Choose your trip length, interests, and pace to build a flexible Annapolis itinerary. Add other destinations, compare experiences, and reserve time for travel between stops.
Browse these experiences as a starting point. The planner considers your interests, pace, and published schedules when building your days.
Ashes and Apparitions of Annapolis Ghost Tour
Embark on this Annapolis ghost tour and step back in time as you stroll through the historic district. Your guide will share chilling tales of hauntings at iconic buildings. Discov…
During The Historic Annapolis Food Tour, you will enjoy a series of dishes from restaurants in downtown Annapolis while weaving through historic sites. The tour lasts approximately…
Tipsy History Tour: 300+ Years of Annapolis Drinking History
Explore Annapolis' vibrant past on this unique historical pub crawl. Over two hours, discover how drinking influenced the city and the nation while enjoying recommended drinks at e…
Annapolis Historic Walking Tour: Harbor and Colonial Downtown
Take a pleasant walking tour through the beautiful historic center of Annapolis, including the picturesque harbor and US Naval Academy. We'll see the Georgian mansions, the iconic …
Cruise through history on the Annapolis Harbor & USNA Cruise. This narrated cruise offers insights into the U.S. Naval Academy and Annapolis' rich maritime heritage while enjoying …
The Original Haunted Pub Crawl by Annapolis Ghost Tours
The only Haunted Pub Crawls permitted inside the oldest and most haunted pubs in Historic Downtown Annapolis. Enjoy a 2-hour guided adventure on our haunted pub crawl. Drink in the…
Start with the number of days you have, then choose an unhurried, balanced, or fuller pace. Review the suggested route before generating your daily plan. Transport allowances are estimates; confirm services and meeting points before booking.
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