Upcoming Events › Specialty Cruises

June 21, 2015

Father’s Day Brunch

Fathers Day Sailing Cruises Annapolis MD

Our Father’s Day Brunch Sail departs Annapolis for a three-hour Brunch cruise at 10:00am and returns at 1:00pm. Sailing cruise includes one free Bloody Mary or Mimosa and delicious food: homemade scones, quiche lorraine squares, baked citrus salmon with hearty bread, grilled flank steak, fresh fruit salad, orange juice and homemade biscotti. $88 per person, …
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Start: June 21, 2015 10:00 am
End: June 21, 2015 1:00 pm
Venue: Annapolis Marriott Waterfront Hotel
Address:
80 Compromise Street, Annapolis, MD, 21401, United States
Adults: $88.00
Children: $48.00
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June 28, 2015

Brews in the Breeze Lunch Cruise

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 …
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Start: June 28, 2015 12:30 pm
End: June 28, 2015 3:00 pm
Venue: Annapolis Marriott Waterfront Hotel
Address:
80 Compromise Street, Annapolis, MD, 21401, United States
Adults: $78.00
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July 4, 2015

Fireworks Cruise

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 Marriott dock at 6:30pm for a sunset sail with live entertainment by “Ship’s Company”. We will then anchor close to the fireworks barge for the 9:15pm fireworks display and return to the dock after the show. Tickets …
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Start: July 4, 2015 6:30 pm
End: July 4, 2015 10:00 pm
Venue: Annapolis Marriott Waterfront Hotel
Address:
80 Compromise Street, Annapolis, MD, 21401, United States
Adults: $84.00
Children: $57.00
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July 12, 2015

July Wine in the Wind

Wine in the Wind, Woodwind in a glass!

Join us for a three hour sail around the Bay sampling wonderful wines.  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: $109 per person. Maximum 35 …
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Start: July 12, 2015 2:00 pm
End: July 12, 2015 5:00 pm
Venue: Annapolis Marriott Waterfront Hotel
Address:
80 Compromise Street, Annapolis, MD, 21401, United States
Adults: $109.00
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July 26, 2015

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 7 albums, toured all 50 states, and seen his popularity swell to half a million Twitter followers, 4 million YouTube views, and nearly 10 million plays …
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Start: July 26, 2015 10:00 am
End: July 26, 2015 1:00 pm
Venue: Annapolis Marriott Waterfront Hotel
Address:
80 Compromise Street, Annapolis, MD, 21401, United States
Adults: $89.00
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Everything Local Dinner Cruise

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 purchase locally or grow yourself. Tickets are $109 per adult and include three course dinner, 3 drink vouchers, and unlimited soda & water. Maximum 35 guests. Menu & Beverages TBD

Start: July 26, 2015 6:30 pm
End: July 26, 2015 9:00 pm
Venue: Annapolis Marriott Waterfront Hotel
Address:
80 Compromise Street, Annapolis, MD, 21401, United States
Adults: $109.00
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August 9, 2015

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, $93 per adult, $56 per child …
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Start: August 9, 2015 11:30 am
End: August 9, 2015 3:30 pm
Venue: Annapolis Marriott Waterfront Hotel
Address:
80 Compromise Street, Annapolis, MD, 21401, United States
Adults: $93.00
Children: $56.00
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August 23, 2015

August 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 2:00pm, return at 5:00pm. Price: $109 per person. Maximum 35 …
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Start: August 23, 2015 2:00 pm
End: August 23, 2015 5:00 pm
Venue: Annapolis Marriott Waterfront Hotel
Address:
80 Compromise Street, Annapolis, MD, 21401, United States
Adults: $109.00
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September 13, 2015

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 13, 2015 5:30 pm
End: September 13, 2015 8:00 pm
Venue: Annapolis Marriott Waterfront Hotel
Address:
80 Compromise Street, Annapolis, MD, 21401, United States
Adults: $109.00
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October 11, 2015

Champagne Brunch

Schooner Woodwind Champagne Brunch Sailing Cruise

Join the Woodwind crew for the most festive brunch on the Bay! Enjoy a very “bubbly” beverage selection, including sparkling wine, and two other champagne cocktails accompanied by delicious food and always entertaining company!   Menu TBD Cruise departs from the Annapolis City Marina in Eastport at 11:30 and returns at 2:30pm.

Start: October 11, 2015 11:30 am
End: October 11, 2015 2:30 pm
Venue: Annapolis City Marina
Address:
410 Severn Ave, Annapolis, MD, 21403, United States
Adults: $109.00
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