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Yacht sailing holidays & skippered tours in Tuscany

Yacht sailing holidays & skippered tours in Tuscany

Discover the magic of sailing holidays in Tuscany! Get onboard with a local skipper and live a unique adventure with your crew: learn to sail, explore incredible places, recharge your batteries and experience the local culture & gastronomy.

  • Sailing Holidays
  • Italy
  • Tuscany

FLEXIBLE CANCELLATION.

Stress-free booking: you can cancel up to 24 hours before departure!

  • 18 reviews
    confirmed

    Pearls of the Tyrrhenian Trophy 2023

    from 22 September - 2 nights
    Tuscany Italy
    4 people
    are onboard
    371€ Per person
  • 18 reviews

    Midweek in the Tuscan Archipelago: Giannutri and Giglio with departure from Civitavecchia

    from 26 September - 2 nights
    Tuscany Italy
    Join in on this experience!
    308€ Per person
  • 26 reviews
    confirmed

    Long weekend of sailing and trekking on the Island of Elba - 2 boats

    from 28 September - 3 nights
    Tuscany Italy
    6 people
    are onboard
    290€ Per person
  • 30 reviews
    confirmed

    The magnificent colors of Elba - Hostess on board! (3cabs-3baths)

    from 28 September - 3 nights
    Tuscany Italy
    2 people interested
    in this holiday
    399€ Per person
  • 99+ reviews
    confirmed

    Wine Experience with Sommelier on the Island of Elba

    from 28 September - 3 nights
    Tuscany Italy
    9 people
    are onboard
    599€ Per person
  • 5 reviews

    A weekend aboard the Goletta dell'Elba

    from 29 September - 2 nights
    Tuscany Italy
    Join in on this experience!
    851€ Per person
  • 78 reviews
    confirmed

    long weekend, sailing with kitchen service!!!

    from 29 September - 3 nights
    Tuscany Italy
    7 people
    are onboard
    154€ Per person
  • 3 reviews
    almost
    confirmed

    Wonderful Elba Island

    from 29 September - 2 nights
    Tuscany Italy
    Join in on this experience!
    297€ Per person
  • 99+ reviews
    confirmed

    Far from everything on the island of Elba, between magic and new friends!

    from 29 September - 2 nights
    Tuscany Italy
    3 people
    are onboard
    262€ Per person
  • 7 reviews

    Weekend between sunsets, aperitifs and sailing to the island of Elba

    from 29 September - 2 nights
    Tuscany Italy
    1 person interested
    in this holiday
    371€ Per person
  • 99+ reviews
    Discounted
    spots until 29 Sep.

    Late summer flotilla on Elba: dips and spritzes to say goodbye to summer!

    from 29 September - 2 nights
    Tuscany Italy
    12 people
    are onboard
    315 299€ Per person
  • 18 reviews

    Weekend in the Tuscan Archipelago: Giannutri and Giglio departing from Civitavecchia

    from 29 September - 2 nights
    Tuscany Italy
    4 people interested
    in this holiday
    308€ Per person
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Reviews - Yacht sailing holidays & skippered tours in Tuscany

2989 reviews
20 / 10
Martina M.

Martina M.

review about Gone with the Wind on Elba September 2023

10 / 10
We have just returned from a we F A N T A S T I C O that could not have gone better! Marco, prepared, sunny and irreverent at the right point allowed us to grasp all the beauties that boat life can give you, its magic and the feeling of freedom that you can not understand if you do not try it. Aria, a Janneau 45, a gem in my opinion, with everything you need on board to make you feel at home. So what can I say, when is the next release?
Martina N.

Martina N.

review about Sailing in the paradise of the Tuscan archipelago August 2023

10 / 10
First experience on a sailing boat and thanks to our commander Luciano it will be the first of a long series! Amazing welcome and competence and a lot of patience in explaining tools, maneuvers and technical language. He gave us the opportunity, together with wonderful travel companions, to enjoy the beauties of Capraia, Elba and Corsica. Always attentive, we felt absolutely safe throughout the trip and never missed a joke to make the experience cheerful. Wonderful person and impeccable commander. A real "Lucio di Mare"! The Beniamina, a splendid boat, has remained in my heart.
Fabrizio B.

Fabrizio B.

review about We navigate safely August 2023

10 / 10
Three unforgettable days of sea and sailing especially thanks to the skipper Orazio who turned out to be not only an excellent sailor but also an excellent travel companion.
Silvia F.

Silvia F.

review about Blue Summer Week in Elba and Capraia August 2023

10 / 10
Week nothing short of fantastic. Mario, the skipper, a character you don't meet every day: we immediately became fond of him and felt part of his crew. He involved us and taught us many notions about the world of sailing. We didn't miss the fun with him!!
Annalisa Z.

