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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.

118

experiences

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5.0

Weekend in Ogliastra, breathtaking Sardinia with skipper and hostess

Duration:

2 days - 2 nights

Italy:

Southern Sardinia

Give this experience a try!

€417

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

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5.0

Weekend on Elba between sea and good food for only 4 guests

Duration:

2 days - 2 nights

Italy:

Tuscany

Give this experience a try!

€350

Per person

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5.0

DODECANESE SECRET: volcanic islands with skipper and kitchen

Duration:

6 days - 6 nights

Greece:

Dodecanese

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+13 travellers

have booked

Starting from

€750

Per person

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Aeolian Islands on a sailing boat: good food between sailing and sea!

Duration:

6 days - 7 nights

Italy:

Sicily

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+6 travellers

have booked

Starting from

€765

€850

Per person

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4.4

Week from South Corsica to North Sardinia - skipper and hostess

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

Give this experience a try!

€830

Per person

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4.8

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

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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+16 travellers

have booked

Starting from

€800

Per person

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5.0

Northern Sardinia - Stintino and Asinara with skipper and hostess/steward

Duration:

6 days - 6 nights

Italy:

Northern Sardinia

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+33 travellers

have booked

Starting from

€835

Per person

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5.0

3 days of sailing and relaxation in the Tuscan Archipelago

Duration:

3 days - 3 nights

Italy:

Tuscany

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+8 travellers

have booked

€350

Per person

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5.0

AEOLIAN ISLANDS with hostess/cook BOAT 16.5 mt exclusive x6 people

Duration:

6 days - 6 nights

Italy:

Aeolian Islands

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+21 travellers

have booked

Starting from

€898

Per person

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5.0

Sailing BenEssere in Ionian Greece

Duration:

6 days - 6 nights

Greece:

Ionian Islands

Give this experience a try!

Starting from

€1,125

€1,250

Per person

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5.0

Sail & Climb in Trieste

Duration:

3 days - 2 nights

Italy:

Venice and the Gulf of Trieste

Give this experience a try!

€420

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

936 reviews

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NATURE & RELAXATION - 7 days on a catamaran with hostess/sailor

03/25/2024

vincenzo P.

-

Italy

Ho fatto tante esperienze di questo genere ma quest’ultima organizzata veramente in maniera eccellente skipper all’altezza della situazione ,chef fantastica posto da sogno da consigliare a tutti
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PHUKET Dream Premium - 8 Days Catamaran ALL INCLUSIVE with Hostess/Cook

03/12/2024

Giancarlo A.

😍😍
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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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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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