Now in our 15th year, Captain Valerie Weingrad welcomes you aboard for your Custom Sailing holiday. Offering “Tailor made” sailing vacations the Greek Islands, Italy, Mediterranean, Caribbean, Bahamas, Florida and New England. Let our knowledgeable, experienced staff and crews show you the “real” islands. With Custom Sailing you travel with friends and experience the islands like a local. We are there with you every step of the way.

Our Captains are U.S. Coast Guard licensed or equivalent, American Sailing Association (ASA) certified, and offers more than 20 years experience in the Greek Islands, the Caribbean, Mediterranean and New England.

Whether you want to explore the islands of the Mythical Grecian Gods, bask in the sun of the Caribbean or sail the playground of the rich and famous in New England remember, there are no limitations with “Custom Sailing.” We will help you choose the right yacht, crew and itinerary to meet and exceed all your expectations.

One guest wrote in our log book that “in your life there are 10 top things, and this was definitely one of them.” Remember, your someday is today…

Our Philosophy

We don’t want you to have any surprises! When you travel with Custom Sailing on our all inclusive trips basically everything is included on the boat except for dinners ashore. Part of the pleasure of travel and sailing is to experience the local culture, people and customs and that is our specialty. In the Caribbean enjoy grilled lobster on the beach and fresh fish while listening to the steel drums of island music. In Greece we may be invited in to a fisherman’s home for dinner or treated to an impromptu feast on the beach with ouzo and dancing, the options and opportunities are endless. Our relationships with “the locals” make your holiday all the more special! Think of it as your private yacht for the week. It’s like “life styles of the rich and famous” without going broke!

We have a large selection of yachts to meet and exceed all of your desires for your ultimate sailing vacation. Choose from a crewed yacht complete with hostess and delectable meals for a real vacation or a bareboat for those who want to “do it yourself.” Indulge in our line of luxury Mega-Yachts from 80′ to 300.’ Please contact us for details on these fabulous opportunities.

Meet the Custom Sailing Crew

Captain Valerie

Captain Valerie

Captain Valerie welcomes you aboard! Holding a US Coast Guard 100T Master Merchant Marine Officers License and current STCW for operation in international waters Valerie is also an ASA certified sailing instructor. Born into a boating family, she has been on the water, in one form or another, her entire life. Her experience includes extensive sailing in the Greek Islands and Turkey and treks along the entire eastern seaboard, from the last lighthouse in Newport to the tip of Florida’s keys and Bahamas. She also brings more than 20 years of experience sailing throughout all of the Caribbean, including the British Virgin Islands, the Grenadine Chain, Trinidad, and Tobago. Between her chef wizardry, her boundless enthusiasm, her far-ranging knowledge, her love of sailing and her distinguished professionalism, you are guaranteed of having fun on Valerie’s watch. Her skill and passion for sailing is contagious and will undoubtedly leave you with remarkable memories.

Captain Ido

Captain Ido

Having spent the first 25 years of his adult life as a Navy Captain (by rank as well as position), Ido now shares his time between cruising his own 40ft sailboat (currently in the Windward Islands) and skippering OPBs (Other People’s Boats) in charters, deliveries and instructions. Altogether he has logged over 200,000 miles and lost count while doing so. He has under his life-vest 4 Atlantic crossings, half a dozen East Coast passages, and numerous criss-crossings of the Med., charters in the Caribbean as well as some Red- and North- seas voyages. While a seasoned captain, Ido sometimes finds it relaxing to be second-in-command under a trustworthy skipper, just to see what it looks like from the crew’s point of view. Ido is also a long-distance runner (only while ashore), a certified bar-tender and an honorary member of the Israeli all-women yacht-racing team.

Captain Tracy

Captain Tracy

Captain Tracy has logged over 100,000 mile in her 21 year sailing career. She is an ASA sailing instructor and has owned her own sailing yachts since 1991. Her first yacht was Auriga, a 51’ Beneteau which delighted students and guests sailing and exploring up and down the island chain from Puerto Rico to Grenada. Her newest yacht and the latest addition in the Custom Sailing fleet is Capella, a 50’ Beneteau Cyclades located in the Caribbean. Tracy’s knowledge of sailing and “where to go” are priceless. Not only is she a great captain, but she is also a gourmand in the galley!

Captain Antonis

Captain Antonis

Captain Antonis is a mentor, friend and wealth of knowledge and experience in everything Greek. He is a graduate of the National Merchant Marine Academy of Hydra which is the first naval academy in Greece, starting its operations in 1749. When he is not busy as captain in his current position on a private 40M motor yacht based in Athens, he is looking after our yacht Maya. You will often find him meeting us at the end of our sailing week in Athens, there to catch our lines and welcome us back from our visit to the islands. Once as I was backing our yacht into her place at the marina I over heard one guest say “I wish I had and Antonis to meet me at the end of each week!”

First Mate Maria

First Mate Maria

Maria welcomes you aboard with her ebullient smile and Greek hospitality. Not only is she a great sailor but she is an amazing cook, using the best of what the markets and sea have to offer! Having spent over 10 years in the charter industry in Greece both as a first mate and hostess she has also developed a training program for others interested in pursuing a career in this industry. Her knowledge of the islands and her network of friends are vast which makes your sailing holiday all the more fun. Let Maria show you her Greek Islands!

The Maya Salon

Whether you want to explore the islands of the Mythical Grecian Gods, bask in the sun of the Caribbean or sail the playground of the rich and famous in New England remember, there are no limitations with “Custom Sailing”. We will help you choose the right yacht, crew and itinerary to meet and exceed all your expectations.

We aim to provide to you the most stress free, relaxing and enjoyable holiday ever, while upholding the highest quality and safety standards. We want you to tell your friends and family what a great time you had with Custom Sailing Worldwide, Inc. We are an equal opportunity vacation provider. We welcome everyone to share in the beauty of an island adventure.

Click here to view a video of a recent sail from Syros to Kea >>