Annapolis is a city of about 40,000 people on the Chesapeake Bay, thirty miles from both Baltimore and Washington, and it holds three things at once: the capital of Maryland, the United States Naval Academy, and the densest surviving eighteenth century streetscape in America. For eight months in 1783 and 1784 it was also the capital of the United States, which is why George Washington resigned his commission in a building you can walk into. It is small, it is walkable, and the water comes up into the middle of it more often than anybody mentions.
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What Is Here
THE NAVAL ACADEMY IS AN ACTIVE MILITARY INSTALLATION AND YOU NEED IDENTIFICATION TO GET IN. This is the single most important thing to know before arriving, because people turn up at the gate without it. Visitors over a certain age must present a valid government-issued photo identification, which for a foreign visitor means a passport, and entry is on foot through the visitor gate rather than by car. THE YARD CAN CLOSE OR RESTRICT ACCESS WITHOUT NOTICE for security reasons or for events, so check before you plan a day around it. Inside, the Chapel is the first image and is worth the visit on its own, with John Paul Jones entombed in the crypt beneath it, and the noon formation of the brigade in term time is the thing to time a visit for.
THE MARYLAND STATE HOUSE IS THE OLDEST STATE CAPITOL IN THE UNITED STATES STILL IN LEGISLATIVE USE, in continuous service since 1772, and it is free to enter. Congress sat here when Annapolis was the national capital: Washington resigned his commission as commander of the Continental Army in the Old Senate Chamber in December 1783, and the Treaty of Paris ending the Revolutionary War was ratified in the same room weeks later.
IT IS THE SAILING CAPITAL OF THE UNITED STATES AND THE HARBOUR IS A WORKING ONE. The second image is the harbour and the tour boat that runs out of it. The Chesapeake is one of the great sailing grounds and this is its centre: charters, schooner trips, the autumn boat shows that take over the whole dock, and a horizon of masts on any summer evening. The narrow finger of water running up to the dock is known locally as Ego Alley, for the parade of boats that come up it to be looked at and then have to reverse out.
THE KUNTA KINTE AND ALEX HALEY MEMORIAL IS AT THE DOCK AND IT MARKS WHAT THIS PORT WAS. Annapolis was a significant point of entry for enslaved Africans, and the memorial marks the 1767 arrival of the ship carrying the man Alex Haley traced as his ancestor in Roots. It sits exactly where the ships tied up, a few metres from the ice cream and the boat tours, which is the honest geography of the place and worth going to deliberately rather than walking past.
THE OLD TOWN IS BRICK AND IT IS GENUINELY OLD. The third image is a brick street at twilight, and the historic district holds one of the highest concentrations of surviving colonial architecture in the country, with several houses of the 1760s and 1770s open to visit. The streets radiate from two circles, State and Church, which is an unusual baroque plan for an American city and is why you keep arriving back where you started.
AND THE DOCK FLOODS ON SUNNY DAYS, which almost nothing written about the city says. Annapolis has one of the highest rates of high-tide flooding in the United States, and it has risen sharply: City Dock now goes under water on dozens of days a year on nothing more than a high tide and an onshore wind, with no rain involved. If you find the lower streets closed and cars rerouted on a cloudless afternoon, that is what is happening, and it is a normal condition here rather than an emergency.
When to Go
May and June, then September and October, are the city at its best: warm without the worst of the humidity, the sailing season in full swing, and the boat shows in October filling the dock.
July and August are hot and genuinely humid, into the thirties with heavy afternoon thunderstorms, which is the Mid-Atlantic summer and is more tiring than the temperature alone suggests. The water is warm and the crowds are at their peak.
Hurricane season runs June to November, and this far up the Chesapeake what usually arrives is the remnant of a storm: wind, a great deal of rain and tidal flooding rather than a direct hit.
Winter is cold, quiet and cheap, with the museums and the State House open and the harbour emptied of boats. January and February can bring snow and the bay can ice at the edges.
Getting There
By car, which is what most people do: about forty minutes from Baltimore, an hour from Washington, and the historic district is best handled by parking in a garage on the edge and walking.
