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Sailboat holidays & skippered tours

The thrill of sailing, the chance to discover places only accessible by sea and to meet new friends are what make a sailing holiday magical. Treat yourself to a week or weekend where you can wake up in the roadstead and have breakfast with the sea around you.

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5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

10 departures available

June - September

Starting from

€825

€743

Per person

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4.8

Let's discover the Aeolian Islands together by sailing

Italy: Aeolian Islands

7 days - 7 nights

19 departures available

May - October

Starting from

€640

€576

Per person

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4.7

In the blue of Capri and the infinity of the Amalfi Coast

Italy: Naples & Amalfi Coast

2 days - 2 nights

8 departures available

May - October

Starting from

€320

€272

Per person

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4.7

Whale watching cruise with WWF guide on an 18-meter schooner between Tuscany and Corsica

Italy: Tuscany

6 days - 6 nights

4 departures available

August - September

Starting from

€1,041

€989

Per person

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4.9

Super!

Gulf of Poets and Cinque Terre

Italy: Liguria

2 days - 2 nights

3 departures available

July - September

Starting from

€390

Per person

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4.9

Super!

Sailing & adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

7 departures available

June - October

Starting from

€700

Per person

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4.8

Super!

May 1st long weekend between Elba and Capraia - 2 boats in company

Italy: Tuscany

3 days - 3 nights

One departure available

April - May

€350

Per person

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4.9

Super!

Trip with photographer to the Pontine - Life changing experiences

Italy: Pontine Islands

4 days - 3 nights

8 departures available

June - October

Starting from

€420

€399

Per person

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4.8

Super!

Barefoot holiday between Elba and Capraia on a 15m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

14 departures available

May - October

Starting from

€230

Per person

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4.8

Super!

All in the family: 5 days between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

5 days - 4 nights

12 departures available

May - September

Starting from

€400

Per person

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4.8

Super!

Barefoot holiday between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

12 departures available

May - October

Starting from

€230

Per person

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4.8

Super!

A week in the Aeolian Islands - 6 islands in seven days

Italy: Aeolian Islands

6 days - 7 nights

7 departures available

June - September

Starting from

€583

€525

Per person

Why book a holiday with Sailsquare?

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80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.

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.

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

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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 - Sailboat holidays & skippered tours

17634 reviews

April 25th: cetacean watching expedition in the Pelagos Sanctuary with WWF guide

04/28/2026

Michele B.

-

Italy

Relatively short but interesting sea outing, with an excellent skipper and WWF experts. On board a nice and multinational company. There has been no shortage of dolphin sightings.
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April 25th long weekend on the Island of Elba

04/27/2026

Andrea T.

-

Italy

3 days on the island of Elba... dream landscapes along the itinerary proposed by Marco and Carmen, a very clean and comfortable boat, which they take care of as if it were their home. Lots of laughter and good music (Sal Davinci ... we joke !!). For me Elisabetta after 23 years that I did not go sailing thanks to Marco I had the pleasure of helping him in navigation and it was a return to the past .... Marco is an excellent professional skipper available in every request ...... my partner Andrea did the baptism on board and it couldn't have gone better .... Carmen as a captain helper always available ready and kind .. We highly recommend trying to sail with them as it's not just seeing Unique places but living a fairy tale thanks Marco and Carmen from Andrea and Elisabetta
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Sailing in the Cyclades

04/22/2026

Miguel M.

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Spain

Exceptional experience!! Yann is a skipper who knows the navigation area and the most suitable anchorages and ports well. In addition to being an excellent sailor, he is an endearing person who seeks the well-being of his "crew", carrying out activities on land such as hikes or visits to interesting places that give added value. His boat "[hidden]" is a sailboat of the highest level, very comfortable and designed to sail in extreme conditions and therefore absolutely safe. Yann keeps it in pristine condition and is spotlessly clean. In short, it is a highly recommended experience.
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Weekend among the most beautiful coves of Elba

04/21/2026

SARA N.

-

Italy

Unforgettable sailing experience with Marco and Carmen! 🌊⛵ From the first moment we felt welcomed as friends: professional, helpful and always attentive to every detail. The weekend was well organized, with breathtaking views, moments of relaxation, aperitifs and lots of laughter. We sailed to the island of Elba, saw dolphins and caught some excellent fish that we then cooked and ate together. All wonderful! Marco is an experienced skipper who conveys safety and passion for the sea, while Carmen adds a special touch with her kindness, sympathy and care for guests. I recommend this experience to anyone who wants to experience the sea in an authentic and relaxing way. Definitely to be redone, we will see each other 😜 again

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