Taste of Tuscany
Bolgheri & Massa Marittima: Coastal Tuscany Meets Maremma
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This journey slips into a side of Tuscany most travelers never quite reach—where mornings carry a hint of salt in the air and days unfold between vineyards, hill towns, and long, satisfying miles on the bike. From Marina di Castagneto Carducci, you roll straight into Bolgheri, riding beneath endless lines of cypress and into the heart of Super Tuscan country, where bold wines and impeccably kept estates set the tone from the very first pedal stroke. Then the landscape begins to shift inland toward Massa Marittima, a striking medieval town shaped by centuries of mining wealth and surrounded by the quieter, more untamed landscapes of the Maremma. Forest roads, ridgelines, olive groves, and peaceful villages create a deeper, more personal side of Tuscany before the journey returns gently toward the Tyrrhenian coast.
Tour Essence
- Ride the iconic cypress-lined road into Bolgheri
- Enjoy a Super Tuscan wine tasting in Bolgheri
- Cycle along Tuscany’s scenic coastline
- Explore medieval Massa Marittima and its cathedral square
- Take part in a hands-on Tuscan cooking class
- Ride through the forests and backroads of the Maremma
- Discover small villages and authentic Tuscan culture
- Relax by the Tyrrhenian Sea in Marina di Grosseto
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
2026
2027
Once you have a trip confirmed, we will feed you a steady diet of additional pre-departure information that includes: How to train, prepare, pack and all the wonderful, inspirational and practical things you want and need to know before you go! Our Travel Advisors will be available to help plan your pre- and post-tour travel.
- Van support
- Expert, bilingual guides
- Cycling clinics and one-on-one coaching
- 1 wine tasting and winery visit
- 1 olive oil tasting
- 1 Tuscan cooking demonstration
- Cultural visits and entrance fees as per itinerary
- Group shuttle at the beginning and at the end of the tour
What’s Included
- Use of our exclusive carbon road bike, La Classica Ribelle (or Equivalent Carbon Road Bike)
- Garmin Edge Explore GPS loaded with the GPX tracks of your rides
- Two water bottles
- Saddle bag with repair kit
- Optional: Map holder on handlebar
Pedal Options
- Flat pedals
- Half-toe pedals (without straps)
What’s Not Included
- Helmet
- Optional: clipless/SPD pedals with shoes
- Optional: your own saddle
- All accommodations
- All breakfasts
- 3 lunches
- 4 dinners
- 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
