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.
26
experiences
26
experiences
4.2
Premium
Duration:
7 days - 7 nights
Thailand:
Phuket, Krabi and Phi Phi Islands
+6 travellers
Have booked
Starting from
€1,905
Per person
4.2
Premium
Duration:
7 days - 7 nights
Caribbean:
Saint Martin
+2 travellers
Have booked
Starting from
€1,630
Per person
4.2
Premium
Duration:
7 days - 7 nights
Pacific Ocean:
French Polynesia
+2 travellers
Have booked
Starting from
€1,280
Per person
4.2
Premium
Duration:
7 days - 7 nights
Caribbean:
BVI - British Virgin Islands
Starting from
€1,760
Per person
4.2
Premium
Duration:
7 days - 7 nights
Caribbean:
Bahamas
+16 travellers
Have booked
Starting from
€1,795
Per person
4.2
Premium
Duration:
10 days - 10 nights
Caribbean:
Grenadines & Martinique
+14 travellers
Have booked
Starting from
€2,055
Per person
4.2
Premium
Duration:
7 days - 7 nights
Caribbean:
Guadeloupe
Fabian M.
Has booked
Starting from
€1,320
Per person
4.2
Premium
Duration:
7 days - 7 nights
Caribbean:
Grenadines & Martinique
+2 travellers
Have booked
Starting from
€1,560
Per person
5.0
Duration:
7 days - 7 nights
Thailand:
Phuket, Krabi and Phi Phi Islands
Be the first one to book!
€1,067
Per person
4.2
Premium
Duration:
10 days - 10 nights
Indian Ocean:
Seychelles
+2 travellers
Have booked
Starting from
€2,235
Per person
4.2
Premium
Duration:
7 days - 7 nights
Indian Ocean:
Seychelles
+12 travellers
Have booked
Starting from
€1,720
Per person
4.2
Premium
Duration:
7 days - 7 nights
Indian Ocean:
The Maldives
+2 travellers
Have booked
Starting from
€1,230
Per person
Why book a holiday with Sailsquare?
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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
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 more about the skipper and travellers who have already booked the holiday, to find out more about the
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
932 reviews
Take part in the 55th Barcolana with everything included
10/11/2023
Peter C.
-
Italy
Weekend on the Island of Elba...Hostess on board
10/9/2023
Barbara B.
-
Italy
All inclusive weekend in the Gulf of Alassio
10/6/2023
John C.
-
Italy
From the Egadi Islands to the Cous Cous Fest of San Vito Lo Capo on a 16-metre boat (private bathroom) with Hostess
10/6/2023
genevieve s.
-
Australia
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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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