Annapolis: America's Sailing Capital and So Much More

By Charles McCool/McCool Travel

Only one hour from Washington, D.C., Annapolis, Maryland is a historic, patriotic, and fun destination, especially when the weather is warm. Home to the U.S. Naval Academy and the Sailing Hall of Fame, it has something for everyone, from billionaires with massive yachts to day trippers looking for sun and fresh seafood. I’ve visited the city many times, and these are my favorite things to do there. What are yours?

Get on the Water

Annapolis calls itself the Sailing Capital of America. Find out why on a schooner cruise. (Photo: Charles McCool)

I could write a separate post entirely about all the great things you can do in Annapolis on the water. Rent a kayak or SUP. Go fishing or crabbing. Take a boat tour on Harbor Queen. Ride on a classic schooner. Walk the plank and shoot water cannons from a pirate ship. Learn to sail at a sailing school. Ride the water taxi (only $3 across to Eastport, $8 maximum). Sail on a private sailboat (OK, you have to know someone). Swim. Water ski. Windsurf or kite surf. Eat, drink, sunbathe.

Join the Navy (Sort of)

The US Naval Academy is located in Annapolis, and you can tour it for $10.50. (Photo: USNAPrep.com)

Speaking of water, there is no denying that Annapolis is a Navy town. While the US Naval Academy is guarded, there are some public entrances and attractions. The easiest and most popular is probably the John Barry gate along Prince George Street near the City Dock area. Commodore Barry was the founder of the US Navy and there is a memorial to him just inside the gate. The nearby visitor center has a short film on the history of the US Navy and Naval Academy, poignant displays, and a gift shop. The Admissions Office is on the second deck (upstairs level) if you want to scare — I mean encourage — your children. Worship services and three dining options and are available to visitors. Public tours cost $10.50 per adult.

Visit the Sailing Hall of Fame

It certainly makes sense that America’s Sailing Capital hosts the National Sailing Hall of Fame. Personally, I like to visit Halls of Fame to be inspired by people who excel at their passion.

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Eat Locally Made Ice Cream

The Annapolis Ice Cream Factory has been named the best in Annapolis every year since it opened in 2004. The lines inside back that up. (Photo: Charles McCool)

The only time I didn’t see several dozen people lined up at the Annapolis Ice Cream Company was on Sunday morning — before it opened. The shop is owned and run by a local couple, and they make fresh ice cream right in the shop almost every day, rotating through 36 flavors including peanut butter Oreo, maple walnut, apple pie, and pumpkin pie for fall. Walking around, I spotted several other ice cream shops. Did I try any? No! Obviously I must return to Annapolis.

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Travel Back in Time

Did you know that Annapolis was the first capital of the United States of America? For nine months at the end of the American Revolution, Congress met at the Maryland State House, and Annapolis is considered the first peacetime capital of the new nation. History oozes from every brick. Visit historic St. Anne’s Church — whose congregation included two Declaration of Independence signers and Francis Scott Key (he wrote the Star Spangled Banner), the cozy alleys, pre-Revolution taverns, and historic homes.

Sip a Few Glasses at a Winery

California and Texas aren’t the only states with good wine. (Photo: Charles McCool)

Visiting a winery in Annapolis was a pleasant surprise. Our wine flight tasting at Great Frogs was accompanied by local artisanal cheeses, fruit, and Marcona almonds. The port wine was my favorite and is sold in cool one-quart maple syrup glass containers. I cringed at the $50 bottle price but, you know what, I should have bought one. When I return for my ice cream adventure, I intend to buy a bottle.

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Go People (and Boat) Watching

Ego Alley, a narrow stretch of water off Spa Creek near the Annapolis City Dock, is among the places to see and be seen. In case it is not obvious, boaters and yacht owners show off their craft along Ego Alley, especially on brilliant weekend days.

Have you been to Annapolis, Maryland? What suggestions do you have for play, do, see, eat, and drink?

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