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 30-Oct 7, 2019
 Sold Out!
Oct 6-13, 2019
Guaranteed to Go

* 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.

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Trip At-A-Glance

  • Length / 8 Days
  • Total Distance / 293 km (181 miles)
  • Avg. Distance / 49 km (30 miles) per riding day
  • Tour Level / 3.0
  • Countries / Italy
  • Begin/End / Volterra / Castiglione della Pescaia (Grosseto)
  • Price / From USD$3795
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  • Tour Summary
  • Daily Itinerary
  • Travel Information
  • Map
  • Reviews
  • Similar Tours
Tour Summary

Tour Summary

  • Highlights
    Fabulous Tuscan culinary specialties (olive oil, tomatoes, basil and rosemary), Thermal spas, Volterra, Ridge rides looking out across vineyards, cypress trees, olives, and the Tyrrhenian Sea, Etruscan tombs and ruins, Two 2-night stays
  • Includes
    8 days, 7 nights' accommodation; 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; and the usual (see below).

    The Usual (Included with every ExperiencePlus! tour)

    • Superb tour leaders who are fun, bilingual and avid cyclists.
    • Help with flights, trains and starting/and or ending hotel reservations.
    • Comfortable lodging in 3-4 star hotels. 
    • All breakfasts and at least half of your dinners.
    • Use of a high quality Titanium road bike, hybrid, or tandem (aluminum road bikes or hybrid bikes in South America) geared specifically to cruise the flats and help ease you over the mountain. Our bikes come with an odometer so you can track your miles, an expandable rear rack pack to carry your stuff, and one water bottle that is yours to keep.
    • Full van support to carry luggage – and tired cyclists, too! 
    • Special events such as wine tastings or cultural visits as described in the trip itinerary.
    • All tips and gratuities at tour hotels and group meals.
    • Unique routes, marked with our famous chalk dust arrows.
    • Daily mileage options on tour.
    • Detailed route map for each day's ride.

    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.

  • Arrive / Depart
    Florence (FRL), Pisa (PSA) or Rome (FCO)
  • Overall Tour Level
  • Daily Ride Summary




    Day Level


    Test ride
    61km / 1293m
    Very hilly
    difficulty level 4.5
    52km / 559m
    difficulty level 3.0
    73km / 825m
    Rolling hills
    difficulty level 3.5
    27km / 335m
    Rolling hills
    difficulty level 1.5
    40km / 627m
    difficulty level 3.0
    44km / 269m
    Mostly flat
    difficulty level 1.0
    Last day

    Tour Level Note:

    **We use Ride With GPS ( to calculate elevation and mileage information. Due to variance between mapping technologies, totals may differ slightly across devices and applications

Terrain Legend

Mostly flat Mostly flat

Rolling hills Rolling

Hilly Hilly

Very hilly Very hilly

Mountainous Mountainous

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.

  • Distance: 61km (38mi)
  • Gain: 1293m (4241ft)
  • Terrain: Very hilly
  • Day Level: difficulty level 4.5
  • Meals: Breakfast
  • Lodging:

DAY 3: Heading towards the coast

Highlights: A great ride through Tuscan hills and coastal lands

Today we head through rich farmland and remote villages where you will have fantastic views of the surrounding 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!

  • Distance: 52km (33mi)
  • Gain: 559m (1834ft)
  • Terrain: Hilly
  • Day Level: difficulty level 3.0
  • Meals: Breakfast, Dinner
  • Lodging:

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.

  • Distance: 73km (46mi)
  • Gain: 825m (2706ft)
  • Terrain: Rolling hills
  • Day Level: difficulty level 3.5
  • Meals: Breakfast, Dinner
  • Lodging:

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.

  • Distance: 27km (17mi)
  • Gain: 335m (1099ft)
  • Terrain: Rolling hills
  • Day Level: difficulty level 1.5
  • Meals: Breakfast
  • Lodging:

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.

