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

4.9

Super!

Ski & Sail at the end of the world!

North Sea: Norway

8 days - 7 nights

One departure available

April

€1,200

Per person

4.0

Sailing and Hiking in the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€1,290

€1,161

Per person

4.6

Yoga, Wind, Sailing and Freedom

Malta: Malta

5 days - 6 nights

One departure available

May - June

€990

€891

Per person

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

4.0

Sailing & Diving in the Small Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

June

€1,290

€1,161

Per person

4.7

Trekking & Sailing to discover Capraia

Italy: Tuscany

3 days - 2 nights

One departure available

May

€299

€269

Per person

4.7

Corsica & Tuscan Archipelago Sailing Yoga & Adventure

France: Corsica

4 days - 3 nights

One departure available

April - May

€490

€441

Per person

5.0

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

4.3

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

Greece: Ionian Islands

6 days - 7 nights

2 departures available

August

Starting from

€750

€675

Per person

4.6

Weekend a Capraia, trekking e natura

Italy: Tuscany

3 days - 2 nights

11 departures available

March - October

Starting from

€200

Per person

5.0

For couples only: BenEssere in Greece!

Greece: Ionian Islands

7 days - 7 nights

One departure available

June

€2,000

Per person

5.0

Wellness Adventure Retreat

Caribbean: San Blas Islands - Panama

10 days - 10 nights

5 departures available

March - June

€3,000

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

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.

1321 reviews

Wellness Adventure Retreat

01/14/2026

Donna S.

Canada

We had an amazing time on board. Great food. Lots of activities. We got to see sharks, dolphins, and many types of tropical fish. Luca was a great host. The boat was beautiful and very clean. The location was absolutely stunning!

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.

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