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Author | Historian | Speaker

Weekly Oak Bluffs Town columnist for the Vineyard Gazette from June 2012 to June 2017, Skip Finley is a retired broadcaster who has written for, been featured or quoted in most media industry trade publications.

Skip built his career in radio, becoming a well-known executive and station owner. He served as Vice Chairman of the National Association of Broadcasters and Chairman of the Radio Advertising Bureau. He served on virtually all broadcasting industry boards of directors, and on their executive committees.

Skip’s career in media since 1971 included responsibility for 43 radio stations (4 that he owned) encompassing 17 markets. His experience includes successes with radio networks, syndicated programs, formats and a satellite channel.

Having attempted to retire since age 50, he keeps returning to communications, currently as Director of Sales and Marketing for the Vineyard Gazette Media Group on Martha's Vineyard, where he summered since 1955 and has lived since 1999, deciding to become a writer.

Skip has written articles for the Vineyard Gazette, Martha’s Vineyard Magazine, Island Weddings Magazine, the Provincetown Banner and the Martha’s Vineyard Museum publications, The Intelligencer and the MV Museum Quarterly.

His book Historic Tales of Oak Bluffs is being published in summer, 2019 by History Press. Whaling Captains of Color – America’s First Meritocracy is to be published by the naval Institute Press in spring, 2020.

A gifted researcher, Finley is also an entertaining speaker with an interesting and highly toned sense of humor.


Skip Finley’s media career in sales and marketing included addresses and presentations to diverse audiences of all sizes, experience that has helped make him an engaging speaker.

For bookings CONTACT HERE.


“At sea, a black master could slap or flog a white sailor.  On land, he couldn't look a white man in the eye..”

- Skip Finley