The tour begins in this walled town in Siena province
Getting to know your fellow tourists is easy on the quiet roads
This will be home for the two days spent on beautiful Elba
A lovely little coastal town along the course
Delightful food and perfect accompanying wines are available throughout this tour
Surround yourself with the rolling hills of Chianti - the origin of the world famous wine
The splendid views never end, even when you're taking a break
It's not going to be a dull ride with all the ascents and descents

Italy Bike Tours Tuscany: From the Hills to the Sea

7 days
Site savings
$3,136 USD

Italy is renowned for being a passionate and proud country. It’s little wonder why, when it boasts delights such as the Tuscan countryside, a fascinating history, and a cuisine that has enraptured the world. All combined it makes for the perfect playground for a cycling adventure. This week-long trip for small groups lets you soak up every last drop of beauty that the hills and sea provide here.

  • Category
    Road Cycling
  • Type
    Fully Guided
  • Duration
    7 days
  • Culture Level
  • Skill Level
    3 - Intermediate
  • Activity Level
    3 - Active
  • Elevation
    3 - Intermediate
  • Terrain
  • Distance
    229.9 miles
  • Avg. Daily Distance
    46.6 miles
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Quick Stats

  • Duration
    7 days
  • Main Destination
  • Distance
    229.9 miles
  • Avg. Daily Distance
    46.6 miles
  • Elevation
    3 - Intermediate
  • Terrain

Route Map (click to view larger image)

Itinerary Details

  1. Day 1Settling into Siena

    The first day of the trip is here and the excitement builds as you swoop into Siena.

    The guides of the tour will run through a briefing of what to expect and help prepare your bikes for the adventure that lies ahead. With the preparations complete, get to know everyone better with some drinks and dinner inside the walls of the breath-taking Monteriggioni Castle.

    • Sangallo Park Hotel
    • Dinner
  2. Day 2Looping around Chianti

    The wait is over as you hop on the saddle and begin a cycling journey through the gorgeous hills of of Chianti. Leaving Siena behind you’ll be wowed by the differing views you get of Radda, a historic Tuscan town with picturesque squares and sumptuous wines.

    The depth of history is palpable, particularly when you learn that the town has been around for millennia. The roads to this charming town will be easy with a continuous ascent and matched with scenic views of vineyards.

    Afterwards, head to Castellina, another Etruscan town with a myriad of wineries offering their world famous Chianti wines. This time, however, the visit to Castellina will be for a delicious cappuccino. It's perfect for re-energising yourself on the ride back to Siena.

    Dinner will be at an acclaimed restaurant to close up an unforgettable day.

    • 40.5 miles
    • Dinner
  3. Day 3Hitting the saddle and history on your first ride

    Leaving Siena behind you’ll be wowed by the differing views you get of the Monteriggioni Castle en route to Abbadia a Isola.

    The depth of history here is amazing especially when you learn how this route of the Via Francigena was previously used in medieval times between Canterbury and Rome. Continuing on you will stop in an array of towns and villages such as Colle Val d’Elsa, which is well known for its glass production. Pass through the likes of San Gimignano as well, where the skyline is dominated by a series of medieval towers.

    Today’s ride will reach its conclusion in the enchanting town of Volterra, which boasts more than 3,000 years of history to dive into. The walled mountaintop town is a clear example of preserving Etruscan heritage.

    You will spend the evening here and be able to explore the town on foot before enjoying into an Italian dinner.

    • 48.5 miles
    • Dinner
  4. Day 4History ebbs and flows as your wheels keep turning

    After wolfing down a delicious breakfast, you’ll have to leave behind Volterra. But fear not as more treats lie ahead. Pedaling onwards you pass through hamlets such as Saline di Volterra, famous for its salt water springs and salt production. As the wheels keep turning, the historical villages keep flowing by and add to a spectacular ride that will eventually conclude in the town of San Vincenzo.

    This spot is well known amongst cycling enthusiasts since Giro d’Italia started and finished there in 1971. Now it is an important tourist resort and it’s the perfect place to relax after a day of riding by the Ligurian Sea. Of course, the evening is capped off with a stunning Italian dinner using the finest local produce.

    • 49.7 miles
    • Breakfast and Dinner
  5. Day 5Elba’s enigmatic charms are all too easy to embrace

    The sunlight, vibrant shades of green, jaw-dropping beaches and picturesque villages make Elba Island an exceptional playground for cyclists to explore. Today marks your chance to soak up the beauty of this Tuscan archipelago. Following breakfast everyone boards a ferry from Piombino to Portoferraio as the adventure kicks into gear.

    It feels like time has stood still in Elba despite it being the third largest island in the country. Elba’s history runs deep, pedaling around you’ll see the remains of outposts and the Necropolis. And if you happen to spot a ‘skull and crossbones’ flag out at sea then it could mean that the dreaded Ottoman corsairs have returned to try and reclaim the island just like they did in the 15th and 16th centuries.

    Cycling the Volterraio road there is much to be seen as you head through some medieval hamlets. Eventually, you will return to the island’s capital, Portoferraio, a Medici town which boasts of museums, mansions and fortresses. After arriving at the hotel, there will be time to embrace Elba at night with another amazing meal.

    • 37.7 miles
    • Breakfast and Dinner
  6. Day 6Pedaling further into Elba’s western frontiers

    After covering the eastern side of Elba it’s only fair to give the western shores a crack too. Top up your energy for the day with breakfast before you start pedaling.

    Today’s riding shows off the Italian hills as you pedal towards the island’s smallest municipality of Marciana Marina. As the spokes turn you will pass through the hamlet of Poggio which is enveloped by century-old chestnut woods.

    From the highs of the hills comes the natural descent leading to some famous beaches and Chiessi, a small hamlet. Riding on you’ll come to a village called Marina di Campo. Situated at the foot of two hills the plain known as Maremma dell’Elba is gorgeous.

    Eventually it is time to return back to Portoferraio where another exquisite dinner awaits to conclude a visit to the island of Elba, a land of diverse landscapes and beauty.

    • 50.6 miles
    • Breakfast and Dinner
  7. Day 7Setting off back to Siena

    A much-needed breakfast awaits before heading back to Siena. The transfer back is included and from Siena it’s time to head somewhere new, packed to the rafters with a lifetime of memories from an amazing ride through the Italian hills and alongside the seas.

    • Breakfast