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. 7/20 to 8/27/21 <------![Homestead Gardens](https://www.eyeonannapolis.net/wp-content/uploads/2021/06/CrapeMyrtle-2021.jpg")
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4/26 to 5/9 <----- ![Homestead Gardens Herb & Veggie Weekend](https://www.eyeonannapolis.net/wp-content/uploads/2021/04/HG-HERB-VEGGIE-APR21.jpg")
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SHamrock Feb 15 to mar 31 2021 
Tag: Sailboat
12th Annual Classic Wooden Sailboat Race
Come out and see a spectacle of beautiful classic wooden sailboats as they race along the mouth of the Severn River to showcase their history and elegant design! The race […]
Narrows Boat Expo
Knot 10 Yacht Sales has coordinated with local restaurants to establish a Spring Expo of boats set on the Kent Narrows waterfront. Giving boat buyers the opportunity to come and […]
Lighthouses of the Chesapeake Bay Sailing Cruise aboard the 74-foot Schooner WoodwindLighthouses of the Chesapeake Bay Sailing Cruise aboard the 74-foot Schooner Woodwind
Sail by as many as 3 different lighthouses while learning about their history, importance, and present day condition from a guest lecturer from the Chesapeake Chapter of the US Lighthouse […]
The Annual Great Chesapeake Bay Schooner Race Start Watch aboard the Schooner Woodwind II
: The Annual Great Chesapeake Bay Schooner Race Start Watch aboard the Schooner Woodwind II: Join in the excitement and watch the start of the race. Tickets* are $89 per […]
Wednesday Night Sailboat Racing Cruise aboard the 74-foot Schooners Woodwind & Woodwind II:
Be part of the action every Wednesday night as the two wooden schooners, Woodwind & Woodwind II, compete in Annapolis’ summer racing series. Help the crew or sit back and […]
Sailing Cruise with live music aboard the 74-foot Schooner Woodwind
Enjoy music performed by Deanna Dove during a two hour sunset cruise aboard the 74-foot Schooner Woodwind. Deanna Dove is best known as the “Island Girl” in her hometown for […]
Sail Away” while learning the history of the Chesapeake Bay aboard the 74-foot Schooner Woodwind
The Key to Annapolis History, by Jeff Holland. The Key to Annapolis history lies right there in the harbor. It can’t be found by looking port; and it can’t by […]
Sailing Cruise with live music aboard the 74-foot Schooner Woodwind
Enjoy music performed by Kyle Offidani during a two hour sunset cruise aboard the 74-foot Schooner Woodwind. Born and raised in the bay area of Delaware- Kyle Offidani is a […]
Sail Away while learning the history of the Chesapeake Bay aboard the 74-foot Schooner Woodwind
Legends and Lore of the Annapolis Waterfront by Dave Gendell Dave brings aboard and entertaining and compelling set of stories and insights around Annapolis history, the Naval Academy, the sailing […]
Sailing Cruise with live music aboard the 74-foot Schooner Woodwind
Enjoy music performed by Mike & Kelly Lange during a two hour sunset cruise aboard the 74-foot Schooner Woodwind. Mike and Kelly Lange are a husband and wife ukulele duo. […]
Wednesday Night Sailboat Racing Cruise aboard the 74-foot Schooners Woodwind & Woodwind II
Be part of the action every Wednesday night as the two wooden schooners, Woodwind & Woodwind II, compete in Annapolis’ summer racing series. Help the crew or sit back and […]
: Beer Tasting Sailing Cruise aboard the 74-foot Schooner Woodwind
Sample beer from Heavy Seas Brewery while enjoying the beautiful sunset under full sail. A brewery representative will be aboard and ticket price includes 3 samples of beer. Beer takes […]
June Wine in the Wind (Italy): Two hour sail on the Chesapeake Bay, sampling wines
A representative from the Tommasi Family Estates will introduce you to four special wines while we are under sail. The cruise will be a relaxing sail including 3-oz samples of […]
Sailing Cruise with live music aboard the 74-foot Schooner Woodwind:
During our 25th Anniversary Celebration Week, we invite you to join us for a special sunset sail to enjoy music performed by Crab Alley Lite during a two hour sunset […]
Wednesday Night Sailboat Racing Cruise aboard the 74-foot Schooners Woodwind & Woodwind II
During our 25th Anniversary Celebration Week, we invite you to join us for a special sunset sail with Captain Jen and Captain Ken as they once again bring on the […]
Sailing Cruise with live music aboard the 74-foot Schooner Woodwind:
Enjoy music performed by The Eastport Oyster Boys during a two hour sunset cruise aboard the 74-foot Schooner Woodwind. Recognized as the City of Annapolis and the Chesapeake Bay’s Musical […]
Sailing Cruise with live music aboard the 74-foot Schooner Woodwind
Enjoy music performed by Don Shappelle during a two hour sunset cruise aboard the 74-foot Schooner Woodwind. Don Shappelle sings and writes many songs about the Chesapeake Bay, it’s people, […]
Chesapeake Light Craft OkoumeFest
A small boat rendezvous for wooden boat lovers. “Okoume” is the plantation-grown African hardwood used in tens of thousands of Chesapeake Light Craft’s build-your-own-boat kits. OkoumeFest features an open house […]
Sailing Cruise with live music aboard the 74-foot Schooner Woodwind
Enjoy music performed by a local artist during a two hour sunset cruise aboard the 74-foot Schooner Woodwind. Cruises depart from the Annapolis Waterfront Hotel at 6:30pm and return at […]
“Sail Away” while learning the history of the Chesapeake Bay aboard the 74-foot Schooner Woodwind:
Enjoy a historically guided 2 hour sunset sailing cruise with one of our local historians. Cruises depart from the Annapolis Waterfront Hotel at 6:30pm and return at 8:30pm. Tickets are […]
May Wine in the Wind
Join us for a two hour sail around the Chesapeake Bay while sampling wonderful wines. A representative from a winery will introduce you to four special wines while we are […]
Mother’s Day Brunch Sailing Cruise aboard the 74-foot, Schooner Woodwind
This wonderful three-hour brunch cruise includes one free Bloody Mary or Mimosa and delicious food: homemade scones, quiche Lorraine squares, baked smoky salmon with hearty bread, grilled flank steak, fresh […]
