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July 2017

Maryland’s Brewer’s Cup Race

$46.00
July 25 @ 6:30 pm - 8:30 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis, MD 21401 United States
Heavy Seas vs. Flying Dog Breweries

Join Heavy Seas and Union Craft Breweries aboard the Seventh 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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Everything Local Dinner Cruise

$109.00
July 30 @ 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 $109 per adult and include three course dinner, 3 drink vouchers, and unlimited…

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August 2017

Brunch Sail with Ernie Halter

$89.00
August 6 @ 10:00 am - 1:00 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. In 2011 Justin Bieber covered…

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Dodon Vineyards Wine Dinner

August 20 @ 6:30 pm - 9:00 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis, MD 21401 United States

Established in 2007, the vineyards at Dodon are fortuitously situated on rolling hills just south of Davidsonville, Maryland. When they began their first experiments with 150 vines, the goal was clear: to practice sustainable agriculture and produce exceptional wines. As ninth generation custodians of this historic farmland, and as demanding winemakers, they are committed to using viticultural practices and winemaking techniques that permit full expression of the unique deep sandy loam ‘Dodon Series Soils’ that lend their wines distinctive aromatics and subtle…

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Solar Eclipse Cruise

August 21 @ 1:30 pm - 3:30 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis, MD 21401 United States

Sail away and watch the event being called the "Great American Eclipse".   While we are not in the area that will see the total eclipse, Annapolis is in the 79% coverage area, and it should be really cool to view from the water, while sailing. The previous time a total solar eclipse was visible across the entire contiguous United States was during the June 8, 1918 eclipse. Click to Enlarge diagram. Depart Annapolis at 1:30pm, return at…

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August Wine in the Wind

August 27 @ 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 Spain.  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 2017

Black Ankle Winery Dinner Cruise

$109.00
September 10 @ 5:30 pm - 8:00 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis, MD 21401 United States
Rolling Hills Black Ankle Vineyards

Due to popular demand, the first boat for this event has sold out... Update- At 9:00pm, now both boats are sold out. Captain Jen fell in love with this winery's location, wine and people that work at Black Ankle Winery. Black Ankle Vineyards is the culmination of a long-time dream of founders Ed Boyce and Sarah O'Herron (that's us). They believe that the central Maryland Piedmont, sitting at the foothills of the Appalachian Mountains, has the right mix of rolling…

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Classic Wooden Boat Regatta

September 17 @ 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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Brunch Sail with Michael Tolcher

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 MICHAEL TOLCHER aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delicious brunch. Michael Tolcher will play acoustically while at anchor in a secluded cove. He will play for about 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 Michael while sailing the Bay. Info about Michael, from Michael: I was born…

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October 2017

Brunch Cruise with Jay Nash and special guest, Natalia Zukerman

October 1 @ 11:30 am - 2:30 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis, MD 21401 United States

An Intimate, All Ages Acoustic Show with JAY NASH and special guest, NATALIA ZUKERMAN aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delicious brunch. Jay Nash will play acoustically while at anchor in a secluded cove. He will play for about 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 Jay while sailing the Bay.…

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