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United StatesMarylandAnnapolis

The Best Boat Rentals & Charters Near Annapolis

Average of 9 reviews in this area.

About Annapolis

Annapolis is the thriving capital city of Maryland and is known for its historic charm and thriving boating culture. It considered the sailing capital of the United States, so if you’re a sailing enthusiast, this is the place to be. A lot of tourism comes in from the surrounding east coast cities like Washington D.C. and Baltimore, and there is a draw for visitors to the Naval Academy.

The best time of year to visit Annapolis is during the late summer and early autumn when the leaves start to change color, and the weather is warm but not stifling. The spring is also a beautiful time, especially if you can catch the flowers blooming. Winter in Annapolis is too cold to enjoy time on a boat.

To get to Annapolis, the easiest way is to catch a flight to the Baltimore International Airport, which is a 30-minute drive from Annapolis. You can also arrive by boat to the City Dock in Annapolis, or by bus on the MTA Maryland. Once in Annapolis, it’s easy to explore most of the city on foot, or you can catch a taxi.

Annapolis Boat Rentals

Annapolis is a big boating hub, with hundreds of stunning motor yachts, sailboats, and more. As the sailing capital of the United States, it stays true to its name with beautiful wooden schooners and sailboats cruising in and out of the many ports around Annapolis. A visit to this city isn’t complete without time spent on a boat, exploring the beauty of Chesapeake Bay. Historic cruises are available to enjoy around downtown, and you can see a lot from the water. The Chesapeake Bay is well known as a unique waterway for cruising on sailboats and motorboats of all sizes. Protected waters, beautiful anchorages, astounding scenery, scrumptious seafood, and historic villages make the Chesapeake an excellent choice for beginning or seasoned boaters.

When you charter a boat out of Annapolis, make plans to visit the docks of EdgewaterTilghman IslandRidgeDealeReedvilleChincoteague IslandNewport NewsNorfolkNew Hampton, and Fenwick Island.

Rent a motor yacht or powerboat while in Annapolis and spend hours cruising and touring. There is so much to discover on the water in Annapolis; you’d be missing out if you don’t rent or charter a boat during your stay. Soak up the sun from the deck of your boat, and explore on your own or let a captain take you to all the best places. A motor yacht will take you to all the great highlights, seeing the skyline from the perspective of the water.

If you don’t want to cruise around on a boat or are traveling on a budget in Annapolis, consider renting a stand-up paddleboard or kayak during your trip. You’ll still have all the fun of being on the water, but you’ll power yourself and get a good workout during your trip. Rent the equipment on your own or take a guided tour or lesson to learn these paddle sports!

For anglers traveling to Annapolis, book a fishing charter to spend a day out reeling in great catches, like the state fish, the striped bass. There are lots of fishing boats and cruises available leaving from the port in Annapolis daily, so no matter when you visit, you’ll be able to book the perfect experience.

Boating Events in Annapolis

Due to its title as the sailing capital of the United States, there are lots of sailing and other boat shows that pop up in Annapolis throughout the year. There are also various sailboat races organized by local marinas, fun events for both sailors participating and spectators watching as white sails fill with wind and race around the Chesapeake Bay.

Other Things To Do

While on land in Annapolis, there is plenty to see and do to enjoy all the awesome things this city has to offer. Enjoy a walk to Sandy Point State Park and admire the Chesapeake Bay Bridge. If you want to dive more into the history - tour the Governor’s Mansion, Kunta Kinte-Alex Haley Memorial, and the Maryland State House or try a historic walking tour of Annapolis.

Be sure to check out the shops in downtown Annapolis if you’re looking for some retail therapy. There are also a lot of great restaurants in Annapolis, some of the best restaurants include the Boatyard Bar & Grill and O’Leary’s Seafood Restaurant.

Marinas in Annapolis

Boat slips at marinas in Annapolis are hot commodities, as this is a popular boating destination for people traveling the east coast. A few of the top marinas to check out include Port Annapolis Marina, Annapolis Yacht Club, and Mears Marina Annapolis. Take a walk on the Annapolis City Dock, one of the top free things to do for visitors, and check out the various marinas. Watch spectacular boats cruise in and out of port, and see the sunset with the beautiful backdrop of the harbor.

Using GetMyBoat to Rent Your Next Boat

Experiencing the water has never been easier thanks to GetMyBoat. GetMyBoat allows you to search quickly, compare prices, submit rental inquiries, and pay for your rental or charter from the convenience of your phone or computer. We offer a secure platform for renters to facilitate a seamless rental transaction. For boat owners, we connect millions of renters to their boat and provide the security and safety checks on each rental transaction.

Search for the perfect experience now and book your dream day out on the water.

15 listings
hourCA$134
MarylandSailing
8 guests

38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

hourCA$134
MarylandPowerboats
6 guests

Cuddy Cabin/Walk Around fishing charter in Annapolis

hourCA$167
MarylandSailing
5 guests

32' Endeavor Cruising Monohull In Eastport Annapolis, Maryland United States

hourCA$214
MarylandSailing
1 guest

Trawler sleep aboard rental in Annapolis

dayCA$1,976
MarylandSailing
10 guests

Cruising Catamaran available starting July 1 - great for captained day charters or bareboat.

dayCA$100
MarylandPowerboats
3 guests

9ft West Marine Ru3 RIB Rental in Annapolis, Maryland

hourCA$1,335
Maryland
49 guests

77ft Liberte Schooner Boat in Annapolis, Maryland

hourCA$112
MarylandFishing
6 guests

40' "Penny Sue" Sport Fisherman In Annapolis, Maryland United States

dayCA$1,603
MD
4 guests

21' Bowrider Fishing Boat in Annapolis, Maryland United States

dayCA$87
MDAdventures
1 guest

Guided Ocean Kayak Tours in Annapolis, Maryland

hourCA$33
MarylandAdventures
12 guests

Stand Up Paddleboard Lesson in Annapolis

dayCA$1,202
Maryland
12 guests

24' Chaparral Bowrider Rental in Annapolis, Maryland

hourCA$134
MarylandPowerboats
12 guests

Bowrider rental in Annapolis

dayCA$67
Maryland
1 guest

Guided Stand Up Paddle Up Tour In Annapolis

dayCA$67
Maryland
1 guest

Guided Kayaking Tour In Annapolis