Tuscany Multi Day Bike Tour History Wine and Local Flavors

Join us on an exclusive cycling journey through Tuscany, where every pedal stroke immerses you in stunning landscapes, rich traditions, and well-being. Your day begins at Casale Chiesina, a haven of tranquility among rolling hills. After a personalized bike fitting, set off on a curated route blending adventure, relaxation, and discovery. Ride through vineyards, medieval villages, and scenic roads, soaking in the authenticity of this land. Along the way, enjoy private tastings at select wineries, savoring fine wines and Tuscan flavors. Pause for a gourmet lunch in an exclusive setting, where local chefs transform fresh ingredients into memorable dishes. Guided by professionals, you’ll enjoy a seamless experience with premium bikes, expert support, and personal care. Whether seeking performance, culture, or relaxation, InGIRO is your gateway to unforgettable cycling moments. Tuscany, as you’ve never experienced it — on two wheels, at your pace, in perfect harmony.

As part of the InGIRO bike tour, a visit to the Monastery of Camaldoli offers a unique moment of serenity and discovery. Nestled in the heart of the Casentino Forests, this historic monastery was founded in the 11th century by Saint Romuald and remains an active Benedictine community. Surrounded by ancient woods, the monastery complex includes the guesthouse, the church with remarkable artworks, and the ancient pharmacy, where monks have crafted herbal remedies for centuries. Cycling through shaded forest roads, you will reach the Hermitage of Camaldoli, a place of silence and deep spirituality, where nature and contemplation blend perfectly. This stop along the InGIRO route is not just a visit, but an experience of cultural richness, peaceful landscapes, and timeless Tuscan heritage — a moment to slow down, breathe, and connect with history in a truly special setting.

The Sanctuary of La Verna is one of the most spiritual and inspiring destinations in Tuscany, and a key stop on the InGIRO bike tour. Nestled in the Casentino Forests at over 1,100 meters above sea level, it is the place where Saint Francis of Assisi received the stigmata in 1224. Surrounded by ancient woods and silence, La Verna offers an atmosphere of peace and reflection. The sanctuary complex includes the Basilica, the Chapel of the Stigmata, and centuries-old corridors carved into the rock. Cycling up to La Verna is both a physical and emotional journey, rewarded by stunning views, quiet forest roads, and a profound sense of history and spirituality. This stop allows guests to experience a unique combination of nature, culture, and deep serenity — a moment to pause, breathe, and connect with the timeless soul of Tuscany.

The Casentino valley is not only rich in history and nature but also home to excellent wineries that are part of the InGIRO bike tour experience. Along the way, guests will visit local vineyards such as Fregnan, Piergentina, and Ornina, each offering a unique expression of Tuscan winemaking traditions. At these wineries, you will meet passionate producers who cultivate their land with care and dedication, transforming local grapes into elegant wines that reflect the character of the valley. Tastings are private and intimate moments where guests can discover refined reds, delicate whites, and special local labels, accompanied by traditional flavors and stories of the territory. These visits are more than simple stops; they are a journey into the heart of Casentino’s culture — moments of pleasure, authenticity, and discovery that make the InGIRO bike tour truly unforgettable.

The Pieve di Romena is one of the most beautiful examples of Romanesque architecture in Tuscany and a special stop on the InGIRO bike tour. Set amidst rolling hills and surrounded by cypress trees and olive groves, this ancient church dates back to the 12th century and welcomes visitors with its simplicity and timeless elegance. Cycling to the Pieve offers a moment of peace and reflection, where history, art, and spirituality blend with the landscape. The stone columns, the perfect arches, and the light that filters through the narrow windows create a serene and intimate atmosphere. This stop allows guests to slow down, admire the beauty of Tuscan heritage, and connect with the deep roots of the Casentino valley. The visit to the Pieve di Romena is not just cultural, but also emotional — a moment to pause and savor the essence of a land where history and nature live in perfect harmony.

The Castle of Romena is an iconic symbol of the Casentino valley and a captivating stop on the InGIRO bike tour. Perched on a hilltop, the castle dates back to the 11th century and once served as a powerful stronghold overlooking the Arno valley. Surrounded by ancient walls and olive groves, the ruins of Romena evoke stories of knights, poets, and noble families. The castle is also connected to Dante Alighieri, who found refuge in the area during his exile and mentioned Romena in the Divine Comedy. Cycling up to the castle rewards guests with panoramic views and the chance to walk through centuries of history. This stop is not just about architecture, but about atmosphere — a place where nature and legend blend, offering visitors a moment of reflection, beauty, and timeless wonder in the heart of Tuscany.

