Things to Do Boating

Annapolis Sailing Cruises: Schooner Woodwind

80 Compromise St., Annapolis, MD 21401
(410) 263-7837
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About Annapolis Sailing Cruises: Schooner Woodwind

Sail the Chesapeake on a 74-foot schooner! Raise the sails, steer the boat, or sit back and relax on a two-hour sail. Special, longer event cruises, too. The Woodwind and Woodwind II offer a real Chesapeake sailing experience for public sails and private events. Buy a ticket, or privately rent the entire boat. Fun, team match racing, corporate outings, crab feasts and catered sunset sails. Sailing is a great way to celebrate birthdays, reunions, and a wedding weekend. Departs from the downtown, Annapolis Waterfront Hotel.

Attraction

General

- Family Friendly

- Maximum Group:

96

- Reservation Recommended

Onsite

- Alcohol Served

- Box Lunch Available

- Group Tours Available

- Private Tours Available

- Restrooms Onsite


General

Pricing

- Payment Methods Accepted

American Express, Discover, Master Card, Visa,

Fall Sailing on the Chesapeake Bay
Annapolis Sailing Cruises: Schooner Woodwind

Fall Sailing on the Chesapeake Bay

October 17, 2019

Help raise the sails, steer the boat or just sit back and relax aboard the Schooner Woodwind. For the month of October, weekday cruises require a 12 person minimum and one day's notice, but no minimums on weekend cruises. Sail times are 12:30-2:30 & 3:00-5:00 and all cruises depart from the Annapolis Waterfront Hotel. Tickets are $48 for adults and $31 for children under 12 years and include a soft drink/bottle of water, snack, and tax.  Beer and wine are available for purchase during the cruise. 

Fall Sailing on the Chesapeake Bay Begins!
Annapolis Sailing Cruises: Schooner Woodwind

Fall Sailing on the Chesapeake Bay Begins!

October 17, 2019

Help raise the sails, steer the boat or just sit back and relax aboard the Schooner Woodwind. For the month of October, weekday cruises require a 12 person minimum and one day's notice, but no minimums on weekend cruises. Sail times are 12:30-2:30 & 3:00-5:00 and all cruises depart from the Annapolis Waterfront Hotel. Tickets are $48 for adults and $31 for children under 12 years and include a soft drink/bottle of water, snack, and tax.  Beer and wine are available for purchase during the cruise. 

Schooner Race Watch Cruise
Annapolis Waterfront Hotel Dock

Schooner Race Watch Cruise

October 17, 2019

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. There will be up to 25 plus schooners at the starting line. Seven of them are at least near 100+ feet. This is going to be incredible. Join the fun! They will be racing to the Norfolk area, we will cheer them on till it’s time to go in. We will be under sail with the schooners (and yes you’ll be sailing on one too). We will not cross the starting line, but we will be sailing around them all as they come down from Baltimore. The cruise departs Annapolis City Marina Dock at Noon and returns to Annapolis City Marina Dock at  3:00pm.  Ticket Price includes bagged lunch, soft drinks, and bottled water and tax.  Our cash bar includes a selection of Craft Beer, Wine & Bubbly! Gourmet Bagged Lunch includes: Adult Bagged Lunches include dill potato salad, charred corn, and fennel slaw & a Cowboy cookie. Sandwiches (Choose 1 per adult ticket) Cranberry Pecan Chicken Salad Wrap Honey Ham with Boursin cheese, rosemary mustard & arugula on a multigrain baguette Vegetarian Hearts & Greens Wrap with artichoke hearts, power greens, almonds & tarragon mayo Child’s Bagged Lunch includes a cluster of grapes & Cowboy cookie Sandwiches served on thick egg bread (Choose 1 per child ticket) Almond Butter & Homemade Blueberry-Pomegranate Jam Turkey & Cheese

Thursday Acoustic Music Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Thursday Acoustic Music Sunset Sail

September 26, 2019

Sit back and relax as Roadside Show entertain you while sailing on the Chesapeake Bay. The cruise departs from the Annapolis Waterfront Hotel dock at 5:30 p.m. and returns 7:30 p.m. Tickets are $48 for adults and $31 for children under 12 years and include a soft drink/bottle of water, snack, and tax.  Beer and wine are available for purchase during the cruise.   

