The Best Boat Hire in Annapolis

Average of 166 reviews in this area.
1 - 18 of 25 listings
25 results

What to Know About Hiring 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 Edgewater, Tilghman Island, Ridge, Deale, Reedville, Chincoteague IslandNewport NewsNorfolkNew Hampton, and Fenwick Island.

Hire 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 hire 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 hiring 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. Hire 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 Hire Your Next Boat

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

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

GetMyBoat customer reviews for boat rentals in Annapolis.

  1. CB
    Cathy
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    We had a wonderful time sailing with Captain Alberto and his wife Grace! My husband and I and two of our friends went for an afternoon cruise as a birthday celebration. The boat was beautiful and they were friendly and gracious hosts. I was interested in learning more about sailing and Captain Alberto (an experienced sailing instructor) was a great teacher. Captain Alberto was also very responsive and helpful when we were making the arrangements for the trip. We hope to have an opportunity to do this again, and highly recommend a trip with Captain Alberto!

  2. KH
    Karen
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    Our group of 6 friends enjoyed a terrific sunset cruise on Captain Alberto's boat. Captain Alberto is clearly an experienced sailor. He and his lovely wife were both very welcoming and we really enjoyed their company. Overall it was a wonderful evening and we all highly recommend it!

  3. SL
    Sarah
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    I booked this trip as a surprise birthday present for my fiancé! I invited a few of his friends and they all had a great time hanging out and learning a little about sailing. Captain Alberto and his wife were great and very knowledgeable. We would definitely recommend to anyone!

  4. NP
    Nicole
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    We celebrated my friend's bachelorette party with a sailing adventure. Captain Alberto and his wife were absolutely wonderful. We had an amazing time on the boat and they were great hosts. The entire process was seamless and extremely enjoyable. They went above and beyond to make it such a great experience. I would highly recommend booking!!!

  5. MF
    Molly
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    Could not have asked for a better day on Captain Alberto's sailboat! My family and I had a wonderful time sailing across the bay, going for a quick swim and got a bonus tour of the Annapolis marina. Alberto and his wife were gracious hosts and let us have some time behind the wheel. It was such a treat sailing with such experienced individuals that will give you impromptu sailing tips and tricks. I highly recommend Captain Alberto for anyone looking to have a fun day on the bay and learn a thing or two about sailing!

  6. JM
    Johannah
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    This was such a great experience!! I brought 4 friends on this boat for my birthday and it was perfect. We all brought snacks and drinks, our bathing suits and a reggae playlist to set us up for a relaxing and fun day. We got to participate in steering the ship, raising the mast, etc. and that was a really cool experience because I like to learn things. Also, Grace and Alberto were so genuine, adventurous, fun, kind and I could go on. I had the best time hearing their life stories and by the end of the trip our relationship felt way more like "old friends" than "customer". We also were able to pull over and swim which to me was the funnest part! I definitely recommend this experience and think it could be anything from "classy and romantic" to "casual and fun" depending on the event and what each group wants and time of day.