Sail and cycle Southern Tuscany’s coastline and islands, from Monte Argentario to Elba and Giglio

When most people picture Tuscany, they imagine vineyards, hill towns, and Renaissance art. But there’s another side to this region, coastal and quieter, where wooded hills meet the sea and small island towns have a long connection to maritime life. This tour takes you through that lesser-seen Tuscany: along the wild coastline of Monte Argentario, across the waters to Elba and Giglio, and into nature reserves, ancient ruins, and small harbors.

Traveling by tall ship and e-bike, you'll explore at a pace that lets you take it all in. One day you're pedaling past Roman ruins and pine forests, the next you're swimming in clear coves or enjoying fresh seafood on deck. You'll ride through landscapes once home to the Etruscans, visit villages that haven't changed in generations, and sail routes that traders and explorers once crossed centuries ago.

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Highlights

• Porto Santo Stefano - Historic harbor town on Monte Argentario
• Porto Ercole - Charming coastal village with Spanish fortresses
• Elba Island - Panoramic cycling and Napoleon’s former exile
• Giglio Island - Quiet roads, beaches, and medieval hilltop town
• Tuscany's Coast & Countryside - Vineyards, olive groves, and sea views
• Local Food & Wine - Regional cuisine onboard and ashore
• Tall Ship Sailing - Cruise the Tyrrhenian Sea under sail

Learn More

Interested in adding to your itinerary? Take a look at our cycling day tours in Italy.

Daily program

Day 1: Arrival in Porto Santo Stefano
Arrive individually in Porto Santo Stefano, a busy harbor town on the northern coast of the Monte Argentario peninsula in southern Tuscany. Boarding begins at 6 pm, but you're welcome to drop off luggage on board as early as 2 pm. If you arrive with time to spare, consider a walk through the historic town center. The Fortezza Spagnola, built in the 17th century to protect the coast from invasions, sits above the harbor and offers excellent views. Dinner is served on board, a good opportunity to meet your fellow travelers, guides, and crew. Overnight in Porto Santo Stefano.

Day 2: Monte Argentario - Orbetello - Cosa - Talamone (25 miles/40 km)
Start the day with a cycling route that begins directly from Porto Santo Stefano, passing through former train tunnels and across a causeway leading to the historic town of Orbetello, located on a narrow strip of land between two lagoons. The Laguna di Orbetello, a protected nature reserve, is known for its birdlife—including flamingoes. Later, visit the archaeological site of Cosa, a Roman colony established in the 3rd century BCE. The route continues through the pine woods of Duna Feniglia, a coastal nature reserve with options for a swim along the way. You return to the harbor for an afternoon sail to Talamone, a fortified fishing village that once played a role in Garibaldi’s 1860 campaign.

Day 3: Talamone - Sailing to Elba - Porto Azzurro
After breakfast on board, the crew sets sail for Elba, Italy’s third-largest island and perhaps best known as Napoleon’s place of exile. If weather allows, you can take part in a short sailing introduction and assist with the sails. After lunch and a swim stop, the boat arrives in Porto Azzurro, located in a sheltered bay on Elba’s southeastern coast. In the evening, take time to explore the town—its origins date to Spanish rule and its streets today are lined with small shops and cafés.

Day 4: Porto Azzurro - Capoliveri - Porto Azzurro (17 miles/27 km)
This afternoon’s ride takes you inland and uphill to Capoliveri, a village perched on a ridge with sweeping views of the island and sea. Once a mining town, Capoliveri is now known for its artisan shops and wine production. The route follows a scenic loop back to Porto Azzurro along a ridge road. After the ride, you have time to walk through the port again or relax onboard.

Day 5: Porto Azzurro - Rio nell’Elba - Volterraio - Enfola Bay (25 miles/40 km)
Today’s ride heads north through Rio nell’Elba, one of the oldest villages on the island. A coffee stop here is a good break before continuing to Volterraio, a lookout point that offers views of Portoferraio, Elba’s capital. Portoferraio was once part of the Grand Duchy of Tuscany and served as Napoleon’s residence during his exile. After lunch, the ride continues to Enfola Bay, a peaceful cove that once served as a military lookout during World War II.

Day 6: Marciana Marina - Monte Perone - San Piero - Marina di Campo (19 miles/30 km)
Today’s route crosses the island and includes the highest elevation of the tour. Starting in Marciana Marina, you'll cycle inland through forested hills to Marciana, one of Elba’s oldest mountain towns. From there, the road ascends to Monte Perone, the highest point of the week, offering panoramic views of the coastline. Afterward, it’s a downhill ride to San Piero in Campo, where you’ll stop for lunch with a view of your ship at anchor. In the afternoon, take a swim before setting sail for Isola del Giglio, a small, mountainous island known for its clear water and quiet natural setting.

Day 7: Giglio Porto - Giglio Castello - Giglio Campese - Porto Santo Stefano (9.5 miles/15 km)
Today’s route explores Isola del Giglio, located at the southern end of the Tuscan Archipelago. From the port, cycle uphill to Giglio Castello, a fortified medieval village that still has its defensive walls intact. From there, a fast descent brings you to Giglio Campese, a small coastal town with a sandy beach that’s ideal for swimming. The return to Giglio Porto follows a winding road with sea views. In the late afternoon, the boat sails back to Porto Santo Stefano. A final dinner on board brings everyone together for a relaxed evening to mark the end of the trip.

Day 8: Departure from Porto Santo Stefano
Your tour officially concludes after breakfast at 9 am.

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Dates & Prices

Questions about pricing or options? Call +1-215-613-0874 to talk to a Tour Advisor now.

Included services

• 7 nights' accommodation in cabin with private bathroom
• 7 x breakfasts, 7 x lunches or dinners
• Bed linens and towels (with one towel change during the week)
• Electric bike rental with pannier
• English and German-speaking cycling tour guide
• Daily cycling route maps and overviews available on board

Tour Company

Map

Maps are for information purposes only and reflect typical routes between overnight locations. They may not reflect your actual route.

Surface and terrain

This tour suits those with a basic fitness level. E-bikes allow you to adjust the difficulty from easy to challenging. Routes range from 15–25 miles (25–40 km) with elevation gains of 660–2,300 feet (200–700 meters), mostly on quiet, paved secondary roads. Some short sections may include gravel or compacted dirt paths through nature reserves. Daily rides include hills, particularly on Elba and Giglio, but e-bike support makes climbs accessible for most riders.

How to get there

Tour start and end -
Porto Santo Stefano, Tuscany

Fly into Rome Fiumicino Airport (FCO) or Rome Ciampino Airport (CIA). From either airport, take a train to Orbetello-Monte Argentario station (approx. 1.5–2 hours), followed by a 20-minute bus or taxi ride to Porto Santo Stefano.