Find The Best Boat Rental in Annapolis, Maryland.

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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.

Annapolis Boat Rental FAQs

How much does it cost to rent a sailboat for a day in Annapolis?

Renting a sailboat for a day in Annapolis starts at $350 a day for an Oceanis Cruising Monohull and goes up to $2,100 a day for a Lagoon Cruising Catamaran.

How much does it cost to rent a boat for a week in Annapolis?

Renting a boat in Annapolis starts at $70 for a sailboat and goes up to $1,600 for a motor yacht rental.

Can you sail in Annapolis without a License?

No, you do not need a license to rent a boat or sail in Annapolis. With GetMyBoat you can rent a boat that includes a licensed captain so that you can enjoy your time on the water. If you want to captain the boat yourself you will need to at the very least have a Boating Safety Certificate. Be aware that owners will have a checkout process to test your competency with their boat, so if you question your ability even if you have your boating safety certificate it is best to go out with a captain.

When does the boating season start in Annapolis?

While boating season can vary a bit depending on the weather it usually starts near the tail end of April and ends in September.

GetMyBoat customer reviews for boat rentals in Annapolis.

  1. AG
    Asia
    41' Lagoon Cruising Catamaran in Maryland, United States

    I celebrated my birthday with a group of 12 people. We absolutely enjoyed ourselves. Planning and communication was a breeze. Captain Jess was a great captain and made us feel welcomed. The boat was clean and spacious. The Bluetooth stereo was loud enough over the wind. It was a such a fun event. I will definitely book again! Can not recommend Captain Jess and Imagine enough!

  2. MY
    Mark
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    Captain Alberto and his 38’ Hunter were perfect for an afternoon sail on the bay! He responded to the inquiry and communications quickly. You help as much or as little as you want, and the Hunter is perfectly setup to take a dip in the bay if you want.

  3. PW
    Pamela
    Charter 41ft "Selina II" Sloop In St. Michaels, Maryland

    We booked this experience for my husbands birthday and it was PERFECT! The Selina II IS STUNNING, and Captain Iris and her crew were absolutely wonderful. Captain Matt was fantastic! He took such good care of us while we sailed across the Chesapeake Bay and celebrated with a couple of glasses of delicious champagne! Look no further and book the Selina II, you won’t regret it, it’s absolutely worth it !!

  4. SS
    Summer
    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

    Joe was absolutely amazing, the yacht was spectacular. It was extremelt clean, spacious, and he did an awesome job with his hospitality & ensuring all of our needs were met. I highly reccommend and will most definitely be returning. We felt right at home here, and didn’t want the trip to end.

  5. KK
    Kristen
    34' Powerboat Charter in Chesapeake, Annapolis MD & South River

    We rented the Cruiser overnight for 2 nights and did a B&B experience. Captain planned the itinerary which included cruise across the Chesapeake to St Michael’s Marina where we stayed, along with stops at 2 lighthouses and creeks all throughout the Chesapeake. We stopped to swim/paddle board at a sandbar and had lovely sunset cruises. And fantastic breakfasts provided from local establishments. Melvin and Stacy are wonderful and great to our family of 6 even going out of their way to make our one daughter have a great birthday onboard. It was a lovely experience

  6. NC
    Nick
    Charter this 42ft Hunter Passage Sailboat in Edgewater, Maryland and sail on the beautiful Chesapeake Bay

    Bill was terrific at helping me learn more about handling a 42' sailboat. I'm trying to get more experience in preparation for taking a bareboat charter, and Bill's experience and mentorship was terrific. I look forward to booking with Bill again in the future.