Tuscany to the Sea Bike Tour | 7 Days
🇬🇧 English-speaking staff
Intermediate+
approx. 250 km
Climb approx. 3,500 m
approx. ¥308,000~
7 days
From hilltop towns to hot-spring villages and old Etruscan towns, all the way to the sea of the Maremma: a ride through southern Tuscany, away from the busiest routes
A self-guided tour to enjoy freely, without a guide 📅 Choose your own departure date.
*Because of the seaside hotel's opening season, departures run from mid-May to June and in September.

A 7-day, 6-night bike tour heading south from Pienza in the Val d'Orcia all the way to the Tuscan coast. Endless rolling wheat fields, ancient woods, medieval villages where time seems to have stopped, and then the Maremma, where Tuscany's wild nature is still intact.
You spend two nights in San Casciano dei Bagni, with hot springs just a short walk away after the ride. Further on, you visit Sovana, Sorano and Pitigliano, towns that still carry traces of the Etruscans, and the hot-water cascades of Saturnia, known since Roman times.
In the wine town of Scansano you stay at a B&B run by producers of Morellino di Scansano. The last day goes from the hills to the sea, almost all downhill, and in the fishing village of Talamone a seafood dinner is waiting.

From the Val d'Orcia to the Sea of the Maremma | 7-Day Itinerary
From Pienza in the Val d'Orcia, through hot-spring villages and Etruscan towns, to Talamone on the sea of the Maremma: a 7-day, 6-night cycling itinerary across southern Tuscany from north to south.
Day 1 | Pienza
Setting off from the Renaissance "ideal town"
Arrive at your hotel in Pienza. After collecting your bike and the bike fitting, you can take an optional test ride to San Quirico d'Orcia.
Pienza was built almost in one go between 1459 and 1462, and it remains a rare example of Renaissance town planning. In the evening, take a slow walk through its cobbled lanes.
Distance: 20 km
Day 2 | San Casciano dei Bagni
Over the hills to a hot-spring village
The first 15 km or so are downhill, followed by gentle rolling hills through open countryside. Stop for lunch in Radicofani, a medieval village crowned by a 13th-century fortress. Beyond it, the small hamlet of Celle sul Rigo, with its 13th-century tower, offers an unforgettable view.
A little further on you reach the hot-spring village of San Casciano dei Bagni, where you stay for two nights. Its spa tradition is very old, and the town keeps a Renaissance town hall and a historic centre of alleys and small squares. Near the springs stands a church dating back to around the year 1000.
Distance: 49.5 km | Elevation: +857 m / -779 m
Day 3 | Cetona and Sarteano
Climbing to medieval villages
A day with more climbing. Cetona sits on the slopes of the mountain of the same name, and you ride up it to get there. Its narrow lanes spiral up to the fortress, and it keeps its medieval layout remarkably well. Then on to Sarteano, known for its distinctive castle.
In the evening you return to the same hotel in San Casciano. A visit to the hot springs is highly recommended.
Distance: 38 km | Elevation: +748 m / -747 m
Day 4 | Sorano
Tiny villages and the Orsini fortress
A more demanding route today, through a string of tiny villages and hamlets.
Sorano is a small town of old houses gathered around its fortress. Built by the Orsini family in the 16th century, it is one of the best-preserved examples of Tuscan military architecture, and from up high you can see far across the valley of the Etruscans. Tonight you stay in Sovana.
Distance: 47 km | Elevation: +682 m / -964 m
Day 5 | Pitigliano and Scansano
Etruscan towns and hot-water falls
You soon reach Pitigliano, a town of elegant palaces and broad cobbled streets. A Jewish community lived here for centuries, earning it the name "Little Jerusalem of Tuscany", and its restored synagogue is well worth a visit.
After a stop in the medieval village of Montemerano, ride on to Saturnia. This sulphurous spa has been known since Roman times: warm water cascades over white rocks, forming natural pools.
Tonight you stay at a B&B in the centre of Scansano, in a converted 17th-century building, where you can taste the Morellino di Scansano wine made by the owners.
Distance: 48 km | Elevation: +909 m / -697 m
Day 6 | Talamone
Through the vineyards to the sea
First, warm up your legs riding to Pereta and Magliano in Toscana, hidden gems of the Maremma surrounded by Sangiovese vineyards, the main grape of Morellino. From the hills to the sea, today is mostly downhill.
Your destination, Talamone, is a small fishing village stretched along a promontory, overlooked by an old Sienese castle and surrounded by the Maremma Natural Park. From the lookout near the lighthouse, the view takes in the whole coast from the Argentario to Punta Ala. In the evening, enjoy seafood at one of the town's restaurants.
Distance: 40.5 km | Elevation: +307 m / -789 m
Day 7 | End of tour
Lingering by the sea
The tour ends after breakfast. The nature and beaches of the Maremma Natural Park (Uccellina) are close by.