Monday Chesapeake Bay History Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Monday Chesapeake Bay History Sunset Sail

September 23, 2019

Enjoy learning about Annapolis with Kevin Brooks.  When you set sail from downtown Annapolis, you see the gorgeous historic skyline that has welcomed ships in for centuries.  We sail past the United States Naval Academy and into the Chesapeake Bay. Come listen to the stories that make up the fabric of history in this terrific town.  Topics change weekly.  Cruises depart from the Annapolis Waterfront Hotel Dock at 5:30 pm and return at 7:30 pm. Sail includes soft drink or bottled water and snack.  Beer & wine are available for purchase. 

Classic Wooden Boat Regatta
Annapolis Waterfront Hotel Dock

Classic Wooden Boat Regatta

September 22, 2019

Participate in the Classic Wooden Boat Regatta. The Woodwinds’ have been invited 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 to win the regatta. This will be an amazing trip for photography (hint B&W or sepia tone) of these old, gorgeous boats. This is going to be a fun, challenging race! Join the crew! Cruise departs Annapolis Waterfront Hotel Dock at 11:00 am and returns to Annapolis Waterfront Hotel Dock at  2:30pm.  Ticket Price includes bagged lunch, soft drinks, and bottled water and tax.  Our cash bar includes a selection of Craft Beer, Wine & Bubbly! Gourmet Bagged Lunch includes: Adult Bagged Lunches include dill potato salad, charred corn, and fennel slaw & a Cowboy cookie. Sandwiches (Choose 1 per adult ticket) Cranberry Pecan Chicken Salad Wrap Honey Ham with Boursin cheese, rosemary mustard & arugula on a multigrain baguette Vegetarian Hearts & Greens Wrap with artichoke hearts, power greens, almonds & tarragon mayo Child’s Bagged Lunch includes a cluster of grapes & Cowboy cookie Sandwiches served on thick egg bread (Choose 1 per child ticket) Almond Butter & Homemade Blueberry-Pomegranate Jam Turkey & Cheese

Thursday Acoustic Music Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Thursday Acoustic Music Sunset Sail

September 19, 2019

Sit back and relax as Deanna Dove entertains you while sailing on the Chesapeake Bay. The cruise departs from the Annapolis Waterfront Hotel dock at 5:30 p.m. and returns 7:30 p.m. Tickets are $48 for adults and $31 for children under 12 years and include a soft drink/bottle of water, snack, and tax.  Beer and wine are available for purchase during the cruise.   

Monday Chesapeake Bay History Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Monday Chesapeake Bay History Sunset Sail

September 16, 2019

Enjoy learning about Annapolis with Jeff Holland.  When you set sail from downtown Annapolis, you see the gorgeous historic skyline that has welcomed ships in for centuries.  We sail past the United States Naval Academy and into the Chesapeake Bay. Come listen to the stories that make up the fabric of history in this terrific town.  Topics change weekly.  Cruises depart from the Annapolis Waterfront Hotel Dock at 5:30 pm and return at 7:30 pm. Sail includes soft drink or bottled water and snack.  Beer & wine are available for purchase. 

Thursday Acoustic Music Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Thursday Acoustic Music Sunset Sail

September 12, 2019

Sit back and relax as Roadside Show entertain you while sailing on the Chesapeake Bay. The cruise departs from the Annapolis Waterfront Hotel dock at 5:30 p.m. and returns 7:30 p.m. Tickets are $48 for adults and $31 for children under 12 years and include a soft drink/bottle of water, snack, and tax.  Beer and wine are available for purchase during the cruise.   

