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July 2016
$44.00

Maryland’s Brewer’s Cup Race

July 26 @ 6:30pm
Annapolis Waterfront Hotel,
80 Compromise Street, Annapolis, MD 21401 United States
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Join Heavy Seas and Union Craft Breweries aboard the Sixth Annual “Maryland’s Brewer’s Cup”. Buy a ticket aboard your favorite brewery’s boat!  Union Craft vs. Heavy Seas! Battle of the Baltimore Brews. During the race, passengers (guest crew) will be able to participate in helping to sail the boat, where appropriate, of course. This will be a “match race” so the competition will be keen between the breweries. Price includes one free beer aboard.  Boats will be filled with three of…

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$109.00

Everything Local Dinner Cruise

July 31 @ 6:30pm
Annapolis Waterfront Hotel,
80 Compromise Street, Annapolis, MD 21401 United States
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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 purchase locally or grow yourself. Tickets are $109 per adult and include three course dinner, 3 drink vouchers, and unlimited soda & water. Maximum 35 guests. Black Ankle Vineyards will be aboard showcasing 2 of their favorite wines. Blackwater Distillery in Kent Island will be showcasing one of their spirits in a unique cocktail aboard.…

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August 2016

August Lighthouse Cruise

August 14 @ 11:30am
Annapolis Waterfront Hotel,
80 Compromise Street, Annapolis, MD 21401 United States
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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 11:30am, return at 3:30pm, includes bagged lunch, soft drinks and snacks, $93 per adult, $56 per child with child’s lunch. Maximum of 35 guests         Gourmet Bagged Lunch includes: Gourmet Sandwich (choose one) Grilled fajita spiced chicken with lettuce,…

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Brunch Sail with Ernie Halter

August 21 @ 10:00am
Annapolis Waterfront Hotel,
80 Compromise Street, Annapolis, MD 21401 United States
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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. Halter has released 6 albums, toured 50 states, and seen his popularity swell to more than 510,000 Twitter followers, 12,000 YouTube subscribers, and nearly 10,000 Facebook ‘Likes’. 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…

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August Wine in the Wind

August 28 @ 2:00pm
Annapolis Waterfront Hotel,
80 Compromise Street, Annapolis, MD 21401 United States
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Join us for a three hour sail around the Bay sampling wonderful wines: The Estate of Louis Latour, Burgundy with Timothe Cousins.  This representative from the winery will introduce you to these special wines. 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.  After the sampling, there will be a small afternoon appetizer buffet that…

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September 2016

Old Westminster Winery Dinner Cruise

September 11 @ 5:30pm
Annapolis Waterfront Hotel,
80 Compromise Street, Annapolis, MD 21401 United States
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Captain Jen fell in love with this winery’s location, wine and people that work at Old Westminster Winery at their grand opening in 2013. The proprietors, the Baker family, are raising a reputation for crafting wines of intrigue. The property is situated on a rocky plot of ground just south of historic Westminster, MD, where patrons enjoy the ambiance of the vineyard and a hands-on winery producing exceptional wines. The Baker family believes this winery represents the American Dream: strong…

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October 2016

Brews in the Breeze Lunch Cruise

October 9 @ 12:30pm
Annapolis City Marina,
410 Severn Ave, Annapolis, MD 21403 United States
+ Google Map

Join the Woodwind crew for an afternoon of beer tasting along with a delicious lunch. 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 $78 per adult and include lunch, four 6 oz. beers, and unlimited soda and water. Additional beer will be available for purchase.  Departs  Annapolis at 12:30pm…

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Schooner Race Watch Cruise

October 13 @ 12:00pm
Annapolis City Marina,
410 Severn Ave, Annapolis, MD 21403 United States
+ Google Map

  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 $83 per adult and $45 per child and include bagged lunch bottled water, soft drinks, and snacks. Beer and wine are available for purchase. *$10 of each ticket purchased will be donated to the Great Chesapeake Bay Schooner Race, a non-profit organization that races to save the Bay in conjunction with the…

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October Lighthouse Cruise

October 15 @ 10:30am
Annapolis City Marina,
410 Severn Ave, Annapolis, MD 21403 United States
+ Google Map

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, $93 per adult, $56 per child with child’s lunch. Maximum of 35 guests Cruise Departs from Annapolis City Marina (Boat Shows are in town)     Gourmet Bagged Lunch includes: Gourmet…

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$900.00 + tax

Annual Great Chesapeake Bay Schooner Race

October 12 @ 8:00am
Watergate Village,
Annapolis, MD United States

Be part of the crew aboard the 74-foot Schooner Woodwind on the race down the Chesapeake Bay from Annapolis to Portsmouth, Virginia! Over 45 schooners participate each year. This is a once in a lifetime experience! $900 plus tax per person includes everything. Space for four guest crew members is available.

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