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August 2016
$109.00

August Wine in the Wind

August 28 @ 2:00 pm - 5:00 pm
Annapolis Waterfront Hotel,
80 Compromise Street
Annapolis, MD 21401 United States
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Wine in the Wind

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
$109.00

Old Westminster Winery Dinner Cruise

September 11 @ 5:30 pm - 8:00 pm
Annapolis Waterfront Hotel,
80 Compromise Street
Annapolis, MD 21401 United States
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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 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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$79.00

Classic Wooden Boat Regatta

September 25 @ 11:00 am - 2:30 pm
Annapolis Waterfront Hotel,
80 Compromise Street
Annapolis, MD 21401 United States
Classic Boat Regatta

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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October 2016
$135.00

Acoustic Brunch with Jay Nash

October 2 @ 10:30 am - 2:30 pm
Annapolis Waterfront Hotel,
80 Compromise Street
Annapolis, MD 21401 United States
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jaynash2-466x368

Announcing a Schooner Woodwind exclusive event!  The influences of being on the water, enjoying great food and beverage can create great memories.  However, when you combine those two elements with live music you are now on a journey. We invite you to join us as Captain Jen navigates us out of Annapolis Harbor for a 4 hour adventure you will not soon forget!  You will be aboard a beautiful 74 foot schooner enjoying a selection of gourmet food prepared by Palate…

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$78.00

Brews in the Breeze Lunch Cruise

October 9 @ 12:30 pm - 3:00 pm
Annapolis City Marina,
410 Severn Ave
Annapolis, MD 21403 United States
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Schooner Woodwind Koozie

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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$83.00

Schooner Race Watch Cruise

October 13 @ 12:00 pm - 3:00 pm
Annapolis City Marina,
410 Severn Ave
Annapolis, MD 21403 United States
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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 $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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$93.00

October Lighthouse Cruise

October 15 @ 10:30 am - 2:30 pm
Annapolis City Marina,
410 Severn Ave
Annapolis, MD 21403 United States
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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, $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

Annual Great Chesapeake Bay Schooner Race

October 12 @ 8:00 am - October 16 @ 5:00 pm
Watergate Village,
Annapolis, MD United States
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.

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$1800.00

The 5-Day Sailing Adventure Cruise

October 17 @ 8:00 am - October 21 @ 5:00 pm
Portsmouth, VA,
Portsmouth, VA United States
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. $1800 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.  Call 410-263-1981 to reserve your spot!

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