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July 2018

Everything Local Dinner Cruise

July 29 @ 6:30 pm - 9:00 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis, MD 21401 United States
Local Everything Dinner Cruise aboard Schooner Woodwind

Enjoy our “Everything Local” themed dinner and drinks while under full sail on the Chesapeake Bay. This cruise will focus on food that you can grow yourself or purchase locally.  Our caterer, Palate Pleasers, prides themselves on getting produce, meats, and many other ingredients from the local area.  For our wonderful selection of alcoholic beverages, we choose independent breweries and distilleries within a 70-mile radius. Tickets are $111 per adult and include three-course dinner, 3 drink vouchers, and unlimited soda…

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August 2018

August Wine in the Wind – Along the Douro

August 12 @ 4:00 pm - 6:00 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis, MD 21401 United States
Wine in the Wind

Join us for a two hour sail around the Chesapeake Bay while sampling wonderful wines from Portugal.  The representative from the winery will introduce you to four special wines while we are under sail. The cruise will be a relaxing sail including 3-oz samples of each of the four wines featured. Along with each wine is a delicious, perfectly paired bite (we call them magnificent morsels) to go with each wine.   Includes a take-home, boat friendly, wine glass by Go Vino with the Woodwind's logo on it.…

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September 2018

Classic Wooden Boat Regatta

September 23 @ 11:00 am - 2:30 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis, MD 21401 United States

Participate in the National Sailing Hall of Fame Classic Wooden Boat Regatta. They have invited the Woodwinds' to participate in the race in the "Spirit of Tradition Class". The course is approximately 5.4 NM and takes place in the Severn River. It is a 3 lap race with pursuit style race. Each boat has a rating, and by the rating they will get a start time. The pursuit style race challenges the competitors to sail through the other race boats…

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September Wine in the Wind – Around the World, New Zealand to California

September 23 @ 3:00 pm - 5:00 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis, MD 21401 United States
Wine in the Wind

Join us for a two hour sail around the Chesapeake Bay while sampling wonderful wines from the Goldschmidt Winery, Alexander Valley & Beyond.  The representative from the winery will introduce you to four special wines while we are under sail. The cruise will be a relaxing sail including 3-oz samples of each of the four wines featured. Along with each wine is a delicious, perfectly paired bite (we call them magnificent morsels) to go with each wine.   Includes a take-home, boat friendly, wine glass by Go Vino…

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Brunch Sail with Ernie Halter

September 30 @ 11:30 am - 2:30 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis, MD 21401 United States

An Intimate, All Ages Acoustic Show with ERNIE HALTER aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delicious brunch. Ernie Halter will play acoustically while at anchor in a secluded cove. He will play for over an hour and after the performance we will set sail on the 74-foot, classic wooden schooner, Woodwind. Raise the sails, steer the boat, sit back, relax and meet Ernie while sailing the Bay. Ernie Halter fell early and…

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October 2018

Brews in the Breeze Lunch Cruise

October 7 @ 11:00 am - 1:30 pm
Annapolis City Marina, 410 Severn Ave
Annapolis, MD 21403 United States

Sail on a lunchtime cruise of beer tasting on the Chesapeake Bay. After we raise all our sails, we will start the tasting with the lightest of the four beers. Lunch will consist of all your Chesapeake favorites, including crab cakes, served buffet style while sailing on the beautiful Bay! Tickets are $86 per adult and include lunch, four 6 oz. beers, and unlimited soda and water. Additional beer will be available for purchase.  Departs  Annapolis at 11:00 am and returns…

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Schooner Race Watch Cruise

October 11 @ 12:00 pm - 3:00 pm
Annapolis City Marina, 410 Severn Ave
Annapolis, MD 21403 United States
Great Chesapeake Bay Schooner Race Start

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. There will be up to 25 plus schooners at the starting line. Seven of them are at least near 100+ feet. This is going to be incredible. Join the fun! They will be racing to the Norfolk area, we will cheer them on till it's time to go in.   We will be under sail…

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October Lighthouse Cruise

October 14 @ 10:30 am - 2:30 pm
Annapolis City Marina, 410 Severn Ave
Annapolis, MD 21403 United States
Schooner Woodwind Chesapeake Bay Lighthouse Sailing Tours in Annapolis, Maryland

Sail to as many as three different lighthouses on the Chesapeake Bay and learn about their history, importance, and present day condition by a guest lecturer from the Chesapeake Chapter of the U.S. Lighthouse Society. Depart Annapolis at 10:30am, return at 2:30pm, includes bagged lunch, soft drinks and snacks, $96 per adult, $58 per child with child’s lunch. Maximum of 35 guests. Scroll down to see menu choices. Cruise Departs from Annapolis City Marina (Boat Shows are in town)  …

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