Unique bike tour Tuscany, off the beaten path cycling tour
From Val d’Orcia to the Tuscan coast get a taste of quintessential Southern Tuscany, where the extraordinary beauty of daily life never fails to delight. Enjoy an introduction to the endless rolling wheat fields, ancient woodland, marvelous medieval villages of Maremma.
WOW Moment
- Ride 30 miles gentle downhill from Scansano wine land to Tuscan coast
- Visit best hot springs and thermal bath of Tuscany: San Casciano dei Bagni and Saturnia
- Cycle through authentic Etruscan villages Sovana and Sorano
the tuscan coast
You will cycle past tiny villages that are frozen in time towards our favorite wine area of Scansano with the Morellino delicious wine. End at seaside enclaves of the coast in Talamone enjoying a mostly downhill stage, after so many hills.
You will appreciate the comfort of our selected charming hotels, but the rustic charms will capture your imagination, Tuscany is magical!
For 2026 Tuscany to the Sea Bike tour will be available only from May 15 to September 30, due to the seasonal opening dates of our hotel in Talamone.
DAY 1
Meet & Greet at your hotel in Pienza, The perfect town almost entirely built between 1459 and 1462, Pienza is a remarkable example of Renaissance-era town planning. If you have even the least appreciation for eautiful architecture, stroll about its cobblestone streets. Bike fitting & Optional bike trip to San Quirico d’Orcia.
Distance 20 km/12,5 miles.
DAY 2
Bike ride from Pienza to San Casciano dei Bagni
Today is a completely country ride: for the first 15 km you will ride downhill and after easy gentle rolling hills. you will see Radicofani medieval and enchanting village with a 1200 dating Rocca After lunch at the hill town continue to small outlying district of Celle sul Rigo with its majestic 13th century tower and an unforgettable view
Few km more and arrive to San Casciano Bagni hot spring. The spa is very old and in town there is impressive town hall of renaissance time. The historic centre worth a visit with its characteristic hill town-plan of alleys and small piazzas. Away from the centre, near the Spa, the Chiesa Basilicale which dates to the year 1000 is of great interest. But though San Casciano, immersed in a lush and uncontaminated nature, is a favourite with farm holiday visitors, it should not be forgotten that a great many tourists come for spa cures such as inhalations, baths and mud treatments.
Distance: 49,5 km / 31 miles | Elevation: +857 m / -779 m
DAY 3
Cetona is situated on the slopes of the mountain of the same name, the mount you will climb to get there! So, prepare for some hills today. Cetona retains the characteristic medieval design that consists of small alley ways and little roads that spiral and wind their way to the fortress. This is a must see town and worth the effort! Later you will also visit Sarteano and can take in the unique castle found there! Return to your same hotel in San Casciano Bagni – and maybe a visit to one of the baths?!
Distance: 38 km / 23,7 miles | Elevation: +748 m / -747 m
DAY 4
Today the ride is more challenging crossing minuscule villages and borgos.
Sorano is barely more than a handful of ancient homes gathered around the fortress which is partly occupied by the Fortezza: Erected in the 16th century by the Orsini family, the castle is one of the best surviving examples of Tuscan military architecture. As we all know, the main function of any fortress is to protect against marauding invaders – because of this, we can see for miles from any window in the hotel, across the valley of the Etruscans.
Distance: 47 km / 29,3 miles | Elevation: +682 m / -964 m
DAY 5
Breakfast at the hotel. Soon you will arrive at Pitigliano: a pristine warren of elegant palaces and surprisingly broad cobble-stoned streets, it is nicknamed Tuscany’s Little Jerusalem in honor of extremely active Jewish community that lived here for centuries. Two of the town’s most interesting attractions are its wonderfully restored Synagogue. After another interesting stop at medieval village of Montemerano reach Saturnia: Terme di Saturnia is a well-known spa of sulphurous water known since roman times. Unique spot to visit: hot water falls cascades over whitened rocks creating natural pools.
