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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

Sailing holiday with yoga and SUP in the Saronic islands

Greece: Saronic Islands and Athens area

6 days - 7 nights

3 departures available

September - October

€990

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

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.

1315 reviews

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

09/16/2025

Paolo S.

Italy

Wonderful experience

Trekking and sailing weekend on the island of Elba

09/16/2025

Fabio B.

Italy

Sailing holiday with yoga and SUP in the Saronic islands

09/15/2025

Nina S.

Finland

Awesome week at sea. Elias knows all the best places to go to. It was just amazing to have this possibility to enjoy yoga, sailing, swimming, Greek food & culture in a relaxing & safe way with good company. I would definetily like to do this soon again.

Sailing holiday with yoga and SUP in the Saronic islands

08/20/2025

madelaine w.

United Kingdom

What a fabulous trip! Everything I'd hoped for and more. A great mix of relaxation and adventure with fabulous company. It was great to learn a bit about sailing whilst exploring some beautiful islands.

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