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Also known as America’s sailing capital, Annapolis and nearby communities have many boating companies that offer public and charter dinner cruises. 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. These well- established local companies provide unique adventures of varying durations – from on-demand water taxis to foodie-favorite wine and dinner cruises. 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.
Annapolis Electric Boat Rentals
Head around Horn Point at the east end of Eastport and cruise up Back Creek to get to Davis’ Pub and other Eastport eateries via a short walk from a street-end dock. We charter the Miss Grace multiple times a year with our business clients and personally. 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. 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.
Cruising
If you decide to head a little farther up or downstream from Annapolis, you’ll find other great choices. The Severn Inn is a classy place with fair-weather docking but gorgeous sunset views of Annapolis. Cantler’s Riverside Inn off Whitehall Bay is a classic crab house with brown paper rolled out on the tables for picking crabs.
Guide Services & Walking Tours
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 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. “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. 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.
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. 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.
The Miss Grace is not just for fishing.
He said no harm no foul if you don’t want to come out today based upon what was going on fish wise. A sunset cruise, a romantic dinner, a family excursion, a wedding proposal….. Seas the Bay will help you design your special day in Annapolis.
From live music cruises to New Year’s Eve, Watermark offers a variety of special and seasonal cruises throughout the year. Join the crew and race Woodwind vs. Woodwind II every Wednesday night from late April through late August. There can be up to 100 other sailboats racing in the Wednesday Night Regatta sponsored by the Annapolis Yacht Club.
Private Chesapeake Bay Charters………..Like No Other………..
Enjoy picturesque views from your very own private yacht. Enjoy a fun music playlist, the sun setting, and a cool beverage from our River Run Bar as you relax on this 60-minute cruise through the Annapolis Harbor. Cruise across the Chesapeake Bay to St. Michaels on the Eastern Shore. Enjoy fresh seafood, boutique shopping, and historic sites all within walking distance. Naval Academy, Annapolis’ role as a historic seaport, the region’s waterways, and catch a glimpse of the Bay Bridge.
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The golden glow reflecting off the sails as the sun descends near the horizon is an unforgettable sight. Welcome Aboard our two beautiful, wooden 74-foot schooners, Woodwind and Woodwind II, for a true sailing experience in Annapolis, Maryland. From School Field Trips to Summer Camps, Watermark is proud to host thousands of students each year on our educational cruises and walking tours. Somehow you’ve got to secure the boat so it’s safe from incoming weather and seas and then make sure your crew moves from the boat to terra firma without getting soaked. We source everything from the Chesapeake Bay Watershed area.
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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. Situated on the Chesapeake Bay near the Severn River, Annapolis is the capital of Maryland and was once the capital of the United States. 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.
Step aboard our cozy launch for an intimate cruise up Spa Creek into the residential area of Old Annapolis, Eastport, and the banks of the U.S.
Woodwind Cruises can accommodate 48 passengers on each ship. 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. In 2011, dinner cruises last three hours and include a murder mystery.
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 you that favorite beverage as you relax watching the sunset over the city skyline. Sunset is a favorite time for a sail on the Woodwinds. The sunset over the Annapolis skyline is breathtaking.
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. 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.
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. 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.
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