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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.



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Get onboard solo, with your family or your friends

Get onboard solo, with your family or your friends

Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.

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Find out before you book who's waiting for you on board

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Sailing holidays that suit all budgets

Sailing holidays that suit all budgets

On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Yacht sailing holidays & skippered tours in Tuscany

2928 reviews

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Weekend on the Island of Elba...Hostess on board


Barbara B.



la professionalità e la compagnia di Vittorio e Giulia ci hanno regalato un week end bellissimo. Affidabili, super disponibili e divertenti Consigliatissimo!!!
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Elba... the scents, the sea and its colors!


Lucia I.



Ivo molto bravo e professionale .beliissima esperienza
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Long weekend of sailing and trekking on the Island of Elba - 2 boats


Roberta M.



Bellissima esperienza, bellissimo equipaggio, ma soprattutto ottimo Skipper!!! Marco mette a suo agio le persone, sempre disponibile e molto preparato. Mi ha permesso di affrontare serenamente la mia prima esperienza in barca a vela. Visitando nuovi posti grazie anche alla perfetta combinazione barca a vela + trekking (e ben organizzata, un ringraziamento anche Francesco "Checco" la nostra guida!) Grazie a tutto il meraviglioso gruppo che mi ha accompagnato in questa nuova avventura!!!
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Long weekend of sailing and trekking on the Island of Elba - 2 boats


giorgio r.



Ottima vacanza, che ci ha permesso di godere sia del piacere di navigare in uno splendido mare, sia di fare delle piacevoli camminate tra i boschi della costa dell'isola, baciati da un caldo sole di inizio Ottobre. Marco (skypper) e Checco (guida trekking) sono 2 persone eccellenti sia per le loro caratteristiche umane, sia per la loro professionalità. Marco è una persona sempre attenta alle necessità e richieste della "ciurma", ci ha assistito e guidato in questa breve (purtroppo) vacanza facendoci scoprire angoli meravigliosi di una natura ancora sorprendente e, non ultimo, i piaceri del palato in ristorantini che non avremmo mai scoperto da soli, ma anche, in barca, dove ci ha cucinato una gustosissima pasta col pesce che aveva pescato lui stesso. Infine un ringraziamento ai compagni di viaggio che hanno reso questa gita quello che speravo: relax, divertimento ed un'ottima esperienza umana. Un saluto a tutti, speriamo di rivederci alla prossima. Buon Vento a tutti.

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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.
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  • 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.
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  • Snorkeling activities that already at a little depth reveal a marine world full of life and history, with remains of Roman and Etruscan ships.
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  • 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.
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  • 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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