Top Arezzo Private and Luxury

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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.

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Cortona Private Hero Experience Luxury E-Bike Lunch and Wine Tour

5 to 6 hours

5.0

(3)

from $433

Cortona - Easy guided eBike tour around the Etruscan City.

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 hoursFree Cancellation

5.0

(63)

from $176

From Cortona Brunello di Montalcino Wine Tour with Lunch

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 hoursFree Cancellation

5.0

from $165

Cortona Private Guided Tour

2 hoursFree Cancellation

4.8

(25)

from $308

Per group

Cortona private walking Tour

2 hours 30 minutesFree Cancellation

5.0

(8)

from $176

Price varies by group size

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 hoursFree Cancellation

4.8

(13)

from $344

Per group

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 hoursFree Cancellation

from $8

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

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Cortona E-Bike Scenic Ride - Private Medieval Countryside tour

3 to 4 hoursFree Cancellation

5.0

(10)

from $331

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 hoursFree Cancellation

5.0

(16)

from $178

Walking Tour in Cortona

1 hour 30 minutes to 2 hoursFree Cancellation

4.6

(20)

from $59

Likely to Sell Out

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.

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Private Tour Siena San Gimignano and Chianti from Cortona

8 to 9 hoursFree Cancellation

5.0

(4)

from $486

Price varies by group size

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.

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Montepulciano Vineyards Wine Tour with 3 Estates Visit

7 to 8 hours

5.0

(22)

from $415

Price varies by group size

Likely to Sell Out

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.

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Private Walking Tour of Pienza with Licensed Tour Guide

2 hoursFree Cancellation

5.0

(4)

from $137

Price varies by group size

Cortona - Sunset eBike Ride Around the Village + Pizza Tasting

- Departure is guaranteed with 4+ guests. - We offer discount codes for each booking — contact us before reserving your spot. - This is a bike tour, so it’s important to feel confident riding for your safety. An Experience that Touches the Soul: Explore Cortona on eBike to have a unique experience beyond the cobblestone streets and history. Discover hidden gems and following a tour inspired by "Under the Tuscan Sun". We'll explore the true essence around the etruscan walls of Cortona, gently ascending the hill to enjoy breathtaking views of the Val di Chiana. We'll guide you through the historic streets of this famous Tuscan town, to reveal not only the iconic landmarks but also those lesser-known and known only to locals. Then we'll relax and enjoy the sunset at the most enchanting and panoramic spot in Cortona. Afterward, we’ll be welcomed at the best pizzeria in the area, where you can indulge in a tasting of four different pizza flavors, accompanied by refreshing drinks.

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Cortona - Sunset eBike Ride Around the Village + Pizza Tasting

3 to 4 hoursFree Cancellation

5.0

(1)

from $219

Tuscany Multi day eBike tour Wine and Pasta

Take a real sip of Tuscany's chill and calm countryside and escape the busy pace of Rome. Come and savor the very best of the Tuscan countryside—its flavors, stories, and breathtaking views. Exclusive & Intimate: Small-group experiences (max 7 per guide) ensure personalized attention and genuine local interactions. Unforgettable eBike Rides: Explore ancient paths, scenic vineyards, and breathtaking landscapes on high-performance pedal-assist bikes. Culinary Immersion: Savor authentic Tuscan flavors through unique dining experiences—from a hillside cheese house picnic to a hands-on cooking class and intimate restaurant dinners. Cultural Insights: Engage with local experts who unveil the hidden stories and history of this iconic destination. Book now for a once-in-a-lifetime adventure through Tuscany—a journey that delights your senses and nourishes your soul! Contact Us: For more detailed information or to receive a discount code for your booking, please contact us before booking.

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Tuscany Multi day eBike tour Wine and Pasta

4 daysFree Cancellation

5.0

from $2,917

Pienza E Bike Discovery the Heart of Val d Orcia

Experience the magic of Tuscany without the sweat! Join us for a half-day e-bike adventure through the rolling hills surrounding the “Ideal City” of Pienza. This tour is carefully designed to take you along the most iconic white roads (strade bianche) in the region, offering panoramic views that look like they’ve been pulled straight from a postcard. Tour Highlights: Effortless Riding: Glide up the Tuscan hills with ease thanks to our premium electric bikes. Iconic Landmarks: Cycle past the famous Gladiator Row (Cipressi di San Quirico) and the charming Vitaleta Chapel. Cinematic Views: Capture the breathtaking landscapes of the Val d’Orcia, a UNESCO World Heritage site. Local Culture: Start and finish in the Renaissance gem of Pienza, with plenty of tips on where to find the best Pecorino cheese or best restaurants.

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Pienza E Bike Discovery the Heart of Val d Orcia

3 to 4 hoursFree Cancellation

from $142

The rolling hills of Tuscany make it a great spot to explore using a motor-assisted e-bike. On this full-day private tour, get picked up at your Florence hotel and delivered to the countryside. Discover the town of Pienza—a UNESCO World Heritage Site—and enjoy an outdoor lunch of authentic local produce, including some wine, before heading off to relax by Bagno Vignoni’s ancient thermal springs.

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Val d'Orcia: eBike Tour Virtual-guided

2 to 3 hoursFree Cancellation

5.0

(3)

from $107

Luch Time Tasting & Winery Tour

2 hoursFree Cancellation

4.6

(8)

from $71

Arezzo Walking Tour with Audio and Written Guide by a Local

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 hoursFree Cancellation

4.5

(11)

from $7

Price varies by group size

Head to an authentic family-run vineyard and winery near the walled town of Castiglion Fiorentino to discover Tuscan wine-making traditions on this private tour. Explore the vineyard (weather permitting), the cellars, and the Vin Santo production area as you hear about the techniques the family has used for generations. Wrap up with a tasting of cheese, salami, extra virgin olive oil, and six different wines.

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Wine & Oil Tasting Experience

1 to 3 hoursFree Cancellation

4.8

(23)

from $42

Price varies by group size

Brunello Wine Tour and Val D'Orcia Landscape

See Tuscany’s loveliest scenery, and discover the history of one of Italy’s most revered wines, on this private, half-day tour. Following pickup from your area hotel, head off the tourist trail to a local, family-owned winery. Taste Brunello di Montalcino—a 100% Sangiovese wine that’s one of Italy’s best—as well as other wines and nibbles. You’ll also tour the idyllic Val d’Orcia, from ancient hill towns to historic monasteries.

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Brunello Wine Tour and Val D'Orcia Landscape

4 hoursFree Cancellation

5.0

(95)

from $261

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

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E Bike Tour on the Lake Trasimeno Cycle Path

4 hours 30 minutesFree Cancellation

5.0

(2)

from $154

Price varies by group size

Kid-Friendly Arezzo Private Guided Tour for Families

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 $270

Price varies by group size

Private Art & Wine Tour in Cortona & Montepulciano, with lunch & 2 wine tastings

8 hoursFree Cancellation

5.0

from $308

Price varies by group size

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