Calendar of Events › Specialty Cruises

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 $69 per adult and $39 per child. Beer and wine are available for purchase.   Newly discounted price does not include lunch.  Please bring your own brown bag …
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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: $69.00
Children: $39.00
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October 12, 2014

Brews in the Breeze Lunch Cruise

P1030987

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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September 21, 2014

September Wine in the Wind

Wine in the Wind, Woodwind in a glass!

Join us for a three hour sail around the Bay sampling wonderful wine. 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 1:30pm, return at 4:30pm. Price: $99 per person. Maximum 35 …
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Start: September 21, 2014 1:30 pm
End: September 21, 2014 4:30 pm
Venue: Annapolis Marriott Waterfront Hotel
Address:
80 Compromise Street, Annapolis, MD, 21401, United States
Adults: $99.00
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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 have invited the Woodwinds’ to participate in the race in the “Spirit of Tradition Class” for the first time, as they have made this a new category/class. The course is approximately 5.4 NM and takes …
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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: $69.00
Children: $39.00
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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 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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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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October 21, 2013 – October 25, 2013

The 5-Day Sailing Adventure Cruise

Join the Schooner Woodwind for a 5 Day Adventure Sail on the Chesapeake Bay October 15-19, 2012

Spend 5 days aboard the Schooner Woodwind sailing from Portsmouth, VA to Annapolis. $1600 plus 10% tax per cabin (double occupancy). Includes accommodations aboard, gourmet meals (4 breakfasts, 5 lunches, and 3 dinners, one dinner is ashore), sail training (if wanted), and absolutely fantastic scenery! Four cabins available. Tickets are not available for purchase online.  …
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Start: October 21, 2013 8:00 am
End: October 25, 2013 5:00 pm
Venue: Portsmouth, VA
Address:
Portsmouth, VA, United States
Adults: $1600.00 + tax
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October 17, 2013

Schooner Race Watch Cruise

Great Chesapeake Bay Schooner Race Start

Tickets available for sale without lunch included 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 $69 per adult and $40 per child and include bottled water, soft drinks, and snacks. Beer and wine are available for …
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Start: October 17, 2013 12:00 pm
End: October 17, 2013 3:00 pm
Venue: Annapolis Marriott Waterfront Hotel
Address:
80 Compromise Street, Annapolis, MD, 21401, United States
Adults: $69.00
Children: $40.00
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October 16, 2013 – October 20, 2013

Annual Great Chesapeake Bay Schooner Race

Blasting along at 10+ knots

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.

Start: October 16, 2013 8:00 am
End: October 20, 2013 5:00 pm
Venue: Watergate Village
Address:
Annapolis, MD, United States
Adults: $900.00 + tax
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