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

4.8

New Year's Eve wandering among the islands of Thailand with hostesses

Thailand: Phuket, Krabi and Phi Phi Islands

11 days - 11 nights

One departure available

December - January

€1,646

Per person

cover image
avatar image

5.0

Split archipelago, Hvar islands, Brac - with Hostess and full board

Croatia: Split Archipelago

7 days - 7 nights

20 departures available

June - October

Starting from

€1,100

Per person

cover image
avatar image

4.8

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

21 departures available

May - October

Starting from

€590

Per person

cover image
avatar image

4.4

Premium

DALMATIAN Paradise - Catamaran cruise with hostess FULL BOARD

Croatia: Split Archipelago

7 days - 7 nights

22 departures available

May - October

Starting from

€1,315

€1,184

Per person

cover image
avatar image

5.0

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

Italy: Aeolian Islands

2 days - 2 nights

2 departures available

October - November

€723

Per person

cover image
avatar image

4.9

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

Italy: Aeolian Islands

6 days - 7 nights

12 departures available

June - September

Starting from

€945

Per person

cover image
avatar image

4.8

Tenerife and La Gomera aboard an 18 m ketch - ALL-INCLUSIVE

Atlantic islands: Canary Islands

6 days - 7 nights

10 departures available

January - December

Starting from

€900

Per person

cover image
avatar image

4.4

Premium

PHUKET Paradise - Catamaran cruise with hostess FULL BOARD

Thailand: Phuket, Krabi and Phi Phi Islands

7 days - 7 nights

39 departures available

January - December

Starting from

€1,390

Per person - min 2 pax

cover image
avatar image

4.4

Premium

BORA BORA Paradise - Catamaran cruise with hostess FULL BOARD

Pacific Ocean: French Polynesia

7 days - 7 nights

75 departures available

January - December

Starting from

€1,535

Per person - min 2 pax

cover image
avatar image

4.4

Premium

RAIATEA - TAHITI Paradise - Catamaran cruise with hostess FULL BOARD

Pacific Ocean: French Polynesia

10 days - 10 nights

26 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

12 departures available

July - September

Starting from

€745

Per person

cover image
avatar image

5.0

Tuscany & Corsica Energy Program between food, sea, sun and adventure

Italy: Tuscany

6 days - 6 nights

6 departures available

July - August

Starting from

€801

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

1692 reviews

avatar image

Sailing paradise in Greece on a big 50 ft boat: the best local experience

10/16/2026

Francesca D.

-

CH

Aga and Jerry are excellent hosts and sailors. Aga goes above and beyond to make guests feel welcome, organising restaurant bookings, taxi boats, recommendations and gorgeous breakfasts. Jerry is an experienced sailor, always calm, with plenty of stories to share, and happy to offer hands-on sailing opportunities to those interested. The boat is comfortable, clean and well maintained. Unfortunately, I cannot give the highest rating due to the high overall cost, lack of transparency around the common fund and poor communication. Having experienced similar holidays, we found the price significantly higher than comparable offers. It was also the first time we encountered a flat per-person common fund with no breakdown of actual expenses. Given the additional €250 per person (including children), totalling €1,750, I would have appreciated a summary of costs, particularly as this covered bed linen, four nights in harbour, breakfasts and lunches, as well as a few restaurant dinners joined by Aga or Jerry. Finally, just days before departure, we were informed of an alleged bedbug outbreak in Athens, which we could not verify through any online sources. This meant sealing all our belongings before boarding, adding considerable packing time and taking up valuable luggage space. Had we been informed earlier, I might have chosen a different holiday.

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

10/15/2026

Lara R.

-

CH

We had a wonderful time and the crew took good care of everything we could have wished for. Thank you very much for the great experience!
avatar image

The Saronic Islands sailing, skippered and on-board kitchen

10/14/2026

Kaija H.

-

FI

Annalisa and Emanuel hosted a very nice and safe sailing trip in their boat involving everyone. Despite the changed route plans due to bad weather the previous week, they were able to replan us a nice trip in the Cyclades Islands. We visited beautiful natural bays, enjoyed sailing, swimming, snorkling, sun bathing, fishing, ancient historical places and delicious fresh home-cooked food. Annalisa and Emanuel are the best and most patient hosts I have ever had!

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

10/12/2026

Fiona B.

-

AU

Andrea was a fantastic skipper and Carol was a great hostess. The week was filled with beautiful beaches, delicious lunches and great conversations and was a perfect way to relax for a week. It was fun sailing along with the second yacht, and we had a great time playing volleyball together. The boat was comfortable and plenty of spots to relax above deck in the sunshine. I highly recommend this trip. Andrea and Alessandro are expert sailors who take the very best care of their customers and always put safety first - but maximize fun and stunning scenery throughout. The hosts on board (Carol and Carlo) were exceptional - making delicious and varied food each day. And little Mattias - the best boat poodle there ever was! What are you waiting for - book this adventure. Thank you Andrea, Carol and Marta for an unforgettable week.

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