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Sailing Charters in Annapolis, Maryland

Sailing Charters in Annapolis, Maryland

Annapolis is a charming, historic and preppy town situated on the Western side of the Chesapeake Bay. Its charm comes from the brick sidewalks and wind washed townhomes. Its historicity is rooted in a three-hundred-year legacy as a colonial state capitol. And finally, the prep is brought to you by all the lacrosse players and sailors that roam the streets and circle the Bay.

Because the city of Annapolis is located on a bit of a Peninsula, it’s been named as America’s ‘sailing capital.’ However, if you’re boatless, or only visiting, fear not--you can still get out on the water. Here are the top three Annapolis-based sailing charters we’d recommend.

1. The Schooner Woodwind Annapolis Sailing Cruises

There are two seventy-four foot schooners, the Woodwind and the Woodwind II, that are available for charter. Both are magnificent and sport sixty-one foot decks. The beauty of this sailing charter is the diversity of packages they offer.

schooner windwind

Schooner Woodwind hosts two hour public sailing cruises, corporate, catered cruises, guided land and Bay “Geocaching” tours for young students and Girl Scouts, and even four-day cruises from Annapolis to Norfolk. Whether you’re visiting Annapolis as a family vacation, anniversary getaway, or an office retreat, this charter could have the program for you!

2. Classic Sail Charters

This Sailing Charter is based in Annapolis, but also has a branch in Puerto Rico. Their sailing yachts are thoroughly refined, and they enjoy guiding visitors through one of the world’s largest estuaries, the Chesapeake Bay! “It is exquisitely appointed, safe, and ready for you to call home while you enjoy the mystique and allure of some of the best sailing grounds in the world,” Their website touts.

Unlike the Schooner Woodwind, the Classic Sail Charter’s Annapolis branch takes a maximum of six guests on each trip. This makes the journey a more intimate one--their website shares that their tours and cruises are ideal for proposals, small family gatherings, and anniversaries.

3. Pirate Adventures on The Chesapeake

If you’ve got young ones tagging along with you, we guarantee this will be a ( if not THE ) highlight of their trip to Annapolis. Pirate Adventures on the Chesapeake is a scavenger hunt cruise that the whole family can enjoy. A day out with this crew involves face paint, pirate names, water cannons, and yes, buried treasure.

If there are no young scallywags in your group, Pirate Adventures of The Chesapeake also offers “Cocktail Cruises for Grown Ups.” So, whichever adventure you choose, it’s sure to result in a lovely day outdoors.

Pain Killer Cocktail

And finally, to look the part, a Montauk button down is the perfect, breezy choice for coastal sailing along the Chesapeake. And our women’s and men’s Sun Hoodies are light weight and have a 50+UPF sun protection for a full day of fun in the sun. Each is made with Montauk’s MTCdryprotect™ smart fabrics, with moisture wicking technology to keep wearers cool and comfortable all day long.

Montauk’s fabrics are made from recycled bottles; an estimated four bottles have been repurposed into each shirt. Further, each is American made. We do this because it allows our performance apparel to tell an amazing story of sustainability, which is traceable and transparent. You can learn more about our recycled yarn and American made clothing at


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