Group Charters

Image: Visitors to Annapolis at the Overlook

Bringing a group to Annapolis? They’ll love our one-hour trolley tour. It’s a great “first thing to do” for a fun overview of all the major points of interest.

Our trolleys are small enough to get around the back streets and boatyards, and feature large, panoramic windows. Enjoy spectacular views of the

U.S. Naval Academy (exterior)
City Dock
State House
colonial mansions
Government House (governor’s residence)
Victorian painted ladies
Maryland’s World War II Memorial.

We’ll cross three bridges–twice–for great water views, and make one stop at the Severn River Overlook. All accompanied by a fun and fascinating narration!

Our vehicles are air conditioned in summer and heated in winter. Tailor the pick-up and drop-off locations to fit your itinerary, helping move your group to and from area attractions and restaurants. Been here before? Special-interest tours are also available for something new and different.

Click here for a profile sheet on our group tour offerings.

Popular Packages & Special Interest Tours

"The Holly Trolley" -- Christmas season offerings

"By Land and By Sea" -- 40-minute harbor cruise

"The Navy Way" -- Walking tour of U.S. Naval Academy

"Gorgeous Gardens" -- Visit William Paca House & Gardens

"Tea & Tour" -- authentic British tea in a 1747 tavern

"The British Connection" -- Medieval Times dinner & show

"African-American Heritage" -- Visit the Banneker-Douglas Museum.

Each package has variable features. Please contact us to discuss your itinerary and pricing.

Here’s an overview of the major group attractions and suggested itineraries.

Click here for all the details on our rates, comp policy, deposits and refunds.

We’ve provided directions and maps to the motorcoach loading zones, and other helps for your driver.

Let us know when you’re planning to visit, and we’ll check our calendar for availability.

We're regularly featured in Smithsonian Associates and Elderhostel tours of Annapolis!

Founded in 1995, Discover Annapolis Tours is a member of these fine organizations:

Image: Spa Creek forms one side of the Annapolis peninsula

CUSTOMER COMMENTS – Unsolicited customer’s views on their tour experience:

“Such a wonderful tour! Our driver/guide was very knowledgeable, witty, and personable, and helped make the city come alive.” - A Tour De Force, Washington DC

Image: Naval Academy Chapel dome from Martin Street.

"Just a note to tell you how much my family and friends enjoyed the trolley tour on Saturday.... The guide was super and the tour quite interesting and fun!"-- Patricia Nalley, Nalley Family Reunion