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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.

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4.8

Super!

Sailing and Freediving in the sea of Sardinia and Corsica

Italy: Northern Sardinia

6 days - 7 nights

One departure available

August

€870

Per person

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5.0

Super!

Long weekend on a sailing boat Cous Cous Festival in San Vito Lo Capo

Italy: Sicily

4 days - 3 nights

2 departures available

September

€345

Per person

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4.8

Super!

Cous Cous Festival tra le Egadi e San Vito Lo Capo in Catamarano

Italy: Aegadian islands

7 days - 7 nights

One departure available

September

€850

Per person

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4.0

Sailing and Hiking in the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€1,290

€1,161

Per person

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5.0

Sailing, Relaxing, Yoga and find your balance

Croatia: Istrian peninsula

7 days - 7 nights

One departure available

August

€950

Per person

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4.7

Voices of the Pelagos: artistic-scientific whale watching expedition with WWF guide

Italy: Tuscany

4 days - 4 nights

One departure available

October

€453

€430

Per person

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4.0

Outdoor and lifestyle exploration

Greece: Peloponnese

6 days - 6 nights

One departure available

September

€815

Per person

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4.6

Cous Cous Fest: weekend of Sailing, Music and Cous Cous!

Italy: Sicily

4 days - 3 nights

2 departures available

September

€350

€315

Per person

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4.0

Sailing & Diving in the Small Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€1,390

€1,251

Per person

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5.0

Yoga, meditation and healthy eating in a natural paradise

Caribbean: San Blas Islands - Panama

5 days - 5 nights

3 departures available

July - August

€1,600

Per person

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4.4

In the sea of Ulysses, all inclusive, yoga instructor on board

Greece: Ionian Islands

6 days - 7 nights

One departure available

August

€850

Per person

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4.7

Weekend a Capraia, trekking e natura

Italy: Tuscany

3 days - 2 nights

One departure available

October

€250

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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.

1325 reviews

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Magic of the Aeolian Islands: yoga and volcanic islands by catamaran

07/19/2026

Francesco R.

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IT

Beautiful islands, impossible to see them all in a week (you will have to come back); Simone, a young but experienced and capable skipper and extremely helpful. Boat with some flaws

Yoga, meditation and healthy eating in a natural paradise

07/10/2026

Uwe D.

-

CH

There are not enough words to describe how grateful I am for this experience with [hidden] Sailing. From the first moment, I felt so much love, warmth, and kindness. It was more than a sailing trip—it felt like coming home to beautiful people with beautiful hearts. Yoga and meditation opened a completely new world for me. They gave me peace, strength, and moments I will never forget. Free diving taught me that true strength comes from a calm mind. It showed me the powerful connection between mental focus and body control, and it changed the way I see myself. Every meal was healthy, fresh, and prepared with so much love and care. You could feel the heart behind everything they did. Thank you for sharing your passion, your knowledge, and your beautiful energy. I leave with unforgettable memories, a full heart, and a different view of life. If you are looking for more than just a vacation, this is the place. It is a life-changing experience that will stay in your heart forever. Thank you, Paola, Kyndera and Luca. I will come back…

Weekend a Capraia, trekking e natura

03/24/2026

Francesco V.

Francesco and Marco are two great professionals, but above all two great travel companions! Highly recommended experience

Weekend a Capraia, trekking e natura

03/23/2026

Niccolò S.

-

IT

Francesco and Marco are two very prepared skippers and the perfect people with whom to embark on this type of adventure. Highly recommended.

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