Top 5 Ways to Enjoy the Water in Annapolis 

A Boat Captain's Guide for Enjoying Annapolis by Water

As a boat captain for Watermark’s Spa Creek tours, I often field questions from visitors and locals about things to do on or near the water in our state capital. Recent construction barricades around the harbor have made it challenging to enjoy water views, yet there are still plenty of opportunities to explore the water in Annapolis. Here are my top five recommendations:


The author’s boat on mooring ball #9, hosting family with views of Annapolis Harbor and the US Naval Academy.

1. Your Own Vessel 
Your sailboat: If you have your own vessel, take advantage of the transient mooring balls, marina slips, or various anchorages in the Annapolis Harbor, Spa Creek, Back Creek, and the Severn River. When the waters are crowded, as they often are during festivals and boat shows, it pays to examine your options. Two years ago, my out-of-town crew member noticed a little-known anchorage off the Severn, just past the Naval Academy Bridge. We easily anchored, with good holding, and were close enough to dinghy into town. It’s now one of my favorite anchorages, with its picturesque view of the bridge lit at night.  

Your small craft: If your larger vessel is anchored or moored, take your smaller craft to any of Annapolis’s public dinghy docks and explore the city on foot. Landlubbers can also launch their paddleboards, canoes, or kayaks from those same docks, located at the end of 22 streets in Annapolis and Eastport. Truxton Park, located farther up Spa Creek, has a boat ramp launch. Find public access points mapped at annapolis.gov/176/Dinghy-Docks, including detailed descriptions and historical facts. 

2. Boat rides with others
Even if you have your own boat, it’s fun to let someone else drive for a change. And sharing the experience with others can be gratifying.

Public cruises: Several public cruises are available from Annapolis or across Spa Creek Bridge in Eastport. Many include historic narration, including 40-minute and 90-minute tours by Watermark, departing from the end of Prince George Street. For those enamored with raising sails, the twin 74-foot Woodwind schooners offer two-hour tours and sunset sails from their base at the Annapolis Waterfront Hotel. If Chesapeake skipjack history is of interest, the Annapolis Maritime Museum in Eastport offers a rare opportunity to climb aboard the historic Wilma Lee.

Water taxi: Whether you’re heading to dinner or meeting friends, the water taxi can whisk you to 25 pickup or drop-off locations in the harbor and along Spa Creek, or 16 locations in Back Creek. The taxis will answer calls (VHF 68) from nearby boats or (410) 263-0033 for those on land. 

Specialty boats: For those seeking a high-spirited experience, you can still find a few party boats operating in the fall. Chesapeake Pirate Adventures offers boisterous fun on weekends through October, and Sea Suite Charters has public cruises on the only tiki boat bar in Annapolis, departing from Nautilus Point on the Eastport side. 


A double rainbow during a Spa Creek Tour on Miss Anne II. Photo by Cheryl Duvall

3. Private Charters 
With a licensed captain: Consider scheduling a private charter for your family and friends through Annapolis-based companies already mentioned, or through smaller businesses such as Chronic Sailing located in Back Creek. Alternatively, the Chesapeake Area Professional Captains Association (CAPCA) offers a free service to connect the public with USCG-licensed captains. Anyone can post a private charter request at capca.net/hire-a-captain by entering the desired date, number of passengers, and preferred vessel type. 

Or bareboat charter: If you don’t own a boat but have the skills and knowledge to explore waters at your own pace, consider chartering with you at the helm. Larger sailing vessels are available through several area businesses, including Chronic Sailing. For those who want to explore waters on a smaller vessel, electric Duffy boats may be reserved for up to 10 guests for one to two hours through Sea Suite Charters.

4. Waterfront Walking
You don’t have to be on the water to enjoy the water. Walking the waterfront can be just as memorable. A popular beginning point is at the end of Ego Alley, along Compromise Street, at the Kunte Kinte-Alex Haley Memorial. From there, a walk to the peak of the Eastport Bridge reveals spectacular views of hundreds of boats in both directions. It’s even more fun if the drawbridge opens while you take in the view. Eastport is just steps away, with a meandering walk past marinas and local businesses.

For those who are curious about the Severn River, consider visiting the United States Naval Academy (consult usna.edu site for up-to-date access information; must show REAL ID). Once on the USNA campus, you may walk along the waterfront, from the harbor around the corner to the Severn River, including views of the Naval Academy’s sailing fleet.


The Annapolis skyline as seen from Spa Creek. Photo by Ted Morgan

5. Waterfront Dining 
Before or after a walk or boat ride, consider dining at one of several waterfront restaurants. Along Ego Alley, you’ll find Choptank and two new restaurants, Marmo and Armada, in the Annapolis Waterfront Hotel (the former Pusser’s). Or cross the Spa Creek Bridge to dine at Carrol’s Creek Café (a personal favorite) or the Chart House. Although not waterfront, the Boatyard Bar & Grill is a universal favorite for sailors. Legendary faces and yachts line the walls, so you’ll feel as if you’re on the waterfront. 

October is the perfect month to enjoy the water in Maryland’s state capital, during or apart from the fall boat shows. Go explore!

About the author: Captain Cheryl Duvall is President of the Chesapeake Area Professional Captains Association (CAPCA). You may see her at the helm of her Gozzard 44 Belle Bateau or on Watermark’s Miss Anne in the Annapolis Harbor. Email her at [email protected].