header cover
sailsquare logo

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

Super!

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

Greece: Ionian Islands

7 days - 7 nights

3 departures available

September - October

Starting from

€550

Per person

cover image
avatar image

4.9

Super!

Small Cyclades

Greece: Cyclades

6 days - 7 nights

One departure available

September

€955

€790

Per person

cover image
avatar image

4.9

Super!

Mykonos to Athens by Fast Cruise

Greece: Cyclades

6 days - 7 nights

One departure available

September

€835

Per person

cover image
avatar image

4.7

Premium

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

Greece: Saronic Islands and Athens area

6 days - 7 nights

6 departures available

September - October

Starting from

€1,100

€1,045

Per person

cover image
avatar image

4.6

Premium

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

Italy: Northern Sardinia

7 days - 7 nights

4 departures available

October - November

Starting from

€1,455

€1,382

Per person

cover image
avatar image

4.8

Sail to the Aeolian Islands with an experienced crew on a catamaran!

Italy: Aeolian Islands

6 days - 7 nights

2 departures available

September

Starting from

€950

€760

Per person - min 2 pax

cover image
avatar image

5.0

Super!

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

Greece: Ionian Islands

7 days - 7 nights

2 departures available

September - October

Starting from

€550

Per person

cover image
avatar image

5.0

Super!

Secret Aegean with skipper and kitchen on board - Rhodes to Kos

Greece: Dodecanese

7 days - 6 nights

One departure available

October

€950

Per person

cover image
avatar image

5.0

Super!

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

Croatia: Split Archipelago

7 days - 7 nights

3 departures available

September

€1,100

Per person

cover image
avatar image

4.9

Aeolian Islands by catamaran, professional skipper/hostess, what else?

Italy: Aeolian Islands

6 days - 7 nights

One departure available

September

€870

Per person

cover image
avatar image

5.0

Super!

Ibiza & Formentera All inclusive week with Cook

Spain: The Balearic Islands

6 days - 6 nights

One departure available

September

€850

Per person

cover image
avatar image

5.0

Super!

Secret Aegean with skipper and kitchen on board - Karpathos to Rhodes

Greece: Dodecanese

7 days - 6 nights

One departure available

October

€950

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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

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 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

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

1313 reviews

avatar placeholder

Elba, all the colors of the big blue - Stewardess on board - 3 Cab/ 3 Bathrooms

09/1/2025

Giovanni C.

-

Italy

Sorry to have to confirm the negative reviews of Samantha and Lorenza. Girls (met on a boat), tough, nice and without the stench under their noses, with other experiences of sailing holidays and spartan trips. The third "girl" is my wife Marie and she is also equally unhappy. Surely the bad weather has negatively influenced the judgment of all of us, but those who go to sea know that with a good galley, good management of the landings and ... of good wine everything is compensated. Unfortunately none of this! If we then add the 3 bathrooms out of order, the punctured tender (...) and no info on safety management, things get complicated and the tension increases. The cost for the galley (NOT agreed) was disproportionate to the quality and quantity offered. It is true that if you find the shopping already done by skipper and hostess, avoid a good fuss ... but how sad !! Furthermore, If you also pay for a Hostess, you expect something more... When they offer you a tour of Elba, it is normal that some port has been booked where you can spend a nice evening on land, have a pleasant breakfast and ... to defuse tensions. Even more so if the weather is bad. Then if due to weather conditions or the crew's desire the program changes, it is canceled and peace. What is certain is that in Elba, you cannot book the day before (but not even a week before) in the middle of August with adverse weather. So in the harbor of Porto Ferraio we caught the storm of wind and rain on August 20th. Crazy gusts and another boat came at us. Most of all, the condition of panic that was generated in part of the crew in seeing how the emergency was handled by the skipper and hostess was bad. The situation was particular but I have seen worse. We were at anchor, without a wave. If only we had had fenders and some more preventive info, everything would have been resolved in a more peaceful way. Finally, I found it strange that we were asked to pay the port for the night after disembarkation, that is the 7^ night, when the holiday was 5 days and 6 nights. Well ! John and Marie
avatar image

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

09/1/2025

Adriano D.

-

Italy

With Riccardo on board the [hidden], you live an experience that is difficult to forget. With attention to every detail, the week with him is to experience the sea, feel good, and why not.. rediscover yourself !
avatar image

ATHENS Dream Premium - All Inclusive Catamaran Cruise with Stewardess

08/31/2025

Marianna C.

-

Italy

The islands are not great, Hydra and Spetzes are the only nice ones. The skipper was definitely unpleasant, he always took us to the ports immediately after lunch and the moorings in the bays were always almost offshore. Fortunately I had my sup to get closer but other older passengers found themselves in difficulty. He was also always nervous and responded very rudely. I was asked for a supplement for gluten and lactose free food of € 240 and for the first two days I was not given any substitute food, things were simply removed. Only after reporting the matter to sailsquare and the hostess did she organize herself a little better. I don't think I will repeat the experience with this group unfortunately.
avatar image

Big and luxurious 60ft catamaran in Cyclades - best local experience with hostess

08/31/2025

Michele L.

-

Portugal

Amazing adventure. Aga, Aja and Greg are supportive and dedicated. Notwithstanding the weather conditions have been challenging for sailing beginners they managed to make our trip amazing. Aga and Aja’s breakfasts and lunchs are healthy, tasty and creative!

Customer Support

nightLifeGeneralInfo

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!

search

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