Included: Experienced cycling guides with extensive knowledge of the area 8-day Tuscany bike & boat tour (with guided or individual cycling tours as in the itinerary) Accommodation for 7 nights aboard the Atlantis (twin-share cabin with ensuite bathroom) 7 breakfasts 7 warm meals onboard Bed linen and towels Overview of maps for the daily tours (on board) SGR Insolvency Protection Add-ons (available to add at checkout) Gravel or or e-bike rental Single occupancy cabin — possible to arrange, contact us before booking Special dietary requirements Not included: Transportation to/from starting/end point Entrance fees & excursions not mentioned in the itinerary Helmet — strongly recommended, smaller number available onboard Lunches and drinks Any transfers not mentioned in the itinerary Beverages on board — tally sheet, to be paid to the captain Insurance — available to add at checkout Guide gratuities — optional

How fit do I need to be?

This Tuscany bike & boat tour is best suited for confident riders who are comfortable cycling in hilly to mountainous terrain . Daily routes involve 200-700 meters (660-2,300 ft) of elevation gain , with some sustained climbs and occasional steep hairpin descents, particularly on Elba and Giglio. The rides are manageable and far more enjoyable with e-bike assistance , which is why most participants choose to ride e-bikes . Excellent bike handling is important, especially on descents and short unpaved sections. Exact daily distances and elevation changes can be found in the itinerary, but in general, the most you’ll cover within a day is 25 mi (40 km) . Routes are primarily on asphalted public roads , with limited traffic outside peak holiday periods. Short stretches of gravel or field tracks may appear on the islands. Traffic is more noticeable near coastal towns and around Portoferraio, but guides prioritize quieter side roads whenever possible. While this is a guided group tour, you’re free to skip a ride, take a rest day on board, or enjoy a swim instead. Riders on non-electric bikes should be prepared to comfortably match the group’s e-bike pace. For more bike adventures in Italy , click here !

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 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.

What do I need to bring?

Here’s a list of the equipment you need to bring: Day pack large enough to carry everything you might need throughout the day (around a 25-40L bag) Water bottle or hydration bladder (2L capacity) Lightweight shoes Comfortable cycling clothes Spare clothes for layering Waterproof rain jacket Sunhat Swimsuit Toiletries (sunscreen, hand sanitizer, bug spray, tissues, etc.) Sunglasses Camera — optional (but recommended) 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 age requirements

Group sizes and pricing For this Tuscany bike & boat tour , there will be 1-3 guides on board, depending on the group size. It takes a minimum of 16 people for this tour to operate. The maximum group size is set at 34 participants . If you’re joining as a solo traveller , a single cabin surcharge is mandatory.It’s not possible to join as a solo traveller and share a cabin with another guest. Tuscany bike & boat tours can be arranged for larger groups. Contact us to make arrangements. Min. age requirements If you are older than 18, you’re good to go. Minors older than 10 may be permitted to join the Tuscany bike & boat tour on a case-by-case basis, but must be in the presence of a parent or legal guardian. If your group has participants under the age of 18 , contact us prior to booking to make arrangements.

Getting there and meeting location

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.

Safety measures and insurance

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.

Check out Early bird options for best sellers here

TUSCANY | ITALY

Sail & Bike Tuscany: Explore the Coast and the Islands

8 days | Moderate

From $2,867 ()

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Italy in summer is timeless, but seeing Tuscany and its islands from the saddle and the sea tells a whole new story. This 8-day journey is shaped by salty air, turquoise water, and hilly Tuscan terrain that makes the riding engaging and rewarding. Our floating home is the Atlantis, a beautifully restored sailing ship blending over a century of history with modern comfort. Life on board is hands-on (as much as you’d like) and relaxed—meals enjoyed outside, sails raised together, swims straight from the deck. Each day, we pedal through the varied landscapes of Elba and Giglio, from lively coastal towns to quiet forests, mountain villages, and medieval hilltops. It’s a side of Tuscany defined by sea, wind, and island life—one that lingers long after the journey ends.

Adventure Highlights

Different side of Tuscany: While most travelers stick to Tuscany’s hilltop villages, on this trip we’re also embracing its sparkling coast and enchanting islands
Sip, savor, cycle: From velvety gelato to bold Tuscan reds, every stop is another excuse to try out yet another Italian specialty
Laid-back holiday by the sea: Trails mapped, dinners waiting, guides leading—leave all logistics to us, relax, and enjoy the ride

Duration

8 days

Season

September through October

Group size

Up to 34 people

The adventure, day by day

Download itineraries

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.

Day 1: Arrival in Porto Santo Stefano

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

Day 2: Porto Santo Stefano — Talamone

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

Day 3: Talamone — Porto Azzurro

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

Day 4: Porto Azzurro — Capoliveri — Porto Azzurro

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: 28 km (17 mi)
Elevation gain: 400 m (1,325 ft)
Accommodation: Cabin aboard the Atlantis

Day 5: Porto Azzurro — Enfola Bay

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

Day 6: Marciana Marina — Marina di Campo

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

Day 7: Island Giglio — Porto Santo Stefano

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: 400 m (1,315 ft)
Accommodation: Cabin aboard the Atlantis

Day 8: Disembarkment

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

Important note

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.

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Life on board

Atlantis

The three-masted barquentine Atlantis is a true showstopper in every harbor, with its impressive size and graceful 14 sails. Built in 1905, it first served as a lightship before beginning a new life as a sailing vessel, beautifully restored and modernized to combine nautical tradition with passenger comfort. Sixteen cozy twin cabins, each with a private bathroom and air conditioning, provide a welcoming retreat, while the warm, nautical-style salon and spacious deck set the stage for shared meals, quiet moments, or simply enjoying the view.

