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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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5.0

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

Croatia: Split Archipelago

7 days - 7 nights

4 departures available

September - October

Starting from

€1,100

Per person

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New

Premium

All inclusive sailing cruise on Excess 11 Catamaran in Croatia with hostess

Croatia: Split Archipelago

7 days - 7 nights

One departure available

September

Starting from

€1,965

Per person

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4.3

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

Malta: Malta

6 days - 6 nights

5 departures available

September - October

Starting from

€690

Per person

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New

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

Italy: Tuscany

3 days - 2 nights

3 departures available

September - October

€275

Per person

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New

Four days of relaxation midweek on the island of Elba with hostess

Italy: Tuscany

4 days - 3 nights

2 departures available

September

€424

Per person

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5.0

New

Cruise in southern Sardinia: charm and turquoise waters in schooner with hostess and full board

Italy: Southern Sardinia

6 days - 6 nights

2 departures available

September

Starting from

€1,200

Per person

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5.0

2 days sailing between Palermo and Cefalù - All inclusive & flexible dates

Italy: Sicily

2 days - 1 night

2 departures available

September

€215

Per person

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4.5

Premium

CORSICA SUD Paradise - catamaran cruise with hostess FULL BOARD

France: Corsica

6 days - 7 nights

One departure available

October

Starting from

€1,485

Per person - min 2 pax

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4.5

Premium

GUADELOUPE Paradise - Catamaran cruise with hostess FULL BOARD

Caribbean: Guadeloupe

6 days - 7 nights

53 departures available

January - December

Starting from

€1,270

€1,143

Per person - min 2 pax

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4.5

Premium

BAHAMAS EXUMA Paradise - Catamaran cruise with hostess FULL BOARD

Caribbean: Bahamas

6 days - 7 nights

50 departures available

January - December

Starting from

€1,815

€1,634

Per person - min 2 pax

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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

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4.5

Premium

KOH SAMUI Paradise - Catamaran cruise with hostess FULL BOARD

Thailand: Phuket, Krabi and Phi Phi Islands

7 days - 7 nights

19 departures available

May - September

Starting from

€1,885

€1,697

Per person - min 2 pax

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Reviews - Sailing or catamaran cruises with hostess or onboard cooking service

1616 reviews

Fabulous Egadi Islands by catamaran - Stewardess on board

09/7/2026

Daniele A.

-

IT

Everything perfect, relaxing holiday. Impeccable skipper. The only note for the hostess: I would recommend every morning to communicate the menu of the day in order to manage small variations for some people who may not like a certain food. For the rest, super recommended holiday.
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Maddalena Archipelago, southern Corsica: wonderful Sardinia

09/7/2026

Alberto Z.

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IT

Exceptional holiday is skipper a true professional !

Sailing among the Islands of Ulysses. Stewardess on board

09/6/2026

Fabrizio D.

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IT

Overall good experience, with room for improvement Positive aspects: the places visited are very beautiful, turquoise water, suggestive bays and pretty villages. Hansel and Léonore are very kind, they go out of their way to try to offer guests a nice holiday, their motto is: "you don't have to think about anything, just relax and have fun, we will take care of the rest". The meals are prepared directly by Hansel, which is unusual on a sailing boat, and we didn't have to think about that either. Léonore at the helm has great control of the boat. Hansel allowed me to sleep outside on the deck as I had requested, and even arranged a mattress and sheet for me to be more comfortable. Negative aspects: the boat is big, but it was designed to do round-the-world regattas, it is not a boat designed to take a vacation. It has been a bit readapted to accommodate people, but it does not have the classic sofa seating in the cockpit, the kitchen is really tiny, it does not have an awning designed to protect from the sun. And when you are in the middle of the sea in the middle of the day with the sun at its peak, you can feel it. Hansel did his best to set up sheets and sheets that certainly helped, but obviously they do not have the same effectiveness and in fact one of these was torn by the wind and we had to replace it, or in any case every time they must be removed and put back on. In the description of the boat it is written that there are 3 bathrooms and 3 cabins and that the boat accommodates up to 6 guests. It is true, but a cabin and a bathroom are reserved for Hansel and Léonore, so for the 6 guests there are in fact 2 bathrooms and only 2 cabins available, so 2 guests do not have a cabin, they have to stay in the dinette. In addition, the boat needs objective maintenance. In addition to a repainting of the deck, the bathrooms both have problems. When using the stern bath, every time the flush pump is activated it is necessary to turn around and pivot with the foot, otherwise the entire toilet bowl is lifted with the pump itself; If you want to open the window, the Plexiglas detaches from the frame. In the forward bathroom the door does not close, so you are forced to use it holding the door closed from the inside with one hand; moreover, the valve does not work well and even when you set it on the outlet it takes in waste water. The SUP has various patches and is always a bit deflated, perhaps it would be appropriate to change it. The tender would also need a leak check: one evening we had used it to go ashore all together but, seeing it deflated, on the way back we preferred to split into two groups and make two turns to avoid risks. In conclusion, the experience was overall positive, Hansel and Léonore are very nice, the places are very nice, but in light of the characteristics of the boat and its state of maintenance I don't know if I would repeat it.

