Embark on an unforgettable tour with a carefully crafted menu of food & drink. Custom built for sailing, comfort and fun, the Liberte is a grand experience for all. Our cruising grounds are some of the most beautiful and historic in the country. The captain and crew are dedicated to your safety, comfort and enjoyment. In addition to our regular afternoon and sunset sails on the Bay, we offer custom charters. We are passionate about sailing and will design a charter for you.
Schooner Woodwind
This historic city is home to the United States Naval Academy, the third-oldest college in the country, St. John’s College, and the homes of four signers of the Declaration of Independence. Also known as America’s sailing capital, Annapolis and nearby communities have many boating companies that offer public and charter dinner cruises. Schooner Woodwind owner and seasoned sailor Jen Kaye is also a “foodie,” who masterminds “Wine in the Wind” evenings. Join Watermark and Ken’s Creative Kitchen aboard Raven for an intimate holiday dinner. Live jazz and holiday classics with Fred Hughes and Paul Langosch will set the mood for appetizers and dinner on the main deck. Then, venture to the open-air top deck to take in the scenery and see the Eastport Yacht Club’s Lights Parade.
Beer Tasting Tuesdays
These well- established local companies provide unique adventures of varying durations – from on-demand water taxis to foodie-favorite wine and dinner cruises. Woodwind sails up to four times daily throughout our summer season from the Annapolis Waterfront Hotel. Let our captains and crew make your trip most enjoyable and memorable. Help hoist the sails (all 4 of them) or take a turn at the wheel. Our specialty sailing cruises are on sale now for this season.
Fishing Seasons
Join us for a two 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. Annapolis Sailing Schooner Woodwind Cruises (schoonerwoodwind.com) operates two boats for public sightseeing cruises and special event sailings. Passengers can help steer, raise the sails or just enjoy the view from Chesapeake Bay.
Father’s Day Brunch Sail
Captain Karl sets the bar high for all others to follow.. Case in point he called me a few hours before the charter and said they are having a slow day fishing due to the wave conditions. He said no harm no foul if you don’t want to come out today based upon what was going on fish wise.
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Have a group of up to 16 passengers?
Included in the ticket are an open beer and wine bar, butler-served hors d'oeuvres, as well as dinner and dessert service at a private table. After fishing with several other bay charters over the years I had an opportunity to fish with Captain Karl & Eric aboard Miss Grace. What a difference, from the spotless boat to the precise way every bait is rigged and deployed. I have taken friends, family & clients and Miss Grace never disappoints. They are the best in the business and the best on the bay.
Woodwind Cruises can accommodate 48 passengers on each ship. Three-hour sail around the Bay sampling wonderful wine. This will be a relaxing sail including afternoon hors d’oeuvres, soft drinks, and four samples of the wine. The Black-Eyed Susan (baltimorepaddlewheel.com), located in Baltimore, is a two-deck paddlewheel riverboat. The lower deck is enclosed while the upper deck has a canopy top and clear sides that will fold down when the weather is not ideal. Able to carry 149 passengers, the Black-Eyed Susan is used mostly for private charters but does offer special theme sailings on the Patapsco River, including dinner cruises.
From special Mother’s & Father’s Day cruises to lighthouse cruises, seeing the Blue Angels overhead, and many other special occasions. View a sampling of our offerings by month below, and check back in mid to late February when our full event calendar becomes available complete with the ability to purchase tickets. Situated on the Chesapeake Bay near the Severn River, Annapolis is the capital of Maryland and was once the capital of the United States.
Wine in the Wind: France
Many alterations were made to the design, including adding a spoon bow, scaling down the lines to meet U.S. Coast Guard parameters, redesigning the deck layout and adjusting the rig to a three-masted staysail design. Reliance Fire Protection has been chartering with Miss Grace for nearly 20 years. We both entertain customers and charter trips to reward employees. The Miss Grace Captain and mate, are very professional, mingle with and entertain our customers and employees, and work hard to make sure the charter is a success. Capt Karl, I just wanted to drop you a quick note thanking you and Eric for another memorable experience on the Miss Grace.
I really appreciate you always taking great care of our employees and customers. I see my good client Dave Smith caught the biggest fish once again…45 inches! We sail rain or shine unless the captain cancels the cruise due to unsafe conditions. The schooner, Liberté, is based on Spa Creek in Annapolis, Maryland.
During the summer months, she’s docked at the Patriot Party Boats pier in Falmouth harbor in Cape Cod, Massachusetts. Captain Chris and Jane had this vessel built just for them. We source everything from the Chesapeake Bay Watershed area. From Maryland Wine to Virginia spirits and all the foods that are found around this area, we create a very special dinner cruise.
Reservation holders are entitled to a Cuzon Rum Punch beverage on board and another at the informal “after party” at the Boatyard Bar and Grill in Eastport. Spirit of Baltimore (spiritcruisesbaltimore.com) sails from Baltimore, along the Patapsco River. Located about half an hour outside of Annapolis, the Spirit of Baltimore offers lunch, dinner, theme, holiday and charter cruises for up to 450 passengers.
This perfect “day on the bay” is a double-edged treat, with fare that includes a complimentary ticket to the Maryland Maritime Museum, the boat’s docking destination in St. Michael’s. Ticket holders for the cruise have a three-hour layover in St. Michael’s, a town with many good restaurants – among them the Crab Claw (super casual) and the elegant Inn at Perry Cabin. Throughout the sailing season, we offer specialty cruises that make any day exceptional. Embark on an unforgettable tour with a carefully crafted menu of food and drink.
Dinner cruises include a DJ, live performers, dancing and a meal. Passengers can dine on salad, beef, pork, chicken, salmon, pasta, vegetables and dessert. Spirit of Baltimore has two enclosed decks and one upper patio deck. We are a family-owned and operated company based in Annapolis Maryland, offering private sails for any occasion on Southerly, our 54 ft. From three-hour day cruises to sunset dinner sails, to wedding proposals and photo shoots, we can customize your sailing charter for an on-the-water experience to remember.
In 2011, dinner cruises last three hours and include a murder mystery. While trying to solve the whodunit, passengers can dine on salad, beef, crab cakes, potatoes, vegetables and a dessert buffet. Being one of the largest charter boats on the Chesapeake Bay, We offer a variety of cruises, tours, and trips, from a variety of pick-up and return locations, North and South of Deale. Our spacious cockpit and salon is the perfect place to enjoy a group outing with friends, birthday party or night out to dinner at one of the local waterfront restaurants. We can handle any and all catering needs, so all you have to do is step aboard and relax. “Party Like a Sailor” events provide a taste of sailboat racing, with both schooners competing with each other during the popular Wednesday Night Races sponsored by the Annapolis Yacht Club.
You must buy a ticket for Boat Show Admission in order to sail aboard Woodwind. We do sell combo tickets which will save you some money. A guided tour exploring the history of the area, the Chesapeake, and the sights you see while on a sail. Each week we will focus on a specific interesting topic with a guest speaker aboard. Groups can reserve space more than six days in advance so you can start planning your event now and know you have that date reserved.
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