Watermark Tours Charters Cruises

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Watermark Tours Charters Cruises Watermark® an Annapolis-based, locally owned and operated business, has been creating authentic experiences since 1972.
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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.

⚓🦪 Ahoy, oyster lovers! 🌊🍻 We’re setting sail for St. Michaels! Join us for OysterFest on November 7th for a shuckin’ go...
10/17/2026

⚓🦪 Ahoy, oyster lovers! 🌊🍻 We’re setting sail for St. Michaels! Join us for OysterFest on November 7th for a shuckin’ good time filled with coastal charm and all the fun! 🦪🎉

🎟️ Tickets are available NOW! Don’t miss the boat, secure your spot and come along for the adventure! 🚢💙

10/08/2026

What’s going on with the elevators at the Maryland State House? 👻

Some say they have a mind of their own. Others believe Thomas Dance might have something to do with it.
Hear his story and discover the spookier side of Annapolis on one of our ghost tours.

Book your tour and see what stories are waiting for you!

👻 Spooky Season is here! 🌊🕯️Set sail on our Haunted Lighthouse Cruise for chilling history, eerie legends, and terrifyin...
09/28/2026

👻 Spooky Season is here! 🌊🕯️

Set sail on our Haunted Lighthouse Cruise for chilling history, eerie legends, and terrifying tales from lighthouses around the world. ⚓️💀

Come aboard if you dare!👀🎟️ Tickets are limited, grab yours NOW before they’re gone! https://watermarkjourney.com/events/haunted-lighthouse-cruise/

09/26/2026

Think Annapolis is all charm and sailboats? Think again. It’s National Ghost Hunting Day and the shadows are calling. Join us a Historic Ghost Tour and see if you leave with a story of your own.

🚨🌅 LAST CHANCE to catch live music on the water! 🌅🚨This Friday, we’re setting sail for ONE MORE Sunset Music Cruise feat...
09/23/2026

🚨🌅 LAST CHANCE to catch live music on the water! 🌅🚨

This Friday, we’re setting sail for ONE MORE Sunset Music Cruise featuring ! 🎶⛵️ Come soak up the sunset, enjoy smooth sailing, and vibe to smooth melodies as we cruise into the weekend. 🌊✨Don’t miss your last chance to experience it, grab your tickets now! 🎟️🔥

https://watermarkjourney.com/events/annapolis-sunset-cruise-with-live-music/

🌅 Friday nights were made for sunsets, live music, and cruising! 🎶🛥️Only a few Friday Night Live Sunset Music Cruises re...
09/15/2026

🌅 Friday nights were made for sunsets, live music, and cruising! 🎶🛥️Only a few Friday Night Live Sunset Music Cruises remain this season, so don’t let FOMO get the best of you! 😎
Join us this Friday as Tommy Perrell takes the stage aboard the Harbor Queen! 🎤✨
Come for the live music, stay for the breathtaking views, and soak up that unforgettable sunset on the water. 🌊🌅

Your perfect Friday night is calling. Are you coming? 🥂🎶
Get your Tickets: https://watermarkjourney.com/events/annapolis-sunset-cruise-with-live-music/

Join Watermark for Defender’s Day, Baltimore’s oldest holiday commemorating the city’s victorious defense against Britis...
09/10/2026

Join Watermark for Defender’s Day, Baltimore’s oldest holiday commemorating the city’s victorious defense against British attack in 1814. Enjoy the sunset as you cruise out of the Inner Harbor, and you may even catch a fireworks display on the way back!

Address

1 Prince George Street
Annapolis, MD
21401

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