Saturday
April 21

Woodwind starts sailing twice a day. (Opening Day)
12:30-2:30 & 3:00-5:00

For the month of April, all weekday cruises require one day's notice. All weekend cruises do not have a minimum. Rates and General Schedule

Saturday
April 28

Woodwind starts sailing three times a day.
12:30-2:30, 3:00-5:00 and a Sunset Sail from 5:30-7:30 pm.
Rates and General Schedule

Saturday
May 12

Woodwind starts sailing four times daily through Labor Day weekend.
11:00-1:00, 1:30-3:30, 4:00-6:00 and a Sunset Sail from 6:30-8:30.
Rates and General Schedule

Sunday
May 20

Lighthouse Cruise: 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 box lunch, soft drinks and snacks, $89 per person, $56 per child with child's lunch. Maximum of 35 guests. See Menu

Sunday
June 10

"Wine in the Wind": A three and a half-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 5:00pm. Price: $99 per person. Maximum 35 guests.

Father's Day Brunch Sail: Depart Annapolis for a three-hour Brunch cruise at 10:00 am and return at 1:00 pm. Cruise comes with a free Bloody Mary or Mimosa and delicious food including homemade scones, quiche lorraine squares, baked citrus salmon with hearty bread, grilled flank steak, fresh fruit salad, orange juice and homemade biscotti. $75 per person, $42 per child. Maximum 40 guests. See Menu

Wednesday
July 4

Fireworks Cruise! Depart from the Marriott dock at 6:30 pm, for a 2 hour sunset sail with live entertainment, then we anchor close to the fireworks barge for the 9:15 show. We return to the dock after the show. $82 per person, $57 per child, which includes a wide selection of desserts and soft drinks. Beer, and wine are extra. See Menu

Sunday
July 15

Lighthouse Cruise: 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 box lunch, soft drinks and snacks, $89 per person, $56 per child w/ child's lunch. Maximum of 35 guests. See Menu

Sunday
July 22

"Wine in the Wind": A three and a half-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 5:00pm. Price: $99 per person. Maximum 35 guests.

Sunday
July 29

Dinner Party Cruise: Enjoy regionally themed food and drinks while cruising the Chesapeake Bay under sail! Depart Annapolis at 6:30 pm, return to the dock at 9:00pm. Includes dinner, 3 drink vouchers, soda and water. Menu will be posted soon. $99 per person, maximum 35 guests.

Sunday
August 12

"Wine in the Wind": A three and a half-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 5:00pm. Price: $99 per person. Maximum 35 guests.

Sunday
August 19

Crafty Brews on the "Heavy Seas" Dinner Cruise: Hugh Sisson, owner of Heavy Seas Brewery (formerly Clipper City) will guide us through a four course dinner pairing great beer, delicious food and fantastic sailing. Depart Annapolis at 6:30 pm, return to the dock at 9:00pm. Includes a glass of beer with each course, soda and water. Menu will be posted soon. $99 per person, maximum 35 guests.

Monday
August 27

Woodwind sails 3 times per day:
12:30-2:30, 3:00-5:00 & Sunset Sail: 5:30-7:30

Rates and General Schedule

Saturday - Monday
September
1-3

Sunday Sept. 23

"Wine in the Wind": A three and a half-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 the wine. Depart Annapolis at 1:30pm, return at 5:00pm. Max 35 guests. Price: $99.

Monday-Wednesday
October 1-3

No public sailing cruises due to Boat Show Setup.

Call 410-263-1981 to book private cruises during this time.

Thursday-Monday
October
4-8

United States Sailboat Show, Woodwind sails four times daily from "E2" Dock in the boat show. We will be running 90 minute cruises, $30 per adult, $20 per child (under 12).

Woodwind's schedule for Boat Show. One of the largest in-the-water shows in the country!

You must buy a ticket for Boat Show Admission in order to sail aboard Woodwind. Buy tickets for Boat Show Admission on their Web Site, here.

Sunday
October 7

Brews in the Breeze Lunch Cruise: Join the Woodwind Crew for an afternoon of beer tasting along with a delicious lunch. After we raise all sails, we'll start with the lightest of our four beers. Lunch will be served buffet style all while sailing on the Bay. Lunch will consist of all your Chesapeake favorites, including crab cakes! $74 per adult includes lunch, four 6 oz. beers, unlimited soda and water. Additional beer can be purchased. 12:30-3:00 pm. Max of 35 people.


Departs from the Annapolis City Marina in Eastport due to Boat Show.

Tuesday-Tuesday October
9-16

No public sailing cruises other than Special Event cruises due to Power Boat Show and the Boat Show Break-Down.
Private Charters and Group Sails can be arranged during this time period.
Call 410-263-1981.

Wednesday- Sunday October
10-14

Annual Chesapeake Bay Schooner Race: Race down the Bay from Annapolis to Portsmouth, Virginia. Over 45 schooners participate each year. Once in a lifetime experience! $900 plus tax per person. Includes everything!
Last year's race.    Previous years.
Three cabins available, call 410-263-1981

Chesapeake Bay Schooner Race Watch: Sail with over 40 other schooners while they start the 130 mile race down the Bay. Depart Annapolis at 12:00 pm, return at 3:00 pm, includes box lunch, soft drinks and snacks, $79 per person, child $45 w/ child's lunch.*$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 Bay Foundation.
See Menu This will sell out very quickly!
Departs from the Annapolis City Marina in Eastport due to Boat Show.

Saturday
October 13

Lighthouse Cruise: 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 box lunch, soft drinks and snacks, $89 per person, child $56 w/ child's lunch. Maximum of 35 guests. See Menu

Departs from the Annapolis City Marina in Eastport due to Boat Show.

Sunday
October 14

Champagne Brunch Cruise: Join the Woodwind Crew for the classiest brunch on the Bay. Enjoy a very "bubbly" beverage selection, including sparkling wine, bellinis and other champagne cocktails. Accompanied by delicious food and always entertaining company! Depart Annapolis at 11:30 a.m., return to the dock at 2:30 p.m. Includes brunch, 3 drink vouchers, soda and water. $99 per person, maximum 35 guests.

Departs from the Annapolis City Marina in Eastport due to Boat Show.

Monday- Friday
October
15-19

Return Cruise from Norfolk to Annapolis

Sold by the cabin, $1600 plus 10% tax. Two people per cabin. Includes accommodations aboard, gourmet meals- 4 breakfasts, 5 lunches, and 3 dinners, one dinner is ashore, sail training (if wanted), and absolutely fantastic scenery! More info & photos.
All cabins available, call 410-263-1981

Wednesday
October 17

Woodwind sails twice a day: 12:30-2:30 & 3:00-5:00

Rates and General Schedule

Sunday
October 28

Public Sailing Season closes at the end of day!

Rates and General Schedule