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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.

653

experiences

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4.3

Mini-cruise on the French Riviera

Duration:

5 days - 5 nights

France:

French Riviera and Porquerolles

Give this experience a try!

€513

€570

Per person

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5.0

May 1st long weekend on the Côte d'Azur

Duration:

5 days - 5 nights

France:

French Riviera and Porquerolles

Give this experience a try!

€625

Per person

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4.9

Sailing & adventure among the Egadi Islands

Duration:

4 days - 4 nights

Italy:

Aegadian islands

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+2 travellers

have booked

€450

Per person

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5.0

May 1st long weekend between sailing, islands and wineries

Duration:

5 days - 5 nights

Italy:

Gulf of Naples

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+2 travellers

have booked

€550

Per person

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4.9

Long live May Day!

Duration:

5 days - 4 nights

Italy:

Aeolian Islands

Give this experience a try!

€382

Per person

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5.0

Orthodox Easter in Greece in the Saronic Islands

Duration:

6 days - 7 nights

Greece:

Saronic Islands and Athens area

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+7 travellers

have booked

€500

Per person

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Weekend in the Magical Pontine

Duration:

3 days - 2 nights

Italy:

Pontine Islands

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Elena S.

has booked

€350

Per person

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4.8

1 May - Whale watching expedition with WWF researcher between Lavagna and Portofino

Duration:

4 days - 4 nights

Italy:

Liguria

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Lily G.

has booked

€449

Per person

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5.0

May Day on Elba

Duration:

4 days - 4 nights

Italy:

Tuscany

Give this experience a try!

€365

Per person

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4.8

Bridge from May 1st to May 5th on a 17 m boat

Duration:

3 days - 3 nights

Italy:

Tuscany

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+3 travellers

have booked

€340

Per person

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5.0

12 Days Sailing Cruise around St. Martin/St. Barth's/Anguilla incl. breakfast and lunch on board

Duration:

10 days - 11 nights

Caribbean:

Saint Martin

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+4 travellers

have booked

€1,995

Per person

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5.0

Weekend in Capraia, the island with timeless sunsets

Duration:

2 days - 2 nights

Italy:

Tuscany

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+12 travellers

have booked

Starting from

€225

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

14263 reviews

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Easter on the Island of Elba

04/22/2024

Antonios S.

-

Italy

Anche se il tempo non ha aiutato, è stata una bellissima esperienza
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Trekking and sailing weekend on the island of Elba

04/22/2024

Sara C.

-

Italy

Bellissima esperienza,grazie alla cordialità e professionalità di Marco e i compagni di avventura. Ho apprezzato molto anche la possibilità di fare trekking. Consigliatissimo!!
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Luxury sailing in the Gulf of Poets

04/15/2024

Antonio C.

-

Italy

Giornata splendida, mare e barca perfetti, altissimo valore aggiunto l’equipaggio, simpatico gentile preparato ma soprattutto disponibile, e Costanza ottima cuoca, esperienza fantastica, da ripetere!!
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Sailing Cyclades

04/15/2024

yannis b.

-

France

Séjour incroyable avec Yann ! Très attentif, drôle et chill dans toutes les situations, dans un bateau très confortable !

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