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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.

25

experiences

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4.2

Premium

TORTOLA Dream Premium - 8 days in catamaran ALL INCLUSIVE with hostess / cook

Duration:

7 days - 7 nights

Caribbean:

BVI - British Virgin Islands

Starting from

€1,760

Per person

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4.2

Premium

PHUKET Dream Premium - 8 days in catamaran ALL INCLUSIVE with hostess / cook

Duration:

7 days - 7 nights

Thailand:

Phuket, Krabi and Phi Phi Islands

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+6 travellers

Have booked

Starting from

€1,905

Per person

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4.2

Premium

BORA BORA Dream - 8 days in catamaran ALL INCLUSIVE with hostess / cook

Duration:

7 days - 7 nights

Pacific Ocean:

French Polynesia

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+2 travellers

Have booked

Starting from

€1,280

Per person

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4.2

Premium

ST. BARTH Dream Premium - 8 days in catamaran ALL INCLUSIVE with hostess / cook

Duration:

7 days - 7 nights

Caribbean:

Saint Martin

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+2 travellers

Have booked

Starting from

€1,630

Per person

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4.2

Premium

EXUMA Dream Premium - 8 days in catamaran ALL INCLUSIVE with hostess / cook

Duration:

7 days - 7 nights

Caribbean:

Bahamas

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+16 travellers

Have booked

Starting from

€1,795

Per person

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4.2

Premium

Dream Premium - 8 days in catamaran ALL INCLUSIVE with hostess / cook

Duration:

7 days - 7 nights

Caribbean:

Grenadines & Martinique

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+2 travellers

Have booked

Starting from

€1,560

Per person

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4.2

Premium

GUADELOUPE Dream Premium - ALL INCLUSIVE catamaran with hostess / cook

Duration:

7 days - 7 nights

Caribbean:

Guadeloupe

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Fabian M.

Has booked

Starting from

€1,320

Per person

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4.2

Premium

MALDIVES Dream Premium - 8 days in catamaran ALL INCLUSIVE with hostess / cook

Duration:

7 days - 7 nights

Indian Ocean:

The Maldives

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+2 travellers

Have booked

Starting from

€1,230

Per person

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4.2

Premium

PRASLIN Dream Premium - ALL INCLUSIVE catamaran with hostess / cook

Duration:

7 days - 7 nights

Indian Ocean:

Seychelles

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+12 travellers

Have booked

Starting from

€1,720

Per person

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4.2

Premium

Dream Caribbean Premium - 11 days in catamaran ALL INCLUSIVE with hostess / cook

Duration:

10 days - 10 nights

Caribbean:

Grenadines & Martinique

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+14 travellers

Have booked

Starting from

€2,055

Per person

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4.2

Premium

SILHOUETTE Dream Premium - ALL INCLUSIVE catamaran with hostess / cook

Duration:

10 days - 10 nights

Indian Ocean:

Seychelles

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+2 travellers

Have booked

Starting from

€2,235

Per person

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4.7

Between sky, sea, volcanoes and trekking in Tenerife. Sailing week - All inclusive with hostess on board!

Duration:

6 days - 7 nights

Atlantic islands:

Canary Islands

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+3 travellers

Have booked

€1,537

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

932 reviews

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Take part in the 55th Barcolana with everything included

10/11/2023

Peter C.

-

Italy

Fantastica esperienza! Nonostante il vento quasi inesistente Alberto e Federica ci hanno fatto sentire tutta l'energia della Barcolana! Grazie!
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Weekend on the Island of Elba...Hostess on board

10/9/2023

Barbara B.

-

Italy

la professionalità e la compagnia di Vittorio e Giulia ci hanno regalato un week end bellissimo. Affidabili, super disponibili e divertenti Consigliatissimo!!!
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All inclusive weekend in the Gulf of Alassio

10/6/2023

John C.

-

Italy

Sarà stata la sfortuna o l’improvvisazione ma non abbiamo navigato con Daniele e nonostante l’impegno di Carmen il we “non ha girato” (barca bloccata in porto da “problemi burocratici”) Mi spiace ma non riproverò
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From the Egadi Islands to the Cous Cous Fest of San Vito Lo Capo on a 16-metre boat (private bathroom) with Hostess

10/6/2023

genevieve s.

-

Australia

Amazing trip with the best crew! Highly recommended.

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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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