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The 74-foot schooner Woodwind and Woodwind II were custom designed and built specifically for sailing on the Chesapeake Bay. Woodwind is a replica of the classic, fast wooden schooners that were built as yachts in the early 1900s. Her handsome mahogany brightwork, gleaming chrome, and roomy cockpit distinguish her from cargo-carrying work vessels.
All "romantic dinner cruise" results in Annapolis, Maryland
Some Annapolis companies offer dinner cruises for private charters. Liberte the Schooner (theliberte.com) carries up to 49 passengers on Chesapeake Bay cruises. Passengers choose when they want to sail and for how long, music played on the cruise, and what food and beverages are served. Some companies, such as Admiral of the Bay (admiralofthebay.com), offer a variety of cruises and ships for trips on Chesapeake Bay. Passengers choose motor, sailing or other type of ship as well as where they want to go and what they want to eat. Admiral of the Bay can arrange cruises for up to 240 people.
Dinner Party Cruise
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.
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Karl and his crew went above and beyond for us on multiple occasions. From helping organize and load up the boat for a surprise birthday cruise to navigating the Severn for the Sherwood fireworks on the 4th of July; cruising on the Miss Grace is second to none. A sunset cruise, a romantic dinner, a family excursion, a wedding proposal….. Seas the Bay will help you design your special day in Annapolis. We charter the Miss Grace multiple times a year with our business clients and personally.
Annapolis Sailing School
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.
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They always take great care of us, put us on the fish and everyone has an awesome time. We highly recommend taking your clients or family on the Miss Grace. Each month we feature a different brewery from the Mid-Atlantic Region, and their representative comes aboard and teaches you about beer. 3 samples of beer come with the cruise, and then order full beers from the brews that you enjoyed the most. The original hull design by Dudley Dix is a Hout Bay 70, a two-masted gaff-rigged schooner intended as a heavy but fast offshore cruiser.
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Special event dinner cruises last two and a half hours and include meal options such as bison, crab, chicken, salad, vegetables and dessert. In addition to the meal, passengers will get food lessons from the chef. This includes where to find locally grown foods, what to look for when shopping, recipes and how to prepare the food served during the cruise.
Our bar is stocked with wine and beer, including a nice selection of local craft beer. July can be steamy or dreamy – hot on land but much cooler on the water. Watermark Cruises and the Schooner Woodwind offers a range of options for getting out on the scenic Severn River or the majestic Chesapeake Bay.
Our employees look forward to our annual Fall trip each year and everyone couldn’t have been happier. There is no specific entertainment on these days of the week. There is so much to see as we sail by the United States Naval Academy and into the Chesapeake Bay. Let the crew serve up your favorite beverage as you relax watching the sunset over the city skyline. Capt Karl, thanks again for a great trip, sorry I missed it. I received many notes from our clients saying what a blast they had with you and Eric.
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Amazing Summer Day Trips to the Eastern Shore and Annapolis.
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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.
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.
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.
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.
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.
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