Italy in the summer is a real classic—but cycling & sailing Tuscany’s islands take it to a whole new level. Welcome to an 8-day dive into all things Italian: the scent of citrus fruit, the tang of sea salt in the breeze, and dishes that taste like summer on a plate. Aboard our floating home, the Atlantis ship, we’ll have the freedom to explore Tuscany’s stunning coast, taking a dip in the sea when we feel like it. And every day, we’ll hop on our e-bikes to wind through lush vineyards, beneath olive groves, along coastal trails high above the sparkling sea, down cobblestone streets, and so much more. You’ll be dreaming of Italy and gelato long after you’ve gone.
This Tuscany bike and boat tour is summer living at its finest—think vineyard-lined hills, sparkling seas, olive groves, and medieval villages frozen in time. By day, pedal your bike past sunflower fields, citrus groves, and cobbled streets before cooling off with a swim in the Tyrrhenian Sea. By night, unwind aboard the three-masted Atlantis, your floating home, where good food, sea breezes, and starlit decks make every evening as magical as the ride.
You can board the boat from 6pm onwards in Porto St. Stefano, a lively harbor town on the northern coast of the Monte Argentario Peninsula. If you arrive earlier, you can check in your luggage after 2pm and enjoy a relaxed wander through the old town’s pastel-colored streets. Want to stretch your legs a little more? Head up to the Spagnola fortress, standing guard since the 17th century, for sweeping views over the harbor. By evening, it’s time for your first onboard meal—the perfect chance to meet your fellow travelers, guides, and crew before settling into your cozy floating hotel for the night.
Meals: Dinner
Accommodation: Cabin aboard the Atlantis
From Porto St. Stefano, we set off on our first bike tour toward the historic town of Orbetello. If luck is on our side, we’ll spot flamingos gathered in the WWF-protected Laguna di Orbetello. The route then leads us to the ancient ruins of the Roman town of Cosa before winding through the Duna Feniglia nature reserve, where a peaceful pine forest makes for an enchanting ride. Mostly following cycle paths, we finish back in Porto St. Stefano, where the Atlantis awaits to carry us across to Talamone.
Meals: Breakfast and dinner
Distance: 40 km (25 mi)
Elevation gain: 200 m (600 ft)
Accommodation: Cabin aboard the Atlantis
After breakfast, we set out on a full day of sailing with a long crossing to the island of Elba. If the winds are on our side, the crew will give us a sailing briefing and we’ll even have the chance to help set the sails ourselves. Elba, Italy’s third-largest island after Sicily and Sardinia, enchants with its lush landscapes, rich history, and laid-back charm. Lunch is served on board, and there’s time for a refreshing swim before we anchor in the sheltered bay of Porto Azzurro. In the evening, we’ll stroll through its lively harbor town.
Meals: Breakfast and dinner
Accommodation: Cabin aboard the Atlantis
Today we explore the many facets of Elba, starting with the lively town of Capoliveri, where we soak in the Italian charm over a coffee and a delicious gelato. Our ride continues along a scenic panoramic route, pausing for a leisurely lunch before heading back to Porto Azzurro. In the evening, we’ll embrace the island vibe with a relaxed wine tasting.
Meals: Breakfast and dinner
Distance: 17 km (11 mi)
Elevation gain: 400 m (1,325 ft)
Accommodation: Cabin aboard the Atlantis
Today we embark on a longer ride from Porto Azzurro to the northern part of Elba. We pause for a coffee break in Rio nell’Elba before continuing to one of the trip’s most stunning viewpoints. From Volterraio, we’ll take in sweeping views over the beautiful bay of Portoferraio, the island’s capital. After lunch, we cycle the final stretch to the picturesque bay of Enfola.
Meals: Breakfast and dinner
Distance: 40 km (25 mi)
Elevation gain: 600 m (1,970 ft)
Accommodation: Cabin aboard the Atlantis
Today is the queen’s stage of our tour! We cycle across the island, stopping in the charming mountain village of Marciana before reaching Monte Perone, the highest point of the trip. From there, a spectacular descent takes us to San Piero in Campo, where we enjoy a delicious lunch with views of our ship. Back on board, there’s time for a refreshing swim right from the boat. Then, with sails set, we make our way to Isola del Giglio, a southern gem of the Tuscan Archipelago, boasting mountains, forests, pristine nature, and crystal-clear waters!
