Embark on Your Unforgettable Journey
Watermark immerses you in the history, culture, and fun of the Chesapeake Bay area more completely than any other tour or charter company.
Cruises and Tours in Annapolis & Baltimore
Experience the best of Annapolis and Baltimore with cruises, walking tours, private yacht charters, and field trips.
Featured Events at Watermark®
Public Cruise
Annapolis, MD
• Dates: March - October
• Departure: Annapolis, MD
• Duration: 40 minutes
Public Cruise
Annapolis, MD
• Dates: Saturdays May -September
• Departure: Annapolis, MD
• Duration: 8 hours
Best Seller
Annapolis, MD
• Dates: April - September
• Departure: Annapolis, MD
• Duration: 1 hour 30 min
Friday Nights in August & September
Friday Night Live Sunset Music Cruises
Enjoy live music and beautiful scenery as you relax with a cool drink on this 90-minute sunset cruise in Annapolis.
Friday, September 11, 2026 at 7pm
Songwriters on the Severn
Celebrate Annapolis Songwriters Festival with a 2.5 hour live music cruise on the Severn River!
Browse Cruises and Tours from Watermark
Public Cruise
Annapolis, MD
• Dates: March - October
• Departure: Annapolis, MD
• Duration: 40 minutes
Public Cruise
Annapolis, MD
• Dates: April - September
• Departure: Annapolis, MD
• Duration: 40 mins
Public Cruise
Annapolis, MD
• Dates: Select dates
• Departure: Annapolis, MD
• Duration: 3 hours
Public Cruise
Annapolis, MD
• Dates: Saturdays May -September
• Departure: Annapolis, MD
• Duration: 8 hours
Best Seller
Annapolis, MD
• Dates: April - September
• Departure: Annapolis, MD
• Duration: 1 hour 30 min
Public Cruise
Annapolis, MD
• Dates: April - September
• Departure: Annapolis, MD
• Duration: 90 minutes
Public Cruise
Baltimore, MD
• Dates: April through October
• Departure: Baltimore, MD
• Duration: 45 minutes
Walking Tour
Annapolis, MD
• Dates: April - October
• Departure: Annapolis, MD
• Duration: 2.25 Hours
Public Cruise
Annapolis, MD
• Dates: Fridays
• Departure: Annapolis, MD
• Duration: 1 hour 30 min
Combo Tour
Annapolis, MD
• Dates: Fridays
• Departure: Annapolis, MD
• Duration: 1 hour 40 minutes
Public Cruise
Annapolis, MD
• Dates: Select dates
• Departure: Annapolis, MD
• Duration: 3 hours
Public Cruise
Annapolis, MD
• Dates: Saturday May - September
• Departure: Annapolis, MD
• Duration: 1 hour 30 minutes
Walking Tour
Annapolis, MD
• Dates: Select dates
• Departure: Annapolis, MD
• Duration: 1 hour 30 min
Public Cruise
Baltimore, MD
• Dates: Saturdays
• Departure: Baltimore, MD
• Duration: 1 hour
Public Cruise
Annapolis, MD
• Dates: Saturdays
• Departure: Annapolis, MD
• Duration: 1 hour
Public Cruise
Baltimore, MD
• Dates: Select dates
• Departure: Baltimore, MD
• Duration: 90 min
Walking Tour
Annapolis, MD
• Dates: Select dates
• Departure: Annapolis, MD
• Duration: 2 hours 15 min
Public Cruise
Baltimore, MD
• Dates: May - September
• Departure: Baltimore, MD
• Duration: 90 mins
Ride the Annapolis Water Taxi
Convenient transportation throughout the Annapolis Harbor — including popular destinations along Spa Creek and Back Creek.
Embark on Your Own Watermark Journey
Public Cruises
- Enjoy being out on the water with a variety of cruises from 40 minutes to a full day.
Private Yacht Charters & Weddings
- Take your next event to the water; the perfect venue for any occasion.
Walking Tours & Guided Experiences
- Discover local history with your period-attired tour guide in Historic Annapolis.
Field Trips &
Youth Programs
- Field trips that meet your curriculum, grade level, and programming needs.
Group Experiences
- Explore a variety of affordable cruises and tours for your group event.
Annapolis
Water Taxi
- Climb aboard the Annapolis Water Taxi — the best way to get around Annapolis!
Why Watermark?
Watermark creates unforgettable journeys for tens of thousands of guests in Annapolis and Baltimore every year.
- A complete Annapolis and Baltimore experience
- Informative and fun, knowledgeable and helpful
- The most refreshing way to see the sights
- Unique educational field trips on land and water
- The most affordable way to get out on the water
- Meticulously maintained classic and elegant yachts
- Customized private yacht charters
- History comes alive in our museum without walls
- Family fun activities for all ages
- Highly trained, certified guides, captains, and crews
- Over 50 years of sharing the best of the Chesapeake
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Watermark Staff over the last 50 Years
Watermark Team Since 1972
A family-owned business since 1972. Learn more about the growth and progression of Watermark.
Our Watermark Team Today
Interested in joining the Watermark family? Get to know our team here and view our open positions.
Guest Journeys
Creating unforgettable journeys for over 50 years.
Cruise was beyond expectations, so happy we decided on Watermark for this event. Always available to answer questions and satisfy special requests…Everyone had a great time. Thanks for a memorable experience!
The group experience was very great, and our crew was phenomenal. Every part of the process was handled by great staff…My experience was so great. I will be bringing my family back to take a tour. Thank you Watermark!
Every aspect of this trip was excellent. Very easy to plan, great and quick communication, all tour guides were wonderful, all students, chaperones, and teachers had excellent feedback to share... We are so thankful!
Thank you to Watermark for helping me to throw the best party of the decade!!! ... It was an amazing evening of dancing, great food, and creating memories!!! The staff was very friendly and accommodating…Highly recommended!!!!
