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Private yacht sailing holidays with skipper in Tuscany

Private yacht sailing holidays with skipper in Tuscany

Discover the magic of sailing holidays in the Aeolian Islands! 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
  • Whole boat with skipper

FLEXIBLE CANCELLATION.

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

  • 2 reviews

    Weekend on the island of Capraia

    from 1 July - 2 nights
    Tuscany Italy
    2 people interested
    in this holiday
    414€ Per person
  • 11 reviews
    almost
    confirmed

    Sailing and trolling on Elba

    from 1 July - 2 nights
    Tuscany Italy
    1 person interested
    in this holiday
    297€ Per person
  • 5 reviews

    Elba Island and Capraia Island, the pearls of the Tyrrhenian Sea .... between splendid waters and characteristic villages

    from 1 July - 7 nights
    Tuscany Italy
    4 people interested
    in this holiday
    679€ Per person
  • confirmed
    whole boat only

    Cruise aboard a 12mt boat to discover the Tuscan archipelago

    from 2 July - 6 nights
    Tuscany Italy
    Reserve this boat!
    (6 spots available)
    725€ Per person
  • confirmed
    whole boat only

    Cruise aboard a 14mt boat to discover the Tuscan archipelago

    from 2 July - 6 nights
    Tuscany Italy
    Reserve this boat!
    (10 spots available)
    655€ Per person
  • 6 reviews
    almost
    confirmed
    whole boat only

    Elba Capraia Corsica Boat 14 mt - Skipper and Hostess on board

    from 2 July - 7 nights
    Tuscany Italy
    Reserve this boat!
    (4 spots available)
    1.232€ Per person
  • 6 reviews

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

    from 2 July - 7 nights
    Tuscany Italy
    1 person interested
    in this holiday
    848€ Per person
  • 4 discounted
    spots

    Comfort week in Tuscany on a 16-meter boat 4 cabins with private bathroom

    from 2 July - 7 nights
    Tuscany Italy
    Join in on this experience!
    944 891€ Per person
  • 4 reviews
    almost
    confirmed

    Week-end in the Gulf of Baratti

    from 2 July - 2 nights
    Tuscany Italy
    3 people interested
    in this holiday
    271€ Per person
  • 7 reviews
    almost
    confirmed

    Tuscan Archipelago Elba Island

    from 2 July - 7 nights
    Tuscany Italy
    Join in on this experience!
    845€ Per person
  • 16 reviews
    2 discounted
    spots

    Sailing in offshore CATAMARAN with the experience of Captain Marco

    from 4 July - One day
    Tuscany Italy
    Join in on this experience!
    159 148€ Per person
  • 2 reviews

    Four midweek days between Elba and Capraia

    from 4 July - 3 nights
    Tuscany Italy
    Join in on this experience!
    435€ Per person
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Why you should book a holiday with Sailsquare?

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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.

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Discover who’s already onboard

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

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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 - Private yacht sailing holidays with skipper in Tuscany

18 reviews
18 / 10
Ivano V.

Ivano V.

review about Sailing for the Argentario, Giglio and Giannutri ... a perfect week July 2021

10 / 10
Great skipper , quiet and helpful . Prepared. He knows when to leave the crew alone, when to have an aperitif together, and he hardly tells you no. Highly recommended.
Elia B.

Elia B.

review about We celebrate Easter on Elba April 2022

10 / 10
Thanks Claudio and Barbara!! Three magnificent days, fun and always sailing! Barbara and Claudio made an exceptional galley and a great menu for all three days.. The atmosphere on board is always pleasant with Barbara helping in the kitchen and Claudio making you try to steer! Very nice boat, always clean and well equipped! Until next time!
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 +++++
Luca C.

Luca C.

review about Between Elba and Corsica-Boat 14 meters exclusively for 4 guests-Hostess on board. July 2021

10 / 10
Ganzissimi: Cinzia, Michel, the boat. Excellent holiday with exceptional skipper and hostess. Cinzia is very nice, always attentive and cooks divinely. Michael is a professional who knows the best places in the area, and is calm and always available. The boat is comfortable and impeccably clean. Return! Luca, Tracy, David, Maria Claudia
Eloise T.