Meals: Breakfast and dinner
Distance: 30 km (19 mi)
Elevation gain: 700 m (2,300 ft)
Accommodation: Cabin aboard the Atlantis
We start our cycling adventure in Campese on the west side of the island, heading for the medieval town of Giglio Castello, perched like a fortress high above the island. A swift descent brings us down to Giglio Porto, where we pause before dinner. Afterward, we set sail around Isola del Giglio, a true southern gem of the Tuscan Archipelago, celebrated for its mountains, forests, pristine nature, and crystal-clear waters.
Meals: Breakfast and dinner
Distance: 15 km (9.4 mi)
Elevation gain: 500 m (1,650 ft)
Accommodation: Cabin aboard the Atlantis
We savor one last breakfast on board before disembarking at 9am. From here, the choice is yours: return home with a treasure trove of Tuscan memories, or extend your stay to explore even more of this enchanting region!
Meals: Breakfast
The itinerary is shaped by the winds, so harbors and anchorages may change depending on the weather each day. Guests are kindly asked to embrace a flexible spirit, as this allows for the most enjoyable and safe sailing experience.
Included:
Add-ons (available to add at checkout)
Not included:
This Tuscany bike & boat tour is perfect for beginners or anyone who wants to enjoy relaxed, easy rides along gentle, relatively flat terrain. All that’s required is a good level of fitness. The most you’ll cover within a day is 30 km (19 mi) with 700 m (2,300 ft) of elevation gain. If you’d like to make your days even easier, your guides offer e-bike rental—you can add road, gravel, or e-bike rental to your booking at checkout.
The routes are mostly on asphalt, with some stretches on gravel roads. This Tuscany bike & boat tour is mainly a guided group experience, but with your guide’s approval, you may choose to cycle independently on recommended routes. You’re also free to take a half or full day to relax on board or enjoy a swim instead of joining a scheduled ride.
The riding pace is set by participants on e-bikes. Guests joining on a regular gravel/road bike should be prepared to match this pace and have the fitness level required to do so comfortably.
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Yes! Skip the hassle of bringing your own bike and simply rent one with your guides. At checkout, you’ll have the option of adding a gravel, road, or an e-bike rental to your booking.
E-bikes are high-quality pedelecs, powered mainly by Bosch motors, built for long distances while staying lightweight and easy to handle. Some bikes may use alternative drive systems. Each e-bike features 28-inch hollow-chamber rims with puncture-resistant touring tires, reliable gears and brakes, a sturdy kickstand, a comfortable touring saddle, mudguards, and a pannier rack. Riders up to 1.79 m (5’10”) can use a trapeze frame, while those taller than 1.80 m (5’11”) are provided a diamond frame.
Note that the riding pace is set by participants on e-bikes, so those joining on a road/gravel bike should be prepared to macth the e-bikes pace.
Here’s a list of the equipment you need to bring:
Dress comfortably and for the weather in clothes you can move in. We suggest bringing clothing appropriate for the season. Layers are best and don’t wear jeans.
Group sizes and pricing
Tuscany bike & boat tours can be arranged for larger groups. Contact us to make arrangements.
Min. age requirements
If your group has participants under the age of 18, contact us prior to booking to make arrangements.
The starting point of your Tuscany bike & boat tour is Porto Santo Stefano. To get there, most people fly into Rome Fiumicino “Leonardo da Vinci” Airport (FCO) or Pisa International Airport (PSA). From there, you can take a shuttle service, public transport, or rent a car to reach Porto Santo Stefano—it should take 2-3 hours.
You’ll meet your guide at 6pm on Day 1 in Porto Santo Stefano. Those who arrive earlier are welcome to drop off their luggage from 2pm onwards.
We highly recommend that you cover all your bases with insurance. To make your booking and traveling experience as carefree as possible, you’ll be offered to simply insure your trip with Redpoint at checkout.
Redpoint—the official 57hours insurance partner—tailors protection packages for adventure travel, offering a comprehensive travel program, even in remote locations! Trip cancellation, natural disasters, pandemic coverage, medical evacuation, primary medical expenses—regardless of the travel interruption that may happen, Redpoint will have you covered.
Deposits
Secure your spot with a 30% deposit upon booking! The remaining 70% of the trip price must be paid 90 days prior to departure at the latest. If booking within 90 days of departure, the full amount is required at the time of booking.
Cancellations
Booking fees are non-refundable after a 48-hour grace period. During checkout, however, you can choose one of 57hours’ flexibility options—Basic, Flexible, or Super Flexible. Depending on which one you choose, a different cancellation policy will apply to your booking.
Basic
Flexible
Super Flexible
