I’ve been to Annapolis, Maryland, Sailing capital of the USA dozens of times, both by boat and by car over the past 15 years. It is the jewel of the bay, a premier tourist attraction of the Mid-Atlantic region loaded with history and offering up unique experiences to a variety of travelers.
I started coming to Annapolis in the mid 90’s when a good friend of mine moved there to get involved in the up and coming regional music scene. Through him I was exposed to the nightlife and gastronomical aspects of the waterfront downtown area. It wasn’t until a few years later that I visited Annapolis by boat, staying at one of the marina’s that surround the harbor.
That’s when I really fell in love with the place.
I’ve been back multiple times every year since then, both when out cruising the bay in my sailboat and also by car to come to the annual boat shows every spring and fall. My better half is also an Annapolis native, so with family still in the area, we visit a few times a year for family functions. Through these experiences I have, at one point or another, hit upon many of the highlights of what Annapolis has to offer.
Recently, I visited by boat on my yearly Chesapeake Bay Cruise aboard my 26 foot sailboat, Pegasus, and spent the day visiting an old friend from up home who had moved to the area a few years back to start a Kayak tour company. It dawned on me that over the years I have probably experienced so much of the good things about Annapolis, that if you put them all together into one days worth of experiences, you would end up having just about the perfect day. Such a perfect day, that I could daydream about it during the low moments of a dreary off season, and maybe keep reliving that day in my mind’s eye, over and over again ala the movie Groundhog Day.
Here I will give you a little rundown of what I would imagine my perfect Annapolis Day would be.
Morning, wake up, early, but too early, say 7am. The water in the harbor is gently rocking the boat as a gentle breeze freshen’s the morning air amidst the warming sun. Stretch out on the foredeck, shake the sleep from my eyes, gather my toiletries into my dry bag and take the dinghy to the shore. Head up to the showers by the Harbormasters office, take a nice long hot shower and dress in crisp clean clothes.
Traipse up the road to Chick N’Ruths Delly, about half way up the main drag heading towards Church Circle. Order up a bagel with cream cheese and tomato, some eggs Benedict perhaps with bacon on the side, and some coffee and orange juice to top things off. Sometime after 8am, it’s time to doth our caps, put our right hand over our heart and recite the “Pledge of Allegiance to the United States of America,” a morning tradition at Chick N’Ruths for years.
Get a cup o’joe to go, hop a bus for the outer reaches of West street to Bacon Sails, a nautical flea market if there ever was one. Almost any sailor could spend hours upon hours needling through the back room, or the bins out front with all manner of used, consignment equipment and sails. There is some new stock as well, and tons of experience and advise at the ready for any boater of any caliber.
Maybe stop by the Goodwill store out by the bus stop to look for some new Hawaiian shirts before heading back downtown. Do some window shopping along the varied storefronts heading down towards the Ego Alley area. Head just a few blocks more and visit the Naval Academy. Free to the public with proper ID, the Naval Academy is rooted to the core of the history of our country and its defense. Inside the Academy, also known as “The Yard,” there are many architecturally profound buildings such as Bancroft Hall, where the Midshipmen reside, the Academy Chapel, and Preble Hall, the Academies museum. John Paul Jones, one or our nations’ first naval war heroes is buried in a crypt underneath the Chapel. His defiant cry of, “We have not yet begun to fight!” is legendary in the annals of naval history.
After a spate of lunch from one of the many shops in the downtown area, head over to Truxton park, on the south side of Spa Creek and register for the afternoon tour from Kayak Annapolis. This two hour kayak tour will take you out the Spa Creek into Annapolis Harbor, with a pit stop across from the Naval Academy, where you will get a short history lesson, then continue on to Ego Alley, and then back through Spa Creek. There is a short paddle school at the beginning of each tour, where you will learn the basics. The tour is accessible for all ages above school age and all skill levels and is ready to accommodate your family or group up to 25 people. The tour highlights some of the lesser known history of boat building in the area and the colonial design of the city and provides an up close look to some of the yachts that call Annapolis home.
Round about happy hour, at least mid week, you can find half price appetizers at Middletons Tavern, located right in the middle of the Ego Alley area of downtown. This Historic tavern has been around since before the Revolutionary war, and has hosted many of America’s Founding Fathers. It features an Oyster bar as well as full service menu items. For me it’s all about a few beers and appetizers.
If the weather is nice, and since this is my dream Annapolis day it most definitely is, then take a stroll over to the Annapolis/Eastport draw bridge and watch the racing sailboats come back from a hard campaign on the bay just before sundown. Hundreds of boats come into the harbor seemingly at once, going this way and that, and remarkably, nobody crashes into anyone else! It’s a sight to behold for sure.
For dinner, take a half an hour walk or so up to Maryland Avenue to Galway Bay, one of the best Irish Pubs around for some traditional Irish fare or great seafood dishes. Along the way you can peruse the many storefronts and walk the circle around the statehouse.
For a nightcap, head back downtown to the world famous Pussers for a frozen rum drink or three, depending on whether you are driving or dinghying around, or if you are walking or taking a taxi, traditional or water back to your accommodations. Pussers is located right along Ego Alley, on the ground floor of the Marriot Hotel. There is a waterfront bar where you can enjoy your “Pain in De Ass” or “Pina Colada.” Pussers is famous for its location in the British Virgin Islands, and is well known for its being the “Official Rum” of the British Navy.
By this time hopefully you haven't had too much to drink or if you did you take the water taxi back to the boat to enjoy a final beverage while enjoying the lights of the city skyline from the harbor. Thus ends the perfect day in Annapolis, according to Yours Truly.