Taste of Tuscany

Overview

Ride from Bolgheri's vineyards to the untamed landscapes of the Maremma. This tour is perfect for the cycling newbies who already enjoy being active, or anyone who just wants to take it easy. Pedal at a meandering pace, stopping to take pictures, savor a leisurely lunch and explore the surroundings. Enjoy quiet roads along flat and rolling terrain zigzagging through vineyards, olive groves and farmland. Average daily distance: 35-45 miles. Terrain: flat and rolling. Our Athletic Beginner tours are perfect for those who aren’t avid cyclists, but are fit and love to exercise regularly. On these trips, you’ll enjoy a flowing pace with plenty of time throughout the day to indulge in the local specialties, take in the local culture and enjoy the magnificent views. There will be an occasional hill, more rolling terrain and higher mileage than an Easy tour. Average daily distance: 35-45 miles. Terrain: flat and rolling. Our guides will offer cycling clinics and one-on-one coaching in cadence, positioning and the art of shifting efficiently on rolling hills. First time bike travelers start with this beloved Italian classic. It's got a bit of everything and it's only six days! Discover a different side of Tuscany on a cycling journey from the vineyards of Bolgheri to the rolling hills of the Maremma. Beginning on the Tuscan coast in Marina di Castagneto Carducci, ride beneath Bolgheri’s iconic cypress-lined roads and through the heart of Super Tuscan wine country, where renowned estates, olive groves, and picturesque villages define the landscape. From there, the route turns inland toward Massa Marittima, a beautifully preserved medieval town surrounded by forests, ridgelines, and quiet country roads. Along the way, enjoy exceptional food and wine, authentic Tuscan culture, and some of the most rewarding cycling in coastal Tuscany before returning to the shores of the Tyrrhenian Sea. Day 1: Tombolo Forest & Bolgheri Loop. Welcome to Italy! The group meets at 12:30 PM at the hotel in Marina di Castagneto Carducci for an introductory lunch and group welcome; a group transfer from Castagneto Carducci–Donoratico train station will be arranged at 12:00 PM. After introductions and a bike fitting, enjoy a first ride through the shaded Tombolo forest along dedicated paths just behind the beach, with the option to continue toward Bolgheri via its iconic cypress-lined road before returning to the coast. Later, settle in and unwind at the hotel’s renowned thalassotherapy facilities. Meals Provided: Lunch, Dinner. Average Mileage: 10 / 15 miles. Elevation Gain: 200 ft. Riding Terrain: Flat coastal bike paths through protected pine forest, then light rolling roads inland on smooth asphalt. Accommodations: Tombolo Talasso Resort (5-star Luxury Level). Day 2: Bolgheri Wine Roads Loop. The ride centers on the landscape surrounding Bolgheri, entering along its iconic cypress-lined boulevard before winding between vineyards and cultivated fields. This is the heart of Super Tuscan country, layered over a territory shaped since Etruscan times, where ancient routes and agricultural patterns still quietly define the land. A winery visit and tasting bring deeper context to the region, before the route gently returns toward the coast. Meals Provided: Breakfast, Lunch, Dinner. Average Mileage: 25 miles. Elevation Gain: 1,400 ft. Riding Terrain: Rolling terrain on smooth secondary roads through vineyards and open countryside. Accommodations: Tombolo Talasso Resort (5-star Luxury Level). Day 3: Castagneto di Massa Marittima. Leaving Marina di Castagneto Carducci, the route gradually leaves the coastal plain behind, heading inland as vineyards give way to olive groves and then to denser woodland. The terrain grows quieter and less cultivated, with long, uninterrupted stretches of riding. Small, often overlooked villages signal the transition into the Maremma—a region once isolated, still defined by a raw, untamed character. Multiple route options offer different approaches to the hills before arriving in Massa Marittima, whose compact medieval center rises unexpectedly above the surrounding landscape, a striking presence after the solitude of the ride. Meals Provided: Breakfast, Dinner. Average Mileage: 30/35 miles. Elevation Gain: 2,100/2,600 ft. Riding Terrain: Transition from coastal plains to inland hills; longer climbs, forested sections, and quieter roads. Accommodations: Tenuta Il Cicalino (Luxury Agriturismo). Day 4: Massa Marittima Loop. A loop from Massa Marittima explores a landscape shaped by mining history, forests, and scattered farmland. The riding shifts between enclosed woodland and open ridgelines, offering constantly changing perspectives. Back in town, time is set aside to wander the cathedral square—one of the most striking in Tuscany—and the narrow streets that reflect a strong and enduring local identity. Along the way, stops may include small producers, with a focus on regional specialties such as pecorino cheese, still crafted in the surrounding hills. Meals Provided: Breakfast, Lunch. Average Mileage: 25 miles. Elevation Gain: 1,500 ft. Riding Terrain: Rolling to hilly with varied gradients on quiet inland roads, alternating between woodland and open sections. Accommodations: Tenuta Il Cicalino (Luxury Agriturismo). Day 5: Massa Marittima to Marina di Grosseto. The final ride leaves Massa Marittima and crosses the Maremma toward the coast, tracing a gradual shift from wooded hills to open plains. This is the land of the butteri, traditional cattle herders, and traces of that heritage remain visible in the landscape—fenced pastures, horses, and wide agricultural expanses. As the route approaches Marina di Grosseto, the terrain levels out and the air begins to change, signaling the return to the Tyrrhenian Sea and the close of the experience. Meals Provided: Breakfast, Dinner. Average Mileage: 45 miles. Elevation Gain: 2,200 ft. Riding Terrain: Gradual transition from inland hills to coastal plains; smoother roads and more open terrain toward the sea. Accommodations: Terme Marine Leopoldo II (4-star). Day 6: Arrivederci! After breakfast at 9:00 AM, we provide a group shuttle to Grosseto train station, approximately 20 minutes away. Meals Provided: Breakfast. The tour includes: Services of expert local bilingual guides throughout the program, full van support throughout the tour, Ciclismo Super Snacks with local specialties and fresh seasonal products, Ciclismo jersey and water bottle, cycling clinics and personalized coaching, group shuttles at the beginning and end of the tour, Bolgheri winery visit and wine tasting, Tuscan olive oil tasting, hands-on Tuscan cooking class, and cultural visits and entrance fees as per itinerary. Included bikes: Use of our exclusive carbon road bike, La Classica Ribelle (or equivalent), Garmin Edge Explore GPS preloaded with daily routes and GPX tracks, Ride with GPS navigation and route access for mobile devices (optional), Ciclismo jersey and water bottle, saddle bag with repair kit, optional map holder on handlebars. Pedal Options: Flat pedals, Half-toe pedals (without straps). What's Not Included: Cycling helmet, Optional clipless/SPD pedals and cycling shoes, Optional personal saddle. Accommodations & Meals: All accommodations, All breakfasts, 3 lunches, 4 dinners. Cultural Experiences & Activities: Ride the iconic cypress-lined road into Bolgheri, Wine tasting in the heart of Super Tuscan country, Hands-on Tuscan cooking class, Olive oil tasting with local products, Explore the medieval town of Massa Marittima, Visit Tuscany’s scenic Maremma region, Relax at coastal spa and thalassotherapy facilities, Discover small villages and authentic local life, Learn about Tuscan agricultural traditions, Enjoy regional cuisine, wines, and pecorino cheese.

Daily Ride Schedule

Accommodation & Services

Accommodation

Hotel

What's Included