Annapolis: Dock, Dine & Play

By May 7, 2021May 29th, 2021Dock, Explore
Snag-A-Slip blog - Annapolis, Maryland
Boat lovers from near and far are attracted to the Chesapeake Bay, and more specifically, its most popular seaside town, Annapolis. Maryland’s capital city, Annapolis is steeped in history, has a rich nautical heritage, and is the “Sailing Capital of the United States.” As a matter of fact, locals will tell you that all roads lead to the water. That’s probably why the United States Naval Academy calls it home.
But the only thing old about this eclectic, lively, and upbeat city is its four centuries of architecture and its love for everything seafaring. Because of its location, it’s also the ideal meeting place for boaters cruising the Chesapeake Bay. Its harbor provides reliable shelter and plenty of marinas to choose from.  
In a city chockfull of truly remarkable marinas, restaurants, and bars, it can be overwhelming to try and choose. Want the scoop on the very best places to dock, dine and play in Annapolis? We’ve got you covered!  This is the list of our favorite marinas and venues. Whether you try one or try them all, we guarantee you won’t be disappointed.

Downtown Annapolis


Annapolis Town Dock is conveniently located right in the desirable heart of historic Annapolis.

Watergate Pointe Marina is a quiet, protected marina away from the hustle and bustle, but packed with amenities.


One of our favorite local haunts is Pusser’s Caribbean Grille on Compromise St. It’s casual and unique waterfront dining and has been awarded the “Best in Dockside Dining” time and time again. And if you dare, try their famous cocktail the Pusser’s Painkiller!

Another winner is Boatyard Bar & Grill in downtown Annapolis, on Severn Ave. & Fourth St.  We call it a winner because it has won the Baltimore Sun’s Critic’s Pick for best crab cake, and is featured on the Travel Channel’s Food Paradise’s Super Sandwiches segment.  That’s a win, win!

The Chart House is also in downtown Annapolis, on Second St., and is a bit more upscale – but worth cleaning up for. It’s set in a historic boathouse and uses only locally sourced ingredients.

Magothy River


Magothy Marina provides top-notch customer service to boaters looking to spend the day on the beautiful Magothy River.

Snag-A-Slip Blog - Annapolis - Magothy River

Podickory Point Marina is nestled in the picturesque state-owned nature preserve of the Sandy Point State Park.


A rare find off the beaten path is The Point Crab House & Grill, perched on a secluded point on Mill Creek Rd.  Its inspiring and refreshing menu changes seasonally, and always surprises and delights.

Known far and wide for its delectable Maryland Crab is Donnelly’s Dockside on Deep Creek Ave. You can get your crab on a sandwich, on a pretzel, in a dip, in a boil, in an imperial, and even on top of jumbo shrimp. No matter how you have it, you’ll love it!

Kent Island


Kentmorr Marina is situated on the historic Kent Island, known as the sport fisherman’s paradise. Kent is the largest island in the Chesapeake Bay, and has bragging rights to quite a history, and is just a short boat ride from Annapolis. The marina is close to the Bay Bridge, for quick car or bike access to Annapolis, Middle Bay, and Eastern Bay.

Snag-A-Slip Blog - Annapolis - Chesapeake Bay Bridge


Kentmorr Restaurant and Crab House, on Kentmorr Road, is a crab fanatic’s dream come true!  It also features one of the finest views of the Eastern Shore. And if you want to catch some rays and dip your toes in the water, there’s even a beach area for your enjoyment.  

One Kent Island landmark has inspired a song to be written about it! The Big Owl Tiki Bar, on Kent Narrow Way South, is the waterside spot for meeting up with friends, grooving to live music, or grabbing a quick nosh or cocktail.  It may even inspire you to write your own little ditty!

Want to learn more about Annapolis before you chart your course? just view or download the interactive visitor’s guide. In it, you’ll see everything Annapolis has to offer, along with upcoming events. Or, if you’re more “hands-on”, wait until you arrive and visit the Annapolis Visitors Center in person.
So, reserve your slip and get ready to trade your docksiders for some walking shoes so you can hit the brick-lined streets of historic downtown Annapolis. See you there!
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Jo Montgomery

Author Jo Montgomery

Jo is a lifelong boat lover and writer. She learned the ropes of boating on her family’s 36’ Carver at the Jersey (joy-see) shore. With over 30 years of writing under her belt, she delights in seeking out, and sharing, the things most important to fellow boating enthusiasts. Jo now lives in Connecticut, near the water she adores, with her husband, two children and large, hairy dog. She is over the moon to be part of the Snag-A-Slip crew!

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