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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.

631

experiences

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5.0

First dives in the Egadi Islands

Duration:

3 days - 4 nights

Italy:

Aegadian islands

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+11 travellers

have booked

Starting from

€360

Per person

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4.5

Sailing in the Gulf of Tigullio

Duration:

4 days - 3 nights

Italy:

Liguria

Give this experience a try!

€450

Per person

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4.3

May 1st on Elba - Stewardess on board -3 Cab./ 3 Bathrooms

Duration:

3 days - 3 nights

Italy:

Tuscany

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susanna s.

has booked

€399

Per person

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4.8

Vang Sheeting and TRIM on a state-of-the-art sailboat

Duration:

1 day - 0 nights

Italy:

Liguria

Give this experience a try!

Starting from

€132

Per person

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The Aeolian Islands in an exclusive boat

Duration:

6 days - 6 nights

Italy:

Aeolian Islands

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+4 travellers

have booked

Starting from

€650

Per person

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5.0

5-day sailing course: discovery and learning

Duration:

5 days - 4 nights

France:

French Riviera and Porquerolles

Give this experience a try!

Starting from

€630

Per person

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4.9

May Day Sailing Bridge in Capraia

Duration:

3 days - 2 nights

Italy:

Tuscany

Give this experience a try!

€265

Per person

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5.0

Discover the beautiful scenery of the Pink Granite Coast

Duration:

4 days - 3 nights

France:

Brittany and Normandy

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Michel H.

has booked

€500

Per person

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4.5

Sailing on the Island of Elba

Duration:

3 days - 4 nights

Italy:

Tuscany

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Elettra

has booked

€350

Per person

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Sailing to the island of Delos

Duration:

4 days - 3 nights

Greece:

Cyclades

Give this experience a try!

Starting from

€594

€625

Per person

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4.9

May 1st long weekend sailing at the Pontine!

Duration:

5 days - 5 nights

Italy:

Pontine Islands

Give this experience a try!

€405

€450

Per person

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4.9

Trekking, E-bike & Sailing Experience, 1 May adventure on Elba.

Duration:

5 days - 5 nights

Italy:

Tuscany

Give this experience a try!

€618

€650

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

14264 reviews

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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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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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