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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

4.8

Super!

Trekking and sailing weekend on the island of Elba

Italy: Tuscany

3 days - 2 nights

One departure available

September

€340

€323

Per person

5.0

Freediving & snorkeling retreat in Marsa Alam Satayah Dolphin Reef

Africa: Egypt & Red Sea

6 days - 6 nights

One departure available

August

€795

Per person

4.7

Weekend a Capraia, trekking e natura

Italy: Tuscany

3 days - 2 nights

2 departures available

September - October

€200

Per person

5.0

Sailing holiday with yoga and SUP in the Saronic islands

Greece: Saronic Islands and Athens area

6 days - 7 nights

5 departures available

September - October

€990

Per person

4.0

Sailing and Hiking in the Cyclades

Greece: Cyclades

7 days - 7 nights

3 departures available

September - October

Starting from

€997

€798

Per person

4.0

Sailing & Diving in the Small Cyclades

Greece: Cyclades

7 days - 7 nights

2 departures available

August - September

€1,020

€918

Per person

Meditation and massage on a sailing boat in Corsica

France: Corsica

7 days - 7 nights

One departure available

August

€1,100

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

€455

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

4.7

COUS COUS FEST: A Weekend of Sea, Sailing, Cous Cous and Music!

Italy: Sicily

4 days - 3 nights

2 departures available

September

€390

€351

Per person

5.0

Selvaggio Blu in Sardinia, Sail & Trek with Alpine Guide on board

Italy: Southern Sardinia

5 days - 6 nights

2 departures available

October - November

€1,450

€1,300

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 - Holidays and cruises on sailboats with organized activities.

1304 reviews

Weekend a Capraia, trekking e natura

07/21/2025

Lorena C.

Italy

A 5 star captain who also caught and cooked an unforgettable tuna for me and the crew for my birthday! Thank you for your professionalism and availability. Until next time... fair winds

Sailing and yoga: discovering Elba and the north of Corsica

07/21/2025

Rossella L.

Italy

Filippo is a very prepared and helpful skipper!! He guided us in a punctual and clear way and immediately made us become familiar with the activities of the boat!! A good cook and speaker, he was able to create a good atmosphere on the boat right from the start!! Thank you Filippo until next :):)

Sailing and Hiking in the Cyclades

07/14/2025

Marco P.

Italy

We had a very nice holiday!

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...

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