Eloise T.

review about A week of pure relaxation, sea and strolls in the Tuscan Archipelago August 2020

10 / 10
Francesco is a very professional and prepared skipper attentive to his guests and with a particular dedication to the kitchen. We spent a beautiful week on the boat with our children and although it was our first experience we found ourselves very comfortable and thanks to the passion for sailing that Francesco has transmitted to us we are sure that there will be many other future experiences. Super recommended!
Marta S.

Marta S.

review about Tuscan Archipelago ... wait for us! An unforgettable sailing week between sport and fun! August 2020

10 / 10
Amazing experience ! Daniele a capable skipper always quiet flanked by his son Andrea a guy available and well prepared. Pina literally spoiled us with her delicacies. They have been able to create a family atmosphere. Seeing is believing . Thank you
Maria Elena  P.

Maria Elena P.

review about Discovering the Gulf of Baratti July 2020

8 / 10
We traveled with Massimo and Joshua, two professional and helpful skippers. Beautiful experience. To be redone!
Mario S.

Mario S.

review about In search of DOLPHINS around the Island of Elba June 2020

10 / 10
It was a short holiday (weekend) but truly unforgettable, even beyond expectations! Beautiful boat, all to ourselves (there were six of us), and perfect weather. With two small children we sailed and also at night, a very suggestive experience. A big thank you to Salvo, excellent skipper, for his availability, competence and attention to our needs! Highly recommended!
Elena D.

Elena D.

review about Circumnavigation of the Island of Elba on a traditional aurica schooner in Tuscany August 2019

10 / 10
We spent 6 days on this fantastic "ecological" boat, in the company of Francesco and his son Alejandro, pleasant travel companions. Staying on this boat is a journey within a journey, it brings you back to the awareness of the world in which we live and how we live it: I advise everyone to try the experience with an open mind and hearts. Safe travel!
Roberta M.

Roberta M.

review about These places in front of the sea 2019 July 2019

10 / 10
Gianpaolo is an excellent skipper, sailing with him gives security. He enforces the rules, but with kindness. He manages to be present, but never intrusive. He is company, chats willingly, and took us to very beautiful places. Beautiful and spacious boat, In short. If you are looking for a smart skipper, and a fun and / or quiet holiday, Gianpaolo is for you.
Francesca A.

Francesca A.

review about The company of new friends ... priceless! June 2019

10 / 10
What can I say! Beautiful sailing experience to discover the pristine sea of the Island of Capraia! Claudio and Nori are people who do not meet easily in life: sunny, available, they immediately put you at ease and make you feel like real "pirates"... to conquer the sea! Perfect weekend (Eolo could have done more but we don't complain)... we were also impressed by the skill of Chef Claudio, who pampered us with delicious specialties! Everything was perfect... too bad that the weekend flies away! Thank you... we hope to see you soon! Good Wind!
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Why rent a sailing boat with skipper in Tuscany

  • Sailing in Tuscany for those who live in northern Italy is really convenient: a few hours of travel by car or train and you are immediately on a boat, ready to sail for a weekend, a bridge or a real summer holiday. Sailing boats for hire in Tuscany depart from one of the many ports in the province of Livorno, from Castiglioncello to Piombino, or further south at Punta Ala and Talamone.
  • If the starting point is easy to reach, the itineraries and destinations can be the most diverse, which is why chartering a sailing boat with skipper in Tuscany is an excellent solution! You're spoilt for choice: Elba, Giglio and Capraia are within easy reach, but if you get the hang of it, you can reach the Corsica or sail around all the smaller islands of the Tuscan Archipelago.
  • The favourable season for renting a sailing boat in Tuscany is quite wide: in summer temperatures are excellent and you rarely suffer from scorching heat, especially on a boat. But even in spring and autumn you can make the most of a sailing holiday, with the cooler weather and brilliant colours of a less harsh sun.
  • Not just sailing! Never before has it been so easy as in Tuscany to combine a sailing holiday with other activities, such as trekking and visits to the islands of the archipelago, dinners in delightful little restaurants and birdwatching... while waiting to spot a dolphin!

Hire a sailing boat in Tuscany and build a tailor-made holiday!

You can rent a sailing boat in Tuscany with a skipper and set the pace of your holiday by the sea: you can enjoy total relaxation with itineraries along the coast, discovering the Argentario and the Island of Elba, even with your children; or you can choose more challenging routes, dedicating a greater number of hours to sailing to reach more distant destinations and test your skills as sea wolves. The choice is yours!