The Castle of Porciano is a hidden gem of the Casentino valley and an exclusive stop on the InGIRO bike tour. Perched on a hilltop overlooking the valley, this medieval fortress dates back to the 11th century and has been beautifully restored, preserving its original charm and history. Cycling up to Porciano rewards guests with breathtaking views of the surrounding hills and the chance to explore ancient stone walls, towers, and courtyards that once welcomed nobles, knights, and pilgrims. Inside, the small museum showcases local artifacts and tells stories of the castle’s rich past, including its connection to Dante Alighieri, who found refuge in this region during his exile. A visit to Porciano is more than a cultural stop; it is a journey into Tuscany’s medieval heart — a place where history, nature, and beauty meet, offering unforgettable moments of discovery, silence, and inspiration.

The Castle of Poppi is one of the most impressive and well-preserved castles in Tuscany, and a key stop on the InGIRO bike tour. Dominating the hilltop town of Poppi, this magnificent fortress dates back to the 13th century and was once the seat of the noble Guidi family. With its elegant towers, grand staircases, and frescoed halls, the castle reflects the rich history and power of medieval Casentino. Visitors can climb the ancient tower for panoramic views of the valley and explore the castle’s library, which houses rare manuscripts and historical documents. Cycling to Poppi and visiting its castle is a journey into the heart of Tuscan heritage, where art, history, and landscape come together. This stop offers guests a unique opportunity to experience the charm of a medieval town and its iconic castle — a highlight of culture and beauty along the InGIRO route.

Ornina Winery is a boutique vineyard in the heart of the Casentino valley and a memorable stop on the InGIRO bike tour. Surrounded by rolling hills and ancient olive groves, Ornina is a place where passion, tradition, and innovation meet to create wines of exceptional character. Guests are welcomed by the owners, who share the story of their land, the winemaking process, and the philosophy behind each bottle. The visit includes a tour of the vineyard and cellar, followed by an exclusive tasting of refined reds, crisp whites, and unique local blends, paired with traditional Tuscan flavors. The atmosphere is intimate and authentic, allowing guests to connect with the essence of this territory, its people, and its products. A visit to Ornina is not just about wine; it is a sensory experience, a moment of beauty and taste that perfectly complements the cycling journey through Tuscany’s hidden gems.

Piergentina Winery is a charming stop on the InGIRO bike tour, offering guests an authentic encounter with the winemaking traditions of the Casentino valley. Set in a peaceful landscape of vineyards and cypress trees, Piergentina is known for its careful craftsmanship, respect for nature, and passion for quality. Visitors are welcomed by the owners, who guide them through the vineyards and cellars, explaining the winemaking process and sharing the stories behind each label. The tasting experience includes elegant reds and fresh whites, paired with local delicacies, creating a perfect balance between flavor and tradition. The visit to Piergentina is more than a tasting — it is a journey into the heart of Tuscan rural culture, where guests can enjoy genuine hospitality, discover unique flavors, and take in panoramic views that make this experience truly unforgettable.

Fregnan Winery is a hidden treasure of the Casentino valley and an exclusive stop on the InGIRO bike tour. Nestled among vineyards and gentle hills, Fregnan is a family-run estate where tradition and innovation come together to produce wines that express the purity and character of the local terroir. Guests are warmly welcomed by the winemakers, who share their philosophy and passion for sustainable viticulture. The visit includes a tour of the vineyards and the cellar, followed by a private tasting of refined wines — from elegant reds to fragrant whites — paired with artisanal products from the region. The experience at Fregnan is intimate and personal, offering not only exceptional flavors but also the chance to discover the heart of Tuscan winemaking culture, surrounded by beauty and genuine hospitality.

The Poppi Golf Club is a charming stop along the InGIRO bike tour, offering guests a relaxing break in the heart of the Tuscan countryside. Surrounded by rolling hills and olive groves, this 9-hole course is beautifully integrated into the landscape, with stunning views over the Casentino valley. During the visit, guests can stroll around the peaceful grounds, enjoy the atmosphere of the club, and experience a different side of Tuscan leisure. The stop includes an easy lunch on the clubhouse terrace, where fresh local ingredients and simple, authentic flavors are served with care. This moment of pause allows cyclists to recharge, enjoy good food, and take in the panoramic scenery before continuing their journey through the beauty and traditions of the region.

