Annapolis has long been called the Sailing Capital of the U.S. – so, it’s no wonder visitors seek out a chance to climb aboard when they’re in town. Our area offers a variety of charter options ranging from fishing trips, overnight cruises, and private parties to get you and your group out on the Bay for a couple hours, for the day, or even overnight. 

A good start is to recognize that a “charter” refers to a private booking of an entire vessel, so your group, along with captain and crew, can enjoy a unique experience on the Bay. Based on the charter and available amenities, you can also choose from many options including drink, food, and music selections that are offered by local charters. Some charters even let you choose your destination and general cruising plan. Be sure to check below this article for a full list of charters in Annapolis and Anne Arundel County.

Tips & Suggestions on Chartering a Boat in Annapolis

After deciding to charter a boat, it’s important to look around for the perfect boat for your occasion. Asking questions is key in figuring out if a boat, its crew, and its captain are the right fit for your excursion. Calling a charter in advance is the best way to get answers to precise questions. How many people can fit on the boat? Is catering included in the booking, or will you have to supply your own? Is there beverage service on board? What happens if it rains on the day of your charter? Does the charter accommodate all of your guests’ specific needs? Is there anything that is explicitly prohibited from being brought aboard? 

Stopping by to check out the boat for yourself is always a good idea. This allows you to get a feel for what your outing will be like, see the size of the boat, and plan for your gathering accordingly. For example, if you’re planning a sunset cocktail cruise with food, it’s a good idea to see ahead of time if the boat sets up well for guests to walk around freely and mingle. It’s also a chance to meet the captain and crew before putting pen to paper and committing to something that may not be exactly what you’re looking for. 

With all this in mind, it’s time to choose your charter!

Get Sailing

There are a number of great schooners – some of the most popular charter choices in the city – to choose from which sail directly from the Annapolis harbor. One of the city’s most beautiful boats boasts three masts and a spacious deck for parties and events of all kinds. There are also two of the fastest schooners on the east coast offering day and sunset cruises, team building programs, and a Boat & Breakfast where guests can spend the night on board before enjoying breakfast with a rising sun. Aside from these schooners, there are many other smaller sailboats available to charter for an overnight cruise or even as a “boatel.” 

Charter a Yacht and Cruise in Style

Yes - a yacht. Boats ranging in length from 24 ft. to 99 ft. are available for charter at Watermark, so there's a vessel perfect for any occasion; whether you have a group of a dozen or a group of a hundred. A yacht charter is a great option for birthdays, anniversaries, weddings, rehearsal dinners, reunions, and corporate events. Watermark Yacht Charters even offer these charters during the Blue Angels Air Show along with the New Years' Eve and Fourth of July firework spectacles that draw in thousands to the Annapolis Harbor each year.

Cast Away 

Another popular charter option is to book a fishing trip and getting out on the bay for a day reeling in rockfish with the whole family or a group of friends. There are a number of options to choose from in Annapolis, however, you can find many others in Southern Anne Arundel County (known to locals as South County). If you head down to Herring Bay, you’ll find the Chesapeake Bay in all its splendor, along with plenty of charter boats to take you out. As the largest estuary in the U.S., the Chesapeake Bay has some of the best fishing in the country, so you’re sure to have a blast bringing in fish all day long. 

Take our suggestions and the listings below to start planning a charter cruise, sail, or fishing trip in Annapolis today!