🔒 Europe Price Lock 🔒Save on France, Italy, Spain & Portugal 2025Book now
8 days
  • guided cycle
  • 7 nights boat
  • 7 Dinners
  • 7 Breakfasts





Trip Code: TSC

Trip highlights

  • Be immersed in the local culture, history and beauty of the Tuscan coast and islands
  • Cycle around Elba, the third largest island in Italy
  • A hands on opportunity to learn about sailing a tallship in the Mediterranean
  • Soaking up the hospitality on board the comfortable sailing boat

Images of Tuscany bring to mind rolling hills, epic architecture, the aromatic scents of herbs and citrus fruits and tasty cuisine and wine. Add to this a journey on a resplendent tallship to discover the islands of Elba,Giglio and the dramatic Tuscan coastline and daily cycles to explore the sights and you have the essence of our Tuscany Bike and Sail trip. Cycle in the footsteps of the Etruscans, and enjoy the Italian 'Dolce Vita!'. Cypress trees, vineyards and olive trees spread across the rolling hills characterising the typical Tuscan landscape. Picturesque medieval towns with small cobbled streets and colorful houses feature as you cycle between ports. Beautiful sandy beaches and remote bays beckon for a swim in the glistening blue water. Aboard the tallship Atlantis with its giant sails, provides a true seafaring ambience. There is nothing better than to jump into the sea directly from the deck of the boat in a quiet bay, help out with hoisting the sails and relax on deck with a cold drink as the sun dips below the horizon.

Trip Grading


More info about grading system

Traveller Rating


Arrive in Porto Santo Stefano, a wonderful, lively harbour town on the northern side of the Monte Argentario peninsula. Boarding takes place at 6pm. Should you arrive earlier, you are welcome to leave your luggage on board from 2pm. Taking a short stroll through the medieval old town, painted in a wash of pink and beige, you will quickly realize that you are now on holiday. We also recommend a walk to the Fortezza Spagnola, built in the 17th century, on the hill above the old town. The first evening meal on board is a great way to get to know your fellow travellers, guides and crew. Overnight in Porto Santo Stefano.

Meals:  D

From Porto St Stefano our first bike tour takes us to the historic town of Orbetello. With a little luck you can admire the spectacular swarm of flamingos in the WWF natural oasis Laguna di Orbetello. Afterwards we will cycle to the ruins of the fortified Roman town of Cosa and later through the Duna Feniglia nature reserve, whose beautiful pine forest will enchant. We cycle mostly on cycle paths and return to Porto Santo Stefano where the Atlantis awaits our arrival for a crossing to Talamone. Cycling: 200m/660ft of elevation

Meals:  B,D

After breakfast we begin cycling through rolling landscapes characterised by grape vines and olive groves. Past the Poggio Perotto Lake we arrive in the medieval town of Magliano. The town's icon is a 2000 year old olive tree, the oldest in Tuscany. This picturesque town, with its two beautiful city gates is very inviting. On our ride back to Talamone we can enjoy the beauty of the Tuscan landscapes once more. Before dinner on board you;re invited to a tasting of typical Tuscan wines. Cycling: 300m/1000ft of elevation

Meals:  B,D

This morning we cross to Elba. After Sicily and Sardinia, Elba is the third largest island in Italy and impresses with its charm, lush nature and rich history. After a light lunch on board we go ashore. The afternoon tour leads along a spectacular panoramic road across the island to Capoliveri. In the evening take the opportunity for a stroll through the charming small harbour town Porto Azzurro. Cycling: 200m/660ft of elevation

Meals:  B,D

A somewhat longer ride today, from Porto Azzuro to the north of the island of Elba. After a coffee break in Rio nell' Elba we will arrive at one of the most impressive viewpoints of the trip. From Voltereio we can look out over the beautiful bay of Portoferreio, the capital of the island. After lunch it is only a few kilometres to the bay of Enfola. Cycling: 500m/1630ft of elevation

Meals:  B,D

Today we cross the island by bike. After visiting the mountain villages of Marciana we reach the highest point of the tour at Monte Perone. We're rewarded with a descent to the village of San Piero in Campo, where you can enjoy a delicious lunch with a view of the boat. After the tour you can take a refreshing swim – directly from the deck. Then the sails are set for our destination, Isola Giglio, located in the very south of the Tuscan Archipelago. This Italian jewel is home to mountains, forests, untouched nature, crystal clear sea! Cycling: 700m/2300ft of elevation

Meals:  B,D

We go ashore in Campese, in the west of the island. Our cycling destination today is the medieval town of Giglio Castello, enthroned high on the island of Giglio like an impregnable castle. A fast descent takes us to Giglio Porto. Enjoy the last cruise on board as we set sail towards Porto St Stefano. A celebratory evening meal in the company of fellow travelers, crew and guides offers a great atmosphere to enjoy our last evening together on board. Cycling: 500m/1650ft of elevation

Meals:  B,D

The tour concludes this morning - disembark at 9am after breakfast.

