A walk around Annapolis can open your eyes to history, cultural heritage, maritime life, and scenic beauty—especially if you’re walking with one of the many tours offered in the historic district. If you’re looking for a walking tour with a knowledgeable guide, Annapolis has lots of purveyors of tours and something for everyone. 

Watermark Tours

The most longstanding and active provider of Annapolis sightseeing tours is Watermark Tours, a professional tourism firm offering all things Annapolis, from boat tours to water taxis to Colonial guides. 

Watermark's experienced guides provide walking tours through historic downtown Annapolis, the Maryland State House, and the United States Naval Academy. The spirited Watermark guides wear Colonial period attire and are very knowledgeable, each receiving fifty hours of annual re-certification training about the history of Annapolis. These guides are also certified by the United States Naval Academy. Click here to learn more about their walking tours. 

Blue Angels Watermark Tours

Watermark offers a variety of walking tours. The Annapolis Four Centuries Walking Tour explores famous landmarks, guiding visitors along the paths traveled by George Washington and other historic figures. The Four Centuries Walking Tour is offered twice daily spring through fall and on Saturdays during winter months.

Other Watermark Tours include the Historic Ghost Walk, with fact-based tales of supernatural events and spirits who haunt centuries-old buildings. Other options are the Colonial Stroll, the African-American Heritage Tour in February, the Historic Hauntings tour in October, and the Holiday Candlelight Stroll in December. 

Watermark’s group tours can include a Chesapeake Cravings food tour, garden tours, and Civil War and War of 1812 tours. In March, you can celebrate Maryland Day with the complimentary "ArchiTrex" Tour exploring vintage architecture in Annapolis. 

If water tours are more to your liking, Watermark offers daily sightseeing cruises available from City Dock. Explore the banks of the United States Naval Academy, to the waterfront homes of Annapolis, to the Chesapeake Bay Bridge and the Thomas Point Shoal Lighthouse. A tour on the water is certainly one of the best ways to experience Annapolis.

United States Naval Academy

Nestled in the heart of Annapolis, the Naval Academy campus is filled with wonderful opportunities for visitors. A guided tour is a terrific way to start. 

Watermark Tours of the USNA

Stop by the Academy’s Armel-Leftwich Visitor Center just inside Gate 1 near the Annapolis City Dock. Chat with a Visitor Center information specialist, view the 13-minute film, The Call to Serve, and take a walking tour of the campus with a professional Naval Academy guide. The tour highlights life at the Academy past and present and includes Lejeune Hall, Bancroft Hall, Tecumseh Court, the Herndon Monument, the Naval Academy Chapel, and the Crypt of Revolutionary War hero John Paul Jones.

Historic Annapolis

The festive Annapolis by Candlelight tour is hosted by Historic Annapolis annually during the holidays. Historic Annapolis is the leading nonprofit preservation and history organization in Annapolis. This fundraiser tour is a rare opportunity to see the interiors of some cherished public and private 18th- and 19th-century architectural icons. You may follow the tour route at your own pace, and informed volunteer guides await visitors in each of the homes.

Paca House Garden

Historic Annapolis also offers advance reservation group tours at the organization’s historic properties, including the William Paca House and Garden, the James Brice House, and Hogshead on Pinkney Street. 

Hammond Harwood House Tours

The beautifully restored 1774 Hammond Harwood House museum on Maryland Avenue offers the annual Secret Garden Tour fundraiser in early June. This self-guided walking tour allows ticket holders a behind the scenes look at some of the most stunning private gardens in downtown Annapolis. 

Hammond Harwood House tours

Capital City Colonial Food Tours

Capital City Colonial’s Historic Annapolis Food Tour winds through historic sites as guests enjoy a series of lunch dishes from restaurants in downtown Annapolis. The food tour combines culture, history, and architecture with a multi-course progressive dining experience. A tour guide leads participants while describing historical landmarks along the way.

Tours & Crawls 

Tours & Crawls offers both family-friendly walking ghost tours and, for the over-21 crowd, a variety of pub crawls and tavern tours. You can spend a fascinating evening learning about ghosts and legendary hauntings in Annapolis. These guided tours include the Walking Ghost Tour of Historic Annapolis, the Haunted Pub Crawl, and the Twisted History Tavern Tour. 

Let Technology be your Guide

Walking tours are one of many ways to see Annapolis. Also look for tours by horse and carriage, trolley, segway, kayak, water taxi, tour boat, and sailing schooner. Whichever one you choose, you’ll be certain to enjoy learning about the rich and compelling history of Annapolis.