Overview

Your Trek Travel guides will meet you at the Palazzo Montebello at 11:00 AM on the first day of your luxurious bike tour in Tuscany. After a one-hour shuttle, you will arrive at the quiet and historic Badia a Coltibuono, or "Abbey of the Good Harvest," to have a delicious local lunch with stunning views of the Chianti hills. Your Trek Travel guides will then spend some time familiarizing you with your Trek bicycle and ensuring you have an excellent fit. A warmup ride will take you along picturesque, winding roads through woodlands and ancient olive groves, before you make your way to the medieval Castel Monastero, magically transformed into a lavish hotel, where you will be hosted for the next three nights. This evening, you'll enjoy a warm welcome to your Tuscany Wine Country bike tour as we gather for drinks on the terrace overlooking Tuscan vineyards before enjoying the first of many exquisite meals together, this one expertly prepared at the hotel's convivial osteria.

Overview

Slowly awaken in your opulent surroundings to another perfect day in Tuscany! Today’s ride traverses the forested hills and olive groves of the celebrated Chianti region. Pedal through the village of Lecchi and enjoy an espresso with the locals before continuing up to Radda, the ancient capital of the League of Chianti. Take time to explore this vibrant village, filled with art galleries, gourmet food, and wine shops—the perfect place to pick up some mementos to take home. Your midday destination is Castello di Volpaia, where the Mascheroni Stianti family personally welcomes you for a spectacular wine-paired lunch in their villa. Afterward, enjoy an exclusive visit of the castle’s cellars and olive oil press. From here, shuttle back to our hotel for a dip in the pool or hop back on your bike to return through the rolling vineyards. This evening, an exquisite Michelin-starred dinner awaits you at be at the celebrated La Bottega del 30, a restaurant nestled in the heart of Chianti that has held a Michelin star for over 25 years.

Overview

Following a relaxing breakfast, this morning you’ll cruise through the Chianti vineyards where you'll be rewarded by rich panoramic views of rolling, sun-drenched Tuscan hills. Choose to stop and explore the Castello di Brolio, the oldest castle and winery in the area, which has belonged to the Ricasoli family for nearly 800 years. Stop for an espresso at their Eroica Caffè, named after L’Eroica, the local cycling event on the strade bianche, with contestants riding vintage bikes on the white gravel roads in full vintage regalia. Then choose to climb up into the hills to Monteluco, one of the highest points in Chianti, or continue on to the quaint village of Villa a Sesta, our lunch destination. Enjoy true Tuscan hospitality as you savor the cuisine of Osteria alla Villa, a small bistro that serves up fresh and creative dishes. This afternoon indulge yourself with some free time at the hotel; enjoy their restorative spa or lounge by the pool with an Aperol Spritz in hand. This evening, we’ll shuttle into the medieval town of Siena where you'll learn the secrets of this historic city from our local guide and see the world-famous Duomo and the Piazza del Campo. Afterward, we’ll wander the cobbled streets as an array of Tuscan specialties unfold before our eyes, to arrive at tonight’s spectacular trattoria. Surrender your tastebuds to culinary favorites like wood-fired pizza or a bowl of cinghiale (wild boar) pasta accompanied by a glass of the finest Brunello and we’ll be sure to finish our fabulous day with a world-class gelato!

Overview

The breathtaking Elsa Valley awaits you today. The quiet roads offer rich, colorful vistas of golden hills dappled with silver olive groves, framed by dark green cypress trees. After a beautiful morning ride descending from the hills of Chianti, you will pedal on quiet country lanes and observe a landscape change as we journey to the stunning 5-star Castello di Casole. This incomparably resplendent hotel is one of Italy's most impressive destination hotels—and formerly an estate to the 10th-century nobility. Along the way, you’ll pause to enjoy a farm to table picnic lunch, featuring hand-cured prosciutto and local cheeses accompanied by delicious Frantoio olive oil. Afterward, choose to climb up to the medieval village of Simignano or pedal directly to your castle hotel. Relax with a cocktail on the hotel terrace and enjoy the spectacular views over timeless Tuscan scenery. Tonight, enjoy a private pizza-making class, where you'll learn how to spin your own pizza dough and make the pie of your choice with a trained pizzaiolo!

Overview

It's pure extravagance to awake at Castello di Casole, and after a leisurely breakfast, you'll mount your bike for one last amazing day on the rolling hills of Tuscany. You will start with a descent from the hotel into the valley below, across vine-covered slopes, and up to the medieval town of San Gimignano, where you're welcomed by the vibrant colors, sights, and sounds of the legendary open-air market. Taste fresh regional olives and take a stroll through the stalls of the local artisans before savoring the famous picci pasta at our favorite local osteria. This afternoon, spin back to the hotel to relax by the infinity pool overlooking the gorgeous Elsa Valley. Or, choose one of the many activities available at the hotel including a ceramics lesson or a watercolor class. You may wish to indulge yourself at their destination spa. Tonight, you'll savor the trip's final gastronomic delight: a perfectly timed aperitif on the hotel’s panoramic terrace as the sun dips below the horizon, followed by a magnificent meal at the hotel's renowned restaurant, La Tosca. Soak in the magical atmosphere of this elegant retreat and raise your glass to an unforgettable luxury bike tour in Tuscany.

Overview

While by now this region is surely starting to feel like home, this morning you'll arise early for your final bike loop through the Tuscan countryside as the sunrise washes over the captivating Elsa Valley. If you’d rather, simply linger over a hot cappuccino and enjoy a leisurely morning soaking in the gorgeous views from the breakfast patio before you bid your farewells and board a private shuttle, taking you to Florence and further adventures.