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Sailing or catamaran cruises with hostess or onboard cooking service

Embark on a vacation where you won’t have to worry about cooking and can fully enjoy the sea without a care. Choose a cruise with a hostess if you want a professional and comprehensive service, from cooking and cleaning to tidying up. If you only want to avoid cooking, select a vacation with cooking service: other tasks, such as setting the table or washing the dishes, will be managed in collaboration with other guests onboard.

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4.3

Premium

ATHENS Dream Premium - All Inclusive Catamaran Cruise with Stewardess

Greece: Saronic Islands and Athens area

7 days - 7 nights

10 departures available

July - October

Starting from

€1,260

Per person - min 2 pax

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5.0

10-Day All Inclusive Ibiza & Formentera Cruise - with Hostess

Spain: The Balearic Islands

10 days - 9 nights

7 departures available

July - October

Starting from

€2,000

Per person

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4.3

Premium

CORSICA SUD Dream - catamaran cruise with hostess FULL BOARD

France: Corsica

6 days - 7 nights

13 departures available

June - October

Starting from

€1,485

€1,337

Per person - min 2 pax

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Sun, sea and relaxation... Discovering the Aeolian Islands - with Hostess

Italy: Aeolian Islands

6 days - 7 nights

One departure available

July

€1,260

Per person

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4.3

Premium

GUADELOUPE Dream Premium - Catamaran ALL INCLUSIVE with hostess/cook

Caribbean: Guadeloupe

6 days - 7 nights

56 departures available

January - December

Starting from

€1,125

€1,013

Per person

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4.3

Premium

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

Caribbean: Bahamas

6 days - 7 nights

9 departures available

July - December

Starting from

€1,865

Per person

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4.7

Premium

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

Greece: Saronic Islands and Athens area

6 days - 7 nights

3 departures available

October

€2,100

€1,995

Per person

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4.9

From the Lighthouse to the Volcano: sailing from Gibraltar to Lanzarote by catamaran

Spain: Andalusia

7 days - 7 nights

One departure available

November

€1,300

Per person

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Full board South Sardinia Cruise with hostess

Italy: Southern Sardinia

6 days - 6 nights

One departure available

July

€1,290

Per person

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5.0

Weekend in Ogliastra, super Sardinia with skipper and hostess

Italy: Southern Sardinia

3 days - 2 nights

One departure available

September

€680

€612

Per person

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4.3

Premium

KOH SAMUI Dream Premium - catamaran cruise with hostess FULL BOARD

Thailand: Phuket, Krabi and Phi Phi Islands

7 days - 7 nights

18 departures available

May - September

Starting from

€1,785

€1,607

Per person - min 2 pax

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4.3

Premium

From TAHITI to RAIATEA Dream - by catamaran ALL INCLUSIVE with hostess/cook

Pacific Ocean: French Polynesia

10 days - 10 nights

31 departures available

January - December

Starting from

€2,295

€2,066

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 - Sailing or catamaran cruises with hostess or onboard cooking service

1180 reviews

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Week of sailing and sea between the Tuscan Archipelago and Corsica with Hostess

07/8/2025

sonia s.

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Italy

-I spent a wonderful holiday with Paolo and Bianca. They are very kind, very nice, Bianca is a very good cook. They are very helpful . My first experience on a sailing boat was very pleasant. I saw beautiful places, coves that otherwise I could not have seen except by boat. I highly recommend a holiday with Paolo and Bianca
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

07/7/2025

Diana U.

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Italy

Amazing experience! It was my first time on a sailing boat, and it was incredible. We visited beautiful places and beaches. Ale and Carlo are the perfect duo to sail with! Ale is professional, knows everything about sailing and the best beaches, and was always available and super friendly. Carlo was also very kind and helpful. I'm a vegetarian, and he always made something special just for me. Thank you for an unforgettable week! Hope to come back soon! :)
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Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

07/7/2025

Eugenia D.

-

Italy

Great experience, great service, very good food and safety on board
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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

07/7/2025

Virginia B.

-

Italy

Beautiful holiday, Andrea precise and very nice skipper made us discover wonderful places and entertained us. Another honorable mention to Marta who fed and pampered us. Mattias a real sea dog! You are missing already!

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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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