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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.

125

experiences

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4.7

The Egadi Islands as you've never seen them before on a 16-meter boat with a professional hostess

Duration:

6 days - 7 nights

Italy:

Aegadian islands

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87 travellers

€1,332

€1,460

Per person

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4.8

Super!

All Inclusive Tour: Capri, Amalfi, Cetara, and Sorrento

Duration:

5 days - 5 nights

Italy:

Naples & Amalfi Coast

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10 travellers

Starting from

€1,059

€1,115

Per person

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4.7

Premium

Big and luxurious 60ft catamaran in Saronic - best local experience

Duration:

6 days - 7 nights

Greece:

Saronic Islands and Athens area

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45 travellers

Starting from

€1,995

€2,100

Per person

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Cannes - Sanremo - Cannes: 7 days cruise with skipper & hostess

Duration:

6 days - 6 nights

France:

French Riviera and Porquerolles

Give this experience a try!

€1,226

€1,290

Per person

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4.7

Premium

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

Duration:

6 days - 7 nights

Greece:

Saronic Islands and Athens area

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137 travellers

Starting from

€998

€1,050

Per person

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4.7

Premium

Sporades one way on a big and comfortable 60ft catamaran with chef

Duration:

5 days - 6 nights

Greece:

Sporades

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2 travellers

€1,898

€1,998

Per person

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4.8

Super!

All Inclusive: Procida, Capri, Positano, Amalfi, Cetara, Sorrento

Duration:

6 days - 6 nights

Italy:

Naples & Amalfi Coast

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8 travellers

€1,316

€1,385

Per person

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Cannes - Tulon - Cannes: 7 days cruise with skipper & hostess

Duration:

6 days - 6 nights

France:

French Riviera and Porquerolles

Give this experience a try!

€1,226

€1,290

Per person

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4.7

Premium

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

Duration:

6 days - 7 nights

Greece:

Cyclades

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49 travellers

Starting from

€2,600

€2,737

Per person

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4.6

Premium

All-inclusive Sardinia & Corsica Cruise (per cabin)

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

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258 travellers

Starting from

€1,197

€1,260

Per person

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4.9

Super!

Corfu to Athens via the exciting Corinth Canal

Duration:

8 days - 8 nights

Greece:

Saronic Islands and Athens area

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4 travellers

€418

€440

Per person

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5.0

Super!

Weekend in the Tuscan Archipelago with PROFESSIONAL COOK SKIPPER

Duration:

2 days - 2 nights

Italy:

Tuscany

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23 travellers

€238

€250

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

1130 reviews

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

05/7/2025

Janette G.

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Australia

After sailing in the teeth of the Meltemi in the eastern Aegean 2 years ago Chris and I were happy to accept an invitation from friends to sail with Sail square in the gentle waters of the southern Corfu strait. Our hopes for a relaxing week on the water were fulfilled, largely due to the sailing skill and the care of Alessandro and his crew. We and our friends were comfortably accommodated in 2 cabins, each with a bathroom. All was clean and well-maintained. Our hostess, Marta, provided delicious Greek breakfasts and lunches. While sailing in the beautiful waters between Corfu, Paxos and Antipaxos, there were many opportunities for swimming at lovely beaches and walking in the islands. Alessandro and his crew, including the ship’s dogs, were exceptionally good hosts and we recommend this experience unreservedly. Lucy and Chris Costas May 2025
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Seychelles paradise by Catamaran

05/6/2025

Fabrizio P.

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Italy

una settimana in catamarano alle Seychelles con equipaggio italiano è pura magia. Ciccio il capitano Peppe vicecapitano e Claudia la cuoca. Accoglienza impeccabile, mare turchese e spiaggie da cartolina. Ospiti Toooooopppppp.
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

04/21/2025

Luna G.

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Belgium

We just had an amazing holiday! Alessandro and his brother Andrea made sure everything was perfect and truly unforgettable. Everything was well-organized and taken care of down to the smallest detail. They constantly checked if we needed anything and made us feel completely at ease. The food on board was absolutely delicious every single time. Thanks to them, it really felt like a dream vacation. Highly recommended!
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BVI TORTOLA Dream Premium - 8 Days Catamaran ALL INCLUSIVE with Hostess/Cook

04/12/2025

Carla P.

-

Italy

ottimo skipper e ottimo servizio di bordo con eccellente cibo

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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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