
Annapolis, Maryland is an iconic sailing town, not only on the east coast but around the sailing world. The number of boats that pepper the shoreline of this little coastal town is astonishing. We have had the pleasure to visit this awesome town a number of times, one of which was when we began this journey of buying a sailboat when we went to the annual Annapolis Sailboat show.
We love Annapolis! It may be one of our favorite places we visited during our entire time sailing the east coast. Everything from the variety of boats, yachts, marinas, the vast history of the area, the Naval Academy, crusty seafood restaurants. The list goes on and on. There are so many reasons to visit Annapolis but visiting on a sailboat takes it to another level.
We have sailed into Annapolis in both July and Mid-October so we have been able to see the town at different times of the year. It always has something great to offer and never disappoints.
Boating Season

One of the many beautiful streets of downtown Annapolis
Annapolis boating season runs from roughly mid-March to mid-November unless you love full foulies and frigid temperatures. Although freezing, the winter has the strongest winds with noreasters commonplace. Spring and fall is the premier time to be sailing around Annapolis as well as the entire Chesapeake Bay. The weather during these seasons is much milder than both summer and winter and offers much more consistent steady breezes for more predictable sailing conditions and weather.
Come summertime, the boating season is full-on and the weather is hot and humid and the breeze can be light out of the south to southwest. With the hot and humid weather comes thunderstorms that can be severe at times with winds up to 60 knots or more.

Approaching thunderstorm on Annapolis Harbor
Seasonally, this town has a few different faces. During winter, the town is reduced down to the local residents and watermen with few visiting boaters, but come summertime, this town is bustling with every type of watercraft. Sailboats, schooners, wood boats, powerboats, trawlers, sailing schools, and everything in between. If it floats, it can be found in Annapolis on any summer day.
Approach and Anchorage
Access to the Harbor and creeks of the Annapolis area is as easy as it gets. If you’re traveling from the south the lighted radio towers on Greenbury Point can be visible from a way out marking the north shore of the Severn River. Traveling from the north, the Chesapeake Bay Bridge will be the first thing you see if you’re coming from the upper bay or the Baltimore area. Once you pass under the bridge you should be able to see those same lighted radio towers to starboard.
Once the towers are located, you’ll want to locate the two buoys marking the inlet to the Annapolis harbor channel. If you are coming from the south you will want to keep the Green #1 AH to port until you round into the harbor channel as it is marking a large shoal that extends from the shore. When coming from the north, look for the Hacket Point shoal Bouy after you have passed under the bridge. If you keep the HP shoal buoy to starboard you will stay well clear of the shoaling near shore. After you pass the shoaling buoy you should start to really see the Lighted Radio towers on Greenbury Point as well as a few NOAA weather buoys. Keep these to starboard as you begin to round the point into the Annapolis Harbor Channel.

View looking up Spa Creek from the Spa Creek Drawbridge
Once in the channel, you will have a wide variety of anchorage options. The north shore of the Severn does not offer that much in terms of anchorages. The majority of anchorages that will allow access to the heart of Annapolis are going to be in Back Creek, Spa Creek and the main Annapolis Harbor.
Back Creek will be the first creek that will appear to port on the south side of the Severn River. Here you have numerous options when it comes to marinas but the anchorages can be a bit tight with docks lining both shores extending well into the creek. The city of Annapolis manages a mooring field towards the end of the creek which would serve as a great spot in the spring and fall when the temps are a little cooler, but it can be downright stifling in the summer. This could also serve well if the weather is up as it is extremely protected with land all around.

Sailing school in Annapolis Harbor
Continuing up the Severn River your next option will be the main harbor of Annapolis and Spa Creek. This is the heart of all the action, whether you choose the municipal mooring field in front of the Naval Academy, a slip in Ego Alley or you head up the creek a bit further you will be in the middle of everything Annapolis. In our opinion, the best option is just grabbing a mooring from the municipal field in front of the Naval Academy. These are first-come, first-serve, so just cruise in, grab a ball and hail the Harbor Master on channel 16. These should be available on all but the most crowded of weekends, i.e., the annual boat show.
Other options up Spa Creek are another municipal mooring field on the other side of the Spa Creek drawbridge that can accommodate boats up to 35 feet. Up the creek, there are two more municipal mooring fields that can accommodate vessels between 45 and 55 feet. Like the mooring field up Back Creek, these could get hot during the summer, but offer good protection in weather. The anchorages past the drawbridge are certainly more spread than the anchorages up Back creek but still packed with boats especially during the summer months.

Sunset over Annapolis Harbor from the municipal mooring field
On calm days, especially in the summer, boats do anchor out towards the entrance of spa creek and Annapolis Harbor, but be aware there are some deep spots right at the entrance of the harbor so you may have to anchor a ways from land and you will need to be wary of fetch.
Further up the Severn River especially past the Baltimore Annapolis Blvd. bridge, you can find a number of quiet anchorages with plenty of room but requires a pretty substantial dinghy to get back to the heart of Annapolis.
HIghlights and Attractions
Annapolis is an awesome walking town. With multiple dinghy docks in town, you can dinghy your way up to either Back or Spa Creek park and hit the streets with your feet. We stayed at the main mooring field when we came to town and just parked the dinghy at either ego alley or right next to the Naval academy and hit the town.

The beautiful grounds of St. Johns College
Besides the obvious tour of the Naval academy and all the other activities available there, Annapolis has a lot to see and explore. Just simply walking up the streets from downtown, you can admire the old, historical townhomes, dotted along mainstreet. One of our favorite walks is just docking the dinghy and heading up the hill to St. John’s College. The grounds of the school are immaculate and it is a great place to take the doggies and let them run around. On the way up the hill or back down, be sure to stop at the Maryland statehouse, which is the oldest U.S. state capitol in continuous legislative use, dating back to 1772.

Looking up East Street toward The Maryland State House
There are all the tourist stores and restaurants along Main street just up from ego alley, but if you want to get the real flavor of Annapolis you will be remiss if you don’t make your way over to Davis’ pub in Eastport. This place is the epitome of local Annapolis and local sailors of Annapolis. We visited in July of 2020 and they had blocked an entire block off to serve people safely and we met so many awesome people that lived in town there or other fellow cruisers, all while just waiting for a table. The food is just as awesome as the atmosphere, highlighted by the crab cakes and the peel-and-eat shrimp.

One of the many gorgeous houses around the Annapolis are
Eastport as a whole is a quieter neighborhood with everything from waterfront restaurants to hole-in-the-wall breweries to high-end dining. Taking a stroll over the Spa Creek Drawbridge is well worth the time and effort.
Sailing around Annapolis and visiting the town should be on the very short list of any cruiser traveling north or south in the Chesapeake Bay. We have always had a wonderful time when we visit and it truly is one of our favorite towns on the eastern seaboard.