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The Best Boat Rental in Annapolis

Average of 15 reviews in this area.
16 listings

What to Know About Renting a Boat in Annapolis

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.

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.

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.

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GetMyBoat customer reviews for boat rentals in Annapolis.

  1. MT
    Michael
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    Great afternoon, the tour was exactly as advertised, captain has tons of experience, even got to learn a bit about sailing. Highly recommend.

  2. TS
    Teri
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    Alberto was an amazing captain. It was a truly enjoyable day on the boat. I will be back again to sail with Alberto

  3. CL
    Collen
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA
  4. DA
    Dan
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    We had a wonderful experience with Alberto. A true professional with a lifetime of experience ready to be shared with aspiring sailors. I would recommend him to anyone looking to enjoy sailing on the bay.

  5. EN
    Erica
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    We had a great time with Captain Alberto. We had a true sailing experience, and one of us even helped drive for quite awhile. He was responsive and knowledgeable and great to hang out with.

  6. GC
    Gil
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    Captain Alberto was great! He is extremely knowledgeable and was more than happy to share his experience with us. We all enjoyed the day and will definitely do it again!