guided wine tour and tasting in Montalcino, Tuscany to discover Brunello and the most amazing wine estates and cellars that give birth to this extraordinary wine.
5.0(63)
8 Hours
Arezzo
- Free cancellation
- Private tour
From
$416
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Viator
Montepulciano Vineyards Wine Tour with 3 Estates Visit
Embark on a private, guided journey through the picturesque vineyards and historic cellars of Montepulciano, the home of the celebrated Vino Nobile di Montepulciano. This exclusive tour offers an immersive experience that captures the essence of Tuscan winemaking tradition. What to Expect Guided Visits to three renowned Wine Estates: Explore estates with centuries of winemaking expertise. Learn about the intricate process of crafting Vino Nobile di Montepulciano from passionate experts. Exclusive Wine Tastings: Savor a curated selection of exquisite wines at each estate. Lunch at the Second Estate: Indulge in a traditional Tuscan meal paired with exceptional wines. This intimate experience blends Tuscan culture, history, and gastronomy into a memorable day amidst the stunning countryside of Montepulciano. Whether you're a wine enthusiast or simply looking to enjoy a luxurious day in Tuscany, this tour is the perfect choice.
5.0(22)
7 Hours - 8 Hours
Arezzo
- Private tour
From
$416
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Viator
Val D'Orcia Dreaming!!
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!!!!!
5.0(18)
4 Hours
Arezzo
- Free cancellation
- Private tour
From
$234
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Viator
Cortona E-Bike Scenic Ride - Private Medieval Countryside tour
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
5.0(10)
3 Hours - 4 Hours
Arezzo
- Free cancellation
- Private tour
From
$332
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Viator
Cortona private walking Tour
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.
5.0(8)
2h 30m
Arezzo
- Free cancellation
- Private tour
From
$176
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Viator
Arezzo Private walking tour
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.
5.0(6)
2 Hours
Arezzo
- Free cancellation
- Private tour
From
$155
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Viator
Private Walking Tour of Pienza with Licensed Tour Guide
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.
5.0(4)
2 Hours
Arezzo
- Free cancellation
- Private tour
- Likely to sell out
From
$137
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Viator
Private Tour Siena San Gimignano and Chianti from Cortona
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.
5.0(4)
8 Hours - 9 Hours
Arezzo
- Free cancellation
- Private tour
- Likely to sell out
From
$487
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Viator
Cortona Private Hero Experience Luxury E-Bike Lunch and Wine Tour
Discover Cortona on a private, fully curated luxury e-bike journey blending breathtaking Tuscan landscapes, culture,and authentic local experiences.Ride premium e-bikes along serene, scenic routes with a professional local expert who brings the region to life with stories, history, and insider knowledge far from crowded paths.Pause to admire charming corners and hidden views, feeling the rhythm of the rolling hills and medieval streets. The journey culminates at a refined, private winery where the owner welcomes you for a curated Tuscan lunch with no overlapping. Savor seasonal appetizers highlighting the finest local products, a thoughtfully prepared first course, dessert or gelato and coffee,paired with at least three glasses of Syrah from different vintages to reveal depth and character.Designed for couples, families, and discerning travelers, this is a seamless, immersive, and unforgettable way to experience Cortona—where every detail is crafted for comfort, privacy, and discovery.
5.0(3)
5 Hours - 6 Hours
Arezzo
- Private tour
- New
From
$434
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Viator
Val d'Orcia: eBike Tour Virtual-guided
Once the tour is booked, you can come to our rental point to collect the bikes, so you can start with our virtual guide, which will accompany you step by step. Start: a smooth hilly loop of about 25 km (2.5-3 hours including stops), with a rolling profile of short climbs and flowing descents on scenic secondary roads. Surface and riding: mixed route on asphalt and white roads. Highlights: pass through the Gladiator filming area and stops near Bagno Vignoni and San Quirico d Orcia, with a very scenic return to Pienza on white roads. Useful notes: this is a tour to enjoy at a steady pace, ideal for a relaxed half day. In the quieter sections, it is a good idea to bring water, a snack, and a charged phone to enjoy the ride with peace of mind.
