Top Annapolis Likely To Sell Out in 2026

This lighthearted, adults-only, tongue-in-cheek, walking tour is presented by a guide in the character of a colonial indentured servant who works odd jobs day and night to make ends meet – colonial style. During your walking tour in Historic Annapolis, you’ll hear scandalous anecdotes and jaw-dropping tales about what went on inside Annapolis’ famed homes and taverns. Colonial Founding Fathers, Annapolis gentry, renowned portrait artists, and regular folk, too, were all up to their tricks! There was revenge, murder, spying, drinking, political discord, and pleasures of the night.

Discover the quirky tales and unusual stories of Annapolis on this engaging walking tour. Led by a colonial-attired guide, explore fascinating anecdotes including the Russian sailor's grave in the Annapolis National Cemetery and the Confederate captain who never conceded defeat. Perfect for those curious about the unconventional side of history, this tour reveals the city's hidden gems and eccentric past. Ideal for adults and middle school-aged children, the tour takes place at 188 Main Street, Annapolis, MD. - Duration: 1 hour and 15 minutes - Suitable for adults and children aged 12 and older - Tours run on the second Saturday of each month - Learn about unique historical figures and events in Annapolis

The Thomas Point Lighthouse is the most iconic lighthouse in Maryland. View this National Historic Landmark on a narrated cruise into the Chesapeake Bay. Not just for lighthouse enthusiasts, everyone loves it during this 1-hour-and-30-minute excursion that blends history, sightseeing, and the great outdoors into a memorable maritime adventure.

Step back in time on this 2-hour guided walking tour through the beautifully preserved Historic District of Annapolis, Maryland. Visit the Maryland State House, once the capitol of the United States, and explore a colonial kitchen and dining room inside a stunning Georgian mansion. Stroll past iconic landmarks including St. Anne's Parish, the Hammond-Harwood House, the Paca House, and the lively Annapolis City Dock. Hear the fascinating story of the friendly rivalry between the U.S. Naval Academy and St. John's College, two institutions that have shaped the character of this unique city. Along the way, your guide will bring everyday colonial Maryland life to vivid detail, from the merchant class to the working poor. Covering less than a mile on foot, this tour is an accessible and immersive introduction to one of America's most historic cities.

Embark on a spectacular, six-mile, narrated cruise from the Annapolis Harbor, past the U.S. Naval Academy seawall and along the banks, wetlands, and waterfront homes of this protected river. As you take in the great outdoors and rich history of the region, this 1-hour-and-30-minute excursion showcases why Annapolis remains a top destination for nature and maritime heritage enthusiasts alike.

Step aboard a classic vessel for a scenic Chesapeake Bay Bridge cruise. As you depart the dock in downtown Annapolis, you will pass along the seawall of the United States Naval Academy and out into open water. As you approach the Bay Bridge, keep an eye out for local wildlife, including osprey, eagles, rays, and even the occasional dolphin, while enjoying great outdoors sightseeing. Then, marvel at the twin spans of the bridge, one of the largest over-water structures in the world. Sit back and relax with a soft drink, beer, or wine available for purchase, and enjoy the sights on this 90-minute journey.

Explore the eerie side of Annapolis with the Spirits & Spirits tour, blending a captivating walking tour through the Historic District with a thrilling cruise on the haunted waterways. Listen to spooky stories from your Ghost Guide, uncover nautical myths, and indulge in beverages available for purchase during the cruise. Perfect for those seeking a unique blend of history and ghostly tales in a fun atmosphere. This tour is suitable for adults and private tours can be arranged upon request. - Combination of a guided walking tour and a scenic ghost cruise. - Hear chilling tales from expert Ghost Guides while exploring Annapolis's Historic District. - Enjoy a variety of beverages and snacks available for purchase once on the boat. - Tours available on select dates, departing from 188 Main Street, Annapolis.

Set sail across the scenic Chesapeake Bay to the charming village of St. Michaels, where travelers can immerse themselves in local culture, fresh seafood dining, boutique shops, and historic sites. Guests enjoy a complimentary non-alcoholic beverage during the cruise before spending around three hours ashore exploring the town before the return journey to Annapolis. Admission to the Chesapeake Bay Maritime Museum is included, making this sightseeing day trip an ideal way to experience Maryland's rich maritime history.