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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.

490

experiences

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4.9

Sailing in the Ocean - Canary Islands

Duration:

4 days - 5 nights

Spain:

Galicia

Be the first one to book!

€399

Per person

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4.0

Pasqua a Vela in Sardegna con Hostess

Duration:

4 days - 3 nights

Italy:

Southern Sardinia

Be the first one to book!

€400

Per person

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4.9

Weekend at the Pontine Islands: Ponza and Palmarola

Duration:

3 days - 2 nights

Italy:

Pontine Islands

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+2 travellers

Have booked

Starting from

€240

Per person

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5.0

Easter and Easter Monday in the Pontine Islands

Duration:

4 days - 3 nights

Italy:

Pontine Islands

Be the first one to book!

€300

Per person

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4.5

Easter and Easter Monday at the Pontine

Duration:

4 days - 3 nights

Italy:

Pontine Islands

Be the first one to book!

€277

Per person

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4.9

Easter and Easter Monday at the Pontine

Duration:

4 days - 3 nights

Italy:

Pontine Islands

Be the first one to book!

€277

Per person

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5.0

Easter in Capraia

Duration:

4 days - 4 nights

Italy:

Tuscany

Be the first one to book!

€455

Per person

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4.5

Easter and Easter Monday 2024 between Ischia, Procida and Capri

Duration:

3 days - 3 nights

Italy:

Gulf of Naples

Be the first one to book!

€294

€309

Per person

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4.8

Let's discover the Aeolian Islands together by sailing

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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+13 travellers

Have booked

Starting from

€531

Per person

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4.9

Easter Trekking & Sailing Experience on Elba, 2 boats

Duration:

3 days - 3 nights

Italy:

Tuscany

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+5 travellers

Have booked

€350

Per person

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EASTER AND EASTER MONDAY SAILING AMONG THE ISLANDS

Duration:

3 days - 3 nights

Italy:

Tuscany

Be the first one to book!

€380

Per person

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4.6

Easter and Easter Monday among the Tuscan Islands. Elba and Capraia.

Duration:

3 days - 4 nights

Italy:

Tuscany

Be the first one to book!

€280

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

14255 reviews

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Guadeloupe and its islands in ten days

02/10/2024

Caterina P.

-

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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Sailing course in the Cyclades

10/18/2023

Antoine B.

-

Belgium

Superbe semaine avec Sylvain. Skipper professionnelle qui vous mets a l'aise et vous explique tout. Il vous emmène a des magnifiques mouillages et nous avons descendu les petites cyclades rapidement. Le bateau est très confortable et très chouette a naviguer même quand le vent est au dessus des 30 nœuds. Je vous recommandes Sylvain pour votre prochaine aventure!

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