Top 5 Things to Do in Annapolis

You know you’re in for an exciting vacation when you visit a historic town like Annapolis, Maryland. Situated right on the Chesapeake Bay, Annapolis is lively and fun. It has lots of fascinating sights to offer the casual tourist and plenty of hidden treasures for the history buff. Between sightseeing and water sports, there’s always time for a fine dining experience. You can feast on a sumptuous meal of fresh crabs that were scuttling across the shore just hours before. So, buckle up and get ready to explore the top things to do in Annapolis.

Graduating sailors throwing hats in the air; things to do in Annapolis
Graduating sailors in Annapolis

Tour the U.S. Naval Academy

This is, hands down, the number one attraction in Annapolis. The US Naval Academy is the pride and joy of the town. It has been educating and training Naval and Marine officers since 1845, and has around 4,000 midshipmen on its grounds at any time. When you’re there, make sure to time your visit with the noon meal formation; it’s like watching a small army making these beautiful formations with precision and majesty.

Naval officers crossing the street in Annapolis
Naval officers crossing the street in Annapolis

After that, take a guided walking tour down the campus. Here you will learn about the history of the academy while you admire the architecture. Speaking of architecture, make sure you visit Bancroft Hall—it’s a must-see for its outstanding design.

Once you’re done with the beautiful campus and the military formations, head over to the U.S. Naval Academy Museum. It’s free, and you can take a self-guided tour through the history of this great establishment. If you plan your visit well, you might catch a music performances by the Naval Academy Band.

Sail Training vessel "Gallant" in Annapolis Harbour
Sail Training vessel “Gallant” in Annapolis Harbour

Flaunt it or watch it on Ego Alley

Yes, that’s what it’s called. There are so many jokes that could fit here right now, but we’ll skip them and get to the alley. Ego Alley isn’t really an alley at all; it’s a waterway that flows into Spa Creek. If you have a beautiful boat that you lavish time, love and resources on, here is where you flaunt it. If you’re a visitor without a boat to flaunt, just take a stroll near the waterway. You’ll watch other proud boat owners parading their beauties in front of your eyes.

If all this beauty makes you hungry, head over to nearby Pussers’ Caribbean Grill. There you can gorge on delicious food, then wash it down with a classic rum cocktail. Make sure to get dockside seating so you can continue to watch the beautiful yachts while you enjoy your meal!

Enjoy an event or festival

Like all towns with a long history behind them, there’s always something to celebrate in Annapolis. Events may be historical, mythical, dubiously cultural, or just plain down silly. The locals just love any opportunity to close their shops and homes and go out and celebrate. Summer in particular is sprinkled with such festivals and special events.

Concerts and live performances have a special place in the cultural scene in Annapolis. In addition, some year-round exhibitions will give you an intimate look into the rich culture of this historic town. There are about 52 exhibits, so it’s easy for you to catch a few no matter when you visit. Also, make sure to check for some of the weekly happenings. These include happy hour, pub quiz nights, pub trivia nights, and live music at the bars across town.

view of Annapolis street with City Hall and red brick buildings; things to do in Annapolis
Annapolis City Hall

Tour Annapolis

Naturally, the best way to experience the real Annapolis is to take a guided tour. Your guide will show you all the attractions and places of interest you might miss on your own. Make sure to include historic Annapolis in your tour. Here you will step back in time and breathe history in every street and alley. The architecture is fascinating and the electric eCruiser is sublime. The waterways provide some of the best panoramic scenes you can set your eyes on in town.

Don’t miss the United States Sailboat Show

Sailboats head to Annapolis from all corners of the globe for this great show. It is by far the largest and most elaborate sailboat show in the world. Of course you will want to make sure to be there when this exceptional event takes place! Boats of all shapes and sizes flock to 1 Dock Street and offer a truly spectacular view to all those interested in boats or sailing.

About Brian Bates


AJ is a travel writer working with At Home Annapolis, a local provider of affordable vacation rentals, to help showcase the great city of Annapolis and help visitors create the vacation of which they’ve always dreamed.

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