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view of main interior cabin of The Maya

About Custom Sailing

Now in our 12th year, Captain Valerie Weingrad welcomes you aboard for your Custom Sailing holiday. Offering “Tailor made” sailing vacations the Greek Islands, Mediterranean, Caribbean and New England. Let our knowledgeable, experienced staff and crews show you the “real” islands.

Meet Our Crew
St Lucia bay

Caribbean

New this year, sail from St Lucia!  Our 50′ yacht Capella  with all the comforts of home, is now based in beautiful Marigott Bay.  Sail the British Virgin Islands on your very own private yacht! Join us in Tortola known as a “sailor’s paradise” for its protected island chain and easy sailing.  Or choose our new 45’ or 50’ yacht as we sail from Blue Lagoon in St. Vincent.  So many options!  Let us help you choose the right one for you.

Come Sail The Caribbean
man piloting a sailing boat

Greek Islands

The Greek Islands: The land of sun, sea and civilization. Your soul will remain in the Aegean Sea! Join us as Custom Sailing Worldwide begins our 12th year of sailing in the magical Greek Islands. Scheduled trips begin in May and run through September.

Explore The Aegean Seas