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

Unforgettable journeys start with Watermark, and we’ve been doing it for more than 50 years.

Experience the best of Annapolis and Baltimore with cruises, walking tours, private yacht charters, and field trips.

This Week's Cruises & Tours

Embark on Your Own Watermark Journey

Why Watermark?

Watermark creates unforgettable journeys for tens of thousands of guests in Annapolis and Baltimore every year.

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The boats may have changed, but Day on the Bay to St. Michaels remains a staple of Watermark 💙

Our president said it best:

“Day on the Bay to St. Michaels has been a staple of Watermark since the company began. It perfectly embodies our mission of immersing guests in the history, culture, and fun of the Chesapeake. Guests enjoy a cruise aboard one of our luxury yachts and exploring the quaint town of St. Michaels, Maryland, making for a spectacular experience.”

Climb aboard for a Day on the Bay every Saturday from May through September🛥️🌊

🎟️ Click the link in our bio for more information and reservations 🎟️

@usnavyblueangels Practice Day 2024 was amazing ✈️ We’re already excited for tomorrow 💙💛 ...

Come along for a cruise through the Inner Harbor 🚢🌊 ...

Yesterday’s rainbow in Annapolis 🚖🌊🌈 ...

Thank you @govwesmoore for making this field trip unforgettable 😊 ...

The best way to get around Annapolis 😎

Water Taxi service is now available seven days a week 🚕🌊

Monday-Friday 10am-10pm
Saturday & Sunday 9am-10pm

📞 410-263-0033 or VHF 68

Help us craft our Mother’s Day mocktail (mom-tail!) 🥂

What’s your pick: 🍊or 💕or 🍍?

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.