Top Arezzo Private and Luxury

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.

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.

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.

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.

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.

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.

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.

- 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.

You will visit with us our winery and vineyard to discover our philosophy and passion. A unique experience in which you can then taste 4 wines from Villa La Ripa, paired with excellent products from the Tuscan tradition in a light three-course lunch. You can also enjoy a wonderful view from the tasting room overlooking the winery and the vineyards of the company.

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

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!

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.

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.

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.

Make the most of your time in Montepulciano with this walking tour that takes in the highlights of the medieval hill town in just hours. Skip the dry guidebook and visit with a guide who can make the Tuscan town’s history to life as you stroll the picturesque lanes and climb to the top of the bell tower (own expense) to admire the views. End with a glass of local wine to cap off your visit.

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.

Brunello di Montalcino is one of Italy's most prestigious wines, but navigating to the rural wineries outside of Montalcino on your own can be stressful. On this private wine tour, let your driver take the wheel and focus on vineyard views as you make your way to the top wine estates and cellars for exclusive tasting experiences. Explore stunning vineyards, learn about traditional winemaking techniques, and savor the rich flavors of Tuscany with guided tastings and a traditional lunch.

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.

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.

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.

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.

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.

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.