Meals:  B



The map and elevation chart are for illustrative purposes only and meant to provide general guidelines.


  • 7 breakfasts, 7 lunches or dinners* (does not include drinks) - meals are provided on a half board basis meaning that breakfast and either lunch or dinner is provided each day - or some days no warm meal is provided while others both lunch and dinner is provided. Usually dinner is provided and lunch is free for you to sample a restaurant along the cycle route. The cook on board is a member of the crew and prepares the meals.
  • 7 nights accommodation in a standard twin cabin with private bathroom on a tallship. The spacious cabins are configured with two lower beds. Supplement applies for single use - limited availability. Or if you are travelling solo you can be matched with another passenger if you are willing to share (subject to availability).
  • Bed linen and towels
  • 21 speed hybrid bike rental with pannier (electric bike, gravel bikes and road bikes available on request - supplement applies).
  • Experienced crew including English speaking cycle guide
  • Information pack including overview maps per cabin

  • Travel to and from Porto Santo Stefano (Monte Argentario Peninsula)
  • 7 lunches or dinners (any meals taken ashore) and beverages
  • Items of a personal nature
  • Tips for guide and crew
  • Travel insurance - mandatory *cruise cover may be required - check with your insurer
  • Helmets - mandatory on all bike tours, you are encouraged to bring your own well-fitted helmet. A limited number of rental helmets are available on board (reservation essential), however we cannot guarantee their suitability.
  • Optional Bicycle insurance. Please note that normal travel insurance often does not cover loss or damage to rental bikes. If you do not take out bike insurance you will need to pay for the cost of the bike or repair of damages.


Bike information



The trip requires an advanced level of fitness from participants, acquired from steady cycling. The terrain is as diverse as the landscapes: the hilly and sometimes mountainous terrain, with some steeps climbs, requires a good physical condition. The tours provide a great range of riding: wide natural paths, small country roads, forest trails, single trails and small paths are all included. You are free to set aside a half or full day to swim or spend on board the boat, instead of taking a planned bike tour. We will traverse mostly asphalted roads, unless you join a mountainbike tour, which are available on selected departures. The standard bike days range between 20 to 45km/12.5 to 28mi, through hilly and mountainous terrain. Ascents will be up to 200-700m / 660-2300ft in elevation. Participants will also have to master extended climbs, during which you may need to push the bike. Most of the roads are asphalted although you will also ride on gravel roads. We believe that only children in a good physical condition and with a minimum age of 10 as well as previous bicycle tour experience would be able to master the cycle tours on their own strength. Please note that the minimum height for a rental bike is 1.50 m (5ft.). Helmets are mandatory on our bike tours. It is advised to bring your own, well fitted, helmet with you as our rental helmet numbers are limited (reservation required).

Departure dates


Itinerary subject to change according to weather conditions.

Want to organise a private group?

Fundraising events, sporting groups, family treats; learn how you can organise a Private Group from just 6 travellers.

Priceper person from


Options & Supplements*
  • Bicycle insurance - standard bike (pp)USD$13
  • Bicycle insurance - electric, mountain bike, e-MTB (pp)USD$32
  • Gravel or Road Bike SupplementUSD$130
  • Electric Bike SupplementUSD$190
  • Single SupplementUSD$1120
*Prices listed are per person

Trip reviews

Why travel with us

Making Europe Affordable

We offer different levels of accommodation and comfort so that even the most budget conscious can treat themselves to active holidays on Europe's most celebrated tracks and trails. Our trips are great value for money because you only pay for what you want.  

Self-Guided Specialists

Our wide range of self-guided itineraries embody the UTracks philosophy of exploring Europe your way. We handle the logistics so all that's left for you to do is enjoy exploring Europe at your own pace. Most depart daily with a minimum of two people, meaning maximum flexibility.

Our Wide Range

With close to 400 trips in almost 50 countries, including the largest range of bike & boat holidays in Europe, we're confident that we can organise an Alps walk, Camino de Santiago or Via Francigena experience, Food Lovers' trip or a tour in a lesser-known pocket of Europe that you will love. 

