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Crewed yacht sailing holidays & cruises

Get on board of a vacation with crew and live the sea without thoughts. Whether you choose a sailboat, a catamaran or a gulet, comfort and gulet, comfort and well-being will be the first place for a holiday of absolute relaxation. vacation of absolute relaxation.

56

experiences

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4.5

Premium

Abaco Dream - Catamaran Cruise with Chef & Full Board

Duration:

6 days - 7 nights

Caribbean:

Bahamas

Starting from

€1,676

€2,095

Per person - min 2 pax

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4.5

Premium

ANDAMAN Dream Premium - 11 days in ALL INCLUSIVE Catamaran with hostess/cook

Duration:

10 days - 10 nights

Thailand:

Phuket, Krabi and Phi Phi Islands

Starting from

€2,144

€2,680

Per person - min 2 pax

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4.5

Premium

BORA BORA Dream Premium on an ALL INCLUSIVE catamaran with hostess/cook

Duration:

7 days - 7 nights

Pacific Ocean:

French Polynesia

Starting from

€1,208

€1,510

Per person - min 2 pax

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4.5

Premium

From TAHITI to RAIATEA Dream - by catamaran ALL INCLUSIVE with hostess/cook

Duration:

10 days - 10 nights

Pacific Ocean:

French Polynesia

Starting from

€1,736

€2,170

Per person

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4.5

Premium

PRASLIN Dream Premium 8 days - Catamaran ALL INCLUSIVE with hostess/cook

Duration:

7 days - 7 nights

Indian Ocean:

Seychelles

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32 travellers

Starting from

€1,560

€1,950

Per person

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5.0

Route to the Egadi Islands: Wind, Flavors and Sea

Duration:

7 days - 7 nights

Italy:

Aegadian islands

Give this experience a try!

Starting from

€585

€650

Per person

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5.0

Super!

Ibiza & Formentera All inclusive week with Cook

Duration:

6 days - 6 nights

Spain:

The Balearic Islands

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73 travellers

Starting from

€675

€750

Per person

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4.5

Premium

GUADELOUPE Dream Premium - Catamaran ALL INCLUSIVE with hostess/cook

Duration:

6 days - 7 nights

Caribbean:

Guadeloupe

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Fabian M.

Starting from

€1,071

€1,190

Per person

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4.5

Premium

KOH SAMUI Dream Premium on ALL INCLUSIVE catamaran with hostess/cook

Duration:

7 days - 7 nights

Thailand:

Gulf of Thailand

Starting from

€1,692

€1,880

Per person - min 2 pax

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5.0

Aeolian Islands - A week on a sailing boat with skipper and assistant

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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3 travellers

Starting from

€786

€873

Per person

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4.5

Premium

ST. BARTH Dream Premium - 8 days in Catamaran ALL INCLUSIVE

Duration:

6 days - 7 nights

Caribbean:

Saint Martin

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2 travellers

Starting from

€1,071

€1,190

Per person

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4.5

Premium

BVI TORTOLA Dream Premium - 8 Days Catamaran ALL INCLUSIVE with Hostess/Cook

Duration:

6 days - 7 nights

Caribbean:

BVI - British Virgin Islands

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8 travellers

Starting from

€1,188

€1,320

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 - Crewed yacht sailing holidays & cruises

1101 reviews

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PHUKET Dream Premium - 8 Days Catamaran ALL INCLUSIVE with Hostess/Cook

12/7/2024

Jess L.

It was an amazing trip. Beautiful places, delicious food, comfortable cabins - would recommend to everyone.
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PRASLIN Dream Premium 8 days - Catamaran ALL INCLUSIVE with hostess/cook

12/3/2024

Frauke K.

It was a great time. We had hoped to sail more and see and experience more of the country and its people. Our skipper had good command of the boat. Unfortunately, he was not very communicative. Apart from a short briefing in the morning, he did not explain or explain anything to us. It was a shame that we could not buy additional wine on the ship. ...we did not want to order wine beforehand - as was offered - because we did not know whether we would actually want to drink it. My husband, I and another guest had birthdays during the tour. We mentioned this beforehand and the other guests pointed it out to the crew again. Unfortunately, we were not even congratulated. That was rather disappointing and does not make you feel welcome. Compliments to the good food. All in all, however, we found in retrospect that the price-performance ratio was not right
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PHUKET Dream Premium - 8 Days Catamaran ALL INCLUSIVE with Hostess/Cook

12/1/2024

Edoardo F.

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Italy

Esperienza fantastica, cibo a bordo sempre abbondante e di buona qualità. Ovviamente si mangia solo thai food. Unica nota negativa spesso c’era cattivo odore di bagno in cabina e le zone comuni non erano molto pulite e ordinate
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Sailing paradise in Greece on a big 50 ft boat: the best local experience

10/30/2024

Santiago D.

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Colombia

A unique and spectacular experience! I sailed for a week and I loved it! Highlights: we sailed every day, the breakfast and lunches were incredible (we all asked for the recipes) and at night we went out to eat at typical restaurants on the Greek islands. I hope to return soon!

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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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