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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.

630

experiences

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Dream Aeolian Islands

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

Starting from

€540

€600

Per person

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4.9

In the blue between Sardinia and Corsica on a sailboat

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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+111 travellers

have booked

Starting from

€650

Per person

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5.0

From Corfù to Lefkas

Duration:

6 days - 7 nights

Greece:

Ionian Islands

Give this experience a try!

€500

Per person

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Intro sail Liguria

Duration:

1 day - 0 nights

Italy:

Liguria

Give this experience a try!

€125

Per person

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4.9

The Channel Islands by sailboat from Saint-Malo

Duration:

6 days - 5 nights

France:

Channel Islands

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+18 travellers

have booked

Starting from

€745

Per person

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4.9

The fantastic Saronic Islands and the surroundings of Athens

Duration:

6 days - 7 nights

Greece:

Saronic Islands and Athens area

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+7 travellers

have booked

Starting from

€618

€650

Per person

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5.0

Sailing Cyclades

Duration:

6 days - 7 nights

Greece:

Cyclades

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+88 travellers

have booked

Starting from

€920

Per person

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5.0

Ibiza & Formentera All inclusive week with Cook

Duration:

5 days - 6 nights

Spain:

The Balearic Islands

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+27 travellers

have booked

Starting from

€570

€600

Per person

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4.8

Sorrento Coast, Capri, Positano, Amalfi. Inclusive.

Duration:

3 days - 2 nights

Italy:

Amalfi Coast

Give this experience a try!

Starting from

€550

Per person

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4.8

An unforgettable sail to discover the Egadi Islands

Duration:

3 days - 4 nights

Italy:

Aegadian islands

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+17 travellers

have booked

€350

Per person

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4.9

Educational course From Athens to Kos on a comfortable and fast Kufner 54

Duration:

9 days - 10 nights

Greece:

North Egean Islands

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+4 travellers

have booked

€890

Per person

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4.4

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

Duration:

4 days - 3 nights

France:

French Riviera and Porquerolles

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+3 travellers

have booked

€440

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

14273 reviews

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

05/2/2024

susanna s.

-

Italy

una splendida vacanza . Fabio e Angela gentilissimi mi hanno offerto ogni confort a bordo e insegnato i primi rudimenti della vela .
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25 April - Whale watching expedition with WWF researcher in Liguria

05/2/2024

Rossella D.

-

Italy

Esperienza complessivamente decisamente positiva, nonostante le importanti difficoltà causate dalle pessime condizioni meteorologiche. L'estrema professionalità dello skipper e delle guide di whale watching, insieme al grande affiatamento e collaborazione che si è creato con tutto l'equipaggio, hanno fatto in modo che l'intera esperienza si vivesse nel migliore dei modi, in totale armonia, portando a casa anche grandi soddisfazioni di avvistamento di delfini, balenottere e tartarughe! Un'esperienza davvero indimenticabile, grazie di cuore!
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LONG WEEKEND 25 April barefoot: 4 days between Capraia and the island of Elba

05/1/2024

Simone D.

-

Switzerland

Prima esperienza in barca a vela , Matteo oltre che essere una bellissima persona è veramente un capitano navigato che sa metterti subito a tuo agio ! Consigliato sia a giovani che famiglie ! Tutto veramente top
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Long weekend in Capraia and North Corsica

04/30/2024

Licio M.

-

Italy

Marco è uno skipper super professionale e accogliente.con l equipaggio. Barca pulita e in ordine. Grazie a Marco e a tutto l equipaggio, super simpatici

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