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Maremma, the coastal & lesser known part of Tuscany, is just as beautiful as the rest of it—but with far less crowds. You’ll see this region in all its glory on this self-guided bike tour, pedaling by rolling wheat fields, cypress trees lining the roads, sun-kissed vineyards, and the most marvelous medieval villages. You’ll also get to know classic Italian dishes and delicious wines during this week in heaven, and you won’t be able to imagine your life without it anymore. With its unmatched beauty of daily life, Southern Tuscany never fails to charm—and it will have your heart, making you forever remember this biking vacation.

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Adventure highlights

  • Travel through time

    Pedal through Etruscan villages, take a dip in hot springs which Romans adored, and explore typical hilltop villages from the Middle Ages

  • Enjoy this carefree itinerary

    A self-guided tour means that you move at your own speed, but enjoy the privileges of arranged accommodation, baggage transfers, routes, and more

  • End the trip on the coast

    Spend a week exploring the beautiful Maremma region and finish the trip in Talamone, a fisherman village

Itinerary

This 7-day, self-guided journey through Maremma is a beautiful way to discover Tuscany. Maremma is one of its most stunning parts and with this bike tour, you’ll move at your own pace and take your time taking in all the beauty around you. Your guiding company will organize accommodation, baggage transfers, breakfasts, routes, and much more—all that’s left to do is pedal and soak in all things Italian.

  • Make your way to Pienza, a wonderful renaissance town in Tuscany. Pienza is a remarkable example of renaissance architecture and it’s truly a treat to just stroll around its cobblestone streets. After a bike fitting, feel free to use the rest of the day as you wish—walk around town, go for a dinner or a cocktail, and settle into your spectacular hotel for the night: a hotel whose building dates back to the 13th century! Tomorrow the cycling begins.

    Accommodation: Hotel Relais Il Chiostro di Pienza

    Pienza in Tuscany
  • Today it’s all about riding through the countryside—for the first 15 km, you’ll ride downhill and after that on gentle rolling hills. You will see Radicofani, a medieval and enchanting village with a fortress dating back before the year 1000. Following lunch, continue to the Celle sul Rigo area with its majestic 13th century tower and an unforgettable view.

    A few kilometers further is the San Casciano dei Bagni hot springs. Here you’ll find old thermal springs, an impressive town hall from the renaissance, and a lovely historic center with its small piazzas and alleys. The Chiesa Basilicale dating back to the year 1000 is also near. San Casciano is set amid lush landscapes and it’s a favorite with visitors—many people come for the healing spa properties, such as inhalations, baths, and mud treatments.

    Accommodation: Sette Querce in San Casciano dei Bagni
    Distance: 49.5 km / 31 miles
    Elevation: +857 m / +2,812 ft | -779 m / -2,555 ft

    San Casciano dei Bagni
  • As Cetona is situated on the slopes of the mountain of the same name, get ready for some hills today! The charming town of Cetona retained the characteristic medieval layout consisting of small alleys and little roads that spiral and wind their way to the fortress. This town is very much worth the effort! Later you’ll visit Sarteano and also see its unique castle. Return to your hotel in San Casciano dei Bagni. If you have time, it’s warmly recommended to relax in the thermal baths!

    Accommodation: Hotel Sette Querce in San Casciano dei Bagni
    Distance: 38 km / 24 miles
    Elevation: +748 m / +2,454 ft | -748 m / -2,454 ft

    Cetona in Tuscany
  • The ride today is a bit more challenging, but the towns and borgos (small Tuscan villages) you’ll see are very much worth it! Sorano is a collection of ancient homes gathered around the fortress that was erected in the 16th century, and is considered one of the best surviving examples of Tuscan military architecture. Continue riding to Sovana, where you’ll stay for the night.

    Accommodation: Sovana Resort
    Distance: 47 km / 29 miles
    Elevation: +682 m / +2,237 ft | -964 m / -3,163 ft

    Sorano, Maremma Tuscany
  • Start cycling to Pitigliano, dubbed as Tuscany’s Little Jerusalem in honor of the Jewish community that’s lived here for centuries, and see its wonderfully restored synagogue. It’s a lovely town to take a break and see its elegant palaces and cobblestone streets. Following a stop at the medieval village of Montemerano, reach Terme di Saturnia—a well known spa of sulphureous waters known since Roman times. This is a truly unique spot so take your time taking in the beauty (maybe even take a dip!) and when you’re ready, head to your accommodation for the night, a lovely B&B that has its own Morellino di Scansano wine.

