Upcoming Events › Specialty Cruises

July 29, 2014

Maryland’s Brewer’s Cup Race

Heavy Seas vs. Flying Dog Breweries

Join Heavy Seas and Flying Dog Breweries aboard the Fourth Annual “Maryland’s Brewer’s Cup”. Buy a ticket aboard your favorite brewery’s boat! 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 …
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Start: July 29, 2014 6:30 pm
End: July 29, 2014 8:30 pm
Venue: Annapolis Marriott Waterfront Hotel
Address:
80 Compromise Street, Annapolis, MD, 21401, United States
Adults: $42.00
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August 10, 2014

August Lighthouse Cruise

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 11:30am, return at 3:30pm, includes bagged lunch, soft drinks and snacks, $89 per adult, $56 per child …
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Start: August 10, 2014 11:30 am
End: August 10, 2014 3:30 pm
Venue: Annapolis Marriott Waterfront Hotel
Address:
80 Compromise Street, Annapolis, MD, 21401, United States
Adults: $89.00
Children: $56.00
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August 24, 2014

August Wine in the Wind (Chile)

Wine in the Wind, Woodwind in a glass!

Join us for a three hour sail around the Bay sampling wonderful wine from Chile. A representative from the wineries will introduce you to these special wines. This will be a relaxing sail including afternoon hors d’oeuvres, soft drinks and four samples of wine. Depart Annapolis at 2:00pm, return at 5:00pm. Price: $99 per person. …
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Start: August 24, 2014 2:00 pm
End: August 24, 2014 5:00 pm
Venue: Annapolis Marriott Waterfront Hotel
Address:
80 Compromise Street, Annapolis, MD, 21401, United States
Adults: $99.00
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September 7, 2014

Brunch Sail with Ernie Halter

Ernie Halter performs aboard the Schooner Woodwind

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 5 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 …
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Start: September 7, 2014 11:30 am
End: September 7, 2014 2:30 pm
Venue: Annapolis Marriott Waterfront Hotel
Address:
80 Compromise Street, Annapolis, MD, 21401, United States
Adults: $89.00
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September 16, 2014

Sailabration Cruise

Taken from 2012 Parade of Sail. Photo Contest Entry from Sue Miller.

SAIL to Sailabration in Baltimore for an all day adventure!: We will set sail from Annapolis at 8:00 am, sail towards Baltimore and rendezvous with the Tall Ship fleet by 11:30 near Fort McHenry. We will return to Annapolis no later than 5:00 pm. Included is: breakfast, lunch, afternoon happy hour hors d’oeuvres and a glass …
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Start: September 16, 2014 8:00 am
End: September 16, 2014 5:00 pm
Venue: Annapolis Marriott Waterfront Hotel
Address:
80 Compromise Street, Annapolis, MD, 21401, United States
Adults: $199.00
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September 21, 2014

Classic Wooden Boat Regatta

Classic Boat Regatta

Brand New Event for Woodwind this Year! Participate in the National Sailing Hall of Fame Classic Wooden Boat Regatta. They are letting the Woodwinds’ participate in the race in the “Spirit of Tradition Class”. They expect to have upwards of 21 classic wooden sailing boats. The smallest boat is 18′, MORGAINE a home built gem, …
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Start: September 21, 2014 11:00 am
End: September 21, 2014 2:30 pm
Venue: Annapolis Marriott Waterfront Hotel
Address:
80 Compromise Street, Annapolis, MD, 21401, United States
Adults: $79.00
Children: $49.00
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Old Westminster Winery Dinner Cruise

old-westminster-wines-3

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 …
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Start: September 21, 2014 5:30 pm
End: September 21, 2014 8:00 pm
Venue: Annapolis Marriott Waterfront Hotel
Address:
80 Compromise Street, Annapolis, MD, 21401, United States
Adults: $99.00
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October 12, 2014

Brews in the Breeze Lunch Cruise

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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 served buffet style while sailing on the beautiful Bay! Tickets are $74 per adult …
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Start: October 12, 2014 12:30 pm
End: October 12, 2014 3:00 pm
Venue: Annapolis City Marina
Address:
410 Severn Ave, Annapolis, MD, 21403, United States
Adults: $74.00
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October 16, 2014

Schooner Race Watch Cruise

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. Tickets* are $79 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 …
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Start: October 16, 2014 12:00 pm
End: October 16, 2014 3:00 pm
Venue: Annapolis City Marina
Address:
410 Severn Ave, Annapolis, MD, 21403, United States
Adults: $79.00
Children: $45.00
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October 18, 2014

October Lighthouse Cruise

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, $89 per adult, $56 per child …
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Start: October 18, 2014 10:30 am
End: October 18, 2014 2:30 pm
Venue: Annapolis City Marina
Address:
410 Severn Ave, Annapolis, MD, 21403, United States
Adults: $89.00
Children: $56.00
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