Tour the U.S. Naval Academy – No visit to Annapolis is complete without a visit to the U.S. Naval Academy. Home of the 4,000-strong brigade of midshipmen, the Naval Academy is the training ground for officers of the U.S. Navy and Marine Corps. On weekdays during the academic year, be sure to catch the midshipmen in noon formation. Don’t miss the recently renovated chapel and its massive pipe organ. Be sure to allow enough time to visit the Naval Academy Museum. It features more than 50,000 artifacts and is home to the famous Gallery of Ships. Guided tours of the USNA begin at the Armel-Leftwich Visitor Center.
Get Out on the Water – Want to get out on the water but don’t know where to begin? The professionals at our world-class sailing and powerboat schools can get you started. If relaxing is at the top of your list, enjoy a 40-minute harbor cruise; relax during a two-hour sail aboard a 74-foot wooden schooner; charter a boat for the day; or unwind on a boat and breakfast getaway. If fishing floats your boat, charter with a seasoned captain or strike out on your own. Want to get closer to the action? Explore the Bay by canoe, kayak, or paddle board.
Pledge your Allegiance at Chick & Ruth’s Delly – The home of the largest milkshakes in the world and the three-pound Super Duper Colossal Burger is also a major seat of patriotism in Annapolis. Every weekday morning at 8:30 a.m. and weekends at 9:30 a.m., owner Ted Levitt invites his patrons to get their day off to a bright start by joining him in reciting the Pledge of Allegiance. If you play your cards right, the master of magic might even do a personalized magic show at your table.
Take a Water Taxi – While Annapolis is a walkable city, sometimes the quickest way to get from point A to point B in America’s Sailing Capital is to hop aboard a water taxi. Use one to get from City Dock to Eastport for an memorable meal along Restaurant Row or drop anchor across from the Naval Academy and call a water taxi to bring you into town. They are a quick, relaxing, and affordable way to work the water into your busy itinerary.
Steer a Duffy Electric Boat – Kick off a fun, environmentally-friendly afternoon on the water with your friends by renting a ten-passenger Duffy electric boat. Board your climate-controlled, 22’ Duffy at the Chart House Restaurant pier at 300 Second Street in Eastport. You can charter the boat with or without a captain for an entire day or as little as an hour. No boating experience is necessary.
Test Drive an Electric Bike – If you want to cycle through the Historic District without breaking a sweat, hop aboard a Green Pedals electric bike. Equipped with high efficiency electric motors, the state-of-the-art vehicles deliver all the fun of standard bikes, but they require only as much effort as you want to put into your ride. The bikes are typically rented for a two-hour period.
Feast on Steamed Crabs – Restaurants serving up nature’s bounty dot the more than 400 miles of shoreline that winds its way through Annapolis and the Chesapeake Bay. Favorites including Mike’s Restaurant and Crab House, Cantler’s Riverside Inn, Skipper’s Pier, and others help contribute to the claim that some 3.9 million crabs are cracked here each year. The Annapolis Rotary Crab Feast held at Navy-Marine Corps Stadium boasts the largest crab feast in the world.
Experience the Roots and Tides Driving Tour – Today, as in the past, the rhythm of life in Southern Anne Arundel County moves with the tides and the seasons. Maritime villages such as Deale, Galesville, and Mayo invite you to escape to a simpler time. Experience the life of a 19th-century waterman at the Captain Salem Avery Museum in Shady Side. Enjoy the quiet of Galesville’s Quaker Burying Ground before wandering past Victorian houses to the Heritage Museum. Historic London Town and Gardens in Edgewater continues to unearth the past at the largest ongoing archaeological dig in Maryland.
Enjoy a Free Concert or Festival – Every First Sunday of the month from May through October, a First Sunday Arts Festival takes place on the first block of West Street from Church Circle to Calvert Street. During the noon to 5:00 p.m. celebration, craft vendors, artists, musical acts, and street performers gather to celebrate the arts. Throughout the summer, outdoor concerts – including free performances by the U.S. Naval Academy Band – abound throughout Annapolis and the Chesapeake Bay.
