Baltimore Metro Region

Summer finds this bayside gem celebrating its 300th birthday in grand style. You can’t squeeze everything into a couple of days, but you’ll have plenty of fun trying. Fun for you, fun for the whole family. And it all takes place in a vacation setting that combines village charm and metropolitan sophistication.

To make your visit memorable, we’ve highlighted some of our favorite attractions. Choose just a few, or go for the gusto in one whirlwind week. For the crowning touch, let an innkeeper pamper you at a bed-and-breakfast.

By the end of your stay, one thing is certain: You’ll have a new favorite vacation spot—right here in Maryland.

Tour, See & Explore

Kick off your visit with a guided tour. Quick, affordable, and highly recommended, these sightseeing excursions are conducted on foot, bicycle, Segway, carriage, trolley, kayak, water taxi, and yacht. All give an excellent lay of the land, allowing you to explore the best of the rest of Annapolis on your own.

Slip on your walking shoes for the Colonial Stroll. Costumed guides regale visitors with fascinating facts and lore about downtown’s “Museum without Walls.” Learn about life in the 18th century. Marvel at the classic buildings. Visit the homes of the four Maryland signers of the Declaration of Independence.

Inside the Maryland State Capitol Building—built, burned, and rebuilt in 1772—you’ll learn this architectural centerpiece hosted the Continental Congress, George Washington’s resignation as military commander-in-chief, and the signing of the Treaty of Paris, which brought an end to the Revolutionary War.

In West Annapolis, the U.S. Naval Academy beckons with its crisp salutes and manicured lawns. Each year, more than 1 million people admire the interior of the Naval Chapel, observe the crypt of hero John Paul Jones, and—while in session—watch midshipmen in their “Noon Meal Formation.” (Remember to be there at 12:15 p.m. sharp.) Nearby Bancroft Hall will amaze. The world’s largest dormitory, this Beaux Arts marvel houses some 4,000 “middies” in 1,700 rooms. Thankfully, a guided tour won’t cover all five miles of corridors, but will help you see why this building rates its own ZIP code.

The History & Food Tour wins rave reviews. Resembling a pub crawl for the history-minded foodie, this three-hour tour wends sightseers past our Founding Fathers’ favorite eateries, stopping here and there for eats and treats. Another must-do: the Women of Annapolis tour, a 90-minute celebration of women from the city’s 18th-century “Golden Age”—be they the gentry, merchants, or indentured servants. Similarly, the African-American Heritage Tour retraces the trials and triumphs of local African Americans since the colonial era, capped with a visit to the dockside spot where, in 1767, slave Kunta Kinte (of Alex Haley ancestry) took his first step onto American soil.

Satisfy your enquiring mind with the Colonial Gossip Tour. Here, guides dish the dirt on their colorful neighbors of yore, reminding us little has changed in 300 years. To satisfy your inner geek, the Segway Safari can’t be beat. Hop about inventor Dean Kamen’s two-wheeled “human transporter” for a one- or two-hour guided tour. Come sundown, make a beeline for the Haunted Ghost Tour. Spooky stories and shadowy streets will thrill kids of all ages. If you’re lucky—or unlucky—you may see the ghosts of the Headless Man, Joe “the enthusiastic gravedigger” Morgue, and Thomas Dance, who long ago fell from the Capitol dome and into the Who’s Who of the Paranormal. Similarly, the Haunted Pub Crawl serves up its share of ghoulish delights all inside several well-stocked bars. Last, set sail aboard the Harbor Queen for a three-hour Sail & Crab Feast (timed to coincide with major sailboat races) or a “pajamas welcome” Moonlight Madness Cruise along the Severn River on July 18.