Watermark has the perfect tour for your group event!

Explore Maryland by Land & Sea

Group Experiences in Annapolis & Baltimore

Watermark offers a wide variety of group experiences in Maryland. Perfect for family gatherings, social occasions as well as military, educational, religious, and fraternal organizations. With seamless itineraries, affordable options, and knowledgeable representatives, we customize your experience to fit your group’s needs.

Request Information
Photo Gallery
FAQs

Browse Tours & Cruises

Guided Historic Tours

Explore centuries of history in Annapolis and Baltimore with our period-attired guides.

U.S. Naval Academy

Walk the grounds of the historic U.S. Naval Academy, home to over 4,000 midshipmen.

Annapolis Harbor

Discover the historic city of Annapolis with a cruise along the harbor and the banks of the U.S. Naval Academy.

Baltimore Inner Harbor

Enjoy all that Baltimore has to offer, including the iconic Domino Sugar sign, Fort McHenry, and more.

Extended Cruises

Take in the views and history of these two picturesque cities with a sightseeing cruise. Narration options available.

Expand Your Itinerary

Enjoy both daytime and evening experiences! Our strong network of partners allows us to plan seamless itineraries that fit your needs.

Why Choose Watermark?

Seamless Itineraries

Watermark has a wide variety of unique experiences and a strong network of partners to help you plan a seamless itinerary.

Close to Major Cities

Annapolis and Baltimore are just a quick trip for major cities including Washington, D.C., Philadelphia, and New York City.

Knowledgeable Staff

Our staff is very knowledgeable about the local area and can help to make recommendations for your trip.

Meal Options

From boxed lunches to sit-down meals to progressive food tours, we have many ways to add meals to your itinerary.

The Destinations

Annapolis and Baltimore are convenient locations to add to your Mid-Atlantic trip!

From narrated sightseeing cruises to guided historic walking tours through the cities’ historic streets, we have many ways to explore the beautiful historic seaports of Annapolis and Baltimore by land and by water.

Close to major airports:

  • 30-minute drive from BWI
  • 1-hour drive from DCA
  • 1½-hour drive from IAD

.

Close to major cities:
  • Less than 1 hour from Annapolis & Baltimore
  • Less than 1 hour from Washington, D.C.
  • Less than 2 hours from Philadelphia
  • Less than 4 hours from New York City
watermark-group

Group Experiences Catalog for Annapolis & Baltimore

Enter your name & email address to receive the 2025 Group Experiences Catalog.

This field is for validation purposes and should be left unchanged.
Name

We love our tour operators!

Watermark is a proud member of the following:

  • American Bus Association
  • Baltimore Tourism Association
  • Maryland Motorcoach Association
  • Maryland Tourism Coalition
  • Pennsylvania Bus Association
  • Student and Youth Travel Association
Schedule an Event

Schedule an Event

"*" indicates required fields

This field is for validation purposes and should be left unchanged.
MM slash DD slash YYYY
Please select all that you are interested in.
Group type, special needs, or anything else we should know.
Would you like to sign up for our e-newsletter?
“John Greene was an extraordinary guide. His knowledge and presentation were exceptional, and he adapted to our group's need to rest after earlier touring, and he spoke to us at a Market House table while everyone rested and got something to drink. We then went on. He is the best. ”
Period-attired guide with group by the Maryland State House.
Lynn K.Annapolis, MD
“Visiting Baltimore for the first time in many years, our 40 retirees, were delighted by the ease of exploring the B&O Railroad Museum, the perfectly-timed delivery of their lunches, and then the narrated cruise of the Inner Harbor. Watermark was the right choice of a tour company as they provided support orchestrating this successful day!”
Anne S., Calvert County Seniors
Anne S., Calvert County SeniorsBaltimore, MD
"Mistress Anna was excellent! She was friendly and really provided a catered tour that was age appropriate and interesting. The facts were great and just the right amount to keep us all engaged and not overwhelmed! We especially loved that she was in 1700's attire which helped to set the tone for the tour!”
Brooke B.
Brooke B.Annapolis, MD

Group Experiences FAQs

Is there bus parking in Annapolis and Baltimore?

There are limited locations in Annapolis for motorcoach unloading. Our team will provide you with detailed bus parking information prior to your event. If participants are arriving in individual vehicles, please allow time for parking and walking distance to your starting point/time.

Watermark cruises and tours rain or shine. In the event of a cancellation on our end due to severe weather, all guests will be notified and refunded in full.

All Watermark vessels are U.S. Coast Guard inspected and certified. They all have emergency equipment, including life jackets, in the unlikely event they are needed. Guests who wish to wear a life jacket during the cruise are welcome to bring one.

Yes, tours visiting the Maryland State House and U.S. Naval Academy require physical government issued photo ID or original passport for adults 18 and over for entry. Guests under 18 without a photo ID must be escorted by a responsible adult. Weapons of any kind will not be permitted at either location.