FIND your perfect trip!
FIND your
perfect trip!
Cycling days
Tuscany Coastal South ride
Tuscany Coastal South ride
Type :
Level :
Duration :
7 days
Cycling days :
Comfort :
Mar Apr May Jun Sep Oct
Seacoast Gastronomy Culture Nature
Price On request
Tuscany Coastal South ride

Tuscany Coastal South ride


Bike Tour: Tuscany Coastal South ride - 7 days

Embark on a picturesque cycling journey along the stunning Tuscan coast, immersing yourself in the natural beauty and cultural richness that defines this enchanting region. Your adventure begins in the charming seaside town of Castiglione della Pescaia, where the azure waters of the Tyrrhenian Sea meet the golden sands of the coastline. Leaving the coastal allure behind, your route takes you inland towards the historic town of Massa Marittima. As you pedal through the Tuscan countryside, you'll be greeted by rolling hills adorned with vineyards, olive groves, and cypress trees, creating a quintessential Tuscan landscape. Massa Marittima, with its medieval charm and well-preserved architecture, invites you to explore its narrow cobblestone streets, vibrant piazzas, and the majestic Cathedral of San Cerbone. Approaching Castagneto Carducci, the landscape becomes more undulating, offering a mix of challenging ascents and rewarding descents. The town itself, perched on a hill with views of the surrounding vineyards and olive orchards, exudes an authentic Tuscan atmosphere.

Day 1: Arrival in Castiglione della Pescaia
Day 2: Loop ride via Marina di Grosseto
Day 3: Loop ride via Vetulonia
Day 4: Cycle from Castiglione della Pescaia to Massa Marittima
Day 5: Cycle Massa Marittima to Castagneto Carducci
Day 6: Loop ride via Bogheri
Day 7: Arrivederci Castagneto Carducci!

Day 1:    Arrival in Castiglione della Pescaia

Arriving in Castiglione della Pescaia, you step into a coastal haven that seamlessly blends historic charm with the allure of the Tyrrhenian Sea. As you approach the town, the sparkling blue waters and sandy shores create a welcoming backdrop for the beginning of your cycling adventure. Your arrival day in Castiglione della Pescaia sets the stage for the adventure that awaits you along the Tuscan coast – a perfect blend of coastal bliss, historic charm, and the warm embrace of Italian hospitality.

Day 2:    Loop ride via Marina di Grosseto
40 km

Starting from Castiglione della Pescaia, your ride follows the coastal road, providing panoramic views of the Tyrrhenian Sea on one side and the rolling hills of Tuscany on the other. The salty breeze accompanies you as you pedal along the sun-kissed shores, with the azure waters glistening under the Mediterranean sun. Upon reaching Marina di Grosseto, the atmosphere changes to a more relaxed seaside vibe. The long sandy beaches stretch out before you, inviting you to take a break and enjoy the sound of waves gently lapping the shore. As you loop back towards Castiglione della Pescaia, the landscape transitions between coastal views and the rustic  beauty of the Tuscan countryside

Challenge: 40km, ascent 10mt, descent 10mt

Day 3:     Loop ride via Vetulonia
60 km

Climb uphill from Castiglione della Pescaia the route takes you through the Tuscan countryside, offering panoramic views of rolling hills adorned with vineyards and olive groves. As you approach Vetulonia, the landscape transforms, and you find yourself in the midst of ancient history. Vetulonia, an Etruscan archaeological gem, welcomes you with remnants of its rich past, including tombs, archaeological sites, and the evocative ruins of the ancient city. Take a moment to explore this historical treasure, immersing yourself in the mysteries of the Etruscan civilization. As you cycle back towards Castiglione della Pescaia, the coastal allure beckons once again. The final stretch may offer glimpses of the Tyrrhenian Sea on the horizon, creating a sense of anticipation as you approach the coastal town.

Challenge: 60km, ascent 425mt, descent 425mt

Day 4:    Cycle from Castiglione della Pescaia to Massa Marittima
50 km

Embark on a captivating cycling journey from the coastal gem of Castiglione della Pescaia to the medieval town of Massa Marittima, weaving through the enchanting landscapes of Tuscany. This ride promises a perfect blend of coastal vistas, rolling hills, and historic charm. The route unfolds through the undulating hills of Tuscany, where vineyards, olive groves, and cypress trees paint a mesmerizing landscape. As you pedal away from the coast, the peaceful countryside offers a stark contrast to the lively atmosphere of the seaside, providing a serene and immersive experience. As you approach Massa Marittima, the silhouette of medieval towers and historic architecture comes into view, perched atop a hill. The town welcomes you with its well-preserved medieval charm, narrow cobblestone streets, and the impressive Cathedral of San Cerbone. Take a break to explore the historic center, where every corner reveals a glimpse of Tuscany's rich cultural heritage.