Annalisa Z.

review about Wild Tuscany and Corsica in Flotilla August 2023

8 / 10
Really nice holiday, nice comfortable boat and super company. Definitely an experience that I recommend and that I would do again
Debora R.

Debora R.

review about Explore the enchantment of the Tuscan Archipelago: Sailing holiday on Elba, Giglio and Giannutri! July 2023

10 / 10
I really appreciated the welcome and friendliness of Francesco and Jeannette, they made us live life on the boat in total serenity and freedom (it was our first experience). Moreover, despite the initially adverse weather conditions, they have continuously looked for alternative solutions so as not to make us miss anything of the initial itinerary.
Claudia  G.

Claudia G.

review about Round Corsica: a sailing adventure July 2023

8 / 10
Very nice experience, I like sailing and I took the boat license recently so it was nice to be able to refresh and put into practice what I had learned and lately put a little aside. Great company I only advise you to specify in the description that it is in effect a high altitude course, the fact that it is on this platform can confuse and make you think that it is a holiday in all respects. Still great experience.
Emanuele B.

Emanuele B.

review about Summer at last... Weekend on the Island of Elba and Pianosa July 2023

10 / 10
It was the first experience on the boat and I must say that it was a special experience, the places recommended by ale were all splendid, then the hospitality on board is spectacular so much that I felt at home. Super also Gianluca's focaccia and aperitifs at sunset. Highly recommended for those who want to experience beautiful landscapes and beautiful people. We hope to see you soon on board ????
Marcello O.

Marcello O.

review about Sailing weekend to discover the Island of Elba June 2023

10 / 10
What can I say... Very nice weekend for the group that participated that helped to spend together 3 wonderful days ... Perhaps the only thing I would have changed is having involved the participants in the choice of stages during the days ... anyway everything wonderful!
Evelin  F.

Evelin F.

review about Wonderful Elba Island June 2023

10 / 10
Super holiday! Everything perfect, nice skipper, helpful and the boat in excellent condition!
David T.

David T.

review about Sailing in a flotilla on the Island of Elba June 2023

10 / 10
I had a great time, before departure she explained all the details of the trip by contacting me, she was very kind and precise, also meeting what were my needs and schedules. During the navigation we participated in a regatta of 20 boats, with a crew of only 3 people including 2 inexperienced, managing to get THIRD! Wonderful! She is very good, super experienced in navigation and knows her boat perfectly (in every little maneuver and weight change). During the return trip we were also able to enjoy the sea and the coasts, also contributing to navigation with many maneuvers, meeting what were my wishes! A contact that I will not miss, a holiday that I will do again! Thanks Sara!
Stefania Z.

Stefania Z.

review about Capraia between sea and tango June 2023

10 / 10
Beautiful bridge of June 2, comfortable boat, fantastic crew and beautiful sea .. What can I say, we can't wait to come back!
Guido F.

Guido F.

review about Weekend between Giglio and Giannutri June 2023

10 / 10
Mirko perfect skipper, combines his technical expertise and experience with interpersonal skills listening to customer needs and managing the team with balance and discretion. I would definitely recommend it.
Sergio S.

Sergio S.

review about Elba Sailing Week, aboard a 15-meter sailboat August 2022

10 / 10
Good morning Fantastic experience, Skipper Alessandro is a special person who loves the sea, helpful and competent. Exceptional group hosted on a comfortable boat and large spaces 110 laude Good wind to all
Marco R.

Marco R.

review about Sailing in the Tuscan archipelago and Corsica August 2022

8 / 10
Through this holiday it was possible to deepen important aspects of sailing and see new places (corsica and elba). The boat is suitable for those who want to deepen this sport and perhaps making two large islands such as Corsica and Elba in the same week can be a bit tiring. After the first days, where Giancarlo met the request of the majority of the hosts (even if he had warned us of weather conditions that were not entirely "touristy"), the holiday took hold in the best way and we were very well on the boat. In addition, by organizing the return crossing (elba-livorno) according to the climatic conditions, the skipper gave everyone security.
Elisa C.

Elisa C.

review about CRUISE IN THE TUSCAN ARCHIPELAGO August 2022

10 / 10
Beautiful holiday! Recommended and to be redone.
Emanuele P.

Emanuele P.

review about Sail to the island of Elba in total relaxation and harmony with nature August 2022

10 / 10
Simply Formidable, responsible and of an extreme kindness, for a week my son listened only to him entering his heart; the only thing I would like to add for Luca is THANK YOU, thank you for the wonderful experience you have passed to my son, me and all the crew!
Roberto C.

