Enjoy a Day Trip to the "Sailing Capital of the World" Annapolis, Maryland

Enjoy a Day Trip to the “Sailing Capital of the World” Annapolis, Maryland

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Whether you seek a day of fun in the sun or a night on the town, Annapolis, Maryland has it all.

Home to the Naval Academy and known as the “sailing capital of the world”, Annapolis’ cultural interests are historic. Day-to-day media reports of bill signings and changes in legislation at the Maryland General Assembly always draws attention from professional politicos, but now that spring has arrived, it’s the leisure activities that are drawing people to this quaint town for day trips and weekend excursions.

Weekends are packed with concerts, water sports, fine arts, and football. A trip down West Street will land you in any number of bars, restaurants and taverns teeming with activity on any given night. So sit tight, here’s the best list of what to do when you decide to visit Annapolis!

Due to its proximity to Baltimore and Washington, D.C., a decision to take a trip to Annapolis can be spontaneous. Whether you want to spend the whole day there just or stop by is up to you.

If you just want to stop by, Westfield Mall in Annapolis offers a huge selection of premium retailers such as Coach, Micheal Kors, Nordstrom, Tommy Bahama, Aldo and Vera Bradley. A shopping excursion is the perfect therapy for an uneventful weekend, and Westfield Mall is one of the better (if not the best) malls in Maryland and is definitely worth a trip.

Retail can be fun, but most people visit Annapolis for one reason – the waterfront. It’s a unique experience that’s incomparable to anywhere else. Weekly sailboat races are held every Wednesday night starting at 6 PM and some 150 boats sail around several checkpoints along the bay. Insider’s tip: a great vantage point is the Spa Creek Bridge.

In addition to sailboats, there are kayaks, paddleboats, and canoe rentals. All of these are great workouts, especially if you paddle against the current. There are guided tours and, of course, plenty of fishing and crabbing options as well. For more information, you should check out Annapolis’ tourism info and don’t forget your sunblock!

If you’re looking for something to do after a day in the sun, a trip to downtown West Street is a great option. There are a number of bars and music venues there that really liven up the scenery.

Rams Head On Stage, Rams Head Tavern, and Stan & Joes serve great house IPAs and offer some fantastic entertainment options. Both Rams Head On Stage and Stan and Joe’s have nightly concerts featuring excellent bands – some of them local, some of them national recordings acts. Upcoming shows at the Rams Head On Stage include Kevin Costner, Maceo Parker, Bret Micheals Martin Short and 10,000 Maniacs.

You can catch a bite to eat to some really good jazz, rock n’ roll, or comedy as well. During the fall, catching some Navy Football at the bar is always a blast. If you do go, parking at the Gotts Parking garage is recommended.

These are just the beginning of ideas for things to do in Annapolis. One final recommendation is to make reservations for most waterfront activities. If you just plan to shop or hang out at one of the many amazing restaurants Annapolis has to offer, you’ll probably be OK with just stopping by. Other than that, just enjoy the scenic and entertaining closeness that is Annapolis!

About the Author: Alan Duckworth is a D.C. area-based entertainment and lifestyle blogger that regularly contributes to The Rogers Revue and Apartments at CityCenter. Along with writing, his skills extend to photography and graphic design.

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