Cruises on the Bay by Watermark
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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.
Rock the Harbor with Tranzfusion 4/26 Spa Creek Cruise — Daily Maryland State House Tour — Fri-Sun
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.
Annapolis Sailing Schooner Woodwind Cruises

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.
United States Sailboat Show
Pssst Mother`s Day is a month away 👀 Have you made plans yet? Treat the moms in your life to a lovely brunch cruise! The really adventurous can travel farther afield to the Magothy River or southward to the South River, West River, or Herring Bay for more fun waterfront restaurants. Or head across the Bay, and you’ll find Hemingway’s and other great dining options along Kent Island’s shore. These destinations are an easy afternoon cruise from Annapolis.
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.
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.
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.
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.
From Maryland Wine to Virginia spirits and all the foods that are found around this area, we create a very special dinner cruise. Reliance Fire Protection has been chartering with Miss Grace for nearly 20 years. We both entertain customers and charter trips to reward employees.

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.
Amazing Summer Day Trips to the Eastern Shore and Annapolis - Washingtonian
Amazing Summer Day Trips to the Eastern Shore and Annapolis.
Posted: Fri, 15 Jul 2022 07:00:00 GMT [source]
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.
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.
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