Calendar of Events › Specialty Cruises

June 15, 2014

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. $86 per person, …
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Start: June 15, 2014 10:00 am
End: June 15, 2014 1:00 pm
Venue: Annapolis Marriott Waterfront Hotel
Address:
80 Compromise Street, Annapolis, MD, 21401, United States
Adults: $86.00
Children: $48.00
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June 8, 2014

June 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 from Tuscan region of Italy.  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: …
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Start: June 8, 2014 2:00 pm
End: June 8, 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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May 21, 2014

Blue Angels Performance Cruise

Blue Angels

Watch the Blue Angels perform their aero-acrobatics during this special cruise. Depart from Annapolis at 11:30am and return at 3:30pm. Advanced ticket purchase required, includes box lunch, soda, and snacks; $89 per person, $56 per child w/child’s lunch. Maximum 40 guests.       Gourmet Bagged Lunch includes: Gourmet Sandwich (choose one) Grilled fajita spiced …
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Start: May 21, 2014 11:30 am
End: May 21, 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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May 20, 2014

Blue Angels Practice Cruise

Blue Angels

Watch the Blue Angels practice their aero-acrobatics during this special cruise. Depart from Annapolis at 11:00am and return at 3:30pm. Advanced ticket purchase required, includes box lunch, soda, and snacks; $89 per person, $56 per child w/child’s lunch. Maximum 40 guests.       Gourmet Bagged Lunch includes: Gourmet Sandwich (choose one) Grilled fajita spiced …
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Start: May 20, 2014 11:00 am
End: May 20, 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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May 11, 2014

Mother’s Day Brunch

Bring Mom aboard the Schooner Woodwind for a memorable Mother's Day Brunch Sail

Our Mother’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. $86 per person, …
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Start: May 11, 2014 10:00 am
End: May 11, 2014 1:00 pm
Venue: Annapolis Marriott Waterfront Hotel
Address:
80 Compromise Street, Annapolis, MD, 21401, United States
Adults: $86.00
Children: $48.00
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May 4, 2014

May 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 person, $56 per child …
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Start: May 4, 2014 10:30 am
End: May 4, 2014 2:30 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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April 26, 2014

Saturday Night Sailor’s Delight Cocktail Cruise

Sunset from Schooner Woodwind II of Schooner Woodwind in lovely Annapolis

Sail away on one of our first sunset sails of the season. Enjoy great appetizers, cocktails, wine and beer as you enjoy the scenery of the Chesapeake Bay. Cruise includes appetizers, three drink vouchers and a sunset sail.  Depart Annapolis at 5:30pm, return at 7:30pm.  Tickets are $59 per adult with a maximum of 35 …
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Start: April 26, 2014 5:30 pm
End: April 26, 2014 7:30 pm
Venue: Annapolis Marriott Waterfront Hotel
Address:
80 Compromise Street, Annapolis, MD, 21401, United States
Adults: $59.00
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April 25, 2014

Friday Night Sailor’s Delight Cocktail Cruise

Sunset from Schooner Woodwind II of Schooner Woodwind in lovely Annapolis

Sail away on one of our first sunset sails of the season. Enjoy great appetizers, cocktails, wine and beer as you enjoy the scenery of the Chesapeake Bay. Cruise includes appetizers, three drink vouchers and a sunset sail.  Depart Annapolis at 5:30pm, return at 7:30pm.  Tickets are $59 per adult with a maximum of 35 …
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Start: April 25, 2014 5:30 pm
End: April 25, 2014 7:30 pm
Venue: Annapolis Marriott Waterfront Hotel
Address:
80 Compromise Street, Annapolis, MD, 21401, United States
Adults: $59.00
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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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