  • Distance: 40km (25mi)
  • Gain: 627m (2057ft)
  • Terrain: Hilly
  • Day Level: difficulty level 3.0
  • Meals: Breakfast, Dinner
  • Lodging:

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: 44km (28mi)
  • Gain: 269m (882ft)
  • Terrain: Mostly flat
  • Day Level: difficulty level 1.0
  • 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
Travel Information

Travel Information

Day 1: Arrival Information

Arrive in Volterra

Your tour starts with a complimentary ExperiencePlus! shuttle pick-up on Day 1 at 12 noon at the Meeting Hotel in Florence, the Hotel Plaza Lucchesi (your spot on the shuttle is already saved for you).

We will be glad to arrange your pre-tour stay at the Meeting Hotel for you upon request. Note that we will not sleep there as a group and the stay there is not included in the tour price.

Flying into Florence (FLR) and continuing to the Meeting Hotel:

  • Taxi from the airport to the Meeting Hotel (25 min/EUR 30)

Or airport shuttle:

  1. Vola in Bus shuttle to the Firenze S.M. Novella train station (20 min/EUR 6)
  2. Taxi from the train station to the Meeting Hotel (10-15 min/EUR 10-12)

Day 8: Departure Information

Shuttle to Grosseto train station

Your tour ends with a complimentary ExperiencePlus! shuttle drop-off at the Grosseto Train station on the final day of the tour at around 10 a.m. (your spot on the shuttle is already saved for you). Schedule your outbound flight for the following day.

The below information will help you plan your departure. For more tips or other routes, you might like Rome2Rio. The fare and timing information listed below is approximate.

We recommend flying out of the Rome Fiumicino Airport (FCO).

From the Grosseto train station to the Rome Airport:

  1. Train from Grosseto to Roma Termini (1.5-2.5 hours/fares vary)
  2. Leonardo Express from Roma Termini to the Rome Airport (32 min/EUR 14) or Taxi (30 min/EUR 48)

Look up Italian train schedules at or Questions? See our information on taking trains in Europe here or ask us.

What's Included

For a full list of what's included before, during and after your bike tour, visit our What's Included page.

Pre-Trip Planning Checklist

To do right after you booked!

6 to 3 Months Prior to Tour Start Date

  • Check the online itinerary of your trip and review the arrival and departure information under the "Travel Information" tab to see meeting place and time, if a reservation on a complimentary ExperiencePlus! Shuttle (if applicable) is required, and other important information to help you plan your arrival and departure.
  • Reserve your flights after you know you have a confirmed tour departure. Please check with our office if you do not know if your trip is confirmed.
  • Book your pre and post-tour hotel nights.
  • Begin your chosen training program:
  • Final payment is due 90 days (120 days for Bike & Barge/Boat tours) prior to the tour start. Please refer to your Deposit Payment Invoice and the Final Payment Reminder e-mail you have received for detailed instructions.

6 to 2 Weeks Prior to Tour Start Date

Day of Your Flight

Get as much sleep on the plane as you can. Pack your one day of cycling gear in your carry-on. See you soon!

What to Expect on Tour


Your bike will be equipped with: a men's or women's saddle, a quick release style seat post adjustment, rear rack and expandable pack, pump, patch kit, spare tube, cable lock, cyclometer, rear lights, a water bottle cage (or two), one water bottle , and a bell. If you would like to bring your own pedals and shoes we recommend doing so—your tour leaders will install them during the bike fitting. We have flat pedals with or without cages available. For safety and hygiene reasons you are responsible for bringing a helmet.


Each day you'll receive a daysheet with information on the day's activities, meals and ride. These also include Tour Leader phone numbers, hotel information and interesting historical and cultural information about sites that you may want to stop and see along the route. Your Tour Leaders will also post daily announcements in the hotel lobby with information about sightseeing in town or restaurant recommendations for dinners on your own as well as important information about breakfast, luggage down and "arrows down" time.

Navigating on Tour

Each day we will provide you with a route map with the day's ride highlighted route. Of course, we also mark the route every day with our signature chalk dust arrows. Our arrows make navigating very easy—you may never need to look at the map! The arrows also allow you to ride at your own pace. There is no need to "keep up" with the group—this is your ride!