Elba Island

Reaching and discovering the coasts of Elba on a sailing boat replaces a seaside holiday with the relaxation and comfort that are often so difficult to achieve in summer, especially if you are on a vacation with children, busy looking for parking, beaches that are not too crowded, shade and cool drinks.

You will have everything you need when you want it on your charter boat: crystal clear waters at any time of day, diving and snorkelling, snacks and naps when you feel like it... and, of course, you will be able to explore new places, beaches and old towns every day.

The coasts of the island of Elba are a constant discovery: the sea varies from blue to green and frames granite cliffs, white pebble beaches or sandy beaches, coloured like the minerals in which the island is rich.
There are many harbours and tourist ports where you can stock up on food and wine delicacies; among the places we recommend you include in your sailing itinerary on the island of Elba are the villages of Portoferraio, Porto Azzurro, Rio Marina and the beaches of Capo Bianco, Marina di Campo and Sansone.

Tuscan Archipelago National Park: seagulls, dolphins, butterflies and a dream seabed

The Tuscan Archipelago National Park, created in 1996, is one of the Italian parks with the strongest integration between land (22%) and sea (78%) and the greatest number of islands, significantly distant and different from each other, rich in endemic species to be safeguarded.
A real dream for nature lovers who, by hiring a skippered sailing boat, can discover a unique biodiversity in total freedom, just a stone's throw from home.

After Elba, the largest islands in the archipelago are Giglio and Capraia, both of which are popular with divers and snorkelers because of their clear waters and wealth of life: try to spot the now rare seahorse among the Posidonia leaves, and keep your eyes peeled for grouper, bream, sea bream and amberjack burrows in the rocky recesses

The Cetacean Sanctuary between northern Italy and France also stretches around the islands of the Tuscan Archipelago, and it is not uncommon in the summer months to spot dolphins and fin whales; but looking up will also give you satisfaction: Corsican Gulls, Peregrine Falcons, Berta and Kestrels fly here.

Gorgona to the north and Giannina to the south. Gorgona to the north and Giannutri to the south are the two wild and mysterious islands that enclose the park area and can become a final destination for your personalised sailing itinerary.

Along the Tuscan coast

For a sailing cruise of a few days or for a family holiday, sailing along the beautiful Tuscan coast gives you a taste of the unique views and sea life.
To the north, you start with a fascinating stretch of coastline over 150 kilometres long that is not easy to explore by land except on horseback: the Maremma, full of coves and long stretches of sandy coastline protected by pine forests.

More southerly, renting a skippered sailing boat can help you discover the Argentario promontory at your own pace, with its sheer cliffs and crags, contrasting with the Orbetello lagoon, a WWF Oasis, and the long beaches of Feniglia and Giannella. The exclusive Capalbio coastline is only a breath away!

From Tuscany around the Tyrrhenian Sea: setting sail

If you're ready to cast off for good, chartering a sailboat from Tuscany allows you to go wherever you want... to Corsica for example. From the island of Elba or Capraia you can set sail, usually towards Cap Corse, always with the best possible advice from your skipper, of course.

Not able to organise a sailing boat rental in Tuscany? Try to look for a boat for rent in Sardinia, in Croatia, or a boat in Turkey. Tuscany is waiting for you at the next opportunity!

How to rent a sailing boat with skipper in Tuscany

  • Letting a whole boat guarantees you total freedom. Many of our proposals for sailing holidays in Tuscany can be exclusive! Choose the right period of time with the filters on the page and enter the holiday that fascinates you most: by moving the cursor to "whole boat" (below the price) you will get an idea of the cost for the charter and what it includes. This is how you start to organise your exclusive holiday, whether with family or friends.
  • Sailsquare allows you to contact the skipper directly in order to receive all the information you need and to define every useful detail for the rental of the sailboat.
  • Time is money! Book early (at least 2-4 months) and you will find great prices and early-booking discounts. If you're not planning to leave during the peak season, the bargain is assured and the choice of boats or catamarans for exclusive charter is certainly wider.
  • The sailboat rental with skipper enables you to experience a carefree holiday. Depending on your wishes and the weather conditions, the professional skipper will make the best decisions every day: itinerary, shore excursions, best swimming spots and moorings. All that's left for you to do is enjoy a relaxing and carefree sailing holiday.
  • If you have any questions about the sailboat and catamaran skippered charter service, or would like more information, please read our frequently asked questions page, or contact us!

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