Wednesday Night Sailboat Races – Looking for an excuse for a mid-week escape from the office? How about the Wednesday Night Sailing Races in Annapolis? More than 130 sailboats slice through shimmering waters, their colorful, wind-filled spinnakers backlit against a golden sky. After racing around several marks in the Chesapeake Bay, they return to Spa Creek for a finish in front of the Annapolis Yacht Club. Races begin the final Wednesday in April and run through the second Wednesday in September. The first gun is at 6:05 p.m.
Annapolis Maritime Museum – Concerned about the environment? Check out Annapolis Maritime Museum's Oysters on the Half Shell exhibit. The interactive display highlights the natural history of oysters and the important role they play in the health of the Chesapeake Bay. The exhibit also chronicles the cultural history of the hard-working people who harvested, shucked, packed, and shipped oysters from the McNasby Oyster Company. Key elements include a 1,000 gallon aquarium with a living oyster reef and the many critters that thrive in such a habitat; a touch tank; a large-scale oyster that opens up to show all the anatomically correct body parts; an exhibit of skimming and processing equipment; and recreated shucking tables. Sections of the work boat, Miss Lonesome, are used to demonstrate how wooden boats were built and used for oyster harvesting.
Maryland State House – Annapolis is home to the oldest State House in continuous legislative use in the nation. It is also the only state house in the country that also served as the nation’s capitol. The Continental Congress met in the Old Senate Chamber from November 26, 1783 to August 13, 1784. During this time, George Washington appeared before Congress to resign his commission as commander-in-chief of the Continental Army. It was here that the Treaty of Paris was ratified, marking the official end of the Revolutionary War.
National Electronics Museum – For an offbeat and off-the beaten-path excursion, try the Historical Electronics Museum. You'll learn about TVs, radios, cell phones, and see a working original Edison cylinder phonograph. The museum houses the first American radar system ever built, a lunar camera similar to the one used to photograph Neil Armstrong’s moon landing, and the SCR-584 – a giant radar unit that visitors can enter and explore.
National Cryptologic Museum – Get a taste of the world of secret codes as you peek behind the curtain at the National Security Agency’s National Cryptologic Museum. Learn of some of our nation’s World War II cryptological triumphs as you trace the development of cryptology from the 1500s to the present day.
William Paca House and Garden – The two-acre reconstructed 18th-century pleasure garden is an oasis in the heart of Annapolis. Located behind the National Historic Landmark home of Declaration of Independence signer William Paca, the garden is the only one of its kind in Maryland. 410-267-8146.
Thomas Point Shoal Lighthouse – Get an up close and personal look at the last screwpile lighthouse on the Chesapeake Bay still in its original location when you take a seasonal tour of the National Historic Landmark Thomas Point Shoal Lighthouse. A boat departing from the Annapolis Maritime Museum takes you on a one-and-a-half mile journey to the 1875 lighthouse at the mouth of the South River. Once there, you can climb into the lighthouse for a docent-led tour. Reservations are required.
Ego Alley – No visit to America’s Sailing Capital is complete without a visit to City Dock and the Annapolis Harbor. Fondly known as Ego Alley, it is here that boats of all sizes strut their stuff before an admiring public. Grab a seat at a dockside eatery, catch an outdoor concert, or treat yourself to an ice cream cone and a stroll along City Dock for a people- and boat-watching experience extraordinaire.
Most Beautiful Doorway in America – Annapolis is home to more 18th-century brick buildings than any other city in the nation. Its five-part Georgian mansions are the crowning architectural jewel in a city that embraces four centuries of architecture. Built by English architect William Buckland in 1774, the Hammond-Harwood House at 19 Maryland Avenue boasts the Most Beautiful Doorway in America.
Woodland Garden at Historic London Town & Gardens – Modeled after the Windsor Great Park in Great Britain, the eight-acre woodland garden features a mile-long path through a variety of garden settings, including a holly grove, dry stream, spring bay, Hosta garden, winter walk, Camellia collection, wildflower walk, Azalea glade, and dell. A wide variety of hollies makes the walk a beautiful place to explore even in the heart of winter.