The Fleet in front of the USNA

Event Planning

Premiere Waterfront Event Venue

Experience the Chesapeake Bay the Watermark® way. With a first-rate fleet of vessels and expert hospitality and service, there’s no better way to explore Maryland’s waterways than with  Watermark®. With a wide-ranging selection of cruise experiences from sightseeing and dining to hosting a private event, you are sure to find the cruise that is right for you.

Unforgettable Events

When you’re looking to create an unforgettable event in the Annapolis, Baltimore, or Eastern Shore area, our vessels allow you to host your next social event, business meeting, wedding, or corporate event on signature yachts. A yacht party aboard a privately chartered boat is just the ticket. Yacht Charters on the Bay℠ by Watermark® has the largest, most meticulously maintained and diverse fleet of yachts on the Chesapeake Bay. Our yachts are available for private events and are catered to meet your specific vision. We create events that your guests will still be talking about for many years to come!

Download our 2022 Charter Planning Guide here.

Download our 2022 Preferred Caterers & Beverage Packages packet here.


Rainbows can be seen from the deck of Lady Sarah

View of Sunset

Why are we considered the best event waterfront venue on the Chesapeake Bay?

Whatever the occasion: yacht charters, boat cruises, wedding yacht charters, company events, cocktail cruises, or private boat cruises for individuals, you will be pleased by our high standard of service for all your luxury needs.

Schedule An Event
Cocktail parties, destination cruises, and more

From cocktail parties to weddings in Annapolis, MD, and destination cruises to St. Michaels, Maryland, we work with the region’s best vendors to plan your event. From event conception to day-of coordination, our experienced event planners will help you plan the details while working with some of the region’s best caterers and vendors. A yacht charter allows you to take your party to many popular waterfront destinations with class and excitement.

Popular Charter Ideas

Group celebrating

View of bay from boat

We make it easy

As operators, we take all the responsibility and effort that goes into planning a successful event. You can be certain we’ll help you plan and execute the best event possible. We take our time to make sure everything is perfect before setting sail. We will be there to welcome you aboard, ensuring that all of your requirements are cared for with professionalism and a smile.

Contact Us

View of sailboats on the bay

Watermark cruise passing under the Chesapeake Bay Bridge