Bicycle Hidden Tuscany

Bicycle Hidden Tuscany

The Etruscans gave Tuscany its name and after the classical age the epicenter of Tuscany moved to the valley of the Arno River to the north of Siena, and this area of (southern) Tuscany was largely forgotten--until today. Modern Italians have re-discovered this scenic area for its landscapes, villages and historical sites and we're happy to offer you an opportunity to discover it, too.

Cycle through important Tuscan towns including Volterra and San Gimignano, visit smaller gems like Massa Marittima and Castiglione della Pescaia, and enjoy spa hotels such as the one near the important Etruscan site of Populonia.

***If this sounds great but you prefer a longer tour check out our Bicycling Hidden Tuscany Plus! Tufa Towns itinerary.***

Tour Dates & Prices

Private Room Fee
Sep 2-9, 2018
Space Running Out!  
May 19-26, 2019
 Book by November 15 and save $200!
Sep 1-8, 2019
 Book by November 15 and save $200!
Oct 6-13, 2019
 Book by November 15 and save $200!

* We are happy to match solo travelers who would like to share a room with someone of the same gender. If no match exists, due to hotel pricing, we will charge 50% of the private room charge. This charge will be collected at the time of the final payment. If a roommate assignment is available it will be refunded at the conclusion of the tour.

Trip At-A-Glance

  • Length / 8 Days
  • Avg. Distance / 49 km (30 miles) per riding day
  • Difficulty / 201
  • Countries / Italy
  • Price / From USD$3795
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  • Tour Summary
  • Daily Itinerary
  • Map
  • Reviews
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Tour Summary

Daily Ride Summary


1 No cycling today.
2 38 mi / 61 km
3 33 mi / 52 km
4 46 mi / 73 km
5 17 mi / 27 km
6 25 mi / 40 km
7 28 mi / 44 km
8 No cycling today.
  • Highlights
    Fabulous Tuscan food grounded in olive oil, tomatoes, basil and rosemary, Thermal spas, Ridge rides looking out across vineyards, cypress trees, olives, and the Tyrrhenian Sea, Etruscan ruins, Two 2-night stays, Volterra, San Gimignano
  • Includes
    8 days, 7 nights' accommodation; van support; 2 to 3 bilingual tour leaders; all breakfasts, 5 dinners with wine; entrance and guided visit Populonia; Day 1 shuttle from Florence to Volterra; Day 8 shuttle to Grosseto train station

    The Usual (Included with every ExperiencePlus! tour)

    • Superb tour leaders who are fun, bilingual and avid cyclists.
    • Help with flights, trains and pre/post tour hotels.
    • Comfortable lodging in 3-4 star hotels. 
    • All breakfasts and at least half of your dinners.
    • Use of a high quality 27-30 speed bike.
    • Full van support to carry luggage – and tired cyclists, too! 
    • Special events like wine tastings, cultural visits and chocolatiers.
    • All tips and gratuities at tour hotels and group meals.
    • Unique routes, marked with our famous chalk dust arrows.
    • Daily mileage options.
    • Detailed route map and free use of our traveling resource library.

    What's not included:

    • Transportation to and from the bicycling tour including airfare, or train travel
    • Helmets - we ask that you bring your own to ensure the best fit
    • Meals not listed in the itinerary
    • Tour Leader gratuity

    See the complete list of what's included with every ExperiencePlus! Tour.

  • Countries
  • Begin/End
    Volterra / Castiglione della Pescaia (Grosseto)
  • Arrive / Depart
    Florence (FRL), Pisa (PSA) or Rome (FCO)
  • Total Distance
    293 km (181 miles)
  • Avg. Distance
    49 km (30 miles) per riding day
  • Difficulty
    The first day of cycling is the most challenging with just over 4,000 feet of climbing. Day 4 has a 10km gentle climb of 2,700+. The rest of the ride is fairly gentle with a few shorter (less than 3 kms) ascents.
  • Terms
Daily Itinerary

DAY 1: Arrive in Volterra

Highlights: Etruscan Volterra

Arrive today in Volterra, one of Italy's most famous Etruscan towns. Volterra was one of the nine most important Etruscan cities in the pre-Roman era; you'll be here two nights so you'll have the chance to explore its Roman theater and cathedrals. We'll take a test ride after we fit bikes today to make sure everything is fitting right.

DAY 2: Loop ride to San Gimignano

Highlights: San Gimignano and its towers. Alabaster shops in Volterra

Our loop ride today takes us to San Gimignano. Famous for its medieval towers, San Gimignano is one of the best-preserved 14th century villages in Europe. Have a rest, enjoy a coffee in the famous Piazza della Cisterna, and explore this fabulous town. We'll offer a shuttle back into Volterra for those who would prefer to avoid the climb! In the afternoon we have a special visit planned inside the Laboratory of an Alabaster carver. You'll learn more about the ancient technique that is still used by these artisans.

DAY 3: Heading towards the coast

Highlights: A great ride through Tuscan hills and coastal lands

Today we head towards the rich farm villages and picture-perfect vineyards of the Pisan hills. You'll note a striking change in the landscape as we leave the central Tuscan hills for the fertile coastal lands. It's a great day for photographs!

Lodging: TBA

  • Distance: 33 mi / 52 km
  • Meals: Breakfast, Dinner

DAY 4: Bicycle through the northern Maremma region

Highlights: Wine village of Bolgheri, Maremma region of Italy, outdoor pools

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 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.