Join Newsletter
<img src='/portals/World%20Expeditions/Icons/brands/small/ADS.jpg' class='brandPopoverIcon' alt="Adventures South"> <div class='brandPopoverBrandName'>Adventure South</div>
Adventure South NZ is unrivalled in their geographic coverage, originality and overall quality of adventures holidays in New Zealand. Choose from walking, cycling, winter or multi-activity holidays, on either the North or South Island.
<img src='/portals/World%20Expeditions/Icons/brands/small/AWH.jpg' class='brandPopoverIcon' alt="Australian Walking Holidays"> <div class='brandPopoverBrandName'>Australian Walking Holidays</div>
Australian Walking Holidays specialises in small group guided walking adventures. Since 1982 we have been guiding small groups of travellers on Australia's finest walks across our tropical, coastal or red centre landscapes.
<img src='/portals/World%20Expeditions/Icons/brands/small/GCT.jpg' class='brandPopoverIcon' alt="Great Canadian Trails"> <div class='brandPopoverBrandName'>Great Canadian Trails</div>
Great Canadian Trails specialises in active holidays in Canada. With both guided and supported self-guided options available, our unique itineraries draw upon some of Canada's most inspiring parks, trails and landscapes from coast to coast.
<img src='/portals/World%20Expeditions/Icons/brands/small/HUM.jpg' class='brandPopoverIcon' alt="Humac Challenge"> <div class='brandPopoverBrandName'>Huma Charity Challenge</div>
Huma enables those with adventurous spirits to challenge themselves and make a difference for a cause close to their heart. Travel, fundraise and meet life-long friends on one of Huma's meaningful and unique challenges around the world.
<img src='/portals/World%20Expeditions/Icons/brands/small/WB.jpg?v2' class='brandPopoverIcon' alt="Walkers’ Britain"> <div class='brandPopoverBrandName'>Walkers' Britain</div>
Walkers' Britain (formerly Sherpa Expeditions) have specialised in walking and cycling trips in the United Kingdom and Europe since 1973. Explore iconic trails and destinations on a self guided or small group active holiday with Walkers' Britain.
<img src='/portals/World%20Expeditions/Icons/brands/small/WB.jpg?v2' class='brandPopoverIcon' alt="Walkers’ Britain"> <div class='brandPopoverBrandName'>Walkers' Britain</div>
Walkers' Britain (formerly Sherpa Expeditions) have specialised in walking and cycling trips in the United Kingdom and Europe since 1973. Explore iconic trails and destinations on a self guided or small group active holiday with Walkers' Britain.
<img src='/portals/World%20Expeditions/Icons/brands/small/TAS.jpg' class='brandPopoverIcon' alt="Tasmania Expeditions"> <div class='brandPopoverBrandName'>Tasmanian Expeditions</div>
Tasmanian Expeditions is the most experienced operator of treks and adventure travel holidays in Tasmania. We own and operate the most comprehensive range of adventure holidays available across Tasmania's varied landscapes.
<img src='/portals/World%20Expeditions/Icons/brands/small/UTX-new.jpg' class='brandPopoverIcon' alt="Utracks"> <div class='brandPopoverBrandName'>UTracks</div>
UTracks are the active European holiday specialists. Whether you prefer cycling or walking, 2-star or 4-star, small groups or self guided, land, river or sea – UTracks can help you to explore Europe exactly the way you want.
<img src='/portals/World%20Expeditions/Icons/brands/small/WYA.jpg' class='brandPopoverIcon' alt="World Expeditions Schools"> <div class='brandPopoverBrandName'>World Expeditions Schools</div>
World Expeditions Schools is our specialist division dedicated to organising tailor made overseas school group adventures. Specialists in Service Learning projects, choose from more destinations than any other school group provider.
<img src='/portals/World%20Expeditions/Icons/brands/small/YOM.jpg' class='brandPopoverIcon' alt="Yomads"> <div class='brandPopoverBrandName'>Yomads</div>
Yomads offers adventures for the 20s and 30s on six continents. Designed as a way to bring young and likeminded travellers together, Yomads caters to those interested in lightly structured and active trips that allow freedom to roam and explore.
<img src='/portals/World%20Expeditions/Icons/brands/small/ACT.jpg' class='brandPopoverIcon' alt="Australian Cycle Tours"> <div class='brandPopoverBrandName'>Australian Cycle Tours</div>
Australian Cycle Tours specialises in high quality self guided and guided cycling experiences in a selection of the most beautiful regions in Australia.
<img src='/portals/World%20Expeditions/Icons/brands/small/WEX.jpg' class='brandPopoverIcon' alt="World Expeditions"> <div class='brandPopoverBrandName'>World Expeditions</div>
The pioneers of original, worldwide adventure travel holidays since 1975
<img src='/portals/World%20Expeditions/Icons/brands/small/TJX.jpg' class='brandPopoverIcon' alt="Trail Journeys"> <div class='brandPopoverBrandName'>Trail Journeys</div>
Self-guided cycling experts on New Zealand's Otago Rail Trail and more
<img src='/portals/World%20Expeditions/Icons/brands/small/BMAC.jpg' class='brandPopoverIcon' alt="Blue Mountains Adventure Company"> <div class='brandPopoverBrandName'>Blue Mountains Adventure Company</div>
The original Blue Mountains canyoning, hiking, climbing and abseiling experts
<img src='/portals/World%20Expeditions/Icons/brands/small/GWNZ.jpg' class='brandPopoverIcon' alt="Great Walks of New Zealand"> <div class='brandPopoverBrandName'>Great Walks of New Zealand</div>
Explore New Zealand's most spectacular wilderness regions with the self-guided hiking experts
<img src='/portals/World%20Expeditions/Icons/brands/small/NAA.jpg' class='brandPopoverIcon' alt="North America Active"> <div class='brandPopoverBrandName'>North America Active</div>
USA Canada hiking & cycling tour specialists, choose from self-guided or guided trips