The best family-friendly activities in Annapolis for parents and kids (Updated October 2026)
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...
$15
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...
$26
Step into Annapolis's rich colonial past on a guided walking tour through the Historic District, led by a guide dressed in authentic colonial attire. Discover...
$26
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...
$28
Sit back and relax on this up-close-and-personal cruise of Annapolis's waterways and scenic city shorelines on one of Watermark's 26-foot, open-aired vessels. Your captain will...
$30
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...
$34
Uncover the rich history of Annapolis on this engaging tour, showcasing Colonial Annapolis, the Maryland State House, and the U.S. Naval Academy. Guided by a...
$34
Historic Ghost Tour of Annapolis
Discover the haunted history of Annapolis on a captivating evening ghost tour. Travelers wander through narrow streets alongside a knowledgeable guide dressed in period attire...
$34
Annapolis Walking Tours provides entertaining and informative tours throughout historic Annapolis. This tour is wonderful for people of all ages and involves approximately 2 miles...
$35
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...
$40
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...
$46
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...
$46
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...
$46
Historic Annapolis Food Tour
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...
$80
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,...
$157
