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Holidays and cruises on sailboats with organized activities.

Do you love to relax but also need to stay active or pursue your greatest passions? On a sailboat, you can enjoy a week or weekend of sailing and sea, combining activities such as trekking, yoga, snorkeling, and even gastronomic tastings.

experiences

5.0

Wellness Adventure Retreat

Caribbean: San Blas Islands - Panama

10 days - 10 nights

6 departures available

February - June

Starting from

€3,000

€2,100

Per person

Arctic New Year: Sailing, Trekking, and Aurora adventures in Norway

North Sea: Norway

14 days - 14 nights

One departure available

December - January

€999

Per person

4.6

Squid Regatta

Italy: Tuscany

2 days - 2 nights

One departure available

October

€180

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.

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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

Find out more about the skipper and travellers who have already booked the holiday, to find out more about the

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 - Holidays and cruises on sailboats with organized activities.

1329 reviews

Squid Festival: let's close the season on a high note! - on board a 17mt boat

11/10/2025

giulia f.

Italy

I participated in the weekend on a sailing boat organized for the Squid Festival and I couldn't ask for anything better! It was a wonderful experience, between sea, wind and excellent company. The crew was great: nice people and with a great desire to have fun. The skipper is super professional, but also helpful and attentive to let us experience sailing in a relaxed and fun way. I can't wait to get back on board for the next adventure! ⚓️🐙✨ Giulia, Eva and Martina

Squid Festival: let's close the season on a high note! - on board a 17mt boat

11/5/2025

Marco F.

Switzerland

Matteo is a professional skipper and above all a pleasant person, who steers the boat and situations with lightness and experience. Luke [hidden] a well-maintained and decidedly comfortable and spacious boat. Nice opportunity and fantastic company / crew, not to be forgotten and to be seen again with pleasure in a next navigation, between sea aperitifs and laughter.

LET'S GO TO TOTANI - Festival in Capria

11/5/2025

Marco D.

Italy

Unforgettable and fun experience, very prepared skipper who tamed a sea that was not exactly docile. The fishing competition is beautiful and suggestive.

Long weekend of whale watching with WWF guide on an 18-meter schooner

10/2/2025

Marco C.

Italy

Unforgettable experience aboard the Schooner Mahayana. An essential and shared life on board. Thanks to Captain Francesco, his crew and WWF guide Ilaria, a serene and pleasant atmosphere was established with all guests from the beginning. Browsing great places. Educational experience on the marine environment with a focus on cetaceans and environmental impact. As a first experience we particularly appreciated the pace of navigation, the life on board and the company.

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