Browse Annapolis Cruises
Discover Scenic Routes and Local History in Annapolis
Annapolis is a beautiful historic seaport that’s great to explore by water!
Immerse yourself in the history, culture, and fun of the Chesapeake. 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.
Annapolis Cruises
Come on down and find us at 1 Prince George St during City Dock Renovations
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
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
Annapolis, MD
• Dates: Saturdays
• Departure: Annapolis, MD
• Duration: 1 hour
Walking Tour
Annapolis, MD
• Dates: Select dates
• Departure: Annapolis, MD
• Duration: 2 hours 15 min
Public Cruise
Annapolis, MD
• Dates: April - September
• Departure: Annapolis, MD
• Duration: 90 minutes
Walking Tour
Annapolis, MD
• Dates: 1st Saturday
• Departure: Annapolis, MD
• Duration: 90 minutes
Public Cruise
Annapolis, MD
• Dates: September 11th
• Departure: Annapolis, MD
• Duration: 2.5 hours
Walking Tour
Annapolis, MD
• Dates: Second Saturday of Month
• Departure: Annapolis, MD
• Duration: 90 min
Public Cruise
Annapolis, MD
• Dates: Select dates
• Departure: Annapolis, MD
• Duration: 1 hour
Walking Tour
Annapolis, MD
• Dates: Private Tour
• Departure: Annapolis, MD
• Duration: 2 hour
Public Cruise
• Dates: November 7, 2026
• Departure: Annapolis, MD
• Duration: 7 hour 30 min
Walking Tour
Annapolis, MD
• Dates: Every 3rd Saturday
• Departure: Annapolis, MD
• Duration: 2 hours
Public Cruise
Annapolis, MD
• Dates: Select dates
• Departure: Annapolis, MD
• Duration: Coming soon
Do you have a group of 20+ people?
Great news. Our team has specialists standing by to assist with your group’s visit.
Annapolis Cruises FAQs
Where do cruises depart?
Our public cruises in Annapolis depart from Annapolis City Dock. The closest address is 1 Dock Street, Annapolis, MD 21401. Keep walking towards the water and look for our red umbrella.
How long are the cruises?
Our cruises vary in duration from 40 minutes up to 7½ hours. Each cruise will list its duration and departure information.
Can we bring our own food and beverages?
You’re welcome to bring a snack or sandwich onto the boat. However, beverages are not permitted. Light snacks, beverages, and cocktails may be purchased on most of our cruises.
What is the weather policy?
We are constantly watching the weather forecast as safety is our number one priority. Our cruises will take place rain or shine. If Watermark cancels a cruise due to severe weather, all guests will be notified and refunded in full.
What is the refund policy?
All tickets are final sale and non-refundable. All cruises are subject to cancellation due to severe weather, lack of participation, or mechanical breakdown. In the event Watermark cancels a cruise, a refund will be provided. Please see specific Day on the Bay to St. Michaels refund policy during checkout.
Are the boats safe?
All Watermark vessels are U.S. Coast Guard inspected and certified. They all have emergency equipment, including life jackets, in the unlikely event they are needed. Guests who wish to wear a life jacket during the cruise are welcome to bring one.
Do I have to purchase tickets online?
Walk-ups are welcome. Tickets for Annapolis cruises may be purchased from the ticket kiosk at Annapolis City Dock. Look for the red umbrella. Tickets for the Spa Creek Cruises aboard Miss Anne may be purchased directly from the captain at Slip 2, Annapolis City Dock. We accept cash, credit card, debit card, and contactless payments at our Annapolis location.
Are the cruises dog-friendly?
We love well-behaved, leashed dogs! In Annapolis, they ride free on our Annapolis Harbor & USNA Cruise, Thomas Point Lighthouse Cruise, Chesapeake Bay Bridge Cruise, Scenic Severn River Cruise, and Spa Creek Cruise. We ask that owners on our boats clean up after their pets in the event that “nature calls.”
Can I bring my stroller?
Strollers are welcome aboard our tour boats. Our cruises are very family-friendly.
Are the vessels wheelchair-accessible?
Most of our boats are wheelchair-accessible with the exception of Miss Anne (Spa Creek Cruise) and the Water Taxis. Not all bathrooms are wheelchair accessible. Please contact our sales office at 410-268-7601 x 100 to discuss any special accommodations. We’re happy to discuss the accessibility of each vessel or tour in detail.
Do the vessels have restrooms on board?
All vessels in Annapolis have restrooms on board with the exception of Miss Anne (Spa Creek Cruise) and the Water Taxis.
Can I bring a bicycle on Day on the Bay to St. Michaels?
Unfortunately, due to limited space, we cannot accommodate bicycles on Day on the Bay to St. Michaels.
Is smoking allowed on board?
To provide the most enjoyable environment for guests, staff, and our beautiful natural surroundings, smoking of any kind is not allowed on board.
Are the vessels climate-controlled?
In Annapolis, our 90-minute cruises, Day on the Bay to St. Michaels, and Bay Lighthouses Cruise are on climate-controlled vessels (main decks). Our 40-minute Annapolis cruises are not typically on climate-controlled vessels.
Do you offer discounts?
For groups under 20 guests, we do not. If you have a group of 20 or more, please inquire about our group experiences. At Watermark, we want to remain a viable option for families to enjoy the history, culture, and fun of this region, so we strive to keep our ticket prices as low as possible for all.