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Sail Inn

Categories: Bar

Features: Beloved dive, Jukebox, Karaoke

Payment options: Credit cards accepted

Alcohol: Full bar

More in this neighborhood: Brooksville / East Hernando

This is a road house in the truest sense of the term, a clapboard building three miles south of downtown Brooksville on what was formerly the main north-south highway in western Florida, U.S. 41. It has been open since 1970, and boasted a jukebox packed with country music classics even when 45 rpm records allowed for a relatively small selection. Look for the sign perched on the top of the 15-foot-high oak tree, where it was moved about a decade ago when U.S. 41 was widened to four lanes.

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Sail Inn - Brooksville / East Hernando