    Accommodation: Morelliana
    Distance: 48 km / 30 miles
    Elevation: +909 m / +2,982 ft | -697 m / -2,287 ft

    Terme di Saturnia, Italy
  • Ride into Pereta and Magliano in Toscana, a real hidden treasure of Maremma, and discover many vineyards of Sangiovese along the way. You’ll reach Talamone, a small fisherman village dominated by an ancient castle. You can enjoy breathtaking views from the Belvedere near the lighthouse of the whole coast, from Argentario to Punta. Maybe use your last evening of the tour to have some delicious seafood in a local restaurant.

    Accommodation: Hotel Baia di Talamone
    Distance: 40.5 km / 25 miles
    Elevation: +307 m / +1,007 ft | -789 m / -2,589 ft

    Talamone in Italy
  • After breakfast at the hotel, the tour comes to an end! Your guide has organized your bike pick-up (if you rented one) in Talamone.

    Talamone beach in Italy
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Meet your guide

Cicloposse
5.00
Cicloposse
Cicloposse is a bike tour operator based in Tuscany, dedicated to delivering unforgettable cycling experiences and active vacations throughout Italy. With their passion for biking and love for travel, they are committed to providing excellent services while being socially responsible and creating low-impact trips that respect the environment. They pride themselves in working with local people and small businesses, enabling their guests not only to experience the authentic essence of Italy, but also to positively impact communities they visit. Cicloposse offers seamless organization, meticulous attention to detail, and fostering genuine connection with their guests.

Accommodation

5.00 (2 reviews)
Mark and Julie (source: Guide’s website)

I would like to thank you for a fantastic trip that you organised for Julie and myself in may last year We have been telling everyone how much fun we had so don’t be surprised if you get a few more Australian enquiries Hope you both have a great year

Bert and Carol B (source: Guide’s website)

Hi Guiliana – Sadly, we are back home but have wonderful memories forever!! Once again you planned a perfect cycle (on tandem) tour of Tuscany. The heart of Tuscany is so very special to cycle through – the quaint old villages,San Casciano – what an incredible panoramic view from this small village – just awesome – lovely suite in that hotel. From there into the Maremma area- with quiet roads and breathtaking veiws. Sovana charming and very special. Then down to the sea – just wow!! Talamone and Porto San Stefano – How beautiful these sea ports are. yes, there are many hills – beautiful vallys/lakes and we just love the villages we go through. Thanks to both you and Marco. Kind regards

Things to know

  • What you get on this adventure:

      • 7-day self-guided Tuscany Maremma bike tour
      • Accommodation for six nights in excellent hotels
      • Six breakfasts (special dietary requirements can be accommodated)
      • All baggage transfers
      • Route notes, maps, elevation gain and city map
      • RidewithGPS App — navigation offline
      • Sightseeing, restaurant and shopping suggestions
      • Delivery bikes at Pienza hotel & bike fitting
      • Pick-up of bikes and gear in Talamone
      • Keepsake Cicloposse water bottle
      • Sales taxes

    What’s not included:

      • Transportation to Italy
      • Lunches and dinners (though you’ll get the best local recommendations)
      • Bikes — available to rent, price per person for the entire tour
        • Gravel or e-bike — $275
        • Hybrid bike — $195
      • Travel and medical insurance — optional
  • If you’d like to join this Tuscany Maremma bike tour, you have to have a good level of fitness and be able to cycle 38-49.5 kilometers (24-31 miles) per day. You’ll be cycling five days in a row, but a great thing about this tour is that you can move at your own pace and stop whenever you feel like it. Still, there are daily routes and different accommodations schedules, so make sure you’re able to cover these distances daily. You’ll gain between 307 to 909 meters (1,007-2,982 ft) per day—check the itinerary for detailed distances and elevation gains.

    If you’re looking for a bigger challenge, check out this self-guided gravel bike tour in Tuscany.

  • This is a list of clothing & footwear we recommend you bring:

      • Cycling shorts (padded shorts recommended, try them out before the tour)
      • Riding jerseys
      • T-shirts and/or casual shirts (quick-dry)
      • Bathing suit
      • Bike socks and/or sports socks (quick-dry)
      • Dress or casual socks
      • Windbreaker or cool-weather jacket (rainproof and breathable)
      • Light rain jacket or poncho (cheap version is fine—insurance on sunny days!)
      • Bike shoes
      • Riding gloves
      • Underwear (quick-dry)
      • Sweater or fleece
      • Slacks or light jeans (quick-dry, wrinkle resistant)
      • Belt
      • Comfortable walking shoes
      • Sandals

    Miscellaneous

      • Passport, wallet and ID
      • Waterproof, zip-lock type plastic bag for your valuables
      • Health insurance card
      • Travel insurance card
      • Cash, credit cards and/or travel cheques
      • Electronic chargers (for camera, MP3 player, e-reader, cell phone)
      • Adaptors or convertors

