Boat rental

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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

Sailing and Hiking in the Cyclades

Duration:

7 days - 7 nights

Greece:

Cyclades

Give this experience a try!

Starting from

€798

€997

Per person

Sailing & Diving in the Small Cyclades

Duration:

7 days - 7 nights

Greece:

Cyclades

10 travellers

Starting from

€816

€1,020

Per person

5.0

Super!

Week in Corsica with wellness programme

Duration:

6 days - 7 nights

France:

Corsica

10 travellers

Starting from

€898

€998

Per person

Seven-Day Yoga & Sailing Retreat in the Small Cyclades

Duration:

7 days - 7 nights

Greece:

Cyclades

Give this experience a try!

Starting from

€990

€1,100

Per person

5.0

Sailing WellEssere in Ionian Greece

Duration:

7 days - 7 nights

Greece:

Ionian Islands

7 travellers

Starting from

€1,215

€1,350

Per person

Yoga Retreat on a Catamaran

Duration:

6 days - 6 nights

Italy:

Naples & Amalfi Coast

2 travellers

€1,950

Per person

5.0

Freediving & snorkeling retreat in Marsa Alam Satayah Dolphin Reef

Duration:

6 days - 6 nights

Africa:

Egypt & Red Sea

8 travellers

€795

Per person

5.0

Aeolian Islands - Volcanoes, Sail & Trekking - Mountain Guide on board

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

11 travellers

€1,430

Per person

Meditation and massage on a sailing boat in Corsica

Duration:

7 days - 7 nights

France:

Corsica

Give this experience a try!

€1,100

Per person

3.7

Weekend YOGA in barca a vela

Duration:

2 days - 2 nights

Italy:

Tuscany

Give this experience a try!

€320

Per person

Sail & Yoga Retreat: relaxing catamaran cruise with full board

Duration:

6 days - 7 nights

Greece:

Saronic Islands and Athens area

Starting from

€2,650

Per person

Sailing and Yoga for the long weekend of June 2

Duration:

4 days - 3 nights

Italy:

Tuscany

Give this experience a try!

€530

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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.

1297 reviews

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!

Capraia under full sail / trekking on the island

07/30/2024

Umberto R.

Italy

Esperienza pazzesca. Josuah è un ragazzo eccezionale, disponibile e appassionato. Consiglio l’esperienza a tutti.

Capraia under full sail / trekking on the island

07/30/2024

AGOSTINO C.

Italy

Esperienza positiva sotto tutti i profili. Grazie a Joshua per la professionalità, disponibilità e cortesia. Il pesce pescato al ritorno è stata poi la ciliegina sulla torta. Esperienza da rifare sicuramente!

Weekend a Capraia, trekking e natura

07/17/2024

Gianluca G.

Italy

Francesco è veramente coinvolgente e si impegna per offrire un servizio ottimo incluso un bel giro sull'isola. Era la mia prima esperienza in barca, molto positiva.

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