Monday Chesapeake Bay History Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Monday Chesapeake Bay History Sunset Sail

September 9, 2019

Enjoy learning about Annapolis with Michael John William.  When you set sail from downtown Annapolis, you see the gorgeous historic skyline that has welcomed ships in for centuries.  We sail past the United States Naval Academy and into the Chesapeake Bay. Come listen to the stories that make up the fabric of history in this terrific town.  Topics change weekly.  Cruises depart from the Annapolis Waterfront Hotel Dock at 5:30 pm and return at 7:30 pm. Sail includes soft drink or bottled water and snack.  Beer & wine are available for purchase. 

Thursday Acoustic Music Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Thursday Acoustic Music Sunset Sail

September 5, 2019

Sit back and relax as the Eastport Oyster Boys entertain you while sailing on the Chesapeake Bay. The cruise departs from the Annapolis Waterfront Hotel dock at 6:30 p.m. and returns 8:30 p.m. Tickets are $48 for adults and $31 for children under 12 years and include a soft drink/bottle of water, snack, and tax.  Beer and wine are available for purchase during the cruise.   

Tuesday Beer Tasting Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Tuesday Beer Tasting Sunset Sail

September 3, 2019

Sample while you sail!  A representative from Union Craft Brewing in Baltimore, MD comes aboard and teaches you about their beer. 3 samples of beer come with the cruise and then order full beers from the brews that you enjoyed the most.  Cruise departs from the Annapolis Waterfront Hotel Dock at 5:30 pm and returns at 7:30 pm. Sail includes a soft drink or bottled water and snack.  Beer & wine are available for purchase. 

Thursday Acoustic Music Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Thursday Acoustic Music Sunset Sail

August 29, 2019

Sit back and relax as Ken Wenzel entertains you while sailing on the Chesapeake Bay. The cruise departs from the Annapolis Waterfront Hotel dock at 6:30 p.m. and returns 8:30 p.m. Tickets are $48 for adults and $31 for children under 12 years and include a soft drink/bottle of water, snack, and tax.  Beer and wine are available for purchase during the cruise.   

Wednesday Night Races
Annapolis Sailing Cruises: Schooner Woodwind

Wednesday Night Races

August 28, 2019

Woodwind and Woodwind II will be match racing every Wednesday night that there is an Annapolis Yacht Club (AYC) Race. Both boats will start on the AYC starting line at 6:45pm, and then race out to a slightly different race course, probably a little longer. During the race, passengers (“guest crew”) will be able to participate in helping to sail the boat and steer the boat, when appropriate of course.

Tuesday Beer Tasting Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Tuesday Beer Tasting Sunset Sail

August 27, 2019

Sample while you sail!  A representative from Port City Brewery in Alexandria, VA comes aboard and teaches you about their beer. 3 samples of beer come with the cruise and then order full beers from the brews that you enjoyed the most.  Cruise departs from the Annapolis Waterfront Hotel Dock at 5:30 pm and returns at 7:30 pm. Sail includes a soft drink or bottled water and snack.  Beer & wine are available for purchase. 

Tuesday Beer Tasting Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Tuesday Beer Tasting Sunset Sail

August 27, 2019

Sample while you sail!  A representative from Port City Brewery in Alexandria, VA comes aboard and teaches you about their beer. 3 samples of beer come with the cruise and then order full beers from the brews that you enjoyed the most.  Cruise departs from the Annapolis Waterfront Hotel Dock at 5:30 pm and returns at 7:30 pm. Sail includes a soft drink or bottled water and snack.  Beer & wine are available for purchase. 

Daily Sailing on the Chesapeake Bay
Annapolis Sailing Cruises: Schooner Woodwind

Daily Sailing on the Chesapeake Bay

August 26, 2019

Help raise the sails, steer the boat or just sit back and relax aboard the Schooner Woodwind. Sail times are 12:30-2:30, 3:00-5:00, & 5:30-7:30 and all cruises depart from the Annapolis Waterfront Hotel. View our website to see about our fun Sunset Sails and Specialty Sails.  Tickets are $48 for adults and $31 for children under 12 years and include a soft drink/bottle of water, snack, and tax.  Beer and wine are available for purchase during the cruise. 