5.0(3)
2 Hours - 3 Hours
Arezzo
- Free cancellation
- Private tour
From
$107
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Viator
Cortona Private walking Tour under the Tuscan sun
Everyone loves Cortona, because it is an authentic and fascinating place. Village of Etruscan origin with stone houses, which stands in the center of an impeccable countryside, hand-sculpted in every corner, pampered by man in every detail. All around there are cypresses, vineyards, olive trees, oaks and fruit trees. Frances Mayes, the very famous writer, made Cortona famous in the eyes of the world thanks to her novel "Under the Tuscan Sun" and the beautiful film based on her novel. So what will we see in this treasure chest of wonders? 1) The Palace of the Captain of the People and the Town Hall, buildings from the medieval era 2) Piazza Signorelli, which owes its name to the famous Renaissance painter who was a friend of Leonardo da Vinci. 3) Piazza del Duomo with its fourteenth-century gothic cathedral 4) the Girifalco Fortress 5) The ancient walls of Cortona with the Porta Bifora, the oldest, as it is of Etruscan origin Enjoy strolling through magic Cortona!
5.0(3)
2 Hours
Arezzo
- Free cancellation
- Private tour
From
$225
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Viator
PRIVATE Hero E-Bike Experience - Cortona and Montepulciano Valley
This experience follows the same high-level luxury format offered in Cortona, reimagined in Montepulciano and the Chiana Valley. Set among Tuscany’s rolling hills, the journey unfolds at a relaxed, immersive pace. Premium Trek e-bikes carry you through vineyards, olive groves, and medieval villages. While Cortona shows refined hilltown elegance, this experience reveals Tuscany’s authentic, expansive soul—quiet country roads, hidden corners, and timeless rhythms. Discover Tuscany’s hidden gems, panoramic vineyards, and medieval villages on a private, immersive tour designed for lasting memories. Led by a certified guide, you explore not just the landscape, but its history, traditions, and soul. As in every Hero-format experience, the journey concludes with a carefully selected lunch, a moment of reward, connection, and authentic Tuscan hospitality. Private, seamless, and deeply personal—where luxury is measured in meaning, not excess, and every ride becomes a lasting memory.
5.0(3)
4 Hours - 5 Hours
Arezzo
- Free cancellation
- Private tour
From
$434
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Viator
Around Lucignano Private ebike tour and Cooking Class
Explore the charming Tuscan village of Lucignano on an exhilarating eBike tour that takes you through picturesque landscapes and hidden gems only locals know. Visit historic landmarks, lush vineyards, and stunning viewpoints, all while enjoying the ease and fun of electric biking. Afterward, immerse yourself in the rich culinary traditions of the region with a hands-on cooking class led by a local chef. Learn how to make the most famous shape of pasta in the area: PICI! Perfect for adventure seekers, food enthusiasts, and families, this tour offers a unique blend of outdoor adventure and authentic cultural experiences that will leave you with unforgettable memories of Tuscany.
5.0(2)
4 Hours - 6 Hours
Arezzo
- Free cancellation
- Private tour
From
$642
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Viator
E Bike Tour on the Lake Trasimeno Cycle Path
Explore Lake Trasimeno on an e-bike tour. Ride through a natural landscape, stop at Punta Navaccia for birdwatching, and visit the fortified town of Castiglione del Lago. Begin your journey at Passignano dul trasimeno and cycle along the lake's shore. Enjoy the natural surroundings, far from the hustle and bustle of city life, as you pedal on a mostly unpaved bike path. Reach Punta Navaccia, a significant natural site dedicated to birdwatching. As you cycle through a wilder area of the lake, keep an eye out for free-roaming animals. Arrive at Castiglione del Lago, a charming fortified town, and take a relaxing break at one of the many lakeside cafes. After your break, continue your ride back to the starting point, completing your scenic loop around Lake Trasimeno. - Guided tour of 56 km, suitable for groups of 4 - 8 people - Includes e-bike and helmet rental - Possibility of Wine Tasting and Typical Products by Reservation
5.0(2)
4h 30m
Arezzo
- Free cancellation
- Private tour
- New
From
$155
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Viator
Private and Guided Walking Tour of Arezzo City of Gold
Walking through the medieval streets of Arezzo is a unique experience. Tradition, history and beautiful landscapes to photograph. Arezzo offers all this and much more. The tour aims to show the truest Tuscany, far from the classic tourist routes. Booking a day in Arezzo allows you to relax in one of the most beautiful medieval cities in Tuscany.
