Cycling Coastal Tuscany

Medieval Towns and Olive-Clad Hills

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The Etruscans gave Tuscany its name and inhabited this coastal area with twelve major settlements.  After the classical age the epicenter of Tuscany moved to the valley of the Arno River to the north of Siena, so coastal Tuscany was largely forgotten – until today.  Modern Italians have re-discovered this scenic area for its landscapes and spas, and we’re happy to offer you an opportunity to discover it too. Come and bicycle through Tuscany’s history as we visit small medieval towns and Etruscan sites, and then relax resorts and thermal spa hotels.  Bicycle this remote region from north to south through low vineyard and olive-clad hills along the Etruscan coast.

Highlights 

  • Relax in thermal spas
  • Enjoy Tuscan foods grounded in olive oil, rosemary, and tomato
  • Ride ridges overlooking the Tyrrhenian Sea
  • Explore small medieval towns

View Itinerary

Skill Levels

  • Sounds Like Fun (easy)
  • I Own Bike Shorts (moderate)

Recent Reviews

Favorite experience on this trip?: The rides, the guides, the food, the visits to pasta and olive oil makers, the weather...it's hard to choose... Read More

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What's Included

  • Six nights’ lodging, plus all lodging taxes and gratuities
  • Most meals – including four dinners with wine and six breakfasts – taxes and gratuities for these meals
  • High quality 27-30 speed hybrid, road, or tandem bike rental
  • Expenses paid for guided visit to Populonia, and entrance to thermal pools
  • Day 1 shuttle from Pisa International Airport
  • Day 7 shuttle to the Grosseto train station
  • Experienced guides who are bilingual, bicultural, and superb cyclists
  • Detailed route map and roads marked with chalkdust arrows
  • Use of “traveling library” so that you can leave your guide books at home
  • Complimentary cycling water bottle and an additional gift of your choice

Tour Map


Itinerary 

Pick Up / Drop Off

Pisa International Airport / Grosseto train station

Day 1 – Arrive in Casciana Terme, near Pisa

Arrive today in Casciana Terme not far from Pisa.  Casciana Terme is one of Tuscany’s many thermal spa towns.  The Romans knew of the hot springs here and the Pisans built a minor spa here as early as 1311.  It wasn’t until the 17th century when the Tuscan aristocracy moved from the cities to the countryside in large numbers, however, that the present spa developed.  Out hotel is close to the spa and we’re happy to help you make reservations.  We fit bicycles this afternoon and you’ll have time to go out for a test ride if your wish.  Dinner is together this evening

  • your choice for the short warm-up ride
  • Meals: Dinner
  • Lodging: First of 2 Nights at The Hotel Margherita

Day 2 – Bicycle a Loop Ride into Upper Maremma Region

Our loop ride today takes us to several of the villages around Casciana Terme.  This is a classic Tuscany in the Pisan hills with small hilltop villages, olive trees, vineyards, and cypress trees punctuating the landscape on the horizon.  For centuries this area was a border region among the historic rival cities of Pisa, Florence, and Volterra.  By 1509 though, Florence consolidated its control over the area.  Our ride takes us through Lari with its sizeable 16th century Medici fortress.  The villages in the area flourished under the Medici family as farm towns and for summer residents of the aristocracy from Pisa and Florence.  Dinner is on your own this evening.

  • 41-49 km (25-27 miles)
  • Meals: Breakfast
  • Lodging: Final Night at The Hotel Margherita

Day 3 – Bicycle from Casciana Terme

Today we leave the rich farm villages of the Pisan hills and head south to ride along a scenic ridge.  Small roads and sweeping views across to the sea lead us to the small town of Pomaia, famous today for the largest Buddhist study center in Europe.  Meditate as needed to prepare for the short 5 km (3 miles) uphill where we’ll reach our highest point – the perched village of Castellina Marittima.  A flat ridge and coasting descent brings us to our hotel.  Dinner is together tonight.

Day 4 – Bicycle through the Northern Maremma Region

We have another scenic ride in store today as we bicycle through the Maremma region of Italy, famous for its “cowboys” and small medieval towns.  The first part of our ride is along the coastal plain; this entire section underwent agricultural reclamation from the late 19th century through Mussolini’s rule in the early-mid 20th century.  Swamps were drained and roads and other infrastructure were built, and the region is now rich in olive oil and wine production.  We pedal through the tiny fortress town of Bolgheri, famous for its red wines, including “Sassicaia”.  Talk with the locals if you can find one – according to one spry 89-year old we met in the town square, there are only twenty-six residents left!  Another gentle forested climb brings us to world-class gelato before a gliding downhill which customers have called, “the best ride in the world” and ends in a tiny stone village, worth a peek before continuing on.  Our hotel pool is perfect for soothing tired muscles after four days of cycling.  Dinner is together this evening.

  • 64 km (40 miles)
  • Meals: Breakfast & Dinner
  • Lodging: First of 2 Nights at the Hotel Calidario

Day 5 – Loop Ride to Populonia and the Beach

We’ve planned a casual bike ride today to give you a sampling of history and geography from the Etruscan time through the Renaissance.  We head first to the ancient Etruscan port of Populonia, the most important Etruscan port town.  We’ll have a guided visit of the tombs and the “industrial” area, learning about the Etruscans’ practice of metallurgy, where they mined tin and iron from local deposits and processed them into valuable commodities for trade throughout the Mediterranean.  After our visit, you can ride to the village for the view, enjoy some beach time, have lunch by the sea, return to the pool or head off for some more mileage.  Dinner is on your own tonight.

  • 25-60 km (15-37 miles)
  • Meals: Breakfast
  • Lodging: Final Night at the Hotel Calidario

Day 6 – Bicycle to our Agriturismo

Today’s ride takes us into the interior as we follow several river valleys before heading south to the small hilltop towns of Gavorrano, Ravi, and Caldana.  We’re headed to our agriturismo, a working farm that produces olives and wine while providing superb lodging and gourmet cuisine.  A dip in the pool before a wine tasting overlooking the view is a perfect end to the day before dinner together.

Day 7 – Tour Ends

Our tour ends after breakfast this morning.  We’ll provide a shuttle to the Grosseto train station where you can head off on further travels or back home.  Enjoy your travels and thanks for joining us to explore the coast of Tuscany!

  • Meals: Breakfast

Customer Reviews 

  • What was your favorite experience on this trip? My husband would say the eating, especially the dinners which included all the local cuisine and made us branch out and try things we never would have. I would say the swimming pools and the thermal hot springs pool at the hotels. They were all beautiful! We also both enjoyed the curvy, beautiful roads through the hill-top towns, especially the cobbled towns, so picturesque!

  • Really loved it. Everything came together to make for a wonderful vacation with an interesting group of co-riders, and great guides. The composite of all experiences reflected one of the nicest vacations I’ve taken. Leaders knew their stuff, and their customers’ needs, and seemed to enjoy the trip as much as we did.

  • Great trip. Guides were superb. Great group!

  • The trip was terrific, especially the guides, the food, the hotels, the countryside, and the bikes. What’s left?

  • The combination of our awesome guides, the small Tuscany towns, the biking and the fun campanions made it just an awesome experience!

  • I had many “favorite” memories; the route was great taking us through picturesque villages on quiet roads. I enjoyed the scenery, the food, the visits to Populonia, swimming in the sea, our hotels, the other group members and our leaders.

  • Favorite experience on this trip?: The rides, the guides, the food, the visits to pasta and olive oil makers, the weather…it’s hard to choose a “favorite”! Thanks so much to you all!! I’d never use a different tour company.

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