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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.

99

experiences

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5.0

Weekend getaway in Capraia

Duration:

2 days - 2 nights

Italy:

Tuscany

Be the first one to book!

Starting from

€290

Per person

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7 Day Greek Sailing Adventure - Dodecanese Islands

Duration:

7 days - 6 nights

Greece:

Dodecanese

Be the first one to book!

€1,653

Per person

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4.0

All-inclusive Sardinia & Corsica Cruise (per cabin)

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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+43 travellers

Have booked

Starting from

€1,511

€1,590

Per person

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5.0

Cruise to the Island of Elba and Capraia

Duration:

6 days - 7 nights

Italy:

Tuscany

Be the first one to book!

€1,200

Per person

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4.9

Crossing from Lefkada to Athens.... Adventure not to be missed!

Duration:

7 days - 8 nights

Greece:

Peloponnese

Be the first one to book!

€430

Per person

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4.8

Pontine Islands by sailboat

Duration:

6 days - 7 nights

Italy:

Pontine Islands

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+3 travellers

Have booked

Starting from

€600

Per person

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4.9

Sailing holiday among the wonders of the Cyclades from Athens

Duration:

6 days - 7 nights

Greece:

Cyclades

Be the first one to book!

€810

Per person

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Sailing, Sea and Cuisine in the Aeolian Islands: good food between sailing and sea!

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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François-Gérald R.

Has booked

Starting from

€738

€820

Per person

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4.9

The Maddalena Archipelago by sail.

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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+18 travellers

Have booked

Starting from

€650

Per person

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4.8

ONE WAY Aeolian Islands by catamaran with hostess - from Palermo to Lipari

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

Be the first one to book!

€1,000

Per person

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4.8

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

Duration:

6 days - 7 nights

Italy:

Aegadian islands

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+2 travellers

Have booked

Starting from

€799

Per person

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4.9

Sailing in the Saronic Islands with hostess on board

Duration:

6 days - 7 nights

Greece:

Saronic Islands and Athens area

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+4 travellers

Have booked

€745

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

934 reviews

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

02/19/2024

Klaembt R.

Boot ist ok, missing in the Night AC, during the day it works but in the Night??
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Dream Grenadines Premium - 8 days on catamaran ALL INCLUSIVE with hostess/cook

02/5/2024

MARIO I.

when I made the reservation I paid for a superior cabin and with the specific request written to you to have a bow cabin. I was assigned a central cabin, I would have liked an official communication from you, informing me of the availability or otherwise of the forward cabin and leaving me the free will to decide whether to accept or not, or withdraw from the contract for which I had paid. commercial and communication incorrectness
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Take part in the 55th Barcolana with everything included

10/11/2023

Peter C.

-

Italy

Fantastica esperienza! Nonostante il vento quasi inesistente Alberto e Federica ci hanno fatto sentire tutta l'energia della Barcolana! Grazie!
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Weekend on the Island of Elba...Hostess on board

10/9/2023

Barbara B.

-

Italy

la professionalità e la compagnia di Vittorio e Giulia ci hanno regalato un week end bellissimo. Affidabili, super disponibili e divertenti Consigliatissimo!!!

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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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