5.0(1)
2 Hours - 3 Hours
Arezzo
- Free cancellation
- Private tour
From
$261
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Viator
E-Bike tour in Montone with visit to the medieval village
This e-bike tour starts from the historic center of Citta' di Castello, to reach Montone classified among "Most Beautiful Villages in Italy". The approximately 45 km long route can be tackled by all people with basic level of supported training of our pedal assisted bikes. We will follow the banks of the Tiber river a totally traffic-free path until we climb the gentle hills that lead to Montone. Here you leave your bikes we will discover the medieval village with a suggestive view of the Tiber Valley. On request it will be possible to visit the Montone Museum inside the magnificent Cloister of San Francesco where paintings and art objects from the history of Umbria are kept. After the visit we will take the Tiber cycle path back to the starting point in Citta' di Castello
5.0(1)
4h 30m
Arezzo
- Free cancellation
- Private tour
From
$155
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Viator
Tour in and bike in Alta Umbria - Citerna and Anghiari
A tour where you can appreciate the beauty of the Umbrian High Tiber and its traditions. You will have at your disposal brand new e-bikes with which it will be possible to reach in the same tour the medieval villages of Citerna and Anghiari. A licensed National Guide will lead the tour in Italian or English presenting the most interesting aspects of the historical and natural heritage of the valley. We will cross the historic center of Citta' di Castello to follow the pleasant cycle path of the Tiber river until we reach Citerna. After a short visit we will resume the route to Anghiari.
5.0(1)
4 Hours - 5 Hours
Arezzo
- Free cancellation
- Private tour
- New
From
$155
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Viator
Private Tuscany Photo Tours
2022 and 2025 EUROPEAN TRAVEL AWARD WINNER - Our photography journey offers a unique opportunity to explore and capture the most captivating landscapes of Tuscany, from early morning light to sunset and dusk. It is a truly life-changing experience, revealing the breathtaking beauty and hidden secrets. During the Tour, you will be immersed in nature and in the authentic Tuscan culture and lifestyle, where history and art blend with outstanding food and wine. Guided by Marco Bulgarelli, an award-winning photographer, you will photograph both iconic views and lesser-known locations: magical landscapes, charming churches, vineyards, rolling green hills, and medieval hill towns and villages. The tour focuses on the finest viewpoints of Val d’Orcia and its surroundings, Crete Senesi, Montepulciano, Chianti, and Montalcino. We will always be in the right place at the right time. Participants will improve their photography skills and take home unforgettable images.
4.9(18)
8 Hours
Arezzo
- Free cancellation
- Private tour
- Likely to sell out
From
$357
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Viator
PRIVATE TOUR: Savor Exquisite Wines, Brunello & Nobile Wine Tour
A superb Experience in the wonderful Val d'Orcia between Noble vines & Medieval cities • Our driver escort will pick you up at your location (hotel, B&B or private apartment) and take you on a drive through the sweet hills of Tuscany. • 1° stop in Montepulciano for a visit of the Historic Cellars. Here you'll find gigantic oak barrels, in which the famous Vino Nobile “rest”. We'll taste wines in 2 different cellars. • For lunch you will taste the famous pasta with "Pici", with delicious meat sauce (Ragù) and tuscan cold cuts • In the afternoon we will drive to Pienza, the town of the Pecorino cheese. The Pecorino is one of the best cheeses in Italy, especially the version 'sotto cenere' - ('under ashes') • Afterwards we will visit another farm in Montalcino. After visiting the spectacular vineyards and cellars, the tour will continue with 5 wine tastings in this prestigious winery, where the Brunello has been produced for generations. Take a look What to expect!
4.8(6)
8 Hours
Arezzo
- Free cancellation
- Private tour
From
$297
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Viator
Arezzo Private Tour with Official Guide
Sitting on top of a hill at the junction of the 4 valleys that compose its province, Arezzo was a great Etruscan and Roman city. In the Middle Ages Guido Tarlati, important Bishop in the XIV century, turned the city into a great cultural and artistic centre.
4.8(13)
2 Hours
Arezzo
- Free cancellation
- Private tour
From
$345
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Viator
Cortona Private Guided Tour
Cortona has become very popular several years ago thanks to the book by Frances Mayes, Under the Tuscan Sun (and the movie with Diane Lane) which is set in Cortona; the protagonist immediately falls in love with the town, its people, and villa Bramasole that she purchases and fixes up.
4.8(25)
2 Hours
Arezzo
- Free cancellation
- Private tour
From
$309
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Viator
Private Tasting of Organic Wines in the Cellar in Mugliano
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.
4.7(11)
2 Hours
Arezzo
- Free cancellation
- Private tour
From
$36
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Viator
Private Guided Tour of Pienza on Foot
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.
4.7(6)
3 Hours
Arezzo
- Free cancellation
- Private tour
From
$250
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