header cover
logo

Log in

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.

cover image
avatar image

5.0

3 days in the wild Aeolian Islands - All inclusive & flexible dates

Italy: Aeolian Islands

2 days - 2 nights

4 departures available

September

Starting from

€723

€650

Per person

cover image
avatar image

3.7

Zakynthos sailing escape - hostess on board (half board)

Greece: Ionian Islands

7 days - 7 nights

2 departures available

October

Starting from

€779

Per person

cover image
avatar image

4.5

Premium

PHUKET Paradise - Catamaran cruise with hostess FULL BOARD

Thailand: Phuket, Krabi and Phi Phi Islands

7 days - 7 nights

40 departures available

January - December

Starting from

€1,390

Per person - min 2 pax

cover image
avatar image

4.3

Week on a 22m maxi-yacht between Pontine and Flegree

Italy: Pontine Islands

7 days - 6 nights

One departure available

August - September

€1,390

Per person

cover image
avatar image

4.5

Premium

BORA BORA Paradise - Catamaran cruise with hostess FULL BOARD

Pacific Ocean: French Polynesia

7 days - 7 nights

76 departures available

January - December

Starting from

€1,535

Per person - min 2 pax

cover image
avatar image

4.5

Premium

RAIATEA - TAHITI Paradise - Catamaran cruise with hostess FULL BOARD

Pacific Ocean: French Polynesia

10 days - 10 nights

29 departures available

January - December

Starting from

€2,330

Per person - min 2 pax

cover image
avatar image

4.3

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

Malta: Malta

6 days - 6 nights

6 departures available

August - October

Starting from

€690

Per person

cover image
avatar image

3.7

Where the blue feels like home: the Ionian islands - hostess on board (half board)

Greece: Ionian Islands

7 days - 7 nights

4 departures available

August - October

Starting from

€779

Per person

cover image
avatar image

4.5

Premium

BORA BORA PARADISE - Mini catamaran cruise with hostess and full board

Pacific Ocean: French Polynesia

4 days - 4 nights

One departure available

October

Starting from

€2,305

Per person - min 2 pax

cover image
avatar image

New

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

Italy: Tuscany

3 days - 2 nights

4 departures available

September - October

€275

Per person

cover image
avatar image

New

Premium

All inclusive sailing cruise on Dufour 54 sailboat in Croatia with hostess

Croatia: Split Archipelago

7 days - 7 nights

4 departures available

August - September

Starting from

€1,830

Per person

cover image
avatar image

New

Gulf of Poets & Cinque Terre by catamaran

Italy: Liguria

1 day - 0 nights

26 departures available

August - September

Starting from

€170

Per person

Why book a holiday with Sailsquare?

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

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 more about the skipper and travellers who have already booked the holiday, to find out more about the

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

1579 reviews

avatar image

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

08/27/2026

Sandra M.

-

IT

The holiday with Andrea was perfect! Andrea is a very good skipper, who makes guests feel at ease with simplicity, always kind and helpful, generous in making the most beautiful bays and beaches known by tender, where we have experienced unforgettable baths and moments. Very clean boat thanks to Carol, the hostess, who in addition to taking care of the spaces, prepares really good breakfasts and lunches, with the added value of having tasted typical Greek dishes. The travel program was nice, I enjoyed dining on land and visiting the delightful villages along the itinerary, it made the holiday even more varied and complete. After many years of sailing holiday, this experience has stood out for its organization, care and quality of service. Thanks to Andrea, Mattias (the loving poodle who conquers everyone) and Carol for the beautiful week. Super-recommended!

Comfortably Aeolian Islands: Catamaran Cruise with Steward

08/26/2026

Jacopo S.

-

IT

Unforgettable experience! Giorgio, the skipper, is an experienced person who gives you confidence and safety in sailing with his deep knowledge of the sea. At the same time, he is committed to creating synergy within the group together with Diego, the sailor cook who offers excellent cuisine and is always attentive to everyone's requests. In addition, the luck of having found great travel companions made the week super fun!

Costa Smeralda and/or Gulf of Orosei on Maxi Yacht with hostess-cook

08/26/2026

Federico F.

-

IT

Overall it was a good experience, especially thanks to the group that was created and the people on board. Marino and the hostess were friendly and pleasant, and we also ate well. As a starting point to make the experience even better, I would first suggest a greater sharing of the itinerary with the guests, of course always respecting the skipper's decisions related to weather and safety. It would also be nice to privilege, when possible, some coves or destinations less accessible by land, enhancing even more the beauty of a boat holiday. On the comfort front, considering the positioning of the experience, a few more attentions could make the difference: more comfortable cushions on deck, more efficient fans in the cabins, easier recharging of devices, a more functional aft shower and some extra care in daily cleaning and in the equipment for the table and aperitif. I would also suggest sharing more about the galley, common expenses and the week's program from the beginning, including the possible night in port. Finally, in the case of items lost due to bad weather or events not attributable to the guests, I would avoid including the cost in the common expenses, leaving the charge to the passengers only in cases of actual negligence. Overall it remains a good memory of the week and especially of the people I met. With a few small tricks, I believe that the experience aboard [hidden] can become even more pleasant and unforgettable. Greetings, Frederick
avatar image

A week sailing in the most beautiful places in the world

08/26/2026

antonella b.

-

IT

Perfect group skipper also... consider that the commander makes lunch and dinner for you!!!

Customer Support

customer support

Do you need support on using the platform or for an online payment? Do you need information or is there something you don't understand? For (almost) any question, we got an answer!

Can't find the perfect holiday for you?

Tell us what you are looking for and let our team find the right solution for you!

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

.

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.

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaGoogle PayApple Pay

© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964