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Popular Combinations

Join us for a walking tour & a cruise!

Popular Combinations Tailored to Your Group

Planning a trip to Annapolis or Baltimore for your family, social, military, reunion, or church group?  Let our experienced group tour specialists put together a comprehensive tour package for your distinct group. We specialize in Baltimore and Annapolis historical, cultural and fun activities.  Watermark offers complete itineraries for your group including meals in the Chesapeake Bay area so you only have to make one call. Most of our tours and cruises can be packaged together to meet your unique Group’s needs.

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Group on a cruise


harbor queen

Annapolis By Land and Sea – Historic Walking Tour & Harbor Cruise

Experience the colonial seaport town of Annapolis, home of the U.S. Naval Academy, with brick-lined streets, 18th century architecture, active boat harbor, several large Georgian mansions and historic pubs.

Your tour begins as you step back in time with a tour guide dressed in colonial attire who will greet your group. During a 2 ¼ hour walking tour, you will visit the exterior of the historic mansions and learn about the distinctiveness of Georgian architecture. You will also view the exterior and interior of the State House, the USNA grounds with interior views of the Chapel, crypt and sarcophagus of John Paul Jones. (Building interiors when available.)

After your walking tour, relax on one of our regularly scheduled 40- or 90-minute narrated cruises onboard one of our tour boats.

Harbor Queen

Coach and Stroll with an Annapolis Harbor Cruise

Great tour and cruise for seniors with limited walking.  Your group will tour the Historic Maryland State House and then take a driving tour on your bus that includes Historic Annapolis and a stop at the WWII Memorial, which provides sweeping views of the United States Naval Academy. The tour also takes you by the Governor’s residence, colonial mansions and gardens, sailboats along the waterfront, homes of the signers of the Declaration of Independence, the City Dock, Victorian bungalows, St. Johns College and much more.  A walking tour of the USNA may be added to this tour.

Your tour will end at the Annapolis City Dock where you will board a tour boat for a narrated cruise on the water. Choose from the 40-minute or 90-minute cruises.  Box lunch option available on the 90 minute cruise.

After your cruise, enjoy some free time in Annapolis to shop the numerous boutiques and antique shops, browse the museums and art galleries and enjoy the charm of the historic sights and spectacular waterfront of Annapolis.

US Naval Academy Chapel

Anchors Away

The United States Naval Academy tour will include the USNA Chapel and Crypt of John Paul Jones, Bancroft Hall, and a walk past many monuments.  The USNA is home to over 4,000 midshipmen. (Building interiors when available)

Have lunch at one of the USNA Restaurants or in one of the many downtown historic restaurants in this lovely seaport town.  Your group may choose to have lunch on their own. End your nautical day with a narrated cruise on the Harbor Queen.  Enjoy a Water-view of Maryland’s Capital and catch a glimpse of the Chesapeake Bay Bridge.

Chesapeake Cravings Tour

Chesapeake Cravings with an Annapolis Harbor Cruise

Enjoy a full day of iconic Chesapeake Bay culinary traditions and history to learn and consume!  Your Colonial attired guide will be with you at the Historic Ram’s Head Tavern where your group will enjoy crab soup and tales of the 300 year old brewery.  You will have a choice of a Maryland State House or Coach tour and then on to an Annapolis Restaurant for a Chesapeake inspired lunch.  After lunch Smith Island Cake, the Maryland State Dessert, will be served at either the Historic PACA House or London Town.

End your day with a Harbor Cruise to get the ultimate Annapolis Experience!

Baltimore Inner Harbor

Aquatic Adventure

Tour the National Aquarium in Baltimore and cruise the Baltimore Harbor for an experience that is Educational, Ecological and Interactive.  An underwater world of beautiful and unusual animals and inhabitants awaits your group at the National Aquarium located in the heart of Baltimore’s Inner Harbor.

After the Aquarium visit and lunch cruise the Baltimore Inner Harbor. See neighborhoods of Federal Hill, Fells Point, Little Italy and Canton, as well as the Baltimore Downtown Skyline and the USS Constellation, See one of our nation’s largest ports with its working docks, shipping and other vessels in the Maritime Industry. You will also get a glimpse of a national landmark, Fort McHenry!

Annapolitan II

Rails & Sails

In Partnership with B&O Railroad Museum. This “All Aboard” tour begins at the Baltimore & Ohio Railroad Museum, the birthplace of American railroading where your group can see, touch, and hear the most important American railroad collection in the world. After exploring the B&O Railroad Museum your group travels a short distance to Baltimore’s Inner Harbor and boards Annapolitan II for a 45-minute narrated harbor cruise to see famous Baltimore neighborhoods like Fells Point, Federal Hill, the downtown Baltimore skyline and historical landmarks like the USS Constellation and Fort McHenry.

Tour available daily April – October beginning at 10am at the B&O Railroad Museum; cruise times vary based on day of week. Confirmed reservations based on tour availability. A 20 minute round trip train ride aboard the B&O Mile One Express is available at the B&O Railroad Museum for an additional cost.

Charm City’s Finest Step-On-Guide and Cruise

Is your group traveling by motorcoach into Charm City? Our period dressed guides will step-on your coach bus and provide live narration on a driving tour of Baltimore city. After exploring the city’s top attractions by land, arrive at the Baltimore Inner Harbor where you’ll step aboard our comfortable climate controlled vessel for a cruise of the Inner Harbor. Cruises on the Bay by Watermark’s 45-minute Inner Harbor Cruise is a great introduction to Baltimore.

Group posing in front of yacht

Reserve your cruise today. Call us at 410-268-7601 x104

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