Life on board is all about atmosphere: relax with a book in the salon, dine under the open sky, or savor a cocktail mixed at the outdoor bar as the sun dips below the horizon. With plenty of space in both sun and shade, and an experienced crew eager to share their love of sailing, the Atlantis offers more than just a trip—it’s a floating escape where tradition, comfort, and adventure meet.

Cabins

The Atlantis features 16 inviting guest cabins, each with its own private bathroom with shower and toilet. Located below deck, the cabins are thoughtfully designed with two separate single beds, central heating, and air conditioning to ensure comfort in every season.

Practical yet elegant, these cabins provide ample space for your belongings while surrounding you with a cozy maritime atmosphere—perfect for unwinding after a day of sailing and sea air.

If you’re joining as a solo traveller, a single cabin surcharge is mandatory.It’s not possible to join as a solo traveller and share a cabin with another guest.

Food

All breakfasts and 7 warm meals onboard are included. Special dietary requirements can be accommodated. Vegetarian and pescatarian diets are free of charge. Gluten-free, dairy-free and dairy-free diets have an additional charge—you can add a special diet to your booking at checkout. Vegan diets cannot be accommodated.

Adventure, packed to go

Sail & Bike Tuscany: Explore the Coast and the Islands

Adventure Brochure

Adventure brochure

Download to share and explore full itineraries, key info, FAQs, and guide details.

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Things to know

Included:
- - Experienced cycling guides with extensive knowledge of the area
  - 8-day Tuscany bike & boat tour (with guided or individual cycling tours as in the itinerary)
  - Accommodation for 7 nights aboard the Atlantis (twin-share cabin with ensuite bathroom)
  - 7 breakfasts
  - 7 warm meals onboard
  - Bed linen and towels
  - Overview of maps for the daily tours (on board)
  - SGR Insolvency Protection
Add-ons (available to add at checkout)
- - Gravel or or e-bike rental
  - Single occupancy cabin — possible to arrange, contact us before booking
  - Special dietary requirements
Not included:
- - Transportation to/from starting/end point
  - Entrance fees & excursions not mentioned in the itinerary
  - Helmet — strongly recommended, smaller number available onboard
  - Lunches and drinks
  - Any transfers not mentioned in the itinerary
  - Beverages on board — tally sheet, to be paid to the captain
  - Insurance — available to add at checkout
  - Guide gratuities — optional
This Tuscany bike & boat tour is best suited for confident riders who are comfortable cycling in hilly to mountainous terrain. Daily routes involve 200-700 meters (660-2,300 ft) of elevation gain, with some sustained climbs and occasional steep hairpin descents, particularly on Elba and Giglio. The rides are manageable and far more enjoyable with e-bike assistance, which is why most participants choose to ride e-bikes. Excellent bike handling is important, especially on descents and short unpaved sections. Exact daily distances and elevation changes can be found in the itinerary, but in general, the most you’ll cover within a day is 25 mi (40 km).

Routes are primarily on asphalted public roads, with limited traffic outside peak holiday periods. Short stretches of gravel or field tracks may appear on the islands. Traffic is more noticeable near coastal towns and around Portoferraio, but guides prioritize quieter side roads whenever possible. While this is a guided group tour, you’re free to skip a ride, take a rest day on board, or enjoy a swim instead.

Riders on non-electric bikes should be prepared to comfortably match the group’s e-bike pace.

For more bike adventures in Italy, click here!
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 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:
- - Day pack large enough to carry everything you might need throughout the day (around a 25-40L bag)
  - Water bottle or hydration bladder (2L capacity)
  - Lightweight shoes
  - Comfortable cycling clothes
  - Spare clothes for layering
  - Waterproof rain jacket
  - Sunhat
  - Swimsuit
  - Toiletries (sunscreen, hand sanitizer, bug spray, tissues, etc.)
  - Sunglasses
  - Camera — optional (but recommended)
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.

Got everything you need? Grab your gear through Active Junky and earn cash back on top outdoor brands — plus a $10 bonus on your first $25+ purchase. Shop now at Active Junky!
Group sizes and pricing
- - For this Tuscany bike & boat tour, there will be 1-3 guides on board, depending on the group size.
  - It takes a minimum of 16 people for this tour to operate. The maximum group size is set at 34 participants.
  - If you’re joining as a solo traveller, a single cabin surcharge is mandatory.It’s not possible to join as a solo traveller and share a cabin with another guest.
Tuscany bike & boat tours can be arranged for larger groups. Contact us to make arrangements.

Min. age requirements
- - If you are older than 18, you’re good to go.
  - Minors older than 10 may be permitted to join the Tuscany bike & boat tour on a case-by-case basis, but must be in the presence of a parent or legal guardian.
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
- - If cancelled within 48 hours of booking, a full refund will be issued.
  - If cancelled 90 or more days before departure, a 70% refund of the total trip price will be issued.
  - If cancelled within 89 days of departure, no refund will be issued.
Flexible
- - If cancelled within 48 hours of booking, a full refund will be issued.
  - If cancelled 90 or more days before departure, a full refund of the total trip price will be issued.
  - If cancelled 60-89 days before departure, a 50% refund of the total trip price will be issued.
  - If cancelled within 59 days of departure, no refund will be issued.
Super Flexible
- - If cancelled within 48 hours of booking, a full refund will be issued.
  - If cancelled 60 or more days before departure, a full refund of the total trip price will be issued.
  - If cancelled within 59 days of departure, a 50% refund of the total trip price will be issued.

Have more questions?

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