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

09/6/2026

Lorenzo A.

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IT

Strongly negative experience and holiday compromised by questionable management to say the least. Our experience was ruined mainly by the management of skipper Andrea and, more generally, by a series of inefficiencies that we consider unacceptable. On the day of boarding, scheduled at 18:00, at 17:55 we were still on the platform without Andrea having shown up. Only a few minutes after boarding we received a phone call in which we were informed that, together with another couple, we had been transferred to a sailboat with another skipper. It was, in fact, a downgrade compared to the catamaran that had been assigned to us, on which we were supposed to live the experience with skipper and co-skipper. The reason we were given was that of "overbooking". A paradoxical situation, considering that Andrea would have directly accepted further personal bookings, thus coming to no longer have room for people who had been regularly assigned to his crew through Sailsquare. The thing that we consider even more serious is that there are conversations, WhatsApp messages, communications via e-mail and via Sailsquare in which Andrea expressly confirms our presence on board, mine and my girlfriend's. It was therefore not an improvised last-minute assignment: our presence on the catamaran had been agreed and confirmed. Our story had already begun with a change of skipper. Initially we were assigned to Emanuele, Andrea's son, who canceled the tour about six days before departure due to problems with the boat. A situation that can certainly happen and that, taken individually, we would have understood. The problem is that we had already organized and paid for four flights and a three-day stay in Stromboli, just for the Sailsquare tour. We had therefore already incurred important expenses and organized our entire holiday, trusting in the alternative that had been proposed to us. To meet the discomfort, Sailsquare had assigned us to Andrea with a catamaran upgrade, together with another couple. The assignment had been regularly accepted and confirmed by Andrea himself through the various communication channels. For this reason, in our opinion, talking about "overbooking" later is not an acceptable justification. In the end we were transferred to a third boat, a sailboat that was filled on the day of embarkation until we reached about 10 people. On board we also met another guy who, like us, had initially been assigned to Emanuele and who confirmed to us that he had experienced the same situation. What made the experience even more unpleasant was the subsequent behavior. The new skipper, Matteo, has repeatedly expressed his problem with the non-payment of fees for the additional people he had embarked. We were asked to urge Sailsquare to resolve the economic situation as soon as possible, despite the fact that we had regularly paid Sailsquare for our trip. The situation has reached the point that we have also been offered the possibility of having to disembark in the middle of the week if the payment was not resolved. Although this eventuality fortunately did not occur, we consider it absurd that a customer who has regularly paid should spend his holiday with the doubt of being able to be disembarked due to administrative problems between the platform, skipper and boat. Andrea's behavior, which we perceived as arrogant, insolent and totally unprofessional, was for us the most serious point of the story. We do not dispute the fact that unforeseen events or changes of plans may occur: we dispute the way they were handled, just a few minutes before boarding and without any real choice. Behind a holiday of this type there are months of work, money, organization and expectations. You work all year round to be able to go on vacation, and being on the quay five minutes before boarding without knowing what would happen is a situation that should never be experienced by a customer. We believe that there have been serious shortcomings of organization, communication and professionalism, both in the management by Sailsquare and in the behavior of the skipper Andrea. A holiday can be changed due to an unforeseen event. What should never change is respect for customers.

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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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