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Welcome to Five O'Clock Charters

Starboard side of a sailboat

Though the phrase "five o'clock" has different meanings for different people, what it means to us is "play time." With life’s busy pace, you need time away from the hustle and bustle that 9-to-5 work schedules create. So we invite you to leave it all behind and come out to play on Maryland's own Chesapeake Bay. Here at Five O' Clock Chartersit’s always 5 O'Clock.

Drop us a line and schedule your getaway sail now!

Get Ready to Sail!

Sunset cruises, watching the races, family time on the water, take your pick.

The Chesapeake Bay is full of amazing sightseeing opportunities.

Photos taken during our charter cruises.

Contact us with any questions you have about chartering.