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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

4.6

Weekend a Capraia, trekking e natura

Italy: Tuscany

3 days - 2 nights

3 departures available

August - October

Starting from

€200

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

Being Together: A Journey of Connection and Presence

Croatia: Kornati Islands

7 days - 7 nights

2 departures available

August

€700

€630

Per person

5.0

Sailing, Reiki Wellness and Meditation in the magic of Corsica

France: Corsica

7 days - 7 nights

One departure available

August - September

€1,200

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.

1300 reviews

Weekend a Capraia, trekking e natura

06/22/2025

Leonardo D.

Italy

Consigliato!

Weekend a Capraia, trekking e natura

06/18/2025

Giovanni N.

Italy

Esperienza bellissima, Capraia Isola magari meno conosciuta di altre dell arcipelago della Toscana, ma affascinante, mare stupendo. Francesco persona competente , affidabile, disponibile, guida la ciurma con il giusto piglio del capitano perché a bordo tutto funzioni al meglio. Anche ottimo cuoco. Barca attrezzata di tutto,

Weekend a Capraia, trekking e natura

06/10/2025

Kristian G.

Italy

Esperienza positiva e skipper disponibile

Sailing WellEssere in Ionian Greece

09/14/2024

Barbara P.

Italy

Splendido viaggio nelle isole Ionie, veleggiando nel mare cristallino in tutto relax, tra bagni, snorkeling, il suo e visitando le isole più caratteristiche. Lo skipper Fabrizio, sua moglie Sari, col gatto Kekku, accoglienti e disponibili, amano profondamente queste isole e ci hanno portato nelle baie più belle, dove ci siamo svegliati nel silenzio; ci è capitato di essere accompagnati da una tartaruga o di provare un trattamento reiki con Fabrizio. La barca è curata in ogni dettaglio e molto confortevole. La cucina vegetariana di Sari è deliziosa. Molto consigliato!

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