Roberto C.

review about Relax in the bays of the island of Elba with my Border Collie August 2022

10 / 10
Nice holiday, beautiful sea. The company was pleasant and the beaches seen were all very nice. The skipper, then, delighted us with some dishes prepared with haute cuisine techniques and with a cream of sugar and milk of her production that, at breakfast, made everyone do an encore. Buffy and Gently gave an extra touch of joy to the whole holiday.
Pascal A.

Pascal A.

review about Sailboat cruise to the Island of Elba and Capraia August 2022

10 / 10
Great skipper with the right advice depending on the weather and the beauties to see and excellent cook + entertainer -:) throughout the week. Excellent Vittorio, congratulations.
Andrea B.

Andrea B.

review about Sailing course at the Marina di Salivoli: learning and navigation on Elba August 2022

10 / 10
Nice course. I learned so many things. Very kind and pleasant also the team on the ground.
Anna P.

Anna P.

review about From La Spezia to Rome, sailing between Capraia, ELba, Giglio, Giannutri August 2022

10 / 10
What a wonder this holiday!!! Even today I daydream when I think back to everything we experienced in this wonderful holiday. Alberto is a perfect skipper, Giulio the best coskipper in the world and Mimme's crew a crazy thing. I left a piece of my heart on that boat at the end of the holiday ??
Alessio P.

Alessio P.

review about FUNtastic cruise Elba Corsica Sardinia July 2022

10 / 10
Great Alfonso! Super prepared and helpful.. Absolutely to be redone! See you soon!
Paola S.

Paola S.

review about ISLAND OF ELBA: SAIL-SWING & DIVE - A week of sailing, swing dancing and diving July 2022

10 / 10
Beautiful holiday! Matteo is a very good skipper, safe and attentive. He perfectly understood the goal of our holiday. Always friendly and helpful! Sweet Silvia, the Hostess. He spoiled and pampered us! Priceless his presence to feel truly on vacation. ...... In short, everything is perfect. Too bad.... only..... that it did not last long!!!!!
Giulia Z.

Giulia Z.

review about A weekend on Elba - Breakfast and lunch included! July 2022

10 / 10
We left with Antony and his sailboat for a weekend on the Island of Elba. Antony is a skipper of the real ones: he knows his boat and the wind, the sea is his home. He gave us confidence, tranquility and his passion for sailing. Witty, agile, excellent cook and with a heart of gold he made us spend beautiful days. We will carry with us forever this beautiful adventure where we learned a lot! The boat is beautiful and conveys just peace and quiet. Experience that we will definitely repeat, thank you very much Antony!! Until next time..

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10 Reasons to go on a sailing vacation in Tuscany

  • Easily accessible from the main cities of northern and central Italy.
  • .
  • An ideal climate and wind for sailing in total relaxation from March to November.
  • Spectacular coves, such as Cala Biodola on Elba and Cala Rossa on Capraia, where you can enjoy sunbathing and diving in the crystal clear waters.
  • .
  • Snorkeling activities that already at a little depth reveal a marine world full of life and history, with remains of Roman and Etruscan ships.
  • .
  • Ideal for trekking to discover ancient fortresses, paths immersed in the Mediterranean and cliffs overlooking the sea.
  • Preferential route for seeing dolphins, minke whales and sperm whales in the Cetacean Sanctuary.
  • .
  • Suitable for a "island-hopping" of a week or only of a weekend with 2/3 days in sailboat.
  • An area of quiet sailing with short distances, full of sheltered ridges and harbors ideal for less or more experienced travelers.
  • Rich in history and culture, everywhere you meet archaeological sites, museums, shipwrecks that can tell the past of the territory.
  • Taste the local culinary specialties and reach Capraia for the traditional Sagra del Totano of November.

The best places to discover by sailing boat or catamaran in the Tuscan Archipelago

A sailing vacation in this angle of paradise will impress you with the beauty of its sea in which the colors of the Mediterranean are reflected.
Situated between the mainland and Corsica, the Island of Elba, Capraia, Giglio, Giannutri, Pianosa, Montecristo and the Island of Gorgona emerge from the crystal-clear waters of the Tyrrhenian Sea and are part of the National Park of the Tuscan Archipelago, the largest marine park in Europe!"

The distances are always limited to 25 miles, so it is often possible to navigate on sight between one island and another making the vacation safe and relaxing.
A cruise on a sailing boat in these islands means sailing with new friends among grottos and coves immersed in the silence, between turquoise waters and sheltered coasts. All this is accompanied by diving, swimming, relaxation and sightings of dolphins and other mammals such as minke whales and sperm whales in the Cetacean Sanctuary.

