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Then, venture to the open-air top deck to take in the scenery and see the Eastport Yacht Club’s Lights Parade. 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. Schooner Woodwind owner and seasoned sailor Jen Kaye is also a “foodie,” who masterminds “Wine in the Wind” evenings. Tickets are still available for August 27, a Spanish-themed two-hour sail featuring four wine samples “perfectly paired with magnificent morsels” provided by prime time Annapolis caterer Palate Pleasers. After fishing with several other bay charters over the years I had an opportunity to fish with Captain Karl & Eric aboard Miss Grace.
Island Chill Yacht Charters

It`s a privilege to be able to share the history, culture, and fun of such a beautiful place 🌎🌸🌊🦀✨ #earthday ... 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. Capt Karl, I just wanted to drop you a quick note thanking you and Eric for another memorable experience on the Miss Grace. Our employees look forward to our annual Fall trip each year and everyone couldn’t have been happier. Our fleet of yachts provide the perfect venue for celebrating your next corporate, social, or wedding event.
The Annapolis Holiday Market Returns on December 7th - Eye On Annapolis
The Annapolis Holiday Market Returns on December 7th.
Posted: Thu, 30 Nov 2023 08:00:00 GMT [source]
All "sunset dinner cruise" in Annapolis, Maryland
Let our captain and crew make your trip an enjoyable and memorable experience. Our bar is stocked with wine, beer and bubbly, including a nice selection of local, independent craft beers available for purchase. Experience the best of Annapolis and Baltimore with cruises, walking tours, private yacht charters, and field trips. Back in Annapolis, the far end of Ego Alley near the Market House has public bulkhead docking for boats up to 17 feet in length. If you’re longer than 17 feet, then your best bet is to grab a mooring buoy, check in with the Harbormaster, and hop on your own dinghy or hail a Watermark water taxi. It is also possible to anchor at no charge on the outside edge of the Annapolis Harbor subject to certain restrictions.
Related Sunset Dinner Cruise Searches in Annapolis, MD
Sign up today and we'll keep you in the loop on upcoming deals, specials, and happenings in and around Annapolis. 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. I really appreciate you always taking great care of our employees and customers.
Private Chesapeake Bay Charters………..Like No Other………..
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.
If you have a dinghy along and you’re tied to a City mooring, you can find City dinghy docks along Spa Creek and Back Creek at several parks and 22 street-end landings wherever public streets meet the water. Except in Ego Alley, the dinghy docks are for boats under twelve feet. 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.
The Boat
Our Annapolis Sunset Cruise takes you out on the water to watch the sunset and see the lights of the Annapolis Harbor. Enjoy a fun music playlist and beautiful scenery as you relax with a cool drink. Beverages and snacks are available for purchase from our full bar. From live music cruises to New Year’s Eve, Watermark offers a variety of special and seasonl cruises throughout the year.
Schooner Woodwind
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.

Das Boot Sailing Charters
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.
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.
Whether it’s a narrated sightseeing cruise or a day trip to St. Michaels, get out on the water with Watermark for an unforgettable journey. Our boats have a full bar service with light snacks available for purchase and restrooms on board. Most of our vessels are handicapped accessible and climate controlled.
You can arrive in Annapolis Harbor by boat and make your way to any restaurant within walking distance of City Dock or Eastport. Chart House and Carrol’s Creek Café are perched on the waterfront, and it’s an easy stroll to the many great restaurants along Main Street, West Street, Maryland Avenue, and Eastport’s Severn Avenue. And we can’t forget the City’s various yacht clubs, which provide unique dining and docking options for their members and guests.
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. Each month we feature a different brewery from the Chesapeake area. A representative from the brewery comes aboard and teaches you about beer. You will taste 3 samples of beer and then you can purchase full beers from the brews that you enjoyed the most. A guided tour exploring the history of the Chesapeake area, and the sights you see while on a sail. Each week we will focus on a specific interesting topic with a guest speaker aboard.
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