Take a Watermark Journey

Watermark immerses people in the history, culture and fun of the Chesapeake Bay area more completely than any tour or charter company.

Harbor Queen

Public Cruises & Water Taxi

From 40 minute cruises to a full Day on the Bay, select yours from our variety of sightseeing cruises in Annapolis Harbor, Baltimore Harbor, and on the Chesapeake Bay.

Book a Cruise
catherine marie yacht

Private Yacht Charters & Weddings

Our fleet of yachts provide the perfect venue for celebrating your next corporate, social, or wedding event. Enjoy picturesque views from your very own private yacht.

Charter a Yacht
Three historic tour guides

Guide Services & Walking Tours

Your period dressed tour guide will engulf you in history and folklore. Select from a variety of tours and programs, from Maryland history to local ghost stories. For visitors of all ages.

Book a Tour
tour guide talking with students

Field Trips & Youth Programs

Where history comes alive! From School Field Trips to Summer Camps, Watermark is proud to host thousands of students each year on our educational cruises and walking tours.

Schedule a Field Trip
Lorem Ipsum

Why Watermark?

Watermark creates unforgettable journeys for tens of thousands of guests in Annapolis and Baltimore every year.

  • A complete Annapolis and Baltimore experience
  • Informative and fun, knowledgeable and helpful
  • The most refreshing way to see the sights
  • Unique educational field trips on land and water
  • The most affordable way to get out on the water
  • Meticulously maintained classic and elegant yachts
  • Customized private yacht charters
  • History comes alive in our museum without walls
  • Family fun activities for all ages
  • Highly trained, certified guides, captains, and crews
  • Over 50 years of sharing the best of the Chesapeake
Making our Mark Employment Opportunities

What’s Happening at Watermark

Looking for things to do in Annapolis and Baltimore? It is always a great time to experience Watermark.
Stay connected with the Watermark community.

Check us out on Instagram

Guest Journeys

Creating unforgettable journeys for over 50 years.

Although we thoroughly enjoyed everything about Annapolis, the tour was the highlight of our trip.

Sandi Jackson

Four Centuries Walking Tour

5 of 5 stars! We went on this tour, without knowing that it was the first of this new cruise, and we enjoyed it immensely. They sell beverages and small snacks at the bar on board. The boat was large, well-equipped, and spotlessly clean. Our Chesapeake Bay Tour Guide was what turned an otherwise very good cruise into a truly memorable excellent experience. Watermark has done a great job with this cruise. This was our first bay cruise, and we highly recommend it to anyone with an interest in the bay's history.

John F

Chesapeake Bay Trio

Thank you for everything you did to make our wedding so memorable!

Steve and Kim

Watermark was flawless – you made sure every detail was perfect

Eileen and Chuck

What a pleasant experience! All crew members were extremely courteous and helpful. Information provided by recording was complemented by the captains additions and made it more enjoyable. The bartender also provided some more explanation when not serving customers. Restrooms were clean and air conditioned lower deck was clean and comfortable. Well worth the price and the time.

Berneda B

Baltimore Harbor Cruise

This cruise was perfect. The entire crew was professional, courteous, and friendly. The captain was outstanding and very personable. I highly recommend this cruise and will take other cruises from Watermark. Thank you.

Mark W

Fireworks Cruise

Relaxing ride on the water We thoroughly enjoyed our trip up and down the river. The staff eased friendly. The pre-recorded information was quite informative about what were were seeing as we moved along. Beverages are available for purchase on the lower level, great for a hot day. Restrooms are also available onboard.

Tanya

Severn River Cruise

As part of my summer plan to do all the Watermark tours, my son and I went this past Friday on the Thomas Point lighthouse tour on their Lady Sarah. It was a heat wave so the choice was perfect. The narration was specific to the landscape we passed and Captain Mike could answer any questions. I never knew about the barge ships for example. The boat comes as close to the lighthouse as possible to avoid its surrounding rocks and ice breaker. The crew will gladly take pictures of you with the lighthouse backdrop. Looking forward to the Severn River tour!

Elly T

Thomas Point Lighthouse Cruise

Took Lady Sarah to St. Michaels to celebrate our special day. CAPTs Dean, Phyllis and Suzy were pleasant, kind and very attentive the entire trip. The Bar Manager (sorry, forgot her name) made sure we received our celebration package after returning to Annapolis, Would repeat the trip in a heartbeat. Thanks to everyone!

Day on the Bay

2023 Holiday Happenings
November & December
Explore holiday events!
This is default text for notification bar
Learn more