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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

4.5

Yoga and Sailing in Costa Smeralda

Italy: Northern Sardinia

7 days - 7 nights

One departure available

July - August

€1,250

Per person

5.0

Freediving & snorkeling retreat in Marsa Alam Satayah Dolphin Reef

Africa: Egypt & Red Sea

4 days - 4 nights

One departure available

October

€1,145

Per person

5.0

Freediving & snorkeling retreat in Marsa Alam Satayah Dolphin Reef

Africa: Egypt & Red Sea

3 days - 3 nights

One departure available

September

€530

Per person

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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

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.

1301 reviews

Weekend a Capraia, trekking e natura

07/5/2025

Sonia G.

Italy

I had never been on a boat before... it was my first time... you have to say that it was a beautiful experience... An unforgettable weekend.. that I will always carry in my heart.... the skipper Francesco a formidable person.... nice... kind...... available... and above all very good in the kitchen too... surprised us with his really very good first courses... Definitely an experience to be repeated...

Weekend a Capraia, trekking e natura

06/22/2025

Leonardo D.

Italy

Advised!

Weekend a Capraia, trekking e natura

06/18/2025

Giovanni N.

Italy

Beautiful experience, Capraia Island perhaps less known than others in the Tuscan archipelago, but fascinating, beautiful sea. Francesco is a competent, reliable, helpful person, he leads the crew with the right attitude of the captain so that everything on board works at its best. Also excellent cook. Boat equipped with everything,

Weekend a Capraia, trekking e natura

06/10/2025

Kristian G.

Italy

Positive experience and helpful skipper

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