Challenge: 50km, ascent 5700mt, descent 210mt

Day 5:    Cycle Massa Marittima to Castagneto Carducci
45 km

Today is your thoughest cycling day from the medieval town of Massa Marittima to the charming hilltop village of Castagneto Carducci, traversing the picturesque landscapes of Tuscany. This cycling journey promises a perfect blend of historic richness, rolling hills, and the timeless allure of the Tuscan countryside. Leaving Massa Marittima behind, the route leads you through the undulating hills of Tuscany, where vineyards, olive groves, and cypress trees decorate the landscape. As you pedal onward, the scenery transforms, and the coastal allure begins to make its presence felt. The Tyrrhenian Sea sparkles in the distance, offering glimpses of the coastal splendor that awaits. The journey takes you through quaint villages and sun-drenched fields, immersing you in the authentic charm of rural Tuscany. Your cycling adventure concludes in Castagneto Carducci, where you can reward yourself with a leisurely exploration of the village's historic sites and perhaps indulge in the flavors of local cuisine at one of its inviting trattorias. Whether you choose to stroll through the narrow streets or relax in a quaint café, Castagneto Carducci welcomes you with its authentic Tuscan hospitality.

Challenge: 45km, ascent 670mt, descent 860mt

Day 6:    Loop ride via Bogheri
40 km

Starting in Castagneto Carducci, the medieval atmosphere of the village sets the tone for your ride. Pedaling through cobblestone streets and past historic buildings, you quickly find yourself immersed in the authentic ambiance of Tuscan hilltop life. The distant sea views provide a scenic backdrop as you leave the village behind and set out towards the renowned wine-producing area of Bolgheri. As you approach Bolgheri, the iconic cypress trees that border the road create a captivating avenue, casting dappled shadows on the sunlit path. The fragrance of the surrounding pine trees and the distant scent of the sea add a sensory dimension to your cycling experience. Arriving in Bolgheri, you're greeted by a quaint hamlet steeped in history and surrounded by vineyards. The cobbled streets and medieval buildings exude charm, while the Castle of Bolgheri stands as a testament to the area's rich past. Take a leisurely break to explore the village, perhaps stopping at a local enoteca to sample the renowned wines produced in the Bolgheri region, such as the prestigious Sassicaia. It's a ride that seamlessly weaves together history, culture, and the pleasures of cycling in the heart of this enchanting region.

Challenge: 40km, ascent 345mt, descent 345mt

Day 7:    Arrivederci Castagneto Carducci!

After breakfast take the local bus to the closest train station in Donoratico, unless you have booked a transfer or extra services with us. 

Hotel L'approdo - Castiglione della Pescaia (GR)
Hotel Girifalco - Massa Marittima
Hotel Zi Martino - San Giusto (LI)



Padlock is included


1 lateral pannier is included






  • Frame: 6061 alloy
  • Brakes: pads
  • Transmission: Shimano 21 gears
  • Wheels: 28 inches
  • Fork: Hi-Ten hard steel
  • Chainset: alloy
  • Chain rings: 48 x 38 x 28 teeth
  • Rear derailleur: Shimano TY300
  • Font derailleur: Shimano TY510
Practical info

6 Nights 

B&B & Hotel ***

Breakfast included

Route notes, maps and App

Bike rental available

7-days a week service-hotline

Luggage transfer included

GPS tracks available 

Medical and luggage travel insurance

Arrival info

Florence or Pisa Airport

Grosseto, Follonica, Castagneto Carducci/Donoratico train station

Italian Bike Tours

Borgo Allegri 16R
50122 Firenze FI
+39 055 2340736 

Italian Bike Tours and its Partners ("We") use cookies to manage the website, to show you personalized content and to manage business goals. Below you can find more information on how we use cookies. You can accept all cookies, select them individually or reject them all. To learn more about our cookie policy, you can visit the dedicated page at any time