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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.

620

experiences

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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

Spring on Lake Garda

Duration:

1 day - 0 nights

Italy:

Lake Garda

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+25 travellers

have booked

€99

Per person

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5.0

A day sailing in the fantastic Gulf of Trieste

Duration:

1 day - 0 nights

Italy:

Venice and the Gulf of Trieste

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+4 travellers

have booked

Starting from

€85

Per person

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5.0

All inclusive day trip sailing around the Golfo Paradiso - flex dates

Duration:

1 day - 0 nights

Italy:

Liguria

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+12 travellers

have booked

Starting from

€126

€140

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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Magic charter Sorrento Capri Amalfi Positano

Duration:

4 days - 3 nights

Italy:

Amalfi Coast

Give this experience a try!

€750

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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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

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

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

14265 reviews

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Sailing cruise in the Greek islands - The Saronic Islands

04/28/2024

ERIC V.

-

France

Pour la seconde fois, j’ai pris énormément de plaisir à naviguer avec Bertrand autour des îles Saroniques. Cette fois ci nous avons poussé jusque Nauplie, situé à l’Ouest du Peloponeise, dans le Golf Argolique. Émettant le désir de faire une navigation de nuit, Bertrand n’a pas hésité à adapter l’´itinéraire pour répondre à ma demande.
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A weekend of sailing between Capraia and the island of Elba

04/24/2024

Angelo C.

-

Italy

Bellissima esperienza, bella gente con uno skipper top!
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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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