By air into BWI, about thirty minutes away, or either Washington airport at an hour or more.
There is no passenger rail to Annapolis, which surprises people. The nearest stations are in Baltimore or at New Carrollton outside Washington, and you continue by bus or car from either. Commuter and intercity buses do run, and there is a seasonal water taxi network inside the harbour.
Once here you walk. The old town, the State House, the dock and the Academy gate are all within fifteen minutes of each other on foot, which is the pleasure of the place and also means the brick and cobble underfoot matters.
The Annapolis Packing List
Humid summers, cold damp winters, uneven brick and cobble throughout, and a lot of time standing on or beside water.
Our merino base layers are 100% Australian merino at 17.5 micron, and a long sleeve merino wool base layer for women solves the specific problem of a Chesapeake shoulder season, where a morning on the water is cold and windy and an afternoon in the old town is warm: wool works damp, which matters on a boat, and does not hold the smell after three days of it. From November to March add a heavyweight merino base layer.
A Marmot PreCip Eco rain jacket in any month, because Mid-Atlantic summer storms arrive fast and hard and because a windproof shell is what you want on the bay even in July.
Walking shoes with grip rather than anything smooth-soled: the historic streets are original brick and cobble, they are uneven, and they are slick in rain. Deck shoes are the local answer if you are sailing.
For summer, a long sleeve sun hoodie and a wide brim sun hat, because a boat has no shade and the glare off the water doubles the exposure, plus a insulated water bottle for the humidity.
Not linked and worth packing: YOUR PASSPORT OR GOVERNMENT PHOTO ID carried on you, because the Academy gate will ask for it and a hotel key card is not it; A LIGHT WINDPROOF LAYER for the evening on the water, which is colder than the land; INSECT REPELLENT for the marshy edges in summer; SUNGLASSES; AND SHOES YOU DO NOT MIND GETTING WET if a high tide puts the dock under while you are on it.
Recommended Tours and Experiences
Essential Resources for Women in Annapolis
Emergency numbers: 911 for police, ambulance and fire, free from any phone including a locked mobile. Calls are answered locally and dispatchers will stay on the line. For non-urgent police matters many cities also run a 311 information line.
The FCDO publishes no advised-against areas anywhere in the United States and no country-level warning. Its guidance concentrates on the practical differences a British visitor meets: entry requirements and ESTA, the cost of healthcare without insurance, extreme weather including hurricanes on the Atlantic and Gulf coasts between June and November, and wildfires, which the FCDO describes as a danger in many dry areas, particularly in canyons, hills and forests. WHAT REACHES ANNAPOLIS IS WATER AND WEATHER RATHER THAN CRIME. THE TIDAL FLOODING IS ROUTINE rather than exceptional, City Dock and the lower streets go under on high tides several dozen times a year, and the practical effect is closed streets, moved cars and wet feet rather than danger. HURRICANE SEASON RUNS JUNE TO NOVEMBER and what reaches the upper Chesapeake is usually a storm's remnant, bringing wind, heavy rain and a storm surge up the bay; the National Hurricane Center is the authority for the track and the National Weather Service for the local warnings, and both are worth checking in late summer. SUMMER THUNDERSTORMS build fast on hot afternoons and the open water is the wrong place to be in one, so a boat trip ends when the crew says it ends. THE BRICK AND COBBLE STREETS are the commonest cause of a turned ankle here. TICKS ARE ENDEMIC in Maryland and Lyme disease is present, which matters if you walk any of the wooded or marshy edges rather than only the town. AND THE ACADEMY'S ACCESS RULES ARE SET BY THE ACADEMY: the United States Naval Academy's own visitor information is where the identification requirements and any closure are published, and it changes without notice. The FCDO's general note that gun crime rarely affects visitors applies, and ordinary urban care in a small, busy, well-lit historic city is the whole of the rest.
US State Department travel advisory: there is none, and this is not an omission. The State Department issues travel advisories for other countries, not for the United States itself, so no US advisory for this destination exists to link. In its place, the Government of Canada advice for the United States gives an equivalent third-country assessment.
