Watermark Tours Charters Cruises

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.

Sunny and 75 with a 100% chance of unforgettable views.Annapolis or Baltimore, today belongs on the water. Hop aboard wi...
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

05/26/2026

Thank you to all who hopped aboard one of our vessels 🚢 to see the Blue Angels ✈️. Very busy week for Watermark, from private charters to public cruises, we had a great time hosting you all!! Can’t wait ‘til Sail250 in Baltimore in June!! Special S/O to all our Captains and Crew, who made it possible! 💐

05/22/2026

Ghost Tours 👻are back, Friday and Saturday nights! Watermark offers two options; Spirits and Spirits Tour explores the spookiest spots by land and by sea 🛥️, and our Historic Ghost Tour explores the spookiest spots by foot in Annapolis. Book on our website.

05/16/2026

Meet Captain Tony. 👋

He’s one of the friendly faces behind the Watermark Water Taxi, helping guests experience Annapolis the way it was meant to be seen: from the water.

A ride on the Water Taxi feels like one of those simple summer memories. The breeze, the harbor views, the little thrill of pulling up to your stop by boat. It’s transportation, but make it Annapolis.

Heading to dinner? Crossing from Downtown to Eastport? Showing off the city to out-of-town guests? Call for easy pickup and make the ride part of the fun.

Call: 410-263-0033 VHF 68

Daily Service
Weekdays: 10 AM to 10 PM
Weekends: 9 AM to 10 PM

💸 Cash, credit card through the Where in Annapolis app , and vouchers accepted.

Baltimore’s waterfront is getting ready for a once-in-a-generation celebration, and the best view is from the water.Sail...
05/14/2026

Baltimore’s waterfront is getting ready for a once-in-a-generation celebration, and the best view is from the water.

Sail250® Maryland & Airshow Baltimore is bringing international tall ships, historic vessels, military ships, flyovers, airshows, and festival experiences to the harbor in honor of America’s 250th anniversary.

Watermark® will be cruising June 25-28 with special Sail250® Maryland experiences, including:

⚓ Baltimore Sightseeing Cruises
Enjoy a 45-minute narrated cruise through the Inner Harbor with views of Fort McHenry, the Domino Sugar sign, Under Armour headquarters, and more.

✈️ Sail250® Flyover and Airshow Cruises
Take in the excitement from the water on a 90-minute cruise featuring views of the visiting ships and possible flyovers during the celebration.

This is Baltimore history, maritime tradition, and America’s 250th from a front-row seat on the harbor.

Book your cruise at WatermarkJourney.com.

Address

1 Prince George Street
Annapolis, MD
21401

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