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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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4.9

Discovering the Breton coast and its islands

Duration:

7 days - 6 nights

France:

Brittany and Normandy

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Jean

has booked

€785

Per person

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5.0

Veleggiata alla Baia dei Saraceni

Duration:

1 day - 0 nights

Italy:

Liguria

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+9 travellers

have booked

Starting from

€115

€121

Per person

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4.8

DISCOVERING THE EGADI ISLANDS on the Routes of the Florio Family

Duration:

6 days - 7 nights

Italy:

Aegadian islands

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+2 travellers

have booked

Starting from

€550

Per person

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5.0

Luxury sailing in the Gulf of Poets

Duration:

1 day - 0 nights

Italy:

Liguria

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+6 travellers

have booked

€90

Per person

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4.9

12-day educational sailing course among the islands of Greece

Duration:

10 days - 11 nights

Greece:

Saronic Islands and Athens area

Give this experience a try!

€859

Per person

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4.8

Gone with the Wind, Corfu and the Poseidon Islands

Duration:

6 days - 7 nights

Greece:

Ionian Islands

Give this experience a try!

€570

Per person

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4.8

Gone with the Wind: 2 boats in Corfu and the Ionian islands

Duration:

6 days - 7 nights

Greece:

Ionian Islands

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+14 travellers

have booked

Starting from

€570

Per person

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4.8

Little sailors grow up: 5 days sailing on the island of Elba

Duration:

4 days - 4 nights

Italy:

Tuscany

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+3 travellers

have booked

€490

Per person

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4.8

All in the Family: 5 days sailing on Elba on a comfortable 17m boat

Duration:

4 days - 4 nights

Italy:

Tuscany

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+7 travellers

have booked

€490

Per person

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5.0

3 DAYS 2 NIGHTS Sailing the Ligurian Coast from GENOVA

Duration:

3 days - 2 nights

Italy:

Liguria

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+5 travellers

have booked

Starting from

€324

€360

Per person

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5.0

A fantastic day on a boat in the blue sea of Tuscany

Duration:

1 day - 0 nights

Italy:

Tuscany

Give this experience a try!

€130

Per person

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4.6

Meditation & Sailing

Duration:

5 days - 5 nights

Italy:

Tuscany

Give this experience a try!

€490

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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