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Watermark Journey

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Experience Annapolis

Journey into the history, culture and fun of one of America’s most eventful destinations with Annapolis’ most skilled event planners and tour coordinators. Only Watermark offers so many ways to celebrate, experience and learn about this special place, both by land and by water.

For more than thirty years, Watermark has offered stunning venues aboard our fleet of luxury yachts for private events, public boat cruises along the Severn River and the Chesapeake Bay and walking tours through historic downtown Annapolis and the U.S. Naval Academy. There’s never been more to do and see!

Go for less than an hour or as long as you like. On land, on water—private event or public outing, your unique Annapolis experience awaits!

Book your private boat charter, custom tour, or sightseeing cruise today!

Video
Journey with Water

Journey with Watermark

Introducing Water

Watermark Luxury Yachts

Coming Events


Ghost Tour
Tours

Annapolis by Land

Walk side-by-side with colonial-attired guides through historic Annapolis and the U.S. Naval Academy’s famous landmarks (and some hidden gems).

Trace the steps of African-American history from the 18th century to present day.

There is a story with every step!

Charters

Wedding, Corporate, Social
Private Boat Charters

ChartersPrivate Events aboard Luxury Yachts: Picture your guests in the most special of settings—a luxury yacht from Watermark—the perfect venue for boat charters, corporate outings, weddings and receptions or social gatherings

All occasions are private and designed to meet your personal tastes. When working with our experienced event planners Watermark takes the art of entertaining to a new level.

Serving the Annapolis, Baltimore, and Washington D.C. area. Providing Annapolis Boat Charters, Baltimore Boat Charters, and Chesapeake Bay Boat Charters.

Cruises

Annapolis by Water

Watermark offers a variety of public boat cruises. Explore the local waterways aboard the Chesapeake’s largest fleet. Cruise for as little as 40-minutes up to a complete Day on the Bay to St. Michaels.

Specialty cruises such as our Bay Lighthouses Cruise and Pirates of the Chesapeake are a great way to see Annapolis with a unique perspective.