The Ancient Pharmacy of Camaldoli is a fascinating stop on the InGIRO bike tour, where history, tradition, and nature come together. Located within the Camaldoli Monastery complex, this historic pharmacy has been in continuous operation since the 16th century. Here, guests can discover ancient recipes and natural remedies created by the monks using herbs and plants from the surrounding forests. The beautiful interiors, with wooden shelves, glass jars, and historical instruments, transport visitors into a world of knowledge and care passed down through generations. During the visit, guests can explore the herbal shop, learn about traditional preparations, and appreciate the link between nature and well-being. This stop is a unique experience, adding a cultural and sensory dimension to the InGIRO tour, where the values of simplicity, wisdom, and nature are still alive today.

The Museum of Wool Art, part of the “Luigi and Simonetta Lombard Foundation” in Stia, is an inspiring cultural stop on the InGIRO bike tour. Located in the heart of the Casentino valley, this museum celebrates centuries of local tradition and craftsmanship in wool production, which has shaped the identity of this region. Inside, guests can explore fascinating exhibitions showcasing ancient looms, textile machines, and handcrafted works, telling the story of the wool industry that once made Stia famous across Europe. Interactive displays and well-curated collections offer insight into the skill and artistry passed down through generations. Visiting the Museum of Wool Art allows guests to connect with the authentic soul of the Casentino — a territory where nature, tradition, and craftsmanship come together in timeless harmony.

Tapinassi Ceramics is a special stop on the InGIRO bike tour, offering guests a unique encounter with Tuscan craftsmanship and artistic tradition. Located in the Casentino valley, this historic workshop has been creating hand-crafted ceramics for generations, combining creativity, skill, and attention to detail. Visitors will have the chance to watch artisans at work, shaping and decorating each piece with traditional techniques and timeless motifs inspired by nature and Tuscan culture. The visit includes a tour of the workshop and showroom, where guests can admire beautiful plates, vases, and decorative objects, each one unique and crafted with care. This stop is not only a discovery of art and tradition, but also an opportunity to bring home a piece of authentic Tuscan beauty — a lasting memory of the InGIRO experience.

Florence, known as the cradle of the Renaissance, is a city filled with art, culture, and timeless beauty. While the InGIRO bike tour focuses on discovering the hidden treasures and landscapes of the Casentino valley, Florence can be included as a special experience, only upon guest request. Walking through its streets means admiring masterpieces like the Cathedral of Santa Maria del Fiore, the Ponte Vecchio, and the Uffizi Gallery, where art and history come alive. This optional visit can be arranged as a private tour or guided day trip, offering guests the chance to explore Florence’s elegance, historic palaces, and charming squares at their own pace, before returning to the peaceful Tuscan countryside. For those who wish to enrich their cycling holiday with art and culture, Florence represents a unique, unforgettable addition — a city where beauty, tradition, and history blend perfectly.

Siena, a jewel of medieval Tuscany, is offered as an optional visit during the InGIRO bike tour, upon specific guest request. Known for its stunning Piazza del Campo, the majestic Cathedral, and narrow winding streets rich in history, Siena captivates with its timeless atmosphere. Strolling through its alleys feels like stepping back in time, surrounded by ancient palaces, traditional shops, and breathtaking views of the Tuscan hills. This exclusive excursion can be arranged as a private visit, allowing guests to discover Siena’s artistic heritage, taste local specialties, and enjoy the charm of this historic city at their own rhythm. For those looking to enrich their cycling adventure with culture and tradition, Siena represents a perfect addition — a city of beauty, art, and centuries-old stories waiting to be explored.

Pisa, world-famous for its iconic Leaning Tower, is available as an optional stop on the InGIRO bike tour, upon guest request. The city offers far more than its famous landmark, with the magnificent Piazza dei Miracoli, the Cathedral, the Baptistery, and charming streets filled with history and life. A walk along the Arno River reveals elegant palaces and peaceful corners where art and architecture blend in perfect harmony. This exclusive visit can be arranged as a private experience, allowing guests to explore Pisa’s treasures, discover local flavors, and enjoy the vibrant yet relaxed atmosphere of this Tuscan gem. For those wishing to complement their cycling journey with cultural highlights, Pisa offers a memorable addition — a place where history, beauty, and Italian charm meet.