Traveling Ted is a blog that takes readers along on my adventures hiking, canoeing, skiing, and international backpacking. Many blogs focus on one aspect of backpacking, but I tackle both the outdoor adventure side and international exploration as well.

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Did you know Annapolis, Maryland is considered far and wide to be the sailing capital of the United States? It’s true. Annapolis is a naval city with a rich history that runs through the story of America itself. Currently, it is a wonderous destination for local food enthusiasts, history buffs, and certainly for anyone who loves sailing.

Annapolis Maryland

Annapolis, Maryland – A charming town – Wikimedia Creative Commons – high limitzz

Whether you have experience sailing, or if you’ve always wanted to learn, Annapolis has a ton to offer. There are numerous reasons you should plan a sailing trip to Annapolis.

Why You Should Plan an Annapolis Sailing Trip

Annapolis is proof that there is more to Maryland than just Baltimore. If you want to get away from the city for a bit, but you still want to take in some local sights and sounds, Annapolis can be ideal. If you happen to love sailing, Easy access to rent a boat in Annapolis makes it a popular boating destination among sailing enthusiasts and even regular travelers looking for a different experience.

Here are 5 reasons to plan a sailing trip in Annapolis soon:


The Chesapeake Bay in general offers some of the finest sailing to be found anywhere in the world. That Bay spans a stunning sixty-four thousand square miles. Annapolis is a small part of that glorious bay. Nonetheless, with its central location within the bay, you can’t argue that Annapolis is an essential piece of the Bay’s enduring appeal. Annapolis has a lot to offer, but it makes clear its deep ties to sailing. For example, this is where you can find the National Sailing Hall of Fame!

Chesapeake Bay Sailing

Old school photo of sailing Chesapeake Bay

Amazing boat shows

Annapolis is a destination for sailing enthusiasts from around the world. Three of the largest in-water boat shows on the planet can be found here. The U.S. Sailboat and Powerboat Show is a perfect example for that. Over 150, 000 people show up! You can also check out the Sailboat Show in October.

Chesapeake Bay sailing

Sailing Chesapeake Bay – Wikimedia Public Domain

It’s easy to get there by boat

There are numerous marinas in the area. You can reach Annapolis with ease by renting a boat. If you take the water taxi, make sure to keep an eye out for Ego Alley. When you find yourself overwhelmed with the sheer variety of ships and boats in the area, you’ll know you’ve arrived.

Related: Acadia Nature cruise in Maine

The races

From April to approximately early September, Annapolis is home to races of all shapes and sizes. Whether you are looking for something with a decided edge of competition, or if you want something that focuses more on fun and leisure, you will almost definitely find what you want. Just keep in mind that certain events only occur on certain days during the season, so make sure you check a calendar before planning any sort of Annapolis sailing trip.

Explore Anne Arundel County

While Annapolis has much to offer in the way of museums and restaurants accessible by boat, you may find yourself looking for a little more in the way of exploration. If that’s the case, keep in mind that there are hundreds of miles of shoreline that make their way through the county. Obviously, such a trip is going to take a good deal of planning. Nonetheless, if you really want to get in some sailing, while exploring some of the best of Maryland, this is a great idea.


Annapolis is unquestionably a stunner. At the same time, there is so much more to this Maryland destination than its scenic beauty. Whether you crave the best local Maryland seafood, or if you just want a day of warm sun and cool waters, Annapolis has something to offer. Our boat rental in Annapolis will make it easy to enjoy everything we have mentioned above.

Just keep in mind that our list only just scratches the surface of a sailing adventure in the iconic city of Annapolis. There is indeed so much to see and do here.

Adventure on!

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