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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.

686

experiences

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4.3

Three days to the Pontine Islands

Duration:

3 days - 2 nights

Italy:

Pontine Islands

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+30 travellers

have booked

Starting from

€399

Per person

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A weekend in the best anchorages of the Mediterranean: the Pontine Islands

Duration:

3 days - 2 nights

Italy:

Pontine Islands

Give this experience a try!

€400

Per person

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5.0

Weekend in Ponza, Palmarola, Ventotene

Duration:

3 days - 2 nights

Italy:

Pontine Islands

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+4 travellers

have booked

Starting from

€250

Per person

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Weekend in the Pontine Islands

Duration:

3 days - 2 nights

Italy:

Pontine Islands

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+2 travellers

have booked

Starting from

€320

Per person

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5.0

Strepitos Pontine!

Duration:

3 days - 2 nights

Italy:

Pontine Islands

Give this experience a try!

Starting from

€390

Per person

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5.0

Sailing, swimming and aperitif at sunset ... What else?

Duration:

1 day - 0 nights

Italy:

Lake Garda

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+80 travellers

have booked

€69

Per person

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Mini-cruise to the Aeolian Islands

Duration:

3 days - 2 nights

Italy:

Aeolian Islands

Give this experience a try!

€230

Per person

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4.9

Crossing to the northwest: sailing weekend in Sicily

Duration:

3 days - 2 nights

Italy:

Sicily

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+8 travellers

have booked

€300

Per person

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5.0

Weekend sailing in the Pontine Islands

Duration:

2 days - 2 nights

Italy:

Pontine Islands

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Federica P.

has booked

Starting from

€280

Per person

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5.0

Weekend in the coves of Ponza and Palmarola

Duration:

2 days - 2 nights

Italy:

Pontine Islands

Give this experience a try!

€300

Per person

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4.9

Weekend on Elba: barefoot among the most beautiful coves

Duration:

2 days - 2 nights

Italy:

Tuscany

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+14 travellers

have booked

Starting from

€270

€300

Per person

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5.0

Sailing and Terme to Ischia

Duration:

2 days - 2 nights

Italy:

Gulf of Naples

Give this experience a try!

€215

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

14308 reviews

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Sailing course on the Côte d'Azur aboard a 15-metre sailboat

05/22/2024

Quentin M.

-

France

Merci à Cyril pour ce stage de voile inoubliable. Gentillesse, bienveillance et transmission de savoir sont de mise. Merci pour les conseils précieux et pour le partage d’anecdotes plus passionnantes les unes que les autres. Le tout dans un cadre magnifique et sur un bateau très agréable à vivre. À recommander sans hésiter!
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Weekend of sea and colors between Ischia, Procida and Vivara

05/21/2024

Juri R.

-

Germany

Se sei ancora indeciso…PRENOTA! Visitare Procida e Ischia con Emiliano e Ida é molto di più di un semplice tour in barca a vela. Emiliano é un velista esperto che conosce bene le coste di Napoli e dintorni, con lui ti potrai sentire al sicuro sulla barca. Potrai decidere dove fermarti, se attraccare al porto per la notte o semplicemente visitare qualche isola e godere del buon cibo. Ad ogni modo non dovrai fare altro che rilassarti e goderti la magica atmosfera che si crea con i tuoi compagni di viaggio perché tanti aperitivi e risate al tramonto sono assicurati. E`stata davvero una bella esperienza, Emiliano e Ida sono fantastici e ci hanno fatti sentire come a casa. Grazie ragazzi per questo indimenticabile Weekend! Agnese e Juri.
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The fantastic Saronic Islands and the surroundings of Athens

05/21/2024

Steve T.

-

Canada

My family and I spent a week onboard with Alessandro exploring the Saronic Islands. We were taken to some amazing places that I will remember forever. Some were busy with people and tourists and some were completely ours - just the bay and our boat. This was a trip of a lifetime with a great skipper!
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Sailing course on the Côte d'Azur aboard a 15-metre sailboat

05/21/2024

Marie-Albane r.

-

France

Superbe stage sur Solal ! Grâce à Cyril et ses très nombreuses connaissances nous nous sommes tous amusés en apprenant beaucoup , nous garderons un très bon souvenir de notre escapade en mer. Un grand merci ,

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