DAY 5: Loop ride to Populonia and the beach

Highlights: Etruscan sites, beaches, Medieval architecture

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.

DAY 6: Bicycle to Massa Marittima

Highlights: Cycling remote country roads, the hilltop village of Massa Marittima

Today's ride takes you into the interior as you follow several river valleys. Our destination tonight is the lively hilltop village of Massa Marittima. Massa Marittima is known as the "figlia nobilissima" (noble daughter) of Pisa and Siena. Its origins lie somewhere in the High Middle Ages, when the hills around the city were mined for minerals. In the 10th century, the city was the seat of the Bishop of Populonia, but the city's golden age came in 1225, when it became an independent municipality. Take time for some sightseeing or relax by the pool.

DAY 7: Castiglione della Pescaia

Highlights: Cycling remote country roads, fishing port of Castiglione della Pescaia

Todays ride takes you further into the interior before bringing you Castiglione della Pescaia on the coast. Although it is a busy seaside resort in July and August, for most of the year Castiglione is a bustling market center and fishing port. Our hotel sits in the old city center under the 17th century walls built by the Medici family's Grand Duke, Ferdinand I.

  • Distance: 28 mi / 44 km
  • Meals: Breakfast, Dinner
  • Lodging:

DAY 8: Shuttle to Grosseto train station

Highlights: Castiglione della Pescaia

Spend an extra day to enjoy this Renaissance fishing port and Medici fortress perched on the hilltop overlooking the village. The town and main square offers an array of cafés and restaurants for lounging and enjoying local foods and wines. For those who must leave we'll offer a shuttle to the Grosseto train station. Arrivederci!

  • Meals: Breakfast




  • Excellent - very well organized, good terrain and fun!

    Sharree, O., Hood River, OR
  • I sure did like soaking in those lovely spas after a day of riding. Fantastic! Trip of a lifetime.

    Janet L., Ayer, MA
  • I keep expecting to have a less than superior trip one of these days, but so far we haven''t!

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

    Suzanne W., Seattle, WA
  • Thanks for making this trip so amazing and memorable!

    Joanna G., Omaha, NE
  • What was your favorite experience on this trip? Too many to single one out. I liked seeing the "Cinghiali" (boar) at the preserve on the way to Massa Marittima. I also loved the pasta demo and the olive oil press, all the dinners, about 10 gelatos, acres of "girasoli" (sunflowers), and the care-free life of the tour. We LOVE ExperiencePlus and hope we can keep taking bike trips into our golden years.

    Sharon S., Eugene, OR
  • We had a fantastic trip. Hotels were excellent. We thought the chalk markings to find the route were really great.

    Sandra L., Miami, FL
  • The meals were, as always, high points. The beauty and variety of the scenery, and the lack or traffic on the route, were great as well.

    David S., Eugene, OR
  • Thanks for a great experience!

    Michael C., Smartswood, NJ
  • My favorite experience on this trip?: Hmmm...the ride from Sesseta to the coast, and back. Also, my two interactions with locals trading our ExperiencePlus! hats.

    Sandy C., Fort Collins, CO
  • Bicycling through beautiful country followed by thermal spa therapy and finished off with a great Italian dinner. Perfect way to spend a day.

    Dan G., Fort Collins, CO
  • 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!

    Willow L., Denver, CO
  • 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.

    Russell B., Arcadia, CA
  • Was a beautiful area of Italy and the "soak" part was exceptional after a hard day''s ride. Cant imagine a better trip. ExperiencePlus Rocks!

    Betsy G., Scottsdale, AZ
  • The format of using chalk arrows and signs on the road allowed us to travel at a pace that we could enjoy the sites and allowed as time to enjoy the tastes along the way each day. Then in the evenings, both the full group dinners and on our free nights the smaller gatherings for dinner were wonderful. The choice of places we had dinner together and the towns and villages we visited were excellent and truly allowed us to appreciate the food and wine of Tuscany.

    John K., Oyama, BC, Canada
  • The trip was terrific, especially the guides, the food, the hotels, the countryside, and the bikes. What's left?

    Brooks Z., Sherborn, MA
  • Spectacular views. Great hotels, spa pools, food and guides.

    Susan S., Fort Collins, CO
  • We had a great experience, a good time, loved the trip, and we think very highly of ExperiencePlus!, this tour, and our tour leaders.

    Calvin M., Fort Collins, CO

    Eric D., Valencia, CA - September 2017
  • Favorite experience on this trip?: The rides, the guides, the food, the visits to pasta and olive oil makers, the's hard to choose a "favorite"! Thanks so much to you all!! I'd never use a different tour company.

    Pamela M., Eugene, OR
  • What was your favorite experience on this trip? The whole trip was incredible. My best day was the ride to and through Bolgheri, Carducci, Sasseta, and Sureveto. What an incredible and wonderful day.

    Bill H., Ft Collins, CO
  • 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.

    Liz T., Napanee, Ontario
  • The tour was a life enhancing experience and we can not wait to schedule our next will be the culinary tour next September!

    Dave M., Manvel, TX
  • Great trip. Guides were superb. Great group!

    Russ A., Seattle, WA
  • Great job! We'll be joining you on another trip in the future.

    Paul B., Issaquah, WA
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