Your accommodation is stylish B&B in town that occupies a totally redesigned building of 17th century. Have a taste of Morellino di Scansano wine of their production
Distance: 48 km / 30 miles | Elevation: +909 m / -697 m
DAY 6
Warm up your legs cycling ride into Pereta and Magliano in Toscana a real hidden treasure of maremma, all around today is wineyards of sangiovese, the main grape of morellino.. You will reach Talamone, a small fishermen village extended along a promontory overlooking the sea, dominated by an ancient sienese castle, hemmed in by the Natural Park of Maremma. The breathtaking view from the belvedere near lighthouse takes the whole coast from the Argentario to Punta ala. Highlight is to enjoy seafood in a restaurant in town.
Distance: 40,5 km / 25,3 miles | Elevation: +307 m / -789 m
DAY 7
End of bike tour. Arrivederci!
INFO TOUR
best period : May, June, September
DIFFICULTY : moderate to challenge
TOTAL DISTANCE : 260 km / 162,5 miles in 5 stages
TOUR REVIEWS
Price & Inclusions
Price
Cost: € 1650 per person – in double occupancy
Single room supplement € 690
Inclusions
Six nights in excellent four & three-star superior hotels
Six breakfasts
All Baggage transfers
RideWithGPS App: tracks, route notes, off-line navigation
Trip notes: Sightseeing & meals suggestions
Delivery bike at Pienza hotel & bike fitting
Pick-up of bikes and gear in Talamone
Keepsake Cicloposse water bottle
Sales taxes
Not Included
Bike Rental per entire tour
Hybrid bike € 190 | Road bike, E-Bike, gravel € 260 | E-Gravel € 350
City Tax each village charges a tax per each day between euro 0,70 and euro 2,00
Cloister is one of those places where you really feel the history of Pienza. Set in a former 15th-century convent directly on Corso Rossellino, the town’s main street, it still retains the atmosphere and character of the original building, with its beautiful cloister at the heart of the property. What we particularly love is the garden at the back, with its swimming pool and wonderful views stretching across Val d’Orcia. You are right in the center of Pienza, with cafés, restaurants and little shops just outside the door, yet once inside, the hotel feels remarkably peaceful.
Sette Querce is a small, family-run property set in a peaceful garden just a few steps from the historic center of San Casciano dei Bagni. The spacious rooms are all junior suites, each with a private entrance and outdoor terrace shaded by oak trees.
We particularly like its relaxed, personal atmosphere and convenient location: after the ride, you can easily walk into the village for dinner or head to the nearby Fonteverde naturla thermal spa to relax in its naturally warm thermal pools – hot spring. Simple, comfortable and welcoming, it fits perfectly with the quiet character of this beautiful Tuscan hill town.
Sovana Hotel & Resort is set right in the heart of one of Tuscany’s smallest and best-preserved medieval villages. Surrounded by a large garden with olive trees and beautiful views towards the Romanesque Cathedral and the surrounding countryside, it has an elegant yet wonderfully peaceful atmosphere.
We particularly like staying here because it gives you the chance to really experience Sovana: after the day visitors have gone, this tiny historic village becomes especially quiet and atmospheric. The spacious garden and swimming pool are perfect for relaxing after the ride, while the village itself is just outside the door – small enough to enjoy entirely on foot.
Morelliana is a small and beautifully designed B&B in the heart of Scansano, with an intimate atmosphere and the kind of warm, personal hospitality that makes a stay feel special. Set in a restored 17th-century building, its rooms combine original Tuscan character with elegant furnishings and thoughtful details.
What we particularly love is the connection with the local wine and food culture. The owners are Morellino di Scansano wine producers, and their restaurant is right next door – a perfect combination after a day on the bike. You can settle in, enjoy a good dinner and a glass of local wine, and experience the genuine hospitality of this little Maremma town.
Hotel Il Telamonio brings you right to the sea, in the historic heart of Talamone – a tiny Tuscan fishing village perched above the coast and surrounded by the natural landscape of the Maremma Regional Park.
We particularly like the location: after arriving by bike, you can forget about transportation and simply wander through the narrow lanes down to the little harbor, restaurants and cafés. The hotel’s panoramic rooftop terrace offers wonderful views across the sea and the Tuscan Archipelago – a perfect place to relax and enjoy the change of scenery after cycling through the hills of inland Tuscany.
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Tour Reviews
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 Regards
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
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