Clang, clang, clang went the trolley and my five-year-old-son was captivated.

We board an early afternoon trolley outside the Annapolis Visitors Center at the top of West Street and immediately, the tour operator, Mark, makes us feel welcome. He asks his guests where they’re from and a connection is made. St. Louis? San Francisco? Connected by trolley, figuratively. New York or Philadelphia? Like Annapolis, former capitals of the United States. He points out that Route 50 stretches over 3,000 miles and goes from Ocean City, Maryland to Sacramento, California, another connection that bonds. It’s obvious he loves this city.

What strikes me right away is his memory and attention to detail. This man knows his facts. And he points out things that I pass all the time but don’t often stop to appreciate: the old time wavy glass on many of the homes, the symmetry architecture (‘what’s on the left is what’s on the right”), Georgian architecture (“this area has the highest concentration of that style in North America”), that four signers of the Declaration of Independence lived here and their homes still stand. He talks about the winter social season and how George Washington once danced and gambled here.

As we pass over the Spa Creek Bridge into Eastport, my son points to the car dealer on the other side of the bridge and says, “Can this tour stop at the Mercedes dealership?” At that moment,

Mark yells out, “Wait a minute!  I remember you!  You were here about two years ago and asked that same question!”

Like I said, Mark has quite a memory. We took the tour when my Li’l Guy was three, and his fascination with cars has not wavered.

Mark reminds us that the Chesapeake Bay is the largest estuary in North America and that the brackish water and winds help to make Annapolis the “sailing capital of America”.

Mark talks about the famed Tug-of-War across the creek between Annapolitans and Eastport residents (jokingly referred to as “slaughter across the water”) and how it’s ‘illegal’ to wear socks in Eastport. In fact, on the vernal equinox (on or about March 20), there’s a sock burning party that helps to kick off boating season.

After taking in a stunning view of the US Naval Academy from Eastport, we are soon in downtown Annapolis. City Dock is the heart of social life in Annapolis and at one time was an international seaport. It fronts Ego Alley, aptly named for the area where a procession of beautiful boats can often be seen.

My son asks if we could stop at Mission BBQ (one of his favorites), but Mark reminds him that this is not a lunch cruise.

We pass the oldest house in Annapolis, on Prince George Street and, nearby, a bed and breakfast that will fly the flag of your home state or country when you stay with them. The history and charm the city exudes is palpable.

The tour stops at the Annapolis WWII Memorial. You’re able to get out, pay your respects and enjoy the view from the site that flies a 48 star flag. Back over the Severn River, there are two important schools in the area. Behind the wall of the US Naval Academy is “the yard”, where midshipmen earn Bachelor of Science degrees. A few blocks away is St. John’s, a private liberal arts college that doesn’t use grades and has “tutors” instead of professors. Their philosophy is that education is not competitive, and their focus is on the study of the 130 “great books”.

We pass a Liberty Bell replica and learn that every state capital and US territory has one. There’s the First Responders Memorial and, as we head around the Maryland Statehouse where The Treaty of Paris was signed, Mark brings the history of Annapolis full circle.

I think I’m going to be taking my Li’l Guy on the Discover Annapolis trolley every couple of years. It’s a wonderful way to learn history and help instill a special pride for his hometown. To find out how you can take the tour, visit the website here.