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

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

cover image
avatar image

4.5

Premium

KOH SAMUI Paradise - Catamaran cruise with hostess FULL BOARD

Thailand: Phuket, Krabi and Phi Phi Islands

7 days - 7 nights

3 departures available

August - September

Starting from

€1,785

€1,339

Per person - min 2 pax

cover image
avatar image

3.0

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

cover image
avatar image

4.5

Premium

TAHITI - RAIATEA Paradise - Catamaran cruise with hostess FULL BOARD

Pacific Ocean: French Polynesia

10 days - 10 nights

11 departures available

January - December

Starting from

€2,560

€2,304

Per person - min 2 pax

cover image
avatar image

New

Premium

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

Greece: Ionian Islands

7 days - 7 nights

4 departures available

August - October

Starting from

€1,785

€1,575

Per person

cover image
avatar image

New

Premium

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

Croatia: Split Archipelago

7 days - 7 nights

3 departures available

August - September

Starting from

€1,645

Per person

cover image
avatar image

New

Premium

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

Greece: Ionian Islands

7 days - 7 nights

4 departures available

August - October

Starting from

€2,060

Per person

cover image
avatar image

4.6

"Boutique" sailing holiday from Athens to Hidra, Spetses and other pearls

Greece: Saronic Islands and Athens area

7 days - 7 nights

One departure available

September - October

€1,200

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

5 departures available

August - September

Starting from

€723

€650

Per person

cover image
avatar image

5.0

Tuscany and Corsica: sailing sun adventure good food energy and well-being

Italy: Tuscany

2 days - 3 nights

One departure available

August

€390

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

11 departures available

October - December

Starting from

€1,430

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

2 departures available

August - September

€1,390

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

1535 reviews

avatar image

A week sailing in the most beautiful places in the world

08/13/2026

Elena T.

-

IT

Piero and Giusy are the best that a sailing experience can offer. Excellent sailors, they give the opportunity to try and apply themselves in maneuvers if you wish. Excellent guides and connoisseurs of the area, it is easy to get lost talking about anything with them. Finally, Giusy's ability in the kitchen and in the management of the kitchen / galley is something that borders on perfection. You can't ask for anything better. Priceless availability, patience and kindness!! ❤️❤️❤️

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

08/13/2026

Florian H.

-

DE

The Tour was great - we had a marvelous time with our family (including two 14-year-old boys) and the other guests. Skipper Tom and our host Aga are very kind and professional. We enjoyed the cuisine and the tour plan including a trip to Hydra. Tom was one of the best skippers I have been with, combining an eye for safety with calm and decisive seamanship. Aga made everything else possible be it recommending places and restaurants but also considering allergies and other specifics. The sea and the landscape are fantastic. Big thanks to the entire team!
avatar image

Midweek sailing trip: two days at sea in Alassio

08/12/2026

Stephanie M.

-

IT

Very well organized weekand Awesome experience
avatar image

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

08/12/2026

David B.

-

IT

Everything was great, nice ride, lots of things to see, and great availability of Skipper and second. Maybe I would have preferred them to dedicate 1 more day to the most beautiful islands such as Antipaxos sacrificing a stop on the way back, and perhaps I would also recommend planning a dinner on board in the roadstead to also enjoy the boat for dinner, but these are details more to give some inspiration to the guys than for anything else. Generally you dine out and you still have the opportunity to see various villages, so even on this nothing to say, I visited beautiful places and also ate well. They also organized excursions and we had fun playing volleyball in the water in a particular place... Congratulations!

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