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

5.0

Vela BenEssere in Grecia dello Ionio

Duration:

7 days - 7 nights

Greece:

Ionian Islands

6 travellers

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€1,125

€1,250

Per person

5.0

Trekking & Sailing - Easter between Elba and Capraia - 2 boats

Duration:

4 days - 3 nights

Italy:

Tuscany

Give this experience a try!

€375

€395

Per person

5.0

Trekking with guide & Sailing - April 25th between Elba and Capraia - 2 boats

Duration:

4 days - 3 nights

Italy:

Tuscany

8 travellers

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€398

€419

Per person

Sailing and trekking in Cap Corse

Duration:

3 days - 2 nights

France:

Corsica

Give this experience a try!

€250

Per person

5.0

Kitesurfing Safari: a unique sporting adventure in the heart of the Caribbean

Duration:

7 days - 7 nights

Caribbean:

Venezuela

Starting from

€3,800

Per person

Sailing and trekking in the Tuscan archipelago

Duration:

3 days - 2 nights

Italy:

Tuscany

Give this experience a try!

€250

Per person

Meditation and massage on a sailing boat

Duration:

7 days - 7 nights

France:

Corsica

Give this experience a try!

€1,100

Per person

4.9

Super!

Ski & Sail at the end of the world!

Duration:

8 days - 7 nights

North Sea:

Norway

Give this experience a try!

€1,200

Per person

5.0

Sailing Yoga and SUP trip in the SARONIC ISLANDS Greece

Duration:

6 days - 7 nights

Greece:

Saronic Islands and Athens area

Give this experience a try!

€990

Per person

5.0

Afternoon sailing and barbecue evening

Duration:

1 day - 0 nights

Italy:

Lake Garda

18 travellers

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Starting from

€129

Per person

4.6

Weekend a Capraia, trekking e natura

Duration:

3 days - 2 nights

Italy:

Tuscany

59 travellers

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Starting from

€180

Per person

5.0

Sailing, relaxation and trekking between Portovenere and the Cinque Terre

Duration:

3 days - 3 nights

Italy:

Liguria

Give this experience a try!

€400

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

Vela BenEssere in Grecia dello Ionio

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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