City Island Yacht Club

Incorporated 1907

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City Island Yacht Club Sailing School

An American Sailing Association (ASA) Affiliate School 

We give you the knowledge and experience to be confident and safe on all your sailing adventures… Whether you charter a boat from a local harbor, go on an exotic sailing vacation, or even buy your own boat.

ASA 101 Schedule 2023

June 9th-11thJuly 7th-9th Aug 4th-6thSept 8th-10thOct 6th-8th
June 23rd-25thJuly 21st-23rdAug 18th-20thSept 22nd-24th 

Call or email for more info:

(718) 885-2487 x 4 or email

Book Online

Pick an event on the calendar:

The CIYC Sailing School provides American Sailing Association curriculum and certification and presents an active sailing community to support you in your sailing endeavor.

Classes Offered

ASA 101ASA 101, Basic Keelboat Sailing
Learn to skipper a 20′ – 27′ sloop-rigged keelboat by day, in light to moderate winds and sea conditions. Learn basic sailing terminology, parts and functions, helm commands, basic sail trim, points of sail, buoyage, seamanship and safety including basic navigation rules to avoid collisions and hazards. Qualifies you for CIYC Club Boat program.
–  $595 (plus $99 for  Coursebook and ASA Certification; instructor gratuity always welcome!)

ASA 103ASA 103, Basic Coastal Cruising Learn to skipper a sloop-rigged auxiliary powered 25′-35′ keelboat by day in moderate winds and sea conditions. Learn cruising sailboat terminology, basic boat systems, auxiliary engine operation, docking procedures, intermediate sail trim, navigation rules, basic coastal navigation, anchoring, weather, safety and seamanship.
–  $595 (plus Coursebook and ASA fees)

ASA104ASA 104, Bareboat Cruising
Learn how to sail a sloop-rigged, auxiliary powered 30′-45′ sailboat during a multi-day cruise upon inland/coastal waters in moderate/heavy winds and sea conditions. Learn about provisioning, boat systems, auxiliary engines, advanced sail trim, coastal navigation, anchoring / mooring, docking, emergency operations, weather, and more.
–  $595 (plus Coursebook and ASA fees)

ASA105ASA 105, Coastal Navigation
Learn the navigational theory and practices for safe navigation of a sailing vessel in coastal and inland waters. On-water coastal navigation skills elements are contained in the ASA103, Basic Coastal Cruising, ASA 104, Bareboat Cruising, and ASA 106, Advanced Coastal Cruising, in progressively increasing levels of detail.
–  $495 (plus $99 for Coursebook and ASA certification fee)

ASA 106, Advanced Coastal Cruising
Learn to safely act as skipper and crew of a sailing vessel about 30 to 50 feet in length in coastal and inland waters, in any conditions. 
– $795 (plus $99 for Coursebook and ASA certification fee) 


Herb d’Entremont (Primary Instructor)

Herb has been sailing for the last 15 years and grew up on the water as an off-shore commercial scallop fisherman. He holds a USCG 100-ton Near Coastal captain’s license, STCW and Safety at Sea certifications, and is a RYA Yachtmaster. Herb has been fortunate enough to sailing in beautiful places like Hawaii, St. Martin, St. Bart’s, Anguilla, Antigua, Grenada, Nova Scotia and of course the USA. He has been a Club Boat and Social Member at CIYC during the last few years and races on a couple of member boats (Eagle & Sanguine). Herb is a certified instructor for ASA 101, 103, 104, 105, 106 and 116. 

Eduardo S. Sanchez (Associate Instructor)

Eduardo is a member of the City Island Yacht Club since 2017 and previously sailed out of the Club Nautique in Sausalito. He obtained his initial American Sailing Association certifications in 2016 and since then he has become an instructor for ASA 101, 103 and 104. He also holds a Master 50 Tons with sailing extension from the United States Coast Guard. His specialty is skippered more than 20 weekly charters throughout the Caribbean, Mediterranean, Great Lakes, San Juan Islands, Florida Keys, Long Island Sound and Martha’s Vineyard/Nantucket.

Eduardo is semi-retired from a career in the software industry where he held various executive positions and currently serves as board member in a handful of software companies. Besides sailing, he keeps fit by jogging, playing tennis, skiing and doing yoga. He also enjoys watching his native Argentina win the Soccer World Cup every few years

David Spiro (Associate Instructor)

In his 55 years of sailing Dave has covered 1000s of miles blue water sailing from the eastern Mediterranean to the Pacific Ocean.  He has delivered boats from US waters to the Caribbean, brought his own boat to cruise in the Bahamas, and cruises a few times a year in the Sea of Cortez off the Baja Peninsula.  This year he was crew on the America II, a 12m America’s Cup boat, on the Princeton team racing Harvard and Columbia in NY Harbor.

David sails a C&C 40 which he keeps at City Island Yacht Club.  Although he is fairly new to ASA  instruction, he spent his career as a teacher at Columbia, Harvard, and the University of Arizona.  David is the CIYC Treasurer and serves on its Board of Directors. He is a certified instructor for ASA 101, 103, and 104. 

Ed Woolsey (Associate Instructor)

Ed is an avid racer and cruiser, who began sailing in 1976. Most of his sail time has been in Eastchester Bay and Long Island Sound, but more recently he has explored the gulf coast of Florida. Over the years, he has owned several boats including a Frers 33, a J-80, an Ericson 38, a Tartan 34, and his current Tartan 41.

In 2015 Ed became a USCG Captain, 100-ton master with a sailing endorsement, and more recently a 200-ton mate of towing. He owns and operates a marine repair and marine electronics business that often takes him to Liberty Landing Marina in Jersey City in New Jersey.

Ed has the following ASA teaching certifications: keelboat, basic coastal cruising, bareboat cruising, coastal navigation, docking and boat handling. Ed sails out of Liberty Landing Marina in Jersey City and City Island Yacht Club where he is an active member. He teaches ASA 103, 104, 105, 106, and 118 (docking) on his boat Five Star

John Baum (Instructors’ Instructor)

John is a professional delivery skipper and a long time member of the club.  He is one of the few people who are certified to train and certify ASA instructors, and he runs periodic clinics at the club for ASA instructors.