Top things to do in Annapolis in Summer (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

Amazing Annapolis Scavenger Hunt
Our very unique, immersive adventures are the only ones of their kind. We, unlike other companies, provide your very own remote, interactive, live host to...
$27

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

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...
$31

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

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

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

