Key West is the last island on a chain of islands, 160 miles from Miami down a highway built on causeways and bridges, and it is closer to Havana than to the Florida mainland's big cities. It is a small place, about two miles by four, with roughly 25,000 residents, tin roofs, wooden Conch houses, roosters in the street and a long habit of not minding what anybody does.
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Two Things Nobody Tells You First
THERE IS ONE ROAD OUT, AND IN A HURRICANE MONROE COUNTY EVACUATES VISITORS BEFORE RESIDENTS. US 1, the Overseas Highway, is the only road off the island chain and it is mostly two lanes for well over a hundred miles. Because of that, Keys emergency management issues a PHASED EVACUATION, and the first phase is for VISITORS AND TOURISTS, typically ordered a day or more before any residential evacuation. A MANDATORY VISITOR EVACUATION IS NOT ADVICE, it is an order, and hotels will close and put you out. If you travel between June and November, carry travel insurance that covers weather disruption, keep your flights flexible and understand that the correct response to a visitor evacuation order is to leave at once, while the road is still moving. HURRICANE IRMA MADE LANDFALL IN THE LOWER KEYS IN SEPTEMBER 2017 as a Category 4, about twenty miles from here, and parts of the chain took years to recover.
AND KEY WEST HAS ALMOST NO BEACH, WHICH IS WHAT ACTUALLY DISAPPOINTS PEOPLE. This is a coral island with no natural sand shoreline, so what exists is small, man-made and shallow: SMATHERS BEACH is the longest, FORT ZACHARY TAYLOR'S is the best and is coarse and rocky underfoot with the clearest water, and HIGGS BEACH is in between. All are fine for an hour and none is the Caribbean beach the brochures imply. IF YOU WANT A BEACH HOLIDAY, GO SOMEWHERE ELSE; if you want a strange, sun-bleached, literary, slightly disreputable island town with a reef offshore, this is the place.
What Is Here
DUVAL STREET IS THE HERO IMAGE AND IT IS A MILE OF BARS, SHOPS AND NOISE. Sloppy Joe's, Captain Tony's and the Green Parrot are the names; it is cheerful, extremely drunk after dark, and it is only part of the island. WALK ONE BLOCK EITHER SIDE and you are in the quiet lanes of OLD TOWN, which hold the largest concentration of wooden nineteenth-century houses in Florida and are the real reason to be here.
THE HEMINGWAY HOME AND MUSEUM is the 1851 house he owned for a decade, where he wrote much of his best work, with a guided tour included in the ticket and roughly SIXTY CATS, many polydactyl, descended from his. THE TRUMAN LITTLE WHITE HOUSE is the naval quarters Truman used for 175 days as a working presidential residence and is a far better museum than it sounds.
THE KEY WEST LIGHTHOUSE IS THE SECOND IMAGE, an 1848 tower across the street from Hemingway's house, climbable, with the best overview of the island, and the keeper's quarters as a small museum.
THE SOUTHERNMOST POINT BUOY IS THE QUEUE PHOTOGRAPH. It is a painted concrete marker, it is not quite the southernmost land, and the line can take an hour in season. GO AT SUNRISE and there will be nobody there.
MALLORY SQUARE AT SUNSET IS THE NIGHTLY RITUAL, a free gathering with buskers, jugglers and food carts starting about two hours before the sun goes down, and it is genuinely good. FORT ZACHARY TAYLOR STATE PARK is the better sunset, quieter, with the fort, a small admission and the island's clearest snorkelling from shore.
THE REEF IS THE BEST THING OFFSHORE. The only living coral barrier reef in the continental United States lies about six miles out, reached by catamaran snorkel trips in a couple of hours. CORAL BLEACHING AND DISEASE HAVE DONE REAL DAMAGE over the last decade and the honest version is that the fish are still excellent and the coral is not what it was.
DRY TORTUGAS NATIONAL PARK IS THE DAY TRIP WORTH PLANNING AROUND AND IT MUST BE BOOKED FAR AHEAD. Seventy miles west, a vast unfinished 1840s brick fort on an island, with superb snorkelling and almost nobody on it. THE YANKEE FREEDOM FERRY SELLS OUT MONTHS IN ADVANCE in high season and seaplanes are the expensive alternative. There is no food or water out there beyond what the ferry provides, and crossings are CANCELLED FOR SEA CONDITIONS with some regularity.
THE CONCH TOUR TRAIN IS THE THIRD IMAGE and, with the Old Town Trolley, is the easiest way to get your bearings on the first morning. Otherwise RENT A BICYCLE: the island is flat, small and made for it.
When to Go
DECEMBER to APRIL is the high season and the best weather: 75F to 80F, low humidity, little rain. It is also the most expensive and the busiest, and it books out.
MAY and NOVEMBER are the value months, warm and mostly dry with lower prices.
JUNE TO SEPTEMBER IS HOT, HUMID AND WET, with daily afternoon storms, 90F with high humidity and voracious mosquitoes. It is also the cheapest.
HURRICANE SEASON RUNS 1 JUNE TO 30 NOVEMBER and peaks from mid-August through September, which is also when the Keys are most likely to be evacuated.
EVENTS FILL THE ISLAND COMPLETELY. FANTASY FEST in late October is a ten-day adult costume carnival, enormous, with widespread public nudity and body paint, and Duval Street is an entirely different proposition during it. Hemingway Days in July, the Powerboat Races in November and spring break in March all book the island out. CHECK THE CALENDAR BEFORE BOOKING, in either direction.
Getting There
KEY WEST INTERNATIONAL, EYW, is on the island, two miles from Old Town, and takes mostly regional flights from Miami, Fort Lauderdale, Orlando, Tampa and some seasonal direct services. It is small, expensive and extremely convenient.
BY CAR FROM MIAMI IS ABOUT 160 MILES AND THREE AND A HALF TO FIVE HOURS, and the drive is the point: 42 bridges, including the Seven Mile Bridge, with water on both sides. ALLOW FOR TRAFFIC, because one accident on a two-lane highway with no alternative route stops everything for hours.
The KEY WEST EXPRESS ferry runs from Fort Myers and Marco Island, about four hours, and is a pleasant alternative that is weather-dependent.
DO NOT RENT A CAR FOR KEY WEST ITSELF. Parking is scarce and expensive, the island is two by four miles and flat, and bicycles, scooters and walking cover all of it. A car is only for arriving and for exploring the other Keys.
Is Key West Safe for Women?
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 wildfire and heat risk in the west and south-west.
Key West is a very safe small town and its crime is overwhelmingly alcohol-related and concentrated on and around Duval Street at night. Old Town is walkable at any hour, the lanes are quiet, and a woman walking home alone here is unremarkable. The honest caution is about drinking: this is a town organised around it, drinks are strong, the bars close at four in the morning, and almost every unpleasant incident involving a visitor starts there. Pace it, watch your own drink, and walk home on Duval rather than through unlit back lanes.
THE SUN IS THE MOST LIKELY THING TO HURT YOU AND IT IS STRONGER THAN ANYWHERE ELSE IN THE CONTINENTAL UNITED STATES. At 24 degrees north on white coral and water, with a constant breeze that hides the burn, people get badly burned here on day one. Reapply, wear long sleeves on the water and accept that a hat is not optional.
THE WATER HAS THREE SPECIFICS. BOAT TRAFFIC is heavy and channels are busy, so swim where marked. SEA URCHINS, FIRE CORAL AND STONEFISH-STYLE SCORPIONFISH are all present on rocky entries, which is the real argument for something on your feet. And FROM ROUGHLY MAY TO SEPTEMBER there are jellyfