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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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4.4

Premium

TUSCANY Paradise - Catamaran cruise with hostess FULL BOARD

Italy: Tuscany

7 days - 7 nights

2 departures available

July - August

Starting from

€2,390

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

12 departures available

January - December

Starting from

€1,940

Per person - min 2 pax

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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

8 departures available

July - September

Starting from

€1,785

€1,339

Per person - min 2 pax

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4.6

Discover the most authentic Greece from Samos to Arki and Agathonisi, with skipper and chef

Greece: Dodecanese

7 days - 7 nights

One departure available

July

€1,200

Per person

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

Greece: Dodecanese

7 days - 7 nights

6 departures available

July - 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

13 departures available

January - December

Starting from

€2,330

€2,097

Per person - min 2 pax

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New

Premium

All inclusive sailing cruise on Dufour 48 in Ionian Greece with hostess

Greece: Ionian Islands

7 days - 7 nights

7 departures available

July - October

Starting from

€1,785

€1,575

Per person

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5.0

Sailing adventures: summer sailing camps IN ENGLISH - for children from 9 to 14 years old

Italy: Tuscany

5 days - 5 nights

One departure available

July

€660

Per person

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5.0

Sail the Pacific: The Milky Way between Fiji and Vanuatu

Pacific Ocean: Fiji Islands

8 days - 8 nights

One departure available

July - August

€1,200

Per person

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5.0

Yoga, meditation and healthy eating in a natural paradise

Caribbean: San Blas Islands - Panama

5 days - 5 nights

4 departures available

July - August

€1,600

Per person

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New

Premium

All inclusive sailing cruise on Dufour 530 sailboat in Croatia with hostess

Croatia: Split Archipelago

7 days - 7 nights

4 departures available

July - September

Starting from

€1,645

Per person

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New

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All inclusive catamaran cruise on a Bali 4.2 in Ionian Greece with hostess

Greece: Ionian Islands

7 days - 7 nights

5 departures available

August - October

Starting from

€2,060

Per person

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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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

1440 reviews

Sail in Menorca with a cook on board!

07/3/2026

Véronique S.

Everything was perfect! Very neat and very clean boat! Delicious Maussi's food and Alex the skipper very attentive and professional. You feel like part of a family. I recommend 100%.

All Inclusive: Procida, Capri, Positano, Amalfi, Cetara, Sorrento

07/2/2026

Luigi C.

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IT

Good evening, the all-inclusive writing is misleading as it is not clear from the program that to go down to Positano and Capri there are other costs to be divided among the participants.

Aeolian Islands on a catamaran, professional skipper/hostess, what else?

07/1/2026

chiara g.

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IT

A simply unforgettable sailing holiday! An experience that exceeded our expectations from every point of view, thanks above all to the sympathy and great professionalism of our skippers. They proved to be an exceptional crew: always attentive to everyone's comfort, they made us discover enchanting coves and breathtaking views that can only be reached by sea. In addition to being excellent navigators, they turned out to be real chefs on board, delighting us every day with fantastic dishes. I highly recommend this adventure to anyone who wants to experience the sea in total relaxation and joy. A big thank you to the skippers for making this week so special!
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Tuscany and Corsica: sailing sun adventure good food energy and well-being

06/29/2026

Melania G.

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IT

My partner and I traveled on board with Daniele and Mariapia in June... They were 4 special days. Boat kept with so much care and attention, itinerary and wonderful places seen! With a few dips in the blue here and there ;) Mariapia pampered us a lot with her healthy and super delicious cuisine, since the morning with the scent of coffee from the mocha. Very nice experience, which I recommend. To be redone!

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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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