Monday Chesapeake Bay History Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Monday Chesapeake Bay History Sunset Sail

August 26, 2019

Enjoy learning about Annapolis with Dave Gendell.  When you set sail from downtown Annapolis, you see the gorgeous historic skyline that has welcomed ships in for centuries.  We sail past the United States Naval Academy and into the Chesapeake Bay. Come listen to the stories that make up the fabric of history in this terrific town.  Topics change weekly.  Cruises depart from the Annapolis Waterfront Hotel Dock at 5:30 pm and return at 7:30 pm. Sail includes soft drink or bottled water and snack.  Beer & wine are available for purchase. 

Thursday Acoustic Music Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Thursday Acoustic Music Sunset Sail

August 22, 2019

Sit back and relax as Dirk Schwenk entertains you while sailing on the Chesapeake Bay. The cruise departs from the Annapolis Waterfront Hotel dock at 6:30 p.m. and returns 8:30 p.m. Tickets are $48 for adults and $31 for children under 12 years and include a soft drink/bottle of water, snack, and tax.  Beer and wine are available for purchase during the cruise.   

Monday Chesapeake Bay History Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Monday Chesapeake Bay History Sunset Sail

August 19, 2019

Enjoy learning about Annapolis with Jeff Holland.  When you set sail from downtown Annapolis, you see the gorgeous historic skyline that has welcomed ships in for centuries.  We sail past the United States Naval Academy and into the Chesapeake Bay. Come listen to the stories that make up the fabric of history in this terrific town.  Topics change weekly.  Cruises depart from the Annapolis Waterfront Hotel Dock at 6:30 pm and return at 8:30 pm. Sail includes soft drink or bottled water and snack.  Beer & wine are available for purchase. 

Thursday Acoustic Music Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Thursday Acoustic Music Sunset Sail

August 15, 2019

Sit back and relax as Don Shapelle & Don Sennett entertain you while sailing on the Chesapeake Bay. The cruise departs from the Annapolis Waterfront Hotel dock at 6:30 p.m. and returns 8:30 p.m. Tickets are $48 for adults and $31 for children under 12 years and include a soft drink/bottle of water, snack, and tax.  Beer and wine are available for purchase during the cruise.   

Thursday Acoustic Music Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Thursday Acoustic Music Sunset Sail

August 8, 2019

Sit back and relax as Deanna Dove entertains you while sailing on the Chesapeake Bay. The cruise departs from the Annapolis Waterfront Hotel dock at 6:30 p.m. and returns 8:30 p.m. Tickets are $48 for adults and $31 for children under 12 years and include a soft drink/bottle of water, snack, and tax.  Beer and wine are available for purchase during the cruise.   

Tuesday Beer Tasting Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Tuesday Beer Tasting Sunset Sail

August 6, 2019

Sample while you sail!  A representative from Port City Brewery in Alexandria, VA comes aboard and teaches you about their beer. 3 samples of beer come with the cruise and then order full beers from the brews that you enjoyed the most.  Cruise departs from the Annapolis Waterfront Hotel Dock at 6:30 pm and returns at 8:30 pm. Sail includes a soft drink or bottled water and snack.  Beer & wine are available for purchase. 

Tuesday Beer Tasting Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Tuesday Beer Tasting Sunset Sail

August 6, 2019

Sample while you sail!  A representative from Port City Brewery in Alexandria, VA comes aboard and teaches you about their beer. 3 samples of beer come with the cruise and then order full beers from the brews that you enjoyed the most.  Cruise departs from the Annapolis Waterfront Hotel Dock at 6:30 pm and returns at 8:30 pm. Sail includes a soft drink or bottled water and snack.  Beer & wine are available for purchase. 