Hotels in Pienza, San Casciano, Sovana, Scansano and Talamone
On this tour you spend one night in Pienza, two nights in San Casciano dei Bagni, and one night each in Sovana, Scansano and Talamone. From a hilltop town to a hot-spring village and a seaside fishing village, each stay reflects the character of its place.
Pienza | Il Chiostro (1 night)
A hotel in a converted 15th-century monastery on Corso Rossellino, Pienza's main street. At its heart is a beautiful cloister, and the atmosphere of the original building is still intact. The garden at the back has a pool and views over the Val d'Orcia. Right in the centre of town, yet very quiet inside.
San Casciano dei Bagni | Sette Querce (2 nights)
A small family-run property in a peaceful garden, a short walk from the historic centre. All rooms are junior suites, each with a private entrance and a terrace shaded by oak trees. After the ride you can walk into the village for dinner or relax in the thermal pools of nearby Fonteverde. Relaxed and welcoming.
Sovana | Sovana Hotel & Resort (1 night)
A hotel right in the heart of Sovana, one of Tuscany's smallest and best-preserved medieval villages. Its large garden with olive trees looks out over the Romanesque cathedral and the countryside. The joy of staying here is enjoying the quiet village once the day visitors have left. The garden and pool are perfect after the ride.
Scansano | Morelliana (1 night)
A small, beautifully designed B&B in the centre of Scansano, in a restored 17th-century building that combines Tuscan character with elegant furnishings. The owners produce Morellino di Scansano wine, and their restaurant is right next door. Enjoy a good dinner, a glass of local wine and the warm hospitality of this small Maremma town.
Talamone | Il Telamonio (1 night)
A seaside hotel in the historic heart of Talamone. Once you arrive by bike, simply wander the narrow lanes down to the little harbour, restaurants and cafés. The panoramic rooftop terrace looks out over the sea and the Tuscan Archipelago, a welcome change of scenery after the inland hills.
Tour price and what's included
Tour price (tax included)
€1,750 per person (sharing a double room)
Single room supplement: €690
*The yen price at the top of the page is an estimate and varies with the exchange rate. Payment is made in euros.
Included
6 nights in hotels (4-star and 3-star superior)
6 breakfasts
All luggage transfers, including between hotels
RideWithGPS app (route data and offline navigation)
Trip notes with sightseeing and food tips
Bike delivery and bike fitting at your hotel in Pienza
Bike and equipment collection in Talamone
Cicloposse water bottle
Taxes
Not included
Bike rental (extra cost)
City tourist tax (€0.70 to €2 per night, depending on the town)
Bike rental prices
Hybrid bike: €190
Road bike, e-bike or gravel bike: €260
E-gravel bike: €350
*Prices cover the whole tour.
Today's price in yen
Support from Japan
Our local staff speak Italian and English. Our Japan office helps you on LINE with questions, bookings and travel documents, in your time zone (not on site).
Even on your first cycling trip abroad, you can join with peace of mind.
What our Japan office offers
• LINE support, reply usually within 24 hours
• In emergencies, our local staff help in English
• Allergies and diets sent to restaurants in advance
• Travel documents also available in Japanese
Ride and taste Italy to the full, with support from Japan.
First cycling tour? Start here
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