The island of Elba

The largest island in Tuscany is Elba, which stretches along 147 kilometers of coastline that can be circumnavigated easily by sailboat.
Your only thought will be to choose the most beautiful bay where to moor. For example, Porto Azzurro, Fetovaia, Viticcio, Cala Biodola, with the perfect transparency of their waters will invite you to bathe for a long time and to spend nights at anchor.
On land, however, there are wonderful excursions, from the summit of Monte Capanne to the mining quarries on the eastern side, not forgetting a visit to the villa di Napoleone. A sumptuous residence where Napoleon Bonaparte lived during his exile and from which you can enjoy a 360° view of the Gulf of Portoferraio.

Island of Capraia

Capraia, the closest to the coast of the Corsica, is characterized by being the only one of volcanic origin: a factor that contributes greatly to the charm of its wild identity and makes it the ideal destination for many trekking activities. Despite the assonance can be misleading, even its name alludes to the rocky nature: Capraia in fact comes from the Latin Capraria which means "rock".

Arriving from the sea you will immediately see Cala Rossa with the unmistakable amphitheater of rock in shades of purple, which dominates the emerald green of the bay and that will welcome you for a dip.
The island offers a number of safe approaches and you can decide whether to sleep in the buoy field or in the harbor. Among the culinary curiosities, a classic event in the month of November is the "Festival of the Squid": in an apotheosis of tastings, along the quay of the port, you can taste the squid cooked in all possible ways.

The island of Giannutri

With its crescent shape, the island of Giannutri is the southernmost island of the Tuscan Archipelago and can be reached in an hour's sailing from Porto Santo Stefano or Porto Ercole.
During the journey you will sail along the Monte Argentario passing by creeks and inlets where luxurious villas of famous people overlook. The island of Giannutri is home to the splendid remains of a Roman residence and the northern part is a protected reserve. Here the contact with nature is total and if you will dive get ready to meet lobsters, small groupers, dentex and dolphins.

The island of Giglio

To the north of Giannutri is the island of Giglio, also a true natural paradise. Surrounded by a turquoise sea and embellished by the villages of Giglio Porto, Giglio Castello and Campese, it is famous for its splendid granite cliffs and its secret beaches and coves. Ideal places to discover by sailing boat and where you can experience the thrill of sailing while practicing its fundamentals.

Gorgona, Pianosa and Montecristo

.

These three islands are visitable only after authorization. In some cases because they are operating penal colonies as on the island of Gorgona, in most because they are naturalistic oases that allow access to restricted groups of visitors. In particular Pianosa, a sheet of land lying on the sea, is today one of the best preserved examples of Mediterranean ecosystem, with its crystalline seabed, the cliffs and the possibility to do trekking going to the discovery of the Baths of Agrippa. Finally Montecristo is the wildest island and inaccessible, where you can approach only from Cala Maestra.

4 Things to know for a sailing vacation in the Tuscan Archipelago

  • Spring is the best time to organize a weekend boating Tuscan even last-minute. The air and the sea become warmer, the bays are quiet and the landscape is green and lively: ideal for sailing-trekking, enjoying every aspect of nature, without stress and taking advantage of great deals. From June onwards the bays begin to come alive with tourists and warm temperatures are perfect for enjoying a week-long holiday of sun, relaxation and social evenings. Finally, in autumn and winter temperatures are never cold and the landscape offers spectacular views and colors.
  • A cruise on a sailing boat in the Tuscan Archipelago is suitable for anyone who wants to spend a vacation in safe waters, in the name of relaxation and contact with nature. The opportunity to sail on the cetacean route and sail with dolphins is a unique experience for young and old alike. Moreover, thanks to the possibility of shelter between the coasts and favorable winds, sailing does not involve great difficulties. So whether it is your first experience on a boat or whether you are already experienced, whether you are in the company of friends or family with children, it is the right choice.
  • The Tuscan Archipelago is the perfect destination to dispel the myth of the expensive sailing vacation. Depending on your needs you can rent an entire boat with skipper or embark individually. The cost starts from 150€ per person for a weekend on a sailing boat to 600€ for a whole week's vacation in high season. The Tuscan Archipelago is a great place to save money thanks to the high quality of life and the availability of safe harbor accommodation without having to incur substantial port expenses.
  • The solutions to reach the Tuscan Archipelago are different, you just have to choose the most congenial. For those arriving from Italy, cars, trains and buses are the main means of getting to Punta Ala, Piombino or San Vincenzo, where most of the cruises begin. Throughout the year there are numerous rail and bus connections that depart from major Tuscan cities (Florence, Livorno, Pisa) and are intensified during the summer. For those arriving from abroad, on the other hand, it is ideal to travel by air to Pisa and Florence where both national airlines and low-cost companies such as Ryanair and easyJet land.

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