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.

FLEXIBLE CANCELLATION.

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

Why you should book a holiday with Sailsquare?

Location point above a wave

The leading sailing holiday marketplace

25,000+ happy travellers, and 10,000+ holidays in 110 destinations worldwide.

Two people with sailor hats

Get onboard solo, with your family, or your friends

Reserve a single spot, a cabin, or a whole boat just for you and your friends or family.

A boat with a magnifier above it

Discover who’s already onboard

Introduce yourselves online, get to know each other onboard, and go home with a bunch of new friends.

Two coins with a currency on top

Sailing holidays that suit all budgets

Rumour has it that sailing holidays are only for the rich or well-connected. With Sailsquare, that's no longer true. Come and discover a world you never thought was accessible!

Reviews - Yacht sailing holidays & skippered tours in Tuscany

2563 reviews
20 / 10
Roberto C.

Roberto C.

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

10 / 10
Bella vacanza, bel mare. La compagnia è stata piacevole e le spiagge viste sono state tutte molto belle. La skipper, poi, ci ha deliziato con alcuni piatti preparati con tecniche di alta cucina e con una crema di zucchero e latte di sua produzione che, a colazione, ha fatto fare il bis a tutti. Buffy e Gently hanno dato un tocco di allegria in più a tutta la vacanza.
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.
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 ??
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..
Ornella V.

Ornella V.

review about Weekend on the island of Capraia June 2022

10 / 10
Wonderful holiday, Matteo a skipper of the highest level and excellent cook, involved us and made us participate throughout the weekend in the maneuvers during navigation and in the movements between one cove and another. Clean, comfortable and well maintained boat. In short, what about a SUPERVACANZA. An experience that will remain an unforgettable memory. Ready to organize another one immediately because for those who love the sea I think there is no better holiday. Thanks again for everything
Elena S.

Elena S.

review about Weekend among the pearls of the archipelago with hostess on board June 2022

10 / 10
Fantastic experience, what to say elba always beautiful but this time in particular, the skipper Edoardo and his partner Irene were very good I dare say of the travel companions albeit short. Edoardo very good and self-confident in steering the boat and Irene an excellent assistant but above all cook. Experience to be redone as soon as possible Everything above all expectations
Ivano Antonio B.

Ivano Antonio B.

review about Long weekend of 2 June in Capraia and Corsica June 2022

8 / 10
Really fantastic boat and with an excellent livability, pity for the lack of the ladder, not a little thing .. and after what happened to our ominous reservation we can only be grateful to the organization for solving the problem So a big thank you to Sailsquare Good morning everyone
Carlo P.

Carlo P.

review about Bridge of 2 June among the wonders of the Island of Elba June 2022

10 / 10
Giacomo is an experienced and prudent professional but also an excellent travel companion. With his boat, excellent and equipped, we sailed where possible and despite the variable weather we spent a perfect holiday.
Italia B.

Italia B.

review about Cruise to discover the Tuscan archipelago and northern Corsica May 2022

6 / 10
I state that I booked qst holiday seen the photo of "monia my boat" but I arrived there in the company of 3 men and I the only woman (skipper, owner and customer like me) average age 50 years I 35. I state that I have already been going on a sailboat for a while but I have never had to deal with a skipper so dictatorial and xnulla attentive to the needs of others (PAYING customers) but very experienced. In 5 days, I took 1 decent bath given the many hours of travel from place to place on average 6 hours a day. As soon as I arrived by boat, I was not given the opportunity to choose the cabin (skipper and owner took the best cabin with bathroom and shower much more capacious) usually the skipper sleeps on the outdoor sofas. The holiday is synonymous with relaxation (at night it was impossible to sleep given the infinity of noises made by the skipper who always came out of the boat checking I do not know what) Professionalism does so much as well as the experience but nowadays the ways are worth above all. --- SKIPPER ANSWER --- Good morning Bruna, I am really sorry that your experience was not optimal, thank you for bringing the problem to our attention, we will carefully examine your opinion to avoid future misunderstandings and to improve ourselves. Below my photo it is indicated that I am the organizer of the cruise, I manage the booking and the various requests of the customers, also always in the description it is highlighted that: "The skipper of this experience will be a professional and trusted skipper, who has been working with us for years: we will communicate more details before departure." No doubt it seems to me about the experience of our skipper. We are always available to clarify any doubt of the customer, before, during and after any booking. You were the first member of the crew, so it was difficult, if not impossible, to know what other members would come on board, men, women and of what age... I remember that the cruise is reserved for all those who like the sea and sailing, and in any case I have not received any request for information on the subject. A few days before the departure on whatsapp chat I put you in touch with the skipper (Stefano) and with the other members of the crew, to have the opportunity to exchange information but also and above all to have the opportunity to clarify any doubt. All the routes, places visited and landings were shared, first on the Sailsquare website and then with all the remaining guests who were very happy to have lived this experience, visiting the island of Elba, Corsica, Capraia and the coast of Tuscany. As mentioned above, I manage the booking, the booking is also part of the assignment of the cabins, we are always very careful when there are "single" travelers not to create situations of embarrassment by staying, always if possible, men with men and women with women, in this case being you in four (skipper included) I thought to do something welcome by entrusting you with the room with double bed for exclusive use and entrusting the cabin to you bow that has 2 beds singles to 2 men (thus avoiding making them sleep in a double bed).
Luigi M.

Luigi M.

review about Sailing in the Tuscan archipelago June 2022

10 / 10
The best skipper I've sailed with. Passionate about sailing and always ready to share and explain what happens on the boat and how to behave. Fun and nice but at the same time professional and balanced. A real sailor, with experiences of ocean crossing, really good and competent. I will be back on the boat with him for sure!
Sailor

Sailor

review about Week-end in the Gulf of Baratti May 2022

10 / 10
Great experience- Marcello was prudent and attentive regarding the management of the boat, very helpful for those who wanted to deepen the theory and practice of the sailboat. He had attention to our needs. Good conversationalist and organizer.
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!!!
Trustpilot

Customer Support

Would you like some support using the platform? We've (almost) always got the answers!

Call us at +44 20351 44220 Check out our Help page

Can't find the perfect holiday for you?

Use our free holiday concierge tool - and let us find your dream sailing experience for you!

Let's find it together!

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.

Tuscany: best travel ideas

Other travel ideas