UK FCDO travel advice: gov.uk/foreign-travel-advice/usa, and read the safety and security page rather than only the landing page, because that is where the substance sits. The FCDO names no advised-against areas anywhere in the United States. The same advice also covers Puerto Rico, the US Virgin Islands, Guam, American Samoa and the Northern Mariana Islands.
Main hospital: Luminis Health Anne Arundel Medical Center is a large hospital in Annapolis itself with a full emergency department, so nothing here requires a transfer to Baltimore or Washington. This is the single biggest practical difference for a visitor: there is no public health system, an emergency room visit without insurance can run into thousands of dollars, and an ambulance is billed separately and is not free. Comprehensive travel insurance with a high medical limit is not optional in the United States, and you should carry your policy number and the insurer's 24 hour number somewhere you can reach them. Urgent care clinics handle anything short of an emergency far more cheaply and quickly than an emergency room, and are the right choice for a sprain, an infection or stitches.
Official health authority: the CDC travellers' health pages, the US federal health authority for visitors, covers vaccination and health advice for visitors to the United States
Embassy contact: the United States is the host country, so there is no US embassy to contact. Your own country's embassy is in Washington DC, with consulates in New York, Los Angeles, Chicago, Houston, San Francisco, Miami and Boston. Find yours before you travel and save the number.
Official tourism authority: Brand USA, the national tourism marketing body, covers the Chesapeake region, and the city's own visitor centre at the dock publishes the boat show dates and the State House hours
Takeaways
Carry photo ID for the Academy. Without it you do not get in.
The State House has been in use since 1772 and is free.
City Dock floods on high tides, with no rain involved.
The streets are original brick. Footwear matters.
Solo women safety assessment: Annapolis is one of the easier American cities to spend time in alone. It is small, affluent and compact, the historic district is busy with visitors and midshipmen into the evening, the restaurants are used to single diners at the bar, and the whole area a visitor uses is walkable and well lit. There is no district here a visitor needs to think about, and the presence of a large military installation in the middle of town makes the centre notably well policed. The practical notes are logistical rather than about personal safety. CARRY YOUR PASSPORT OR A GOVERNMENT PHOTO ID if the Naval Academy is on your list, because the gate will ask and nothing else substitutes; check the Academy's own visitor page the morning you go, since the Yard closes without notice. THERE IS NO TRAIN, so getting here and away is a car, a bus or an airport transfer, and planning the last leg matters more than usual. THE REAL HAZARDS ARE ENVIRONMENTAL AND MOSTLY MILD: uneven colonial brick that turns ankles, tidal flooding that closes the dock on clear days, violent summer thunderstorms that end boat trips, and ticks on any wooded or marshy walk. Hurricane season brings remnants up the bay between June and November, and the National Hurricane Center and the National Weather Service are the two things to watch in that window. 911 REACHES EVERYTHING, and the city has its own large hospital with a full emergency department. Medical care in the United States is expensive and billed, so insurance with a high limit is not optional.
Reading On
Annapolis sits between two large cities and makes sense alongside either, so the Washington DC packing list covers the capital an hour west and the Baltimore packing list the harbour city forty minutes north, which is the closest relative this post has in the library: another Chesapeake port whose waterfront is its subject. Further up the coast, the Philadelphia packing list covers the other city where the Revolution was argued out and the Boston packing list the one where it started. South, the Charleston packing list covers the other great preserved American port whose history includes the slave trade it was built on. For the country, the United States travel guide for women carries the regions, the driving and the seasons in full. For why wool is the right first layer for a cold morning on the water and a warm afternoon on land, read the guide to merino wool base layers for women. Every destination we cover is indexed at the travel packing guide for women, and the base layers are at the Roman Trail collection. North east up the same coast, the Cape May packing list covers the other great preserved Mid-Atlantic waterfront, a Victorian resort at the bottom of New Jersey that is also one of the best bird migration sites on Earth.
If the outer journey is calling you, the inner one usually is too. Explore SoulMap at romantrail.com/blogs/soulmap.
