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The Woodwinds, Sailing into Spring

Bears aren't the only ones who hibernate throughout the winter. As soon as the birds begin to chirp and the flowers begin to blossom, the boats around Annapolis begin to find their way out of their plastic shrink wrap and into the cold waters of the Chesapeake Bay. When Annapolis Discovered…

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The Wilma Lee Skipjack Sets Sail

The Wilma Lee sails into City Dock in Annapolis. Photo courtesy of Visit Annapolis. Built in 1940 and restored in 2019, the Wilma Lee was unveiled this past summer as the latest boat to set sail on the shores of the Chesapeake. This historic boat resides at the Annapolis Maritime Museum and…

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A Quick History: Annapolis Sailing School

View of the Rainbow Dinghy Dock looking out onto the Chesapeake Bay. Photo courtesy of the author. Back in 1959, Annapolis resident and sailor, Jerry Wood was in the toy business. But, he realized there were no facilities available in the area for the rental of boats, he opened Annapolis Boat…

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Get to Know Captain Jennifer of Schooner Woodwind

You can’t miss the beautiful, 74-foot schooner docked outside of Pusser’s, taking locals and visitors out on the Bay from Tax Day through Halloween. As they get ready to put in for a new season, kicking off their 16 th season on April 13, here’s a little more about Captain Jennifer Kaye, one of the…

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Boat Maryland Week Preview

The boating season in Annapolis arrives with the spring equinox, and by April the town is absolutely bursting with pent up energy. Sailors, powerboaters, paddlers, one and all, have looked longingly out at the water all winter. At long last the sun is shining, the Bay is thawing, and the warm days…

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Aboard the Woodwind Celebrating 25 Years!

What better way to celebrate the warm weather in Annapolis than hoping aboard one of two, beautiful 74-foot schooners – Schooner Woodwind and Woodwind II – for a fun sailing experience in Annapolis! I had the pleasure of joining Captain Jennifer Kaye of Annapolis Sailing Cruises for their Wednesday…

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A Recap of the Annapolis Boat Shows

Welcome to the Annapolis Boat Shows! The largest in-water boat shows in the country each take place biannually at City Dock in downtown Annapolis. Over the course of two weeks, vendors, boat owners, manufacturers, and visitors come together to shop and explore the vast display of sailboats and…

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The Sailing Academy at Herrington Harbour North

I’ve always been a ‘try anything once, twice if you like it’ type person. I’ve been skydiving, bungee-jumping, have had the opportunity to fly a Cessna, fly an airship. Though my extreme adventure days may be over, I look for every opportunity to explore with my son and give him as many different…

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