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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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4.8

Catamaran with chef in the magical sea of the Ionian Islands

Greece: Ionian Islands

7 days - 7 nights

3 departures available

July - September

Starting from

€1,250

Per person

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4.3

Premium

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

Caribbean: Grenadines & Martinique

6 days - 7 nights

75 departures available

January - December

Starting from

€1,250

€1,125

Per person

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Cannes - Sanremo - Cannes: 7 days cruise with skipper & hostess

France: French Riviera and Porquerolles

6 days - 6 nights

4 departures available

August - October

€1,290

Per person

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SAILING & IDLENESS Argo-Saronic Gulf

Greece: Saronic Islands and Athens area

7 days - 7 nights

One departure available

August - September

€1,960

Per person

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4.3

Premium

New Year's Eve catamaran in the golden triangle of the Caribbean - Full board with hostess

Caribbean: Saint Martin

6 days - 7 nights

2 departures available

January

Starting from

€2,490

Per person - min 2 pax

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Full board South-East Sardinia Cruise with hostess

Italy: Southern Sardinia

6 days - 6 nights

One departure available

July

€1,290

Per person

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3.0

Southern Sardinia on a beautiful 16m boat with HOSTESS

Italy: Southern Sardinia

7 days - 7 nights

7 departures available

July - August

Starting from

€1,400

€1,260

Per person

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4.6

Sailing in the most beautiful Saronic with chefs: Hydra and Spetses

Greece: Saronic Islands and Athens area

7 days - 7 nights

One departure available

September

Starting from

€1,300

Per person

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5.0

Overwhelmed by an unusual destiny in the blue sea of Corsica

Italy: Tuscany

6 days - 7 nights

One departure available

August - September

€700

Per person

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4.3

Premium

Dalmatian Dream - week on catamaran ALL INCLUSIVE with hostess/cook

Croatia: Split Archipelago

7 days - 7 nights

6 departures available

July - September

Starting from

€1,885

Per person

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5.0

Week in Corsica with wellness programme

Italy: Tuscany

6 days - 7 nights

One departure available

August

€1,559

Per person

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4.9

Families sailing: north-western Sicily with exclusive boat!

Italy: Aegadian islands

7 days - 7 nights

5 departures available

July - September

Starting from

€817

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

-ho trascorso con Paolo e Bianca una vacanza stupenda . Loro sono gentilissimi simpaticissimi Bianca è una cuoca bravissima. Sono molto disponibili . La mia prima esperienza in barca a vela è stata piacevolissima. Ho visto posti stupendi, calette che altrimenti non avrei potuto vedere se non in barca . Consiglio vivamente una vacanza con Paolo e 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.

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Italy

Ottima esperienza, servizio ottimo, mangiato molto bene e sicurezza a bordo
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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

07/7/2025

Virginia B.

-

Italy

Vacanza bellissima, Andrea skipper preciso e simpaticissimo ci ha fatto scoprire posti meravigliosi e ci ha intrattenuti. Altra menzione d’onore a Marta che ci ha cibati e coccolati. Mattias vero lupo di mare! Mancate giá!

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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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