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Crewed yacht sailing holidays & cruises

Get on board of a vacation with crew and live the sea without thoughts. Whether you choose a sailboat, a catamaran or a gulet, comfort and gulet, comfort and well-being will be the first place for a holiday of absolute relaxation. vacation of absolute relaxation.

80

experiences

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5.0

Vela BenEssere in Grecia dello Ionio

Duration:

7 days - 7 nights

Greece:

Ionian Islands

Give this experience a try!

€1,250

Per person

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4.7

Big and luxurious 60ft catamaran in Cyclades - best local experience

Duration:

6 days - 7 nights

Greece:

Cyclades

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+10 travellers

have booked

Starting from

€1,796

Per person

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4.9

Fantastic sailing cruise between Capraia and the North of Corsica

Duration:

5 days - 4 nights

Italy:

Tuscany

Give this experience a try!

€450

Per person

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4.7

Sun, sea, wind Sardinia and Corsica

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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+29 travellers

have booked

Starting from

€850

Per person

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5.0

Giglio Giannutri Talamone Week with Cook on board

Duration:

7 days - 6 nights

Italy:

Tuscany

Give this experience a try!

€900

Per person

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4.9

Super!

From Corfu sailing between turquoise sea and white beaches - hostess on board

Duration:

7 days - 7 nights

Greece:

Ionian Islands

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+3 travellers

have booked

Starting from

€810

Per person

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5.0

Super!

SECRET DODECANESE: at full roadstead with skipper and kitchen

Duration:

6 days - 6 nights

Greece:

Dodecanese

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+9 travellers

have booked

€1,300

Per person

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4.3

Elba, all the colors of the big blue - Stewardess on board - 3 Cab/ 3 Bathrooms

Duration:

5 days - 6 nights

Italy:

Tuscany

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+10 travellers

have booked

Starting from

€599

Per person

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5.0

The perfect island-hopping in Greece! Skipper & Hostess - All included

Duration:

6 days - 6 nights

Greece:

Saronic Islands and Athens area

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+40 travellers

have booked

€1,590

Per person

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4.7

Big and luxurious 60ft catamaran in Saronic, the best local experience

Duration:

6 days - 7 nights

Greece:

Saronic Islands and Athens area

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+15 travellers

have booked

Starting from

€1,424

Per person

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5.0

Super!

An exciting holiday between Lampedusa and Malta

Duration:

6 days - 6 nights

Italy:

Pantelleria and Lampedusa

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+4 travellers

have booked

€850

Per person

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4.8

Lampedusa-Malta one way. Inclusive

Duration:

6 days - 7 nights

Malta:

Malta

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+4 travellers

have booked

€1,000

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 - Crewed yacht sailing holidays & cruises

990 reviews

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An all-inclusive day on a sailing boat

07/22/2024

Giulia D.

-

Italy

Bellissima giornata. Luigi e Federica con la loro professionalità, accoglienza e simpatia hanno contribuito a rendere questa esperienza ancora più bella e divertente. Mio nipote di 10 anni si è divertito molto. Consiglio a tutti questa gita in barca, anche perché via mare si vedono panorami e acque meravigliosi e unici.
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All Inclusive Cruise to the Egadi Islands

07/22/2024

paola z.

Ho trascorso una settimana nella quale ho vissuto emozioni speciali: gli skipper hanno creato un’atmosfera di pura energia. La barca molto comoda e pulita; la loro organizzazione ci ha permesso di ammirare luoghi magici. Il cibo è stato: memorabile. La natura e il vento hanno fatto il resto. Grazie di cuore Agata e grazie Leonardo!!! Spero di ripetere la crociera
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Aeolian Islands: wellness, taste, fun with a fabulous cook on board

07/22/2024

Lily J.

-

United States

10/10 for any first timers doing sailing trip over a week! Highly recommend!
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Eolie a vela: buon cibo e comodità, imbarco a Capo D'Orlando

07/22/2024

Pietro P.

-

Italy

Settimana indimenticabile. Le Isole Eolie offrono tanto…mare incredibile, natura inesplorata, borghi magici e tramonti unici, una vera avventura. Nila e Emiliano sono delle ottime guide che consentono di assaporare quello che c’è di autentico in queste meravigliose isole. Attraverso una profonda conoscenza dei luoghi da parte di Emiliano, vero uomo di mare, e alla grande sensibilità e conoscenza di Nila, ci hanno anche deliziato con piatti e preparazioni siciliane. Barca super confortevole e in eccellenti condizioni, è diventata casa dal primo momento. Esperienza super consigliata. Non vedo l'ora di tornare!

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Why choose a sailing vacation with hostess or crew

  • Do you want to enjoy an all-round relaxing vacation, without having to think about anything? On board these vacations you will find a crew who will brighten up your stay.
  • Find the perfect vacation for you: choose a vacation with a hostess who will take care of the all-round service or choose a vacation with an on-board chef who will prepare the best local dishes for the guests.
  • Enjoy the vacation you've been dreaming of for a long time after a year of work: devote your time only to having fun and relaxing, without having to lift a finger.
  • Are you planning your vacation with children and don't want to have any thoughts other than enjoying time with your family? A vacation on a boat with a crew is ideal!

The best destinations for a sailing vacation with crew

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Sailing vacations with hostess or crew in the Mediterranean: discover the wonders of our sea, following the advice of the skipper, perhaps sipping a cocktail prepared by the staff on board. You'll be spoiled for choice for a cruise on a sailing boat or catamaran or gulet with family, friends or new people met on board. Marinas and marinas, historic and lively villages, islands full of small restaurants or almost deserted islands, waters from green to turquoise, wide beaches and hidden coves: a boating vacation in the Mediterranean offers everything!

In Italy the best destinations are the Tuscany from whose coast to reach the island of Elba and the Giglio but also the Corsica. The Northern Sardinia, trendy and exclusive, but also the wild Southern Sardinia, or the Aeolian Islands, the Egadi Islands, the Pontine Islands and the Amalfitan Coast.

Do you prefer to go abroad? Choose a sailing vacation with hostess or crew in Croatia or in Greece, choosing a custom itinerary among the dozens and dozens of islands. But that's not all: Côte d'Azur, Corsica, Balearic Islands are all fantastic experiences, surpassed perhaps only by a vacation aboard a gulet in Turkey with crew for maximum comfort!

Hosted or crewed sailing vacations in the Caribbean: sailing on a catamaran in the Caribbean is the best way to enjoy the winter sea in Martinica, Grenadines, Cuba, Antigua and Barbuda, British Virgin Islands, Guadeloupe: excellent sailing conditions and a unique atmosphere characterize each island of the archipelago. Whether by catamaran or by sailboat, in the Caribbean your skipper will take you to explore small deserted bays even in high season, so that your cruise will be a unique and unforgettable experience.

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