The best family-friendly activities in Annapolis for parents and kids (Updated October 2026)

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...

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...

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...

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...

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...

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...

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,...

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...

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...

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...

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...

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...

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...

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...

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...