    First aid kit

      • Insect repellent
      • Antiseptic cream or antibiotic ointment
      • Antihistamine tablets for hay fever
      • Sunscreen and total bloc
      • Throat lozenges or hard sweets
      • Painkillers
      • Band-aids and ‘Second Skin’ for blisters
      • Rehydration salts
      • Multi-vitamins
  • Yes! If you’d like to skip the hassle of bringing a bike for your Tuscany Maremma bike tour, your guides offer bike rental. Prices are per person and for the entire week of cycling:

      • Hybrid bike — $195
      • Gravel or e-bike — $275
  • A self-guided tour is an independent exploration without a formal guide leading the way. Instead of being part of a group with a tour leader, you will navigate the tour yourself, using resources provided by the operator, such as maps, guidebooks, audio guides, or digital apps.

    For this Tuscany Maremma bike tour, your guide will arrange terrific accommodation for you with six breakfasts. All your baggage will be transferred from one accommodation to the next. You’ll get detailed route notes, maps, daily elevation gains and distances, and a city map. For navigation offline, you’ll use the RidewithGPS app.

    Another great thing about going on a self-guided journey is that your local guide will provide you with all the sightseeing, restaurant, and shopping suggestions you could imagine! This way you can be sure you’re truly getting the authentic Tuscan experience.

  • Group sizes and pricing

      • It takes a minimum of 2 people for this self-guided Tuscany Maremma bike tour to operate.
      • The maximum group size is set at 16 people.

    Tuscany Maremma bike tours can be arranged for larger groups. Contact us to make arrangements.

    Min. age requirements

      • If you are older than 18, you’re good to go.
      • Minors older than 16 may be permitted to join the Tuscany Maremma bike tour on a case-by-case basis, but must be in the presence of a parent or legal guardian.

    If your group has hikers under the age of 18, contact us prior to booking to make arrangements.

  • To get to your Tuscany Maremma bike tour, the nearest airports are Rome Fiumicino (FCO) and Florence Airport (FLR). It’s up to you whether you’d like to rent a car to reach Pienza, the starting point of your tour, or you’d like to use public transport. Driving with a car takes between 1.5-2.5 hours to Pienza, depending on where you land.

    For the public transport option, after landing you have to reach Chiusi. The easiest option would probably be to take the train. Once in Chiusi, you can take a bus or a taxi to Pienza, the starting point of your Tuscany Maremma bike tour.

  • We highly recommend that you cover all your bases with both emergency medical and travel insurance.

    With medical insurance, if you have an accident or medical emergency on or off the mountain, you’ll avoid paying out of pocket for costly expenses. This covers everything from hospital treatments to emergency air transportation and more. Travel insurance covers canceled flights, natural disasters and other scenarios that may interrupt your travel plans.

    We also expect you to respect local regulations and take measures to protect yourselves, your guides, and the communities you’re traveling to. If you need assistance selecting the right insurance for your group, let us know and we will be happy to help!

  • Deposits

    You can secure one of the set dates with a 30% deposit upon booking. The remaining 70% of the trip price is to be paid 90 days prior to departure, at the latest.

    Secure your early bird spot with a 10% deposit! This tour gets sold out very quickly, but with early-bird booking, you will be the first one to know about any new upcoming dates. Pick your preferred dates without the risk of your bucket list adventure selling out!

      • Only 10% of the total amount should be paid as a deposit upon booking. This deposit is non-refundable, but can be transferred to another 57hours adventure anytime in case the dates don’t suit you.
      • Once the dates are set, you can confirm your booking by paying another 20% of the total amount.
      • The final balance is due 3 months (90 days) prior to departure.

    Cancellations

    Booking fees are non-refundable in all cases. During checkout, however, you can choose one of 57hours’ flexibility options:

    Basic

      • In case of cancellation within 48 hours after booking, the amount paid is fully refundable.
      • For cancellations 60 or more days before the trip, you are eligible for a 70% refund of the trip price.
      • For cancellations 0-59 days before the trip, there is no refund.

    Flexible

      • In case of cancellation within 48 hours after booking, the amount paid is fully refundable.
      • For cancellations 60 or more days before the trip, you are eligible for a full refund of the trip price.
      • For cancellations 30-59 days before the trip, you are eligible for a 50% refund of the trip price.
      • For cancellations 0-29 days before the trip, there is no refund.

    Super Flexible

      • In case of cancellation within 48 hours after booking, the amount paid is fully refundable.
      • For cancellations 30 or more days before the trip, you are eligible for a full refund of the trip price.
      • For cancellations 0-29 days before the trip, you are eligible for a 50% refund of the trip price.
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