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July 2017

Fireworks Cruise

July 4 @ 6:30 pm - 10:00 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis, MD 21401 United States
Celebrate the 4th of July in Annapolis enjoying a sunset sail complete with fireworks from the water

Join us for a festive cruise celebrating the 4th of July. We will depart from the Annapolis Waterfront Hotel dock at 6:30 pm for a sunset sail with live entertainment by "Ship's Company". We will then anchor close to the fireworks barge for the 9:15 pm fireworks display and return to the dock after the show. Tickets are $89 per adult, $62 per child and include bottled water, soft drinks, and a wide selection of desserts including fresh fruit. Beer…

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$107.00

Brunch Sail with Tony Lucca

July 9 @ 10:00 am - 1:00 pm
Annapolis Waterfront Hotel, 80 Compromise Street
Annapolis, MD 21401 United States

Back for a 5th performance on the Schooner Woodwind! An Intimate, Acoustic Show with TONY LUCCA aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delicious brunch and a relaxing sail. Tony Lucca captured America’s hearts in 2012 as the Team Adam finalist on NBC’s hit TV show “The Voice.” Lucca’s duet of “Yesterday” by The Beatles with coach Adam Levine (Maroon 5) landed Top 5 on iTunes Overall and Pop Singles sales charts.…

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Everything Local Dinner Cruise

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 prides itself 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 soda &…

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August 2017

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.  The 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.   Includes a take-home, boat friendly, wine glass by Go Vino with the Woodwind's logo on it. Raise the sails, steer the boat…

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September 2017

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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October 2017

Brews in the Breeze Lunch Cruise

October 8 @ 11:00 am - 1:30 pm
Annapolis City Marina, 410 Severn Ave
Annapolis, MD 21403 United States

Sail on a lunchtime cruise of beer tasting on the Chesapeake Bay. 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 $84 per adult and include lunch, four 6 oz. beers, and unlimited soda and water. Additional beer will be available for purchase.  Departs  Annapolis at 11:00 am and returns…

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Schooner Race Watch Cruise

October 12 @ 12:00 pm - 3:00 pm
Annapolis City Marina, 410 Severn Ave
Annapolis, MD 21403 United States
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 $86 per adult and $48 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 Chesapeake…

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October Lighthouse Cruise

October 14 @ 10:30 am - 2:30 pm
Annapolis City Marina, 410 Severn Ave
Annapolis, MD 21403 United States
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. Scroll down to see menu choices. Cruise Departs from Annapolis City Marina (Boat Shows are in town)  …

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Brews in the Breeze Lunch Cruise

October 15 @ 11:00 am - 1:30 pm
Annapolis City Marina, 410 Severn Ave
Annapolis, MD 21403 United States

Sail on a lunchtime cruise of beer tasting on the Chesapeake Bay. 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 $84 per adult and include lunch, four 6 oz. beers, and unlimited soda and water. Additional beer will be available for purchase.  Departs  Annapolis at 11:00 am and returns…

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