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

Super!

Barcolana 58: a day at the most famous regatta in the world

Italy: Venice and the Gulf of Trieste

1 day - 1 night

One departure available

October

€280

Per person

4.7

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

Italy: Tuscany

4 days - 4 nights

One departure available

October

Starting from

€453

Per person

4.8

Super!

Squid Festival on the Island of Capraia - 2 boats in company (22 seats)!

Italy: Tuscany

3 days - 2 nights

One departure available

October

€280

Per person

4.7

Squid Regatta

Italy: Tuscany

2 days - 2 nights

One departure available

October

€180

Per person

4.7

Madeira, the pearl of the Atlantic: sailing, trekking and adventure

Atlantic islands: Portugal

5 days - 6 nights

One departure available

November - December

Starting from

€1,200

Per person

4.8

LET'S GO TO TOTANI - Festival in Capraia

Italy: Tuscany

3 days - 3 nights

One departure available

October - November

€375

Per person

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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.

1328 reviews

Sailing, Relaxing, Yoga and find your balance

08/24/2026

Roberto C.

The most beautiful bays of the Kvarner islands. The right mix of relaxation, active holiday and meditation.

Sailing, Relaxing, Yoga and find your balance

08/17/2026

Andrea P.

Perfect organization, quality of everything without flaws, top skipper in every respect, holiday that guaranteed fun, sailing, lots of laughter, fantastic places to visit and lots of sport!

Sailing, Relaxing, Yoga and find your balance

08/16/2026

Marco M.

Everything perfect! Max great skipper, experienced sailor. Self-confident. Very easy-going and funny. Precise and always available. The location, company and activities carried out, all excellent! Beautiful holiday. Thank you Max!

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

07/19/2026

Francesco R.

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

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