The “Maritime Republic of Eastport” as it’s fondly known (you’ll see the flags and probably want one too, trust me) is just a short boat ride or walk across the bridge from Downtown Annapolis. Here you’ll find a neighborhood with a charming, nautical personality of its own. With great views of the Naval Academy and charming historic houses and views of the water all around, Eastport boasts some of the best dining in the city. Below, we give you just a few of my favourite restaurants in Eastport for every occasion! 

If You’re Looking For …

Fun & Casual Dining: Boatyard Bar & Grill

Restaurants in Eastport, Annapolis

With its boat house design & nautical decor, and lively atmosphere, Boatyard is where you can go when you get off your boat in your board shorts and flip flops and have a fun time with friends and family. Throughout the year, Boatyard also hosts many events, from live music nights, to Bands on the Sand to a fishing tournament. Currently, there are no events happening but they do have an outdoor tent and heaters to accommodate guests for the winter. A must stop for all types of seafood, from oysters, scallops to crab cakes to fish tacos, their menu is as extensive as it is delicious. A true local favorite. 

See Boatyard Bar & Grill Menu Here

Address: Boatyard Bar & Grill 400 Fourth St, Annapolis, MD 21403

Pub Grub (and Drinks!): Davis’ Pub

Davis’ Pub Annapolis

A local legend, Davis’ Pub is a favorite of the sailing community and truly all of Eastport. A small and cozy place with great food and great prices, everyone remarks on how friendly the staff is and how you feel like you’re part of the Pub family even on your first visit. If you’re looking for great drinks and true Pub food in Annapolis, Davis’s is the spot. Absolute must-trys include the crab pretzel and steamed shrimp! Check on Facebook for their daily specials before you go. 

See Davis’ Pub Menu here

Address: Davis’ Pub 400 Chester Ave, Annapolis, MD 21403

A Date Night Spot: Chart House

Eastport Annapolis waterfront restaurant

If you’re looking for something a little bit more upscale, look no further than Chart House, located right on the water in Eastport. This is one of 26 locations across the country, with a recent million dollar renovation of this location, it is an elegant spot if you’re looking for a romantic night out. A surf & turf location, you can choose from amazing Snapper Hemingway to prime rib and steaks. Don’t forget to end the night with their famous Hot Chocolate Lava Cake. 

See Chart House Menu here

Address: Chart House 300 Second St, Annapolis, MD 21403

To Celebrate A Special Occasion/Anniversary: Lewnes Steakhouse 

Annapolis Restaurant Lewnes Steakhouse

If you’re passed just dating and looking to celebrate your anniversary (or any other special occasion!)  Lewne’s Steakhouse is the spot in this Maritime Republic. With it’s dim-lighting, leather, and high-booths, this place is perfect for an intimate and celebratory affair. And what is a celebration without wine? Lewne’s offers a selection of 450 different wines. Beyond its reputation for incredible food and ambiance, the service is also notably exceptional. If you’re looking for a special evening and service, Lewnes should not be skipped. 

See Lewnes Steakhouse menu here

Address: Lewnes Steakhouse 401 Fourth St, Annapolis, MD 21403

A Place If you’re a Baller: Eastport Yacht Club

Waterfront Restaurants Eastport Annapolis Maryland

Now, Annapolis Yacht Club is a members-only club, so you’ll need to be a member, know a member,or be a member in another club that offers reprecipriocity. If money is object to you, AYC is certainly more than worth it. With it’s beautiful location and design, amazing award-winning service, and truly delicious food, you will never have a bad time here. And if you are, just get out there and go sailing, who has a bad day on the water after all?  A staple of the Annapolis community and yachting community truly all over, this is THE place to be in town.

Learn more here

Address: Annapolis Yacht Club 2 Compromise St, Annapolis, MD 21401