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Annapolis Cruises

Annapolis is a beautiful historic seaport that’s great to explore by water!

Whether it’s a narrated sightseeing cruise or a day trip to St. Michaels, get out on the water with Watermark for an Unforgettable Journey. Our boats have a full bar service with light snacks available for purchase and restrooms on board. Most of our vessels are handicapped accessible and climate controlled.

Come on down and find us at Annapolis City Dock, 1 Dock Street and look for the Red umbrella!

Annapolis Cruises

Miss Anne decked out for the holidays

Jolly Express

Hop aboard Miss Anne, all decked out for the holidays. Enjoy hot cocoa, holiday music, and good cheer. Bring your own blankets and enjoy Captain Santa’s “sleigh ride.”

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Holiday Stroll & Cruise

Colonial Stroll & Cruise – Holiday Style

Traditions of the holiday season will be highlighted along with our classic Colonial tales as you stroll the quaint streets of the Historic District. Your guide will deliver you to enjoy a cruise aboard the festively decorated “Miss Anne”.

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Captain Santas's Cruise

Captain Santa’s Cruise

Bring the family on this water ride where cheery holiday music will be playing. Captain Santa will hand out candy canes to all.

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Spirits & Spirits

Spirits & Spirits

You’ll be led through haunted waterways by boat and brave the Historic District by foot while your guide entertains you with nautical myths, pirate tales, and ghost stories.

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Harbor Queen

Annapolis Harbor & USNA

Step aboard to experience a narrated cruise of historic Annapolis and the banks of the U.S. Naval Academy. An Annapolis tradition and fun for the whole family.

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Miss Anne

Spa Creek Tour

Step aboard our cozy launch for an intimate cruise up Spa Creek into the residential area of Old Annapolis, Eastport, and the banks of the U.S. Naval Academy.

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Water Taxi Service

Hop on a taxi to visit your favorite restaurant or to get downtown from Eastport.  Taxi’s operate in the Annapolis Harbor, including Spa Creek and Back Creek

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Fireworks cruise

Special or Seasonal Cruises

From live music cruises to New Year’s Eve, Watermark offers a variety of special and seasonal cruises throughout the year.  Click below to learn more.

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Boat near Domino Sugar Factory

Baltimore Cruises

From live music cruises to New Year’s Eve, Watermark offers a variety of special and seasonl cruises throughout the year.  Click below to learn more.

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Lady Sarah Severn River

Scenic Severn River Cruise

A spectacular 6-mile cruise on the beautiful Scenic Severn River and historic Annapolis Harbor; includes the banks of the United States Naval Academy

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Lady Sarah Bay Bridge
Chesapeake Bay Bridges

Cruise through Annapolis’ historic harbor, by the United States Naval Academy, and under the twin spans of the famous Chesapeake Bay Bridge.

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Thomas Pt Lighthouse

Thomas Point Lighthouse

View this National historic landmark as you cruise the Chesapeake Bay on a narrated cruise.  Not just for lighthouse enthusiast; everyone loves it!

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Watermark Cruise Boat

Day on the Bay to St. Michaels

Cruise across the Chesapeake Bay to St. Michaels on the Eastern Shore.  Enjoy fresh seafood, boutique shopping, and historic sites all within walking distance.

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Annapolis Sunset Cruise

Annapolis Sunset Cruise

Enjoy music playing, the sun setting, and a cool beverage from our River Run Bar as you relax on this hour long cruise through the Annapolis Harbor.

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