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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

The perfect holiday on Europe's hottest and most glamorous island

Malta: Malta

6 days - 6 nights

4 departures available

September - October

Starting from

€690

Per person

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New

Weekends immersed in the blue of the sea and the green of the island of Elba

Italy: Tuscany

3 days - 2 nights

2 departures available

September - October

€275

Per person

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New

Four days of relaxation midweek on the island of Elba with hostess

Italy: Tuscany

4 days - 3 nights

One departure available

September

€424

Per person

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4.8

New

Cruise in southern Sardinia: charm and turquoise waters in schooner with hostess and full board

Italy: Southern Sardinia

6 days - 6 nights

One departure available

September

€1,200

Per person

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5.0

2 days sailing between Palermo and Cefalù - All inclusive & flexible dates

Italy: Sicily

2 days - 1 night

5 departures available

September - October

Starting from

€215

€194

Per person

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4.4

Premium

CORSICA SUD Paradise - catamaran cruise with hostess FULL BOARD

France: Corsica

6 days - 7 nights

One departure available

October

Starting from

€1,485

Per person - min 2 pax

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4.4

Premium

GUADELOUPE Paradise - Catamaran cruise with hostess FULL BOARD

Caribbean: Guadeloupe

6 days - 7 nights

53 departures available

January - December

Starting from

€1,270

€1,143

Per person - min 2 pax

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4.4

Premium

BAHAMAS EXUMA Paradise - Catamaran cruise with hostess FULL BOARD

Caribbean: Bahamas

6 days - 7 nights

50 departures available

January - December

Starting from

€1,815

€1,634

Per person - min 2 pax

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New

Premium

All inclusive sailing cruise on Lagoon42 Catamaran in Croatia

Croatia: Split Archipelago

7 days - 7 nights

One departure available

September

Starting from

€2,150

Per person

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4.4

Premium

KOH SAMUI Paradise - Catamaran cruise with hostess FULL BOARD

Thailand: Phuket, Krabi and Phi Phi Islands

7 days - 7 nights

19 departures available

May - September

Starting from

€1,885

€1,697

Per person - min 2 pax

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4.2

Aegean dreams: sailing around Rhodes - hostess on board (half board)

Greece: Dodecanese

7 days - 7 nights

2 departures available

October

Starting from

€829

Per person

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4.4

Premium

TAHITI - RAIATEA Paradise - Catamaran cruise with hostess FULL BOARD

Pacific Ocean: French Polynesia

10 days - 10 nights

27 departures available

January - December

Starting from

€2,490

€2,241

Per person - min 2 pax

Why book a holiday with Sailsquare?

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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

Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.

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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

1645 reviews

Wellness, sun, sea and adventure: a weekend full of sailing!

09/15/2026

rosanna n.

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IT

We had a beautiful we on a sailing boat. Daniele and Maria Pia are wonderful in putting everyone at ease. Excellent company, the itinerary and the food prepared by Pia who is a wonderful cook, able to find any variation she is asked for. Daniele gladly lent himself to a change of cove for an unforgettable swim, due to the headwind compared to the established itinerary. Everything perfect.
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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

09/15/2026

AnnMarie S.

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US

Amazing vacation! I would compare it to somewhere between camping and glamping, but on the sea! We saw the most beautiful beaches, sunsets, and sunrises. We sailed along side dolphins, explored caves, and even saw sea urchins and octopus when we were snorkeling. Caroline was our chef an overall caretaker. She catered to our every need and the best meals we had all week were the breakfasts and lunches that she cooked for us! The boat fits up to six guests. Two of the three rooms are extremely small so if you go with friends, you will be sleeping in the same bed since there is only one bed per room. There is also no indoor shower. You shower in your bathing suit out in the open on the back of the boat. I would highly recommend privatizing the boat if you go with a group of friends. We thought we had done so, but then we found out at the last minute that there was miscommunication and a man was joining us four girls. He was very nice, but we would’ve preferred to only have one girl per small room versus doubling up and having to share space/a bathroom with a man. Overall it was a fabulous experience and I would most definitely do it again!

Catamaran cruise in Sardinia & Corsica with chef - full board (per cabin)

09/14/2026

Lendell S.

-

US

Outstanding crew, beautiful locations and amazing food on the boat created a very memorable experience.

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

09/14/2026

Elizabeth B.

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AR

Spectacular week, Alessandro super friendly, courteous, organized and fun. He took us to amazing places. Carlo: wonderful person, excellent cook and always available with his smile and unique warmth. The group climate on board was optimal. Unbeatable week!!!!

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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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