Plan A Trip To This Historic US City For Your Next Sailing Adventure

For a short time between 1783 and August 1784, Annapolis was the capital of the fledgling United States. During that period, Congress met at the State House to ratify the Treaty of Paris, bringing an end to the Revolutionary War and recognizing America as an independent nation. Nowadays, the small city, just a 30-minute drive from Washington D.C. and Baltimore, is content to be the capital of Maryland and, thanks to its prime location on the Chesapeake Bay, "America's Sailing Capital." This makes it a must-visit for anyone who loves boats and the water.

With a population of just 40,000, Annapolis provides a charming getaway from the bustle of the big nearby cities, with a compact downtown area rich with the nation's largest concentration of gorgeous 18th-century buildings. All roads lead to the water in a community steeped in maritime and naval traditions — Annapolis is a town passionate about sailing. Thousands of boats registered worldwide line the docks and marinas, and spectators crowd the shore to follow sailboat racing every Wednesday night from April to August, while regular food festivals and events give visitors a chance to sample the region's famous seafood. Let's take a look at what the city, affectionately known as Crabtown, has to offer sailing enthusiasts looking for their next adventure.

Annapolis truly is a sailor's paradise, offering something for everyone, from landlubbers who are toying with the idea of getting their sea legs to seasoned pros. The Annapolis Sailboat Show, held every October, is one of the oldest and largest events of its kind in the United States. With hundreds of boats of all shapes and sizes converging on the town's marinas, it gives potential buyers a chance to climb aboard and check out a variety of crafts or even take them for a spin!

Naturally, anyone with some sailing experience will be itching to get on the water. Annapolis is a great starting point for exploring the Chesapeake Bay or further afield. Around the Bay, sailors can enjoy the beautiful scenery and stop off at a variety of locations from historic towns like St. Michaels and Norfolk, indulge in a little fishing around Tangier Island, or check out the wildlife at the Wye Island nature reserve.

For a longer trip, you can take the popular journey along the East Coast between Annapolis and Newport, Rhode Island, another historic sailing town. Several routes are available depending on whether you want to challenge yourself or take a more leisurely approach, dropping into the many points of interest along the way — a layover in Manhattan is a major highlight for many. If you really want to test your skills, the route also hosts the biennial Annapolis to Newport race.

If you're not a sailor, you might be reading this and wondering how to get in on the action during a trip to Annapolis. If you have a little time on your hands, you can take a course at the Annapolis Sailing School, which offers instruction ranging from the basics to advanced certification. Another way to get involved is to book a cruise on a beautiful 74-foot schooner, where you can muck in with the crew or just kick back and enjoy the ride.

Aside from sailing, there are plenty of other activities for lovers of the water, including kayaking, canoeing, and surfing on windy days. The Chesapeake Bay has been a source of commercial fishing for hundreds of years, and sport fishing is a popular pastime in the area. Chartering a boat gives you the chance to see what you can catch under the guidance of an experienced crew.

The Bay is home to the famous Maryland blue crab, which finds its way into many of the region's favorite dishes, from crab dip to crab cakes. If you fancy catching your own, there are several crabbing spots where you can even do it from dry land. To truly eat like a local, your best bet is to order a bunch of freshly steamed crabs at one of the city's old-school crab shacks and tuck in straight from the shell.