Annapolis- Maryland’s Maritime Destination

Known as “America’s Sailing Capital” and also the “Sailing Capital of the World,” Annapolis, Maryland is best experienced from both land and water.

Have you ever taken a sail on the Chesapeake Bay? It’s an exhilarating experience punctuated by a flotilla of interesting sights, sounds and sensations both from the shore and the bay. Whether you’re taking a sail with Annapolis Sailing Cruises or motoring along in your own boat, time spent on the bay will allow you to fully appreciate how and why Annapolis became such an important maritime destination centuries ago. It will also help you to understand why that standing has endured in today’s world of modern tourism and travel.

It’s no wonder the United States Naval Academy was founded here in 1845 on the site of Fort Severn. You can take a tour of this revered institution–and hit their gift shop (check out the coupon for it on your Annapolis Discovery Map)–most days of the year. For this–as well as for all kinds of other visits to Annapolis–it’s best to park at the Navy Marine Corps Memorial Stadium and take the short shuttle ride into the historic center of town. It’s said that “all roads lead to the water” here but keep in mind that those narrow streets can be clogged with traffic, so there’s no sense adding to that situation.

A separate ticket will afford you entrance to the U.S. Naval Academy Museum, located on the grounds of the academy. Home to one of the world’s best model ship collections, a visit here will also help you to learn the stories of the men and women that have served their country at sea. Speaking of midshipmen (and midshipwomen!), how about those uniforms? That’s one of the best parts of hobnobbing around Annapolis–there’s nothing like a man or a woman in a naval uniform. That’s what you call sharp and snappy!

Be sure to visit the historic Main Chapel also on the grounds of the U.S. Naval Academy. A venerable location for weddings and funerals, this cathedral-like structure will woo you by its beauty and grace. Here you can also visit the crypt of John Paul Jones. You likely remember that name but do you recall who this illustrious person was? Well, this Scottish-American naval captain is recognized as having been the first well-known naval commander for the American colonists during the Revolutionary War.

If you’re not ready to apply to the Naval Academy but still want to learn more than what is the difference between leeward and windward or tack and jibe, consider signing up for a lesson with the Annapolis Sailing School. This place is so cool and comprehensive that they even have a powerboat school! Check out their online gift shop too.

Speaking of shopping, you’ll find plenty of it in and around Annapolis. For authentic nautical-themed goods, go to Resails, a Newport, Rhode Island-based company that handcrafts a variety of bags, totes and duffels from old sail cloth. They even produce doggy rain jackets!

And who doesn’t love gazing at a painting of an old seafaring scene? You can find one of these and much more, including a ship’s cargo full of interesting sea-themed collectibles, at Annapolis Maritime Antiques. This unique emporium also specializes in custom furnishings for your yacht, deck or dining room.

When in Annapolis, be sure to check out Eastport. Does that make sense? Sure it does, especially since from Eastport you can enjoy some of the best views of Annapolis and also feast on delicious seafood served up in one of the many establishments on “Restaurant Row.” Just take a water taxi to Eastport from City Dock or saunter across the Spa Creek Bridge. Either way, traveling here is half the fun.

This is also where you can rent a kayak, canoe or paddle board for experiencing the Chesapeake up close and personal. Go early in order to visit the Annapolis Museum & Park, another must-see for marine history buffs and landlubbers alike. In the summer, you can even tour the oh-so adorable (and historic) Thomas Point Shoal Lighthouse, a National Historic Landmark built in 1875.