Taste of Tuscany
Bolgheri & Massa Marittima: Coastal Tuscany Meets Maremma
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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.
Tour Essence
- Ride the iconic cypress-lined road into Bolgheri, heart of Super Tuscan wine
- Enjoy wine and olive oil tastings at renowned estates along the Tuscan coast
- Cycle from the Tyrrhenian coast into the rolling hills of the Maremma
- Explore medieval Massa Marittima and its stunning cathedral square
- Take part in a hands-on Tuscan cooking experience with local ingredients
- Relax in exceptional spa hotels and finish by the Tyrrhenian Sea
Savor Tuscan specialties such as cured meats, wild boar, pecorino cheese, black truffles, fresh Mediterranean seafood, handmade tortelli filled with sheep’s milk ricotta and herbs, grilled lamb, wild herbs from Monte Amiata, and rustic chestnut dishes rooted in local tradition.
What to Expect
Terrain
Flat to RollingStart Location
Marina di Castagneto CarducciEnd Location
Marina di GrossetoMileage
Average Daily: 30 miles Total: 140 milesElevation
Average Daily: 1,500 ft Total: 7,400 ft
Start Location
Marina di Castagneto CarducciFly Into
Rome (FCO)End Location
Marina di GrossetoFly Out Of
Rome (FCO)Tombolo Forest & Bolgheri Loop
Meals Provided
Lunch, DinnerAverage Mileage
10 / 15 milesElevation Gain
200 ftRiding Terrain
Flat coastal bike paths through protected pine forest, then light rolling roads inland on smooth asphaltMeals Provided
Lunch, DinnerAccommodations
Tombolo Talasso Resort
The Tombolo Talasso Resort is a 5-star hotel has wonderful Etruscan beauty, containing vineyards and olive groves right between where the hills meet the sea. The resort has a magnificent private beach and outdoor pool as well as a high quality spa. This resort has all the modern amenities you would expect.
Bolgheri Wine Roads Loop
Meals Provided
Breakfast, Lunch, DinnerAverage Mileage
25 milesElevation Gain
1,400 ftRiding Terrain
Rolling terrain on smooth secondary roads through vineyards and open countrysideMeals Provided
Breakfast, Lunch, DinnerAccommodations
Tombolo Talasso Resort
The Tombolo Talasso Resort is a 5-star hotel has wonderful Etruscan beauty, containing vineyards and olive groves right between where the hills meet the sea. The resort has a magnificent private beach and outdoor pool as well as a high quality spa. This resort has all the modern amenities you would expect.
Castagneto di Massa Marittima
Meals Provided
Breakfast, DinnerAverage Mileage
30/35 milesElevation Gain
2,100/2,600 ftRiding Terrain
Transition from coastal plains to inland hills; longer climbs, forested sections, and quieter roadsMeals Provided
Breakfast, DinnerAccommodations
Tenuta Il Cicalino
A charming countryside agriturismo set in the rolling hills of the Maremma near Massa Marittima, Tenuta Il Cicalino offers an authentic Tuscan stay focused on nature, relaxation, and outdoor activity. Spread across traditional farmhouses with apartments and rooms, the property features swimming pools, a wellness center with sauna and spa services, and a restaurant serving local cuisine.
Massa Marittima Loop
Meals Provided
Breakfast, LunchAverage Mileage
25 milesElevation Gain
1,500 ftRiding Terrain
Rolling to hilly with varied gradients on quiet inland roads, alternating between woodland and open sectionsMeals Provided
Breakfast, LunchAccommodations
Tenuta Il Cicalino
A charming countryside agriturismo set in the rolling hills of the Maremma near Massa Marittima, Tenuta Il Cicalino offers an authentic Tuscan stay focused on nature, relaxation, and outdoor activity. Spread across traditional farmhouses with apartments and rooms, the property features swimming pools, a wellness center with sauna and spa services, and a restaurant serving local cuisine.
Massa Marittima to Marina di Grosseto
Meals Provided
Breakfast, DinnerAverage Mileage
45 milesElevation Gain
2,200 ftRiding Terrain
Gradual transition from inland hills to coastal plains; smoother roads and more open terrain toward the seaMeals Provided
Breakfast, DinnerAccommodations
Terme Marine Leopoldo II
A contemporary 4-star spa hotel set among pine trees just steps from the beach in Marina di Grosseto, Terme Marine Leopoldo II combines seaside relaxation with thermal wellness. The property features extensive spa and wellness facilities with natural thermal waters, indoor and outdoor pools, a full-service beauty center, and a restaurant, along with spacious rooms and easy access to the Tyrrhenian coast.
Arrivederci!
Meals Provided
BreakfastMeals Provided
BreakfastAccommodations
2027
Once your trip is confirmed, we’ll provide everything you need to prepare for your adventure—from training and packing tips to practical travel information and inspiration for the journey ahead. Our Travel Advisors are also available to help you plan your pre- and post-tour travel.
- Services of expert local bilingual guides throughout the program
- Full van support throughout the tour
- Ciclismo Classico Super Snacks with local specialties and fresh seasonal products
- Cycling clinics and personalized coaching
- Group shuttles at the beginning and end of the tour
What’s Included
- 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
- Ciclismo Classico 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
- All accommodations
- All breakfasts, 3 lunches, and 4 dinners
- Ride the iconic cypress-lined road into Bolgheri
- Bolgheri winery visit and wine tasting
- 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
