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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.

545

experiences

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5.0

Smart working by boat in Santa Margherita Ligure and Sestri Levante

Duration:

1 day - 1 night

Italy:

Liguria

Give this experience a try!

Starting from

€119

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 in Las Palmas for the carnival

Duration:

3 days - 4 nights

Spain:

Galicia

Give this experience a try!

€150

Per person

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4.5

Weekend di vela e Trekking all'Isola d'Elba

Duration:

2 days - 2 nights

Italy:

Tuscany

Give this experience a try!

€280

Per person

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4.9

Weekend on Elba between Sailing, E-bike and Tasting in a farmhouse

Duration:

2 days - 2 nights

Italy:

Tuscany

Give this experience a try!

€390

Per person

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4.9

E-bike & Sailing Experience with wine tasting on Elba - 2 boats

Duration:

2 days - 2 nights

Italy:

Tuscany

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+3 travellers

have booked

€314

€330

Per person

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5.0

E-bike & Sailing Experience con degustazione vini all'Elba - 2 barche

Duration:

2 days - 2 nights

Italy:

Tuscany

Give this experience a try!

€314

€330

Per person

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4.8

Barefoot holiday: Weekend between Elba and Capraia

Duration:

2 days - 2 nights

Italy:

Tuscany

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+3 travellers

have booked

Starting from

€250

Per person

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4.6

Weekend a Capraia, trekking e natura

Duration:

2 days - 2 nights

Italy:

Tuscany

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+8 travellers

have booked

Starting from

€180

Per person

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5.0

Sailing weekend to the Columbretes Islands

Duration:

2 days - 2 nights

Spain:

The Balearic Islands

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+14 travellers

have booked

Starting from

€200

€210

Per person

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Week End Basic and Advanced Sailing Course

Duration:

2 days - 2 nights

Italy:

Liguria

Give this experience a try!

€200

Per person

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5.0

Tartare, prawns and bubbles in Santa Margherita Ligure - ALL INCLUSIVE

Duration:

2 days - 2 nights

Italy:

Liguria

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Claudia D.

has booked

Starting from

€224

€249

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

14252 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.

-

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.

-

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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