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Sailboat holidays & skippered tours

The thrill of sailing, the chance to discover places only accessible by sea and to meet new friends are what make a sailing holiday magical. Treat yourself to a week or weekend where you can wake up in the roadstead and have breakfast with the sea around you.

598

experiences

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5.0

Easter in the Phlegrean Islands

Duration:

4 days - 4 nights

Italy:

Gulf of Naples

Give this experience a try!

€350

Per person

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5.0

Educational Cruise

Duration:

3 days - 2 nights

Italy:

Tuscany

Give this experience a try!

€380

Per person

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Sailing day Genoa, Camogli and San Fruttuoso

Duration:

1 day - 0 nights

Italy:

Liguria

Give this experience a try!

Starting from

€110

Per person

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4.9

Sailing & adventure among the Egadi Islands

Duration:

5 days - 4 nights

Italy:

Aegadian islands

Give this experience a try!

Starting from

€450

Per person

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Weekend nelle Magiche Pontine

Duration:

5 days - 4 nights

Italy:

Pontine Islands

Give this experience a try!

€350

Per person

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4.5

Weekend di vela e Trekking all'Isola d'Elba

Duration:

2 days - 2 nights

Italy:

Tuscany

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+2 travellers

have booked

€280

Per person

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4.0

Pasqua a Vela in Sardegna con Hostess

Duration:

4 days - 3 nights

Italy:

Southern Sardinia

Give this experience a try!

€400

Per person

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4.9

Sailing in the Ocean - Canary Islands

Duration:

4 days - 5 nights

Spain:

Galicia

Give this experience a try!

€399

Per person

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4.3

Easter and Easter Monday on board a 14-meter boat in the Pontine Mountains

Duration:

4 days - 3 nights

Italy:

Pontine Islands

Give this experience a try!

€440

Per person

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4.3

Easter and Easter Monday 2024 aboard a 22-meter boat

Duration:

4 days - 3 nights

Italy:

Pontine Islands

Give this experience a try!

€600

Per person

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5.0

An all-inclusive day on a sailing boat

Duration:

1 day - 0 nights

Italy:

Liguria

Give this experience a try!

€180

Per person

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5.0

Easter and Easter Monday in the Pontine Islands

Duration:

4 days - 3 nights

Italy:

Pontine Islands

Give this experience a try!

€300

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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

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 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

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 - Sailboat holidays & skippered tours

14253 reviews

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A weekend of sailing between Capraia and the island of Elba

03/20/2024

davide C.

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Italy

Enrico è un comandante che sa mettervi a proprio agio in un equilibrio di libertà e professionalità . Se vi piace oltre al vento il buon cibo siete sulla barca giusta ..
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Guadeloupe and its islands in ten days

02/10/2024

Caterina P.

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Italy

At first, from my son Guglielmo , a special thanks to J.B. for his prompt interest and kind concern when we had problems to get in touch because of my smartphone (next time better an e sim). Than, even if i'm not exactly the best guest to have on bord, i received any kind of support to make me feel confortable and enjoy my stay.. You'll find someone who loves his job and who knows how to do it at best. Really good experience thanks also to Adriana, LuLu e Franco. See you soon!
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Guadeloupe and its islands in ten days

02/9/2024

Franck P.

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France

J’ai passé un super séjour sur le Mango qui est un voilier de voyage hyper abouti. Des vrais sensations de Voile…..! Merci à Jean Baptiste pour son accueil authentique qui aime partager ces connaissances et qui m a fait les beaux sites traversés…. À très bientôt. Franck
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Guadeloupe and its islands in ten days

02/8/2024

Lucie C.

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France

Super accueil. Jean Baptiste est très agréable très professionnel et surtout très securisant en.mer. il connaît son bateau dans tous les détails. Très bon séjour avec une bonne ambiance. Jean Baptiste nous a fait decouvrir de très beaux endroits. . nous le recommandons vivement. Adriana Lucie et Franck

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