For sailors looking to explore the Chesapeake Bay, this suggested 4-day itinerary provided a perfect mix of scenic anchorages and charming small towns. The journey starts and ends at The Sailing Academy’s base at Herrington Harbour North in Tracy’s Landing, Maryland. Day 1: Herrington Harbour to Harness Creek (18 NM) ⛵️Sail: Depart Herrington Harbour and head north to Harness Creek on the north side of South River. Watch out for the pound nets (fish trap pilings) between Herring Bay G1 and 83a.

For just $75, you can go sunset sailing on the Chesapeake Bay in Annapolis onboard one of the few operating Skipjacks left in the country. @annapolismaritimemuseum runs these boats all summer and I gotta say it’s a must if you’re in town. In addition to these sunset cruises, they also offer heritage tours, where you can learn about the ecology of the Bay, and Wednesday night races where you can watch the weekly Annapolis sailboat racing up close and personal. Book on their website! #annapolis #s

We’re not ashamed to admit The Chesapeake Bay is our FAVORITE place to teach sailing, ESPECIALLY in the fall. Miracle forecasts of cool consistent breeze, sunshine, and easy tides are common throughout September-Oct. Its not too late to experience it for yourself! Jump aboard one of our weeklong learn-to-cruise courses and liveaboard, or come for a weekend stay! ⚓️ABOUT US⚓️ The Sailing Academy is an ASA sailing school for those who want to learn to sail, cultivate sailing skills, or begin a lif

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