But what if it rains? What happens to the arrows? In a light rain, the arrows actually "set up" and become more permanent. In a heavy rain, they do wash away. If that happens, we'll re-group to cycle together for those who want to continue cycling while those who prefer to stay dry can shuttle.

For the tech-loving riders out there we offer the opportunity to download GPS tracks of most tour routes to your personal GPS device using

Van Support

The van carries luggage and supports cyclists. It also has water, fruit and snacks. Though the van has snacks, we encourage you to stop and enjoy markets and find your own favorite local specialty.


We have carefully chosen all of our accommodations for their charm and location. They are typically small, family run hotels that offer you a glimpse into the local culture.

We prefer hotels near interesting sites in the center of town located along the best cycling route in the area. Because many of the hotels are small not all of the rooms will be exactly the same. We keep this in mind and do our best to distribute rooms fairly by the end of the tour. Our itinerary lists our primary hotels. On rare occasions, listed hotels are subject to change.

Meals and Restaurants

Breakfasts: we work hard to arrange complete breakfasts but some hotels still serve continental style breakfasts; cycling is energy intensive so we do recommend you plan for a morning or mid-morning snack on the road at a local café or market.

Water is OK in almost all hotels and in country fountains; if there is a problem, we will advise you.

We'll recommend lunch locations en route and most itineraries include a few group picnics. We limit the number of picnics so you don't feel pressured to be at a certain place in the middle of your ride.

Dinners together are often pre-planned and pre-ordered. We'll ask you prior to your trip if you have special dietary requirements. Preplanned meals allow us to provide a variety of regional specialties and facilitate efficient service. Water, wine and beer are included.

Tipping Your Tour Leader Team

If you feel your tour leader team has demonstrated great expertise and service, common practice within the travel industry is to tip. Tipping is voluntary and greatly appreciated, and gratuity amounts vary widely. Should you decide to leave a tip, as a guideline, we suggest 5% of the tour cost per traveler – this for the entire tour leader team, not each Tour Leader. If you’d like to show your gratitude for your Tour Leaders’ excellent service you can give the tip to any member of the tour leader team, as they share it evenly. In order to avoid social tensions, we encourage you to tip as individuals and not as a group. If you feel your Tour Leaders did not quite meet your expectations, then we would like to know about it. You will also have the opportunity to leave your comments in our evaluation survey which we email to you after your trip.


By reserving space on tour, you agree that ExperiencePlus! Bicycle Tours may use, re-use and reproduce any images, photos or videos that you send to us, or that are taken by our guides and/or other travelers of you individually or in a group, in any medium, including but not limited to print, electronic media, or Internet, free of charge and without your right to inspection, for promoting and publicizing our travel products and services worldwide. If you do not want us to use any images of you that are taken by us or other participants during the tour, you must inform us or your tour leader in writing at the start of the tour.





  • 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
  • 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
  • Thanks for making this trip so amazing and memorable!

    Joanna G., Omaha, NE
  • We had a fantastic trip. Hotels were excellent. We thought the chalk markings to find the route were really great.

    Sandra L., Miami, FL
  • 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
  • Thanks for a great experience!

    Michael C., Smartswood, NJ
  • 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
  • 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
  • Great job! We'll be joining you on another trip in the future.

    Paul B., Issaquah, WA
  • 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
  • We had so many! The evening meals were wonderful and riding through such beautiful country was just breathtaking! Our guides were fun, knowledgeable and paid attention to of every detail.

    Cindy K., Greeley, CO - September 2018
  • 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
  • The trip was terrific, especially the guides, the food, the hotels, the countryside, and the bikes. What's left?

    Brooks Z., Sherborn, MA
  • Excellent - very well organized, good terrain and fun!

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

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

    Ellen L., Boulder, CO
  • Great trip. Guides were superb. Great group!

    Russ A., Seattle, WA

    Eric D., Valencia, CA - September 2017
  • 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
  • Spectacular views. Great hotels, spa pools, food and guides.

    Susan S., Fort Collins, CO
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