Tuesday Beer Tasting Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Tuesday Beer Tasting Sunset Sail

August 6, 2019

Sample while you sail!  A representative from Port City Brewery in Alexandria, VA comes aboard and teaches you about their beer. 3 samples of beer come with the cruise and then order full beers from the brews that you enjoyed the most.  Cruise departs from the Annapolis Waterfront Hotel Dock at 6:30 pm and returns at 8:30 pm. Sail includes a soft drink or bottled water and snack.  Beer & wine are available for purchase. 

Tuesday Beer Tasting Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Tuesday Beer Tasting Sunset Sail

August 6, 2019

Sample while you sail!  A representative from Port City Brewery in Alexandria, VA comes aboard and teaches you about their beer. 3 samples of beer come with the cruise and then order full beers from the brews that you enjoyed the most.  Cruise departs from the Annapolis Waterfront Hotel Dock at 6:30 pm and returns at 8:30 pm. Sail includes a soft drink or bottled water and snack.  Beer & wine are available for purchase. 

Tuesday Beer Tasting Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Tuesday Beer Tasting Sunset Sail

August 6, 2019

Sample while you sail!  A representative from Port City Brewery in Alexandria, VA comes aboard and teaches you about their beer. 3 samples of beer come with the cruise and then order full beers from the brews that you enjoyed the most.  Cruise departs from the Annapolis Waterfront Hotel Dock at 6:30 pm and returns at 8:30 pm. Sail includes a soft drink or bottled water and snack.  Beer & wine are available for purchase. 

Thursday Acoustic Music Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Thursday Acoustic Music Sunset Sail

August 1, 2019

Sit back and relax as Matt & Katie of Stick Mob entertain you while sailing on the Chesapeake Bay. The cruise departs from the Annapolis Waterfront Hotel dock at 6:30 p.m. and returns 8:30 p.m. Tickets are $48 for adults and $31 for children under 12 years and include a soft drink/bottle of water, snack, and tax.  Beer and wine are available for purchase during the cruise.   

Thursday Acoustic Music Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Thursday Acoustic Music Sunset Sail

July 25, 2019

Sit back and relax as the Eastport Oyster Boys entertain you while sailing on the Chesapeake Bay. The cruise departs from the Annapolis Waterfront Hotel dock at 6:30 p.m. and returns 8:30 p.m. Tickets are $48 for adults and $31 for children under 12 years and include a soft drink/bottle of water, snack, and tax.  Beer and wine are available for purchase during the cruise.   

Monday Chesapeake Bay History Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Monday Chesapeake Bay History Sunset Sail

July 22, 2019

Enjoy learning about Annapolis with Tom Guay.  When you set sail from downtown Annapolis, you see the gorgeous historic skyline that has welcomed ships in for centuries.  We sail past the United States Naval Academy and into the Chesapeake Bay. Come listen to the stories that make up the fabric of history in this terrific town.  Topics change weekly.  Cruises depart from the Annapolis Waterfront Hotel Dock at 6:30 pm and return at 8:30 pm. Sail includes soft drink or bottled water and snack.  Beer & wine are available for purchase. 

Thursday Acoustic Music Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Thursday Acoustic Music Sunset Sail

July 18, 2019

Sit back and relax as Dirk Schwenk entertains you while sailing on the Chesapeake Bay. The cruise departs from the Annapolis Waterfront Hotel dock at 6:30 p.m. and returns 8:30 p.m. Tickets are $48 for adults and $31 for children under 12 years and include a soft drink/bottle of water, snack, and tax.  Beer and wine are available for purchase during the cruise.   

Monday Chesapeake Bay History Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Monday Chesapeake Bay History Sunset Sail

July 15, 2019

Enjoy learning about Annapolis with Jeff Holland.  When you set sail from downtown Annapolis, you see the gorgeous historic skyline that has welcomed ships in for centuries.  We sail past the United States Naval Academy and into the Chesapeake Bay. Come listen to the stories that make up the fabric of history in this terrific town.  Topics change weekly.  Cruises depart from the Annapolis Waterfront Hotel Dock at 6:30 pm and return at 8:30 pm. Sail includes soft drink or bottled water and snack.  Beer & wine are available for purchase. 

