Watermark Tours Charters Cruises
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Watermark® an Annapolis-based, locally owned and operated business, has been creating authentic experiences since 1972.
Watermark® has immersed people in the history, culture, and fun of the Chesapeake area more completely than any other tour or charter company for more than 50 years. Whether you want to learn or just enjoy the Chesapeake Bay area, no one else offers so many ways to experience this special place, both by land and by water, in less than an hour or as long as you like. Offering historic walking tours, cruises, and special events for individuals and groups in both Annapolis and Baltimore.
06/22/2026
Naptown Brass Band is back aboard Harbor Queen, bringing the energy, the music, and the party during Sail250 in Baltimore! 🎶💃🕺
From nonstop brass beats to incredible harbor views, this is one celebration you won’t want to miss. Grab your friends, hit the dance floor, and make unforgettable memories on the water!
🎟️ Tickets are selling fast—secure yours today at: https://watermarkjourney.com/events/sail250-naptown-brass-band-cruise/
Behind the Journey continues with Mistress Kate ✨
One of our wonderful guides, Mistress Kate brings Annapolis history to life with heart, humor, and a deep love for this city. We chatted with her about why she loves Annapolis, her favorite place in town, and even her favorite person from the past.
Come along as we get to know the people behind the stories.
Sometimes fun can be educational too, check out some of our enchanting walking tours that immerse you in the stories of Annapolis past along side extremely knowledgeable tour guides decked out in their colonial garb!
06/17/2026
Still trying to figure out what to do for Dad? How about a Day on the Bay to St. Michaels. Dad can enjoy fresh seafood, check out the Boat Festival, visit historic sites, you know, "Dad Stuff" Get Tickets: https://watermarkjourney.com/events/fathers-day-on-the-bay-to-st-michaels/
06/16/2026
📣ATTENTION‼‼ ATTENTION‼� will provide the sounds and vibes for this Friday Night's Sunset Music Cruise!! Get your tickets now! https://watermarkjourney.com/events/naptown-brass-band-cruise/
06/11/2026
A wonderful night celebrating Historic Annapolis at the Paca Girlfriends Party. Several members of our Watermark team attended and had such a fun time.
Watermark is proud to be an Annual Corporate Partner of Historic Annapolis and grateful to be part of a community that values history, connection, and unforgettable local experiences.
06/01/2026
Friday Night Live is back on the water this week! Check out GroundRent this Friday! Get Tickets: https://watermarkjourney.com/events/annapolis-sunset-cruise-with-live-music/
05/29/2026
Sunny and 75 with a 100% chance of unforgettable views.
Annapolis or Baltimore, today belongs on the water. Hop aboard with Watermark and make the most of this picture-perfect day.
Book your cruise at WatermarkJourney.com
Click here to claim your Sponsored Listing.
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Address
1 Prince George Street
Annapolis, MD
21401