While Annapolis is worth visiting year-round, the first two weeks of October bring a special level of excitement as the Annapolis Boat Shows transform the harbour into a boating enthusiast’s dream.
During the Annapolis Sailboat and Powerboat Shows, temporary floating docks form an impressive marina filled with the latest models, while hundreds of land exhibits display gear, electronics and more.
The sail show is the largest and the only all-sailboat show in the US, while the powerboat show is known for its welcoming vibe that attracts water sports enthusiasts, anglers, long-distance cruisers, and those curious about the boating lifestyle.
Annapolis, known as America’s sailing capital, has deep maritime roots, a lively recreational boating scene and easy access to the Chesapeake Bay, the country’s largest estuary. So, for sailors wishing to visit an idyllic sailing community in the United States, there is a strong case for Annapolis, Maryland, to be at the top of the list.
The city is also Maryland’s state capital and holds a unique place in US history, having served briefly as the nation’s capital, especially noteworthy this year as the United States commemorates the 250th anniversary of the signing of its Declaration of Independence. Annapolis has since evolved into a vibrant modern destination but the heart of the town, its historic district, still maintains its 18th and 19th century charms.
A must for sailors: The Annapolis Sailboat Show
Sailors from around the world will descend upon Annapolis from 15 to 18 October for the Annapolis Sailboat Show – the largest and only all-sailboat show in the US – where manufacturers debut their latest models and sailors may climb aboard sleek racing boats, offshore monohulls and luxurious cruising catamarans. World-class educational seminars are offered by industry professionals. Charter companies and tourist board representatives help plan dream vacations and top manufacturer experts provide boat-specific advice. These four days, however, deliver much more than great shopping for boats and gear; they are a reunion of sailing friends and a celebration of all things sailing.
From its earliest days, Annapolis has been shaped by the water and has drawn boatbuilders and watermen to its shores. Visitors can experience this heritage firsthand aboard the skipjack Wilma Lee, a traditional sailing workboat operated by the Annapolis Maritime Museum. Public sailing trips and private charters are offered in addition to museum exhibits (amaritime.org). Visiting sailors can also be a spectator or crewmember during the annual Great Chesapeake Bay Schooner Race in October, when a fleet of tall ships race 100 miles from Annapolis to Norfolk, VA, in mid-October (gcbsr.org).
The city is famous for its competitive sailboat racing culture and Annapolis yacht clubs host several prestigious regattas each year. Highlights for 2026 include the Helly-Hansen Sailing World Regatta (1-3 May), the J/30 North American Championships (18-20 September) and the J/70 North American Championships (27 October - 1 November).
Local weeknight racing takes place five days a week during sailing season but peaks on Wednesdays, when more than 100 boats gather and spectators can watch dramatic finishes on Spa Creek. There, as boats cross the finish line, crews scramble to drop sails and quickly turn 180 degrees to avoid a drawbridge just metres away, threading back through oncoming racers and spectator boats.
A variety of local charter companies offer skippered or bareboat charter on monohulls, catamarans and powerboats for visitors who want to see Annapolis or the Chesapeake Bay by water. For a classic sailing experience, the schooner Woodwind offers two-hour daytime and sunset sails, often featuring local guest speakers such as historians, authors and environmentalists (schoonerwoodwind.com).
More unforgettable sightseeing opportunities are available through the locally owned company, Watermark, which operates boat cruises and unique walking tours (watermarkjourney.com). Non-sailors will find plenty to enjoy in Annapolis, too. The US Naval Academy offers guided tours and is home to Preble Hall, the US. Naval Academy Museum (usna.edu). History buffs might choose to tour colonial era buildings. All visitors will enjoy strolling the quaint streets, shopping at locally owned boutiques, visiting the historic state house and sampling the local cuisine; be sure to try a Maryland crabcake. (visitannapolis.org).
Beyond Annapolis, the nation's capital city Washington DC, and Baltimore, another historic port town, are easy day trips. Both offer revitalised waterfront promenades, world-class museums, professional sports and fine arts venues, and exceptional dining. Come and see all the Annapolis region has to offer.