July Wine In The Wind Sail
Annapolis Waterfront Hotel Dock

July Wine In The Wind Sail

July 14, 2019

Join us for a two-hour sail around the Bay to celebrate Bastille Day by sampling wonderful wines from France - A representative will introduce you to several 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. You will be able to raise the sails, steer the boat or just sit back and relax with your wine and food. Menu & Wines TBD Cruise departs from the Annapolis Waterfront Hotel at 4:00 pm, returning at 6:00 pm.  Tickets are $83 Maximum 40 guests. 

Thursday Acoustic Music Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Thursday Acoustic Music Sunset Sail

July 11, 2019

Sit back and relax as Mike & Kelly Lange entertain you while sailing on the Chesapeake Bay. The cruise departs from the Annapolis Waterfront Hotel dock at 6:30 p.m. and returns 8:30 p.m. Tickets are $48 for adults and $31 for children under 12 years and include a soft drink/bottle of water, snack, and tax.  Beer and wine are available for purchase during the cruise.   

Wednesday Night Races
Annapolis Sailing Cruises: Schooner Woodwind

Wednesday Night Races

July 10, 2019

Woodwind and Woodwind II will be match racing every Wednesday night that there is an Annapolis Yacht Club (AYC) Race. Both boats will start on the AYC starting line at 6:45pm, and then race out to a slightly different race course, probably a little longer. During the race, passengers (“guest crew”) will be able to participate in helping to sail the boat and steer the boat, when appropriate of course.

4th of July Fireworks Cruise
Annapolis Sailing Cruises: Schooner Woodwind

4th of July Fireworks Cruise

July 4, 2019

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 $93 per adult, $66 per child and include bottled water, soft drinks, and a wide selection of desserts including fresh fruit. Beer and wine will be available for purchase. Maximum 40 guests. 

Tuesday Beer Tasting Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Tuesday Beer Tasting Sunset Sail

July 2, 2019

Sample while you sail!  A representative from Hysteria Brewery in Columbia, MD comes aboard and teaches you about their beer. 3 samples of beer come with the cruise and then order full beers from the brews that you enjoyed the most.  Cruise departs from the Annapolis Waterfront Hotel Dock at 6:30 pm and returns at 8:30 pm. Sail includes a soft drink or bottled water and snack.  Beer & wine are available for purchase. 

Monday Chesapeake Bay History Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Monday Chesapeake Bay History Sunset Sail

July 1, 2019

Enjoy learning about Annapolis with Tom Guay.  When you set sail from downtown Annapolis, you see the gorgeous historic skyline that has welcomed ships in for centuries.  We sail past the United States Naval Academy and into the Chesapeake Bay. Come listen to the stories that make up the fabric of history in this terrific town.  Topics change weekly.  Cruises depart from the Annapolis Waterfront Hotel Dock at 6:30 pm and return at 8:30 pm. Sail includes soft drink or bottled water and snack.  Beer & wine are available for purchase. 

Thursday Acoustic Music Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Thursday Acoustic Music Sunset Sail

June 27, 2019

Sit back and relax as the Eastport Oyster Boys entertain you while sailing on the Chesapeake Bay. The cruise departs from the Annapolis Waterfront Hotel dock at 6:30 p.m. and returns 8:30 p.m. Tickets are $48 for adults and $31 for children under 12 years and include a soft drink/bottle of water, snack, and tax.  Beer and wine are available for purchase during the cruise.   

Monday Chesapeake Bay History Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Monday Chesapeake Bay History Sunset Sail

June 24, 2019

Enjoy learning about Annapolis with Kevin Brooks.  When you set sail from downtown Annapolis, you see the gorgeous historic skyline that has welcomed ships in for centuries.  We sail past the United States Naval Academy and into the Chesapeake Bay. Come listen to the stories that make up the fabric of history in this terrific town.  Topics change weekly.  Cruises depart from the Annapolis Waterfront Hotel Dock at 6:30 pm and return at 8:30 pm. Sail includes soft drink or bottled water and snack.  Beer & wine are available for purchase. 

Thursday Acoustic Music Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Thursday Acoustic Music Sunset Sail

June 20, 2019

Sit back and relax as Jason Ager entertains you while sailing on the Chesapeake Bay. The cruise departs from the Annapolis Waterfront Hotel dock at 6:30 p.m. and returns 8:30 p.m. Tickets are $48 for adults and $31 for children under 12 years and include a soft drink/bottle of water, snack, and tax.  Beer and wine are available for purchase during the cruise.   

Monday Chesapeake Bay History Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Monday Chesapeake Bay History Sunset Sail

June 17, 2019

Enjoy learning about Annapolis with Dave Gendell.  When you set sail from downtown Annapolis, you see the gorgeous historic skyline that has welcomed ships in for centuries.  We sail past the United States Naval Academy and into the Chesapeake Bay. Come listen to the stories that make up the fabric of history in this terrific town.  Topics change weekly.  Cruises depart from the Annapolis Waterfront Hotel Dock at 6:30 pm and return at 8:30 pm. Sail includes soft drink or bottled water and snack.  Beer & wine are available for purchase. 

Tuesday Beer Tasting Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Tuesday Beer Tasting Sunset Sail

June 4, 2019

Sample while you sail!  A representative from DC Brau in Washington, DC comes aboard and teaches you about their beer. 3 samples of beer come with the cruise and then order full beers from the brews that you enjoyed the most.  Cruise departs from the Annapolis Waterfront Hotel Dock at 6:30 pm and returns at 8:30 pm. Sail includes a soft drink or bottled water and snack.  Beer & wine are available for purchase. 

Wednesday Night Races
Annapolis Sailing Cruises: Schooner Woodwind

Wednesday Night Races

May 15, 2019

Woodwind and Woodwind II will be match racing every Wednesday night that there is an Annapolis Yacht Club (AYC) Race. Both boats will start on the AYC starting line at 6:45pm, and then race out to a slightly different race course, probably a little longer. During the race, passengers (“guest crew”) will be able to participate in helping to sail the boat and steer the boat, when appropriate of course.

Wednesday Night Races
Annapolis Sailing Cruises: Schooner Woodwind

Wednesday Night Races

May 15, 2019

Woodwind and Woodwind II will be match racing every Wednesday night that there is an Annapolis Yacht Club (AYC) Race. Both boats will start on the AYC starting line at 6:45pm, and then race out to a slightly different race course, probably a little longer. During the race, passengers (“guest crew”) will be able to participate in helping to sail the boat and steer the boat, when appropriate of course.

Daily Sailing on the Chesapeake Bay
Annapolis Sailing Cruises: Schooner Woodwind

Daily Sailing on the Chesapeake Bay

May 11, 2019

Help raise the sails, steer the boat or just sit back and relax aboard the Schooner Woodwind. Sail times are 11:00-1:00, 1:30-3:30, 4:00-6:00, & 6:30-8:30 and all cruises depart from the Annapolis Waterfront Hotel. View our website to see about our fun Sunset Sails and Specialty Sails.  Tickets are $48 for adults and $31 for children under 12 years and include a soft drink/bottle of water, snack, and tax.  Beer and wine are available for purchase during the cruise. 

Wednesday Night Races
Annapolis Sailing Cruises: Schooner Woodwind

Wednesday Night Races

May 1, 2019

Woodwind and Woodwind II will be match racing every Wednesday night that there is an Annapolis Yacht Club (AYC) Race. Both boats will start on the AYC starting line at 6:45pm, and then race out to a slightly different race course, probably a little longer. During the race, passengers (“guest crew”) will be able to participate in helping to sail the boat and steer the boat, when appropriate of course.