The Chesapeake Bay is the largest estuary in the U.S., spanning 64,000 square miles and six states—and offering sailors everything from quiet retreats in calm inlets to full-on national sailing regattas in open water. Located in the heart of the Bay (38 degrees, 58 minutes, 35 seconds north and 76 degrees, 28 minutes, and 46 seconds west), it’s no surprise Annapolis is considered the Sailing Capital of the U.S.

We’re home to the National Sailing Hall of Fame; marinas packed year-round with boats of all shapes and sizes; dockside restaurants, sailing schools and charters; plus boat dealers and maintenance facilities to help with everything from repairs to purchases. There’s also the Boatyard Bar and Grill, a popular local sailors hangout that Sail Magazine calls one of the Top 12 Sailing Bars in the World.

Needless to say, whether you’re a veteran sailor or are considering dipping your toe in the water for the very first time, Annapolis has something to offer. 

Annapolis Boat Shows

Annapolis is home to three of the world’s largest in-water boat shows: The Annapolis Spring Sailboat Show, the U.S. Powerboat Show, and the U.S. Sailboat Show. Since 1970, Annapolis has hosted the U.S. Sailboat and Powerboat shows, bringing in over 150,000 boat lovers from around the world each year. Every October, the Sailboat Show takes over Annapolis’ City Dock for four days, followed by the Powerboat Show for another four days in the same location. Featuring the industry’s leading manufacturers and the latest in electronic equipment, gear, and essentials in vendors’ tents lining Ego Alley, the boat shows offers everything a sailor could think of. 

Spring Sailboat Show at Sunset

The Annapolis Spring Sailboat Show is the world’s greatest showcasing stage for sailboats. Bringing in thousands from around the world, it showcases the latest sailboats from manufacturers around the world. Each April, Annapolis’ City Dock is once again inundated with vendors selling the year’s best in equipment, gear, essentials, and boats. Pick a spot on the globe and book a charter; buy that chart-plotter you’ve had your eye on all year, or that catamaran you’ve always wanted. It’s all at the Annapolis Spring Sailboat Show.

All three exhibits are put on by the Annapolis Boat Shows.

Annapolis Charters, Cruises, and Sailing Schools

 Annapolis Sailing Cruises: Schooner Woodwind

Whether you’re looking simply to spend an afternoon out on the Chesapeake Bay relaxing, staying overnight on a boat in the Annapolis Harbor, or learning to sail on your own, it’s in Annapolis. 

With a handful of charters and cruises available, getting out on the water is easy. You’ll find sunset tours, day tours, historic water tours, even fishing charters to take you out. Many depart right out of the Annapolis Harbor in historic downtown, making booking a trip on the Bay easy and convenient when visiting. 

There are also a number of sailing schools in the area where you can learn the basics and test your sea legs. Grasp the fundamental navigation skills needed to set sail alone or learn about the basics of racing through the schools’ seminars and classes offered throughout the year. 

National Sailing Hall of Fame and Museum

National Sailing Hall of FameThe National Sailing Hall of Fame (69 Prince George Street [38 58.5’N 76 29.0W]) is a not-for-profit educational institution located on Annapolis’ City Dock. Dedicated to preserving America's sailing legacy and engaging sailing’s next generation, the Hall of Fame offers special events, sailing classes and programs, exhibits, and 530 feet of docks on the Annapolis waterfront. Here, you’ll find a little sailing art as well as a catalogue of Hall of Fame inductees ranging from railroad tycoon, Harold Vanderbilt, to local Annapolis sailing legend, Gary Jobson.  

More Reasons to Visit Annapolis: From Serious Sailing to Leisure Travel

Annapolis also is renowned as a global sailing powerhouse. Annapolis hosted U.S. Sailing's Rolex International Women's Keelboat Championship in 2005, and Volvo Ocean Race organizers selected Baltimore/Annapolis as the only official U.S. Stopover in the 2005-2006 around the world race. Maryland's capital city is also well known for Labor Day Weekend Races. More than 200 boats in fifteen classes compete in this annual Labor Day Weekend event that attracts boaters from across the country. 

Annapolis Harbor

It's easy to visit Annapolis if you’re arriving by boat. Sailors can drop anchor at a mooring ball right in front of the Naval Academy and catch a water taxi into town, or dock at one of the marinas in the area. One of the first things you are likely to see is a host of sail and power boats strutting their stuff at City Dock, affectionately known as Ego Alley. 

Part of Annapolis' appeal to boaters is the fact that it is located where the mouth of the Severn meets the powerful sailing winds of the Chesapeake Bay. Many boaters choose to keep their boats in Annapolis so they can head down after work on a Friday night. If you are among them, you could find yourself spending the evening dining and exploring the Historic District. The next day, it's off for a day sail or for a weekend getaway to St. Michaels on the Eastern Shore. Solomons, Baltimore, Rock Hall, Havre de Grace, Chesapeake Beach, and Herrington Harbor are all popular places within easy boating reach of Annapolis. By Sunday, don't be surprised to find yourself back in Annapolis enjoying a roll-up-your-sleeves, steamed crab feast.

If you’re a sailor, Annapolis is one for the bucket list. Whether its maritime history or sailing races you’re after, Annapolis has something for every sailor.