Top Annapolis Sightseeing Tours

Put a ghoulish twist on your night out with a haunted pub crawl through historic Annapolis. Visit three bars over the course of the night, each with a ghost story behind it that will scare you sober. Drinks available at your own purchase.

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 seawall of the United States Naval Academy and out into open water. As you approach the Bay Bridge, keep an eye out for local wildlife, including osprey, eagles, rays, and even the occasional dolphin, while enjoying great outdoors sightseeing. Then, marvel at the twin spans of the bridge, one of the largest over-water structures in the world. Sit back and relax with a soft drink, beer, or wine available for purchase, and enjoy the sights on this 90-minute journey.

Take a pleasant walking tour through the beautiful historic center of Annapolis, specially designed for the US 250th Anniversary. Discover the fascinating role Annapolis played in the fight for and achievement of American independence! We will begin along the city dock and harbor that received many founding fathers in the 1700's, admiring the view to the Chesapeake Bay and wider world. We'll see two Georgian mansion built in the 1770's, as well as the iconic Maryland State House, where the Treaty of Paris was signed (bringing to a conclusion the Revolutionary War) and where General Washington resigned as general, thus becoming the "greatest man in the world" and the "American Cincinnatus. " We'll also explore the campus of St. John's College, which dates back to 1696, and talk about other Annapolis customs and traditions, as well as bars, restaurants, and more. All questions are welcome!

We depart right from downtown Annapolis, putting you immediately in the heart of the waterfront, Spa Creek, Ego Alley, and the harbor scene without needing to travel to an outlying marina. Enjoy a customized experience tailored to your group with a USCG-licensed captain. Whether you want to cruise Spa Creek, sail the Bay, anchor for a swim, stop at a waterfront restaurant, or enjoy a sunset picnic, the classic teak-appointed Nauticat offers a refined and relaxed way to enjoy the water. Bring your own food and drinks or opt for catering to make your outing extra special. Enjoy a private boat experience with just your group and no crowds. Depart from downtown Annapolis, right in the heart of the waterfront. Choose from two vessels: the classic Nauticat 331 or the nimble AB Oceanus RIB. Suitable for family outings, casual celebrations, or intimate getaways. Flexible trip lengths and itineraries to match your preferences.

This private walking tour offers a calm and comfortable introduction to historic Annapolis at an easy pace. You explore the city as residents once did, along flat streets and quiet waterfront paths shaped by daily life and civic tradition. Clear storytelling brings forward the voices of merchants, lawmakers, families, and sailors who defined early Annapolis. Your walk begins near the harbor where trade and community met. The route continues through peaceful public spaces with time to pause, sit, and enjoy the surroundings. Stories focus on early American governance, maritime heritage, and local customs explained in a relaxed and engaging way. This experience suits travelers aged 50+ who value culture, history, and thoughtful narration without rushing. Please note: The program and attractions may vary based on booking date/time and crowd conditions, ensuring each visit is a unique experience.

This private walking tour introduces historic ghost stories through the calm streets of Annapolis at a relaxed and comfortable pace. You explore the city where colonial history and long-shared legends quietly intersect. Storytelling focuses on documented events, respected local traditions, and the people who shaped early America. Beginning near the Maryland State House, you hear how politics, power, and personal lives left traces still discussed today. Around Church Circle, stories reflect faith, daily life, and the rhythm of an 18th-century town. Near the William Paca House, refined society and private lives reveal another layer of Annapolis history. The walk concludes by the City Dock, where maritime life and waterfront legends complete the experience. This tour is designed for travelers who value history, and storytelling without haste. Please note: The program and attractions may vary based on booking date/time and crowd conditions, ensuring each visit is a unique experience.