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 t... More

Celebrate the holiday season with a delightful 45-minute cruise along Spa Creek, guided by Captain Santa or Mrs. Claus. This family-friendly adventure includes hot cocoa served by an onboard elf and cozy blankets to keep warm as y... More

Discover the profound legacy of African American history in Maryland on an enlightening two-hour walking tour in Annapolis. Starting near Market House Park, journey through time to encounter significant landmarks such as the Alex ... More

The original 90-min Annapolis Ghost Tours are the only tours created by our owner, noted local Maryland historian, and author of "Haunted Annapolis". Don't be fooled by national chains pretending to be locally owned and run. Take ... More

Our very unique, immersive adventures are the only ones of their kind. We, unlike other companies, provide your very own remote, interactive, live host to assist and encourage you along through your phone. We are an Austin, TX-bas... More

Get ready to discover why Let’s Roam is the ultimate in app-led adventure hunt excitement! Picture this: strolling through Annapolis, hitting up all the iconic landmarks and uncovering hidden gems, all while tackling trivia ques... More

Embark on a thrilling adventure in Annapolis! Unravel the city's rich history, from its days as the US capital to its vibrant present. Discover the tales of Princess Anne, Abraham Lincoln, and Duke Ellington. Marvel at the city's ... More

Take a pleasant walking tour through the beautiful historic center of Annapolis, specially designed for the US 250th Anniversary. Discover the fascinating role Annapolis played in the fight for and achievement of American independ... More

Celebrate the holiday season with the Holiday Candlelight Stroll, a delightful 75-minute walking tour through Annapolis. Led by a period-attired guide, this tour takes you through Maryland’s capital, adorned in festive greenery.... More

Welcome the holidays with Watermark's Christmas in the Capital Tour: Annapolis Traditions and State House Trees. Meet your period-attired guide inside our cozy office before embarking on your tour. Stroll with your colonial guide ... More

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 tou... More

This private walking tour offers a calm and comfortable introduction to historic Annapolis at an easy pace. You explore the city as residents once did, along flat streets and quiet waterfront paths shaped by daily life and civic t... More

This private walking tour introduces historic ghost stories through the calm streets of Annapolis at a relaxed and comfortable pace. You explore the city where colonial history and long-shared legends quietly intersect. Storytelli... More