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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!

  • confirmed
    whole boat only

    Cruise aboard a catamaran to discover the Tuscan archipelago

    from 21 May - 6 nights
    Tuscany Italy
    Reserve this boat!
    (8 spots available)
    925€ Per person
  • confirmed
    whole boat only

    Cruise aboard a 12mt boat to discover the Tuscan archipelago

    from 21 May - 6 nights
    Tuscany Italy
    Reserve this boat!
    (6 spots available)
    625€ Per person
  • confirmed
    whole boat only

    Cruise aboard a 14mt boat to discover the Tuscan archipelago

    from 21 May - 6 nights
    Tuscany Italy
    Reserve this boat!
    (10 spots available)
    555€ Per person
  • 7 reviews
    almost
    confirmed

    Tuscan Archipelago Elba Island

    from 21 May - 7 nights
    Tuscany Italy
    Join in on this experience!
    739€ Per person
  • 6 reviews

    Week between sunsets, aperitifs and sailing on the island of Elba

    from 21 May - 7 nights
    Tuscany Italy
    Join in on this experience!
    689€ Per person
  • 2 reviews
    confirmed

    An unforgettable weekend in the Tuscan Archipelago

    from 21 May - One night
    Tuscany Italy
    Join in on this experience!
    297€ Per person
  • Discounted
    spots until 22 May.

    Cruise to discover the Tuscan archipelago and northern Corsica

    from 22 May - 7 nights
    Tuscany Italy
    1 person interested
    in this holiday
    530 371€ Per person
  • 31 reviews
    confirmed

    Leave with us: 2 boats to discover the splendid Capraia

    from 26 May - 3 nights
    Tuscany Italy
    5 people
    are onboard
    265€ Per person
  • 41 reviews
    confirmed

    Isola di Capraia .. "I'll walk around you until you return" :-)

    from 26 May - 3 nights
    Tuscany Italy
    5 people
    are onboard
    318€ Per person
  • 17 reviews

    Week end Exploring the Tuscan Archipelago

    from 27 May - 2 nights
    Tuscany Italy
    Join in on this experience!
    318€ Per person
  • 12 reviews
    confirmed

    A weekend on the most fascinating island of the Tyrrhenian Sea: Capraia - Tuscany

    from 27 May - 2 nights
    Tuscany Italy
    4 people
    are onboard
    240€ Per person
  • 9 reviews
    4 discounted
    spots

    Weekend sailing and relaxation in the wonderful Tuscan Archipelago

    from 27 May - 2 nights
    Tuscany Italy
    Join in on this experience!
    275 260€ Per person
  • 1
  • 2
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Reviews - Yacht sailing holidays & skippered tours in Tuscany

2286 reviews
20 / 10
Fabio  A.

Fabio A.

review about Sailing in company between Elba, Giglio and Giannutri August 2021

10 / 10
Thanks to Daniele I lived, together with my wife, not only one of the most beautiful holidays of our life but he managed to let us enter in a way known really by few (the sea), thanks skipper it was all fantastic
Francesca S.

Francesca S.

review about Tuscany and Northern Corsica: blue sea and wild bays April 2022

10 / 10
Week of perfect season began: sea, wind and beautiful sails to Corsica. Leonardo does his job with great professionalism and passion and the result is excellent. Kalekoy (the boat) is very beautiful, comfortable and organized in every detail. Highly recommended, all nice!
Spartaco M.

Spartaco M.

review about CrazySail Skipper Academy Lite: Punta Ala - April 30th April 2022

10 / 10
Great Inti! The most ''ganzo'' skipper (tuscan like me) I have met so far. Really engaging and dynamic person from a human point of view, but technical at the same time in pointing out some dangerous situations to the skipper or helmsman on duty, always with a smile or a joke that does not hurt. I hope to have the opportunity to sail with you again Good wind and see you soon
Spartaco M.

Spartaco M.

review about CrazySail Skipper Academy Lite: Punta Ala - April 30th April 2022

10 / 10
Great Matthew! Really good person and skipper. Calm and security are the words that certainly distinguish him. Words that very often unfortunately are missing in a sailing trip. Thanks to him, among other things, I had the opportunity to understand with how much intelligence and little excitement, you can operate maneuvers even apparently very difficult, made such by the frenzy of having to do them in a short time, which is almost always bad counselor. To the next Matthew, thank you for the teachings and good wind!
Spartaco M.

Spartaco M.

review about CrazySail Skipper Academy Lite: Punta Ala - April 30th April 2022

10 / 10
Beautiful experience on board with CrazySail skippers! Competent, technical and professional people! But what struck me most was the human aspect and empathy that Matteo (skipper designated for the day), Inti and Daniele have been able to create since before the sailing and the beautiful climate, created thanks to them, on the boat among perfect strangers such as we were guests. I recommend to everyone, experienced sailors but also and above all newbies who want to approach this world, an experience with CrazySail and its skippers! ????
Romina V.

Romina V.

review about Relaxation and luxury sailing between Versilia and Liguria January 2022

10 / 10
Fabrizio is an excellent skipper with a great sailing experience and makes the crew feel in absolute safety. We spent a very pleasant day in wonderful company. The boat is brand new, comfortable and very performing! Five-star experience!!!
Sallustio F.

Sallustio F.

review about Capraia a marvel of the Tuscan archipelago September 2021

10 / 10
I recommend everyone to try at least once a long week end with Fabrizio and Anna You won't just find what you can expect from a sailing trip, specifally: - clean boat - in-depth knowledge of the area - excellent navigation skills - something to eat and drink - etc you will see that everything is done with an high level of care to make you happy, which is the extra I raraly find from my any previous trip "How" things get done make an huge difference, there is not something to eat ... it's super well prepared to make sure you enjoining it when sharing, Wine.... much above any medium expectation! Grazie Fabri and Anna, be sure i'll be back soon...
Sara G.

Sara G.

review about Week between the island of Elba and Capraia - Relax, sun and good wine September 2021

10 / 10
Unforgettable holiday! Luca dedicated himself completely to us putting us at ease. Super helpful, prudent, kind, polite, proactive. He cradled us for 7 days on the coast of the Island of Elba without missing anything!!! Wonderful sunrises and sunsets, hidden coves where we could only get there by swimming. Endless aperitifs with background music. In short... Fun!! Luca introduced us to the island in a different way and pampered us as best we could wish for!!! THANK YOU!!!
Emanuela M.

Emanuela M.

review about Tuscan Archipelago Elba Island September 2021

10 / 10
Fantastic captain! Able to amalgamate the group, instill tranquility and follow everyone's wishes. We have always sailed safely, also being able to actively participate in navigation maneuvers. Return from Elba sailing, from the upwind to the wind in the stern and butterfly sails. Complete experience and lots of fun. Thanks again for everything!
Elena G.

Elena G.

review about Exclusive cruise between Capraia, Elba Island and Corsica! August 2021

10 / 10
Beautiful holiday. The boat is really spacious, elegant, sporty. Simón is very attentive, kind and helpful, and we went sailing whenever the weather allowed. We had fun and relaxed. In short, we recommend everyone a week on Sean with Simón! Elena and Fabio
Massimiliano T.

Massimiliano T.

review about A week to discover the Tuscan islands August 2021

10 / 10
I spent this holiday among the Tuscan islands and in the wonderful blue waters of the Island of Elba. With a fantastic crew and a wonderful skipper giving me and the whole crew the memory of a week at sea that will remain indelible in our hearts. Thank you so much Ilario I think it is for me and on behalf of all Thank you Until next time Good wind
MILENA P.

MILENA P.

review about Sailing flotilla between the Island of Elba, Capraia and Corsica August 2021

10 / 10
Super captain! Always attentive and alert, even in wind at 40 knots Not to mention the excellent mussels that he prepared for us ! How can you not get attached !
Monica B.

Monica B.

review about Have fun and relax while discovering Elba and Capraia islands August 2021

10 / 10
An unforgettable week: our first sailing experience was exciting thanks to the competence, availability and passion of the skippers. Excellent accommodation on the boat that was comfortable and always clean.
Paolo C.

Paolo C.

review about Capraia and Elba - unforgettable mid-August! August 2021

8 / 10
It has been a wonderful week. The boat is nice and comfortable. Pietro despite not being on board with us, was always available and valuable even at a distance. Skipper Leonardo did an impeccable job.
Laura M.

Laura M.

review about On a sailing boat between the Tuscan archipelago and Corsica, discover the heart of the Mediterranean from the sea August 2021

8 / 10
Our skipper was Guido who accompanied us on a nice ride between Elba, Corsica and Capraia. Although we did not know the other members of the crew, we immediately found ourselves in full harmony and this cooperation allowed us to overcome even some unexpected and difficulties that arose during the week (limited space on board for 9 people, some problems of the boat a little dated, long wait to moor in Capraia). For me it was a wonderful experience and I keep an unforgettable memory of it.
Marine C.

Marine C.

review about Elba ... An endless summer July 2021

10 / 10
Alfredo ("Il Capitano"!) is an outstanding skipper! Not only does he perfectly master his sailboat, the itinerary and the weather hazards specific to the Mediterranean (sales rotating constantly that week), which provides a permanent feeling of security and invites to great relaxation, but he is also a person worthy of being known as he is warm, generous, attentive, and bon vivant! We spent an amazing week with Alfredo and the very friendly crew we had the chance to meet on the sailboat! Sailing, swimming, many nights at anchor without going ashore, tasty meals from morning to evening prepared in turn by sharing the secrets of recipe (viva la pasta!), bursts of laughter, songs: what more could you ask for! The real Italian dolce vita that we love so much! We are already looking forward to sailing with him on the new boat he is looking for next season to provide more comfort on board!
Marco S.

Marco S.

review about Sailing week in the Tuscan Archipelago: relaxing bays and beautiful islands! August 2021

8 / 10
Alessandro is a skipper with experience and competence as well as being very sociable and nice to review some functional things on the ?...
Pietro S.

Pietro S.

review about 3 boats from Genoa to Rome: Cinque Terre, Porto Venere, Capraia, Elba, Giglio, Argentario July 2021

10 / 10
Young, fun and helpful. Wonderful holiday
Ilaria M.

Ilaria M.

review about Mid-August sailing along the coasts of the island of Elba August 2021

10 / 10
Is Umberto a great person?? Many experiences to tell, very nice and prepared. He is a real ship commander!!!
Marco M.

Marco M.

review about Elba and Capraia a Vela August 2021

10 / 10
Our week with Levantades & Captain Marco was magnificent. A rare professionalism in a skipper in love with his work that he transmits with the heart and a lot of experience. With a mix of lots of fun and relaxation, we highly recommend climbing Levantades! Gabriela &Marco, Varese
Max C.

Max C.

review about Sailing flotilla between the Island of Elba, Capraia and Corsica July 2021

8 / 10
Alessandro is very experienced and very cautious. I hope to sail with him again for all he has to teach and for sympathy. I would only suggest that he probe more into the expectations of the crew on the relationship between sport and relaxation and be more explicit about what is calibrating the activities. For example: weather and sea, fatigue, less experienced or uncomfortable crew members, other flotilla boats.
Valentina G.

Valentina G.

review about Elba Capraia and Corsica on 50 feet! July 2021

10 / 10
Person of the highest professionalism and great human qualities has been able to create an excellent harmony in the crew helping to make the holiday magical and very fun. The sailings were wonderful. Skipper really recommended, a really smart person!
Isabelle S.

Isabelle S.

review about A dream for two ... Elba and its magic, bays and coves! July 2021

10 / 10
Everything was perfect Giacomo can make your dream comes true. He is very profesional and considérate with his customers. He cooks almost as a chief ???? The boat is not only very Nice but charming and each detail is made with Amore. I recommend Thais fabulosa Cruise +++++
MARINIG A.

MARINIG A.

review about Whale watching cruise with WWF researcher between Elba, Capraia and Northern Corsica! July 2021

10 / 10
Gianni skipper good and capable. He did everything he could to please everyone. We managed to see the whale and sperm whales, as well as bottlenose dolphins and dolphins. Not to mention the skill of the biologist who with her enthusiasm and her knowledge of cetaceans, made us live a beautiful and very interesting week. Brava Silvia!!
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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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