Annapolis, MD 

Some places are beautiful. Others become a part of who you are. Annapolis manages to do both. From the waterfront views, to the crab cakes to the United States Naval Academy; Annapolis feels captures the true essence of coastal living. Not only is Annapolis one of our favorite places on the entire east coast, it was one of Mr. Buffett’s as well.

Let’s take it back to the very beginning.

Annapolis, Maryland. Founded in the 1600’s, Annapolis carries history beautifully and timelessly. From the cobblestone streets, to the colonial architecture, down to the waterfront taverns, this town creates a setting that feels both refined and relaxed. Everyday life in Annapolis revolves around the water, hence it being one of our favorite places. From early morning fishing trips to sunset cruises across the Chesapeake Bay, boating isn’t just an activity here; it’s part of the culture. The harbor is lined with beautiful yachts and classic sailboats.

Our mornings, before early morning fishing trips, start at Iron Rooster. If you have been, you know where this is going. If you have not been, just plan on cancelling any other breakfast reservations you have already made during your stay. They are known for their World Famous RoosTarts. You cannot go wrong ordering any flavor and they also have seasonal flavors, as well.

After your overconsumption from breakfast, you have plenty to keep you occupied in downtown Annapolis. The area is filled with boutique shopping, seafood restaurants, rooftop bars, and hidden gems tucked into historic alleyways. From the Spice & Tea Exchange of Annapolis to the beautiful boutiques to the views and duck feedings at Ego Alley, Annapolis’ charming downtown has enough to keep you entertained throughout your stay.

In any part of Maryland, crab cakes are practically a requirement. There is no other place you should attempt, other than our and Mr. Buffett’s favorite, Boatyard Bar & Grill. Boatyard Bar & Grill has the most exceptional crab cakes we may have ever had and it is a must visit every time we are in Annapolis. The Boatyard Bar & Grill was founded in 2001 by Dick Franyo. We are convinced that he is the best at crab cakes because Dick grew up fishing on the Chesapeake Bay. Who better to make your crab cakes than someone who has lived in the crab cake state of the world their entire life?! The crab cakes are so popular, you can even have them shipped nationwide.

A must visit, is the United States Naval Academy. Mr. Buffett had a true appreciation to the USNA, the midshipmen and his amazing friends at the USNA. Naval Academy tours are a must! You can purchase tickets for guided tours and view the Yard’s picturesque walkways by foot or electric car. You will get a behind-the-scenes tour and a day in the life insight of a midshipman as well as the history and tradition of one of the greatest fighting forces on Earth!

There’s something about Annapolis that feels timeless. We hope you enjoy it as much as we do!

-Written by Sarah LaSorsa