Top Arezzo Private and Luxury - page 2

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 breathtaking Chianti hills on a day trip filled with stunning landscapes and rich culture. Begin with a visit to the UNESCO-listed city of Siena, renowned for its exquisite architecture. Enjoy a delicious lunch at a traditional Tuscan farmhouse, featuring homemade pasta and five tastings of the finest Chianti wines. Then, discover the secrets of local wine production in a picturesque setting.

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

Once the tour is booked, you can go to the rental point to pick up the bicycles and start the experience with virtual navigation. The e-bike loop tour starts in Pienza and measures about 26 km with 350 m of positive elevation gain: medium-easy level. The route alternates secondary roads, paved sections, about 6 km of state road, and short paths. Some sections are open to vehicular traffic and it is therefore important to have good confidence with the bicycle and feel safe on shared roads. The itinerary crosses the landscapes of Val d'Orcia among estates, open fields, and panoramic viewpoints, also passing near a famous location from the film Gladiator. The main stop is Bagno Vignoni, a thermal village famous for the large water basin in the center of the square. During the return towards Pienza, the route passes near the Cappella di Vitaleta. The road alternates between asphalt, secondary roads, dirt roads, and short easy gravel paths.

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.

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.

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.

Discover Cortona through an exclusive private journey for travelers seeking the highest level of authenticity and comfort. Ride premium e-bikes along quiet panoramic routes guided by a local expert who shares stories, culture, and hidden perspectives of Tuscany.Enjoy privileged access to a family-owned olive oil estate dating back to the 1800s, where a private visit reveals traditional production methods, historic tools, and centuries of heritage rarely experienced by visitors. Conclude the day with a refined winery experience with a curated lunch and exceptional wines in an intimate setting, with no overlapping groups.As a final gesture, guests receive a personally selected bottle of estate olive oil — a lasting memory of Tuscany. Designed as a fully private experience, every detail is tailored to create rare access, genuine connection, and unforgettable moments.Ideal for travelers who prefer meaningful experiences over crowded tours and value time, privacy, and true Tuscan elegance.

A private professional photo and video experience in the Val d’Orcia, designed for elegant and authentic visual memories. I personally guide you through the most iconic locations starting from Pienza, selecting the best light and cinematic angles to create natural, high-quality photos and videos. What’s included: – 30 professionally edited photos – 1 cinematic video trailer (approx. 2 minutes) with professional editing and color grading – Video delivered in both 16:9 and 9:16 formats – Professional equipment and aerial drone footage (where permitted) – Digital delivery via email within 3 days

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.

Optimize your logistics and make the most of your time with this private transfer from Florence to Assisi that includes stops to visit the Tuscan hill towns of Montepulciano and Cortona. Enjoy the ease of pickup at your Florence hotel and explore towns worry-free while your driver stays with the vehicle and your luggage. Sightsee, shop, and dine at your own pace, then end your day with seamless drop-off directly at your Assisi hotel.

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.

Hosted personally by a local curator specialized in private experiences. Not a tour, but a privately curated day through the hidden treasures of Cortona Valley. Access medieval castle, historic abbey, and secret estates normally closed to visitors, all at a relaxed pace. Along the way, you’ll pick and collect hidden local treasures, from artisanal products to olives and specialty ingredients, later enjoyed with a refined Tuscan wine pairing. Enjoy a private lunch and tasting with a curated itinerary, ensuring no overlapping groups and a premium pickup experience. Every moment is designed to delight your senses and create memories that last. Fully private, each step is carefully crafted to immerse your group in Tuscany’s culture, traditions, and seasonal delights — far from the crowds and tailored entirely to your experience.

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

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!!!!!

This isn’t just a vacation — it’s an immersive Tuscan journey where you’ll: Taste Italian cuisine and recipes passed down through generations. Wander cobblestone streets in Cortona and beyond Indulge gelato daily. Share sunsets over rolling hills with friends and family.

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.

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.

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.

Arezzo is famous because Giorgio Vasari was born here, the disciple of Michelangelo, who designed the famous Uffizi and the Vasari Corridor in Florence on behalf of Grand Duke Cosimo I De' Medici. Our tour's principal stops are as follows: The city's center square, Piazza Grande, is uniquely typical with its porticoes dating from the sixteenth century. Piazza del Duomo: this stunning medieval structure, dominating the plaza, houses priceless artwork by Donatello and Piero della Francesca. Arezzo's ancient lanes and streets, where the ambiance of the old goldsmith shops is still palpable. The most well-known painting by 15th-century painter Piero della Francesca is located in the Basilica of San Francesco, Cappella Bacci. Based on the advice of Dominican priest Jacopo da Voragine, these frescoes tell the story of the True Cross! How could anyone possibly miss a tour this thorough? Now let's move!

Book for an unforgettable cycling experience in Tuscany — carefully designed routes, top-quality equipment, and private tastings in authentic local settings.

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!

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.

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.