
Colonial Annapolis & U.S. Naval Academy Walking Tour
Enjoy the rich stories of historic Annapolis, the Maryland State House, and the U.S. Naval Academy on this 2¼-hour walking tour.
Book NowEnjoy the rich stories of historic Annapolis, the Maryland State House, and the U.S. Naval Academy on this 2¼-hour walking tour.
Book NowFollow our spirited guide through the timeless narrow streets of this old and creaky town. Stopping at spooky spots, you'll hear stories told with dramatic zeal of those that have passed.
Book NowDuring this walking tour and cruise combination experience, you’ll brave the Historic District by foot and hear spooky stories from your Ghost Guide. You’ll then continue on through the haunted waterways of Annapolis and be entertained with nautical myths and pirate tales.
Book NowThis 90-minute lighthearted, tongue-in-cheek 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.
Book NowOn this 2-hour walking tour, our knowledgeable guide in period attire will share the fascinating history of the contributions made here and regionally by African Americans.
Book NowSpecial Historic Hauntings takes you back to a time of superstition and legend. And who knows, after a trip inside Hogshead, your own story may be added to the history of Annapolis!
Book NowEnjoy a three-course dinner at the Maryland Inn. Then, you’ll follow your spirited guide for a leisurely stroll through a small section of the Historic District of Annapolis packed with haunted stories.
Book NowHear tales about the Russian sailor buried in the Annapolis National Cemetery, the historic “mobile homes” of Annapolis, the Confederate captain who kept fighting the Civil War long after the South surrendered then built a home in Annapolis, the missing State House cornerstone … and so much more!
Book NowWelcome the holidays with an evening walking tour of Annapolis. Hear holiday traditions of times past as you walk by colonial mansions, Victorian homes, and quaint shops.
Book NowStroll through Maryland's state capital, trimmed in greenery, with your period-attired guide. Then enjoy authentic, colonial, holiday decorations, and learn about early nineteenth-century holiday traditions at the Hammond-Harwood House.
Book NowLearn more about our special or seasonal walking tours here.
Learn MoreAnnapolis Tours by Watermark offers visitors to the Annapolis and Baltimore region the opportunity to tour some of the nation’s most historic streets with knowledgeable guides that are dressed in period attire.
Watermark is the authentic provider of guided historic walking tours in Annapolis, Maryland. With our company’s origins dating back to the 1970’s, our period dressed Colonial guides keep U.S. and Annapolis history alive and have been sharing their passion for history and folklore to adults, students, and groups of all types for decades. Our tours are a unique and fun option when looking for things to do in Annapolis.
True Annapolis historians! They walk the streets in colonial attire sharing their wealth of knowledge of Maryland’s state capital. Our guides go through an extensive training program that exposes them to authors, professors, specialists, and historic sites. They enjoy spreading the word on how our city came to be with facts, stories, and sheer delight. Many of our Squires and Mistresses have been guiding with Watermark for decades. We are proud to have such a loyal and gifted group ready to show you around town.
Watermark’s walking tours provide a great experience for a private group. Whether you are looking for a family. Social, military, or church outing, all of our walking tours are available as a private tour. Click below to contact our group tour specialist or learn more about popular group and private packages.