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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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4.8

Discover the Ionian Islands, Lefkada, Meganisi, Kalamos, Atokos and Itaque

Duration:

6 days - 6 nights

Greece:

Ionian Islands

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+16 travellers

have booked

€585

Per person

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4.9

Sailing cruise in the Greek islands - The Saronic Islands

Duration:

7 days - 7 nights

Greece:

Saronic Islands and Athens area

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+28 travellers

have booked

Starting from

€523

€550

Per person

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4.8

Let's discover the Aeolian Islands together by sailing

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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+23 travellers

have booked

Starting from

€625

Per person

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Discovering the wonderful Hvar - Vis - Korcula

Duration:

6 days - 7 nights

Croatia:

Split Archipelago

Give this experience a try!

Starting from

€518

€575

Per person

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5.0

Venice and the Venetian Lagoon

Duration:

2 days - 2 nights

Italy:

Venice and the Gulf of Trieste

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+4 travellers

have booked

€188

Per person

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5.0

EOLIE IN RELAX - Boat with 3 cabins and 3 bathrooms

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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+6 travellers

have booked

Starting from

€433

Per person

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4.8

Aeolian Islands: wellness, taste and fun

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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+12 travellers

have booked

Starting from

€551

€580

Per person

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5.0

Sea, sailing and relaxation in the beautiful Aeolian archipelago

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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Mauro

has booked

Starting from

€333

Per person

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4.0

Discovery of southern Corsica, Sardinia and this sublime archipelago

Duration:

6 days - 7 nights

France:

Corsica

Starting from

€1,476

Per person

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3.5

Egadi Islands, Zingaro Nature Reserve, San Vito lo Capo

Duration:

6 days - 7 nights

Italy:

Aegadian islands

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+2 travellers

have booked

Starting from

€585

€650

Per person

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4.8

Scopello, San Vito and Egadi: friends, good food sailing

Duration:

6 days - 7 nights

Italy:

Aegadian islands

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+12 travellers

have booked

Starting from

€523

€550

Per person

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5.0

Pack your suitcase and we'll take care of the rest!! Stewards on board!

Duration:

6 days - 6 nights

Greece:

Ionian Islands

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+15 travellers

have booked

Starting from

€510

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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