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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

ST. BARTH Dream Premium - 8 days in Catamaran ALL INCLUSIVE

Caribbean: Saint Martin

6 days - 7 nights

51 departures available

January - December

Starting from

€1,125

€1,013

Per person

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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

21 departures available

May - October

Starting from

€1,260

Per person - min 2 pax

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4.3

Premium

CORSICA SUD Dream - catamaran cruise with hostess FULL BOARD

France: Corsica

6 days - 7 nights

9 departures available

June - October

Starting from

€1,485

€1,337

Per person - min 2 pax

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4.3

Premium

GUADELOUPE Dream Premium - Catamaran ALL INCLUSIVE with hostess/cook

Caribbean: Guadeloupe

6 days - 7 nights

49 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

7 departures available

October - December

Starting from

€1,985

€1,787

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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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

€1,339

Per person - min 2 pax

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4.3

Premium

From TAHITI to RAIATEA Dream - Catamaran cruise with hostess FULL BOARD

Pacific Ocean: French Polynesia

10 days - 10 nights

26 departures available

January - December

Starting from

€2,295

€1,721

Per person - min 2 pax

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4.6

Aeolian Islands: wellness, taste, fun with fabulous cook on board

Italy: Aeolian Islands

7 days - 7 nights

8 departures available

July - August

Starting from

€910

€865

Per person - min 2 pax

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5.0

12 days of sailing from Martinique to Guadeloupe

Caribbean: Guadeloupe

11 days - 11 nights

One departure available

January - February

Starting from

€1,795

Per person - min 2 pax

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4.3

Premium

Capri Dream Premium - Catamaran cruise full board

Italy: Naples & Amalfi Coast

6 days - 7 nights

26 departures available

May - October

Starting from

€1,320

€1,188

Per person - min 2 pax

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4.3

Premium

Cruise to discover Corfu and Ionian Greece - Hostess & Half Board

Greece: Ionian Islands

7 days - 7 nights

17 departures available

May - October

Starting from

€845

Per person - min 2 pax

Why book a holiday with Sailsquare?

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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

1368 reviews

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

10/7/2025

Sharron G.

-

United Kingdom

We were the last group to sail this year & enjoyed reading the other reviews as everyone had such positive feedback. We weren’t disappointed and although the weather wasn’t kind to us we couldn’t have had a better experience. Alessandro is an amazing skipper, he’s young but he’s been sailing forever & certainly knows his way around his boat and the waters & islands we sailed around. He made you feel safe & well looked after. Carlo couldn’t do enough for us all & his food & hospitality were excellent, making us laugh as we tried to speak Italian. We couldn’t believe how he was able to serve up the dishes from the tiny galley kitchen. Something different every day and he even caught a tuna & that was served up for lunch, you don’t get fresher than that. We couldn’t have had a better adventure with better crew. Thank you Alessandro & Carlo! PO5 will return xxxxx
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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

10/6/2025

Corinne W.

-

Switzerland

It was very nice and beautyful, when the sun was shining.☀️We had a good time and the crew was very nice, helpful. And kind. Thank you!
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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

10/1/2025

Arina R.

-

Spain

It was an unforgettable journey 🤩 I totally recommend it to everyone. Andrea is very professional skipper with a lot of experience, he takes care about safety of the guests and carefully plan the route. And the most important he is an awesome person to have great conversation with. We learned so much about the sailing during the week. The hostess Marta is very kind and cooks delicious lunch. It was so comfortable that we don’t have to worry about what to eat for the breakfast or the lunch, everything was prepared by her. We visited incredible bays, had so much swim and slept under the stars sky in the sea, nothing else to ask for. But the special mentioning is to their dog Matthias, real marine dog who stole our hearts ❤️ During raining winter days I will think about Matthias that he is sailing somewhere in the Mediterranean Sea and smile! We will be missing this week, but for sure one day we will come back!
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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

10/1/2025

Arina R.

-

Spain

It was an unforgettable journey 🤩 I totally recommend it to everyone. Andrea is very professional skipper with a lot of experience, he takes care about safety of the guests and carefully plan the route. And the most important he is an awesome person to have great conversation with. We learned so much about the sailing during the week. The hostess Marta is very kind and cooks delicious lunch. It was so comfortable that we don’t have to worry about what to eat for the breakfast or the lunch, everything was prepared by her. We visited incredible bays, had so much swim and slept under the stars sky in the sea, nothing else to ask for. But the special mentioning is to their dog Matthias, real marine dog who stole our hearts ❤️ During raining winter days I will think about Matthias that he is sailing somewhere in the Mediterranean Sea and smile! We will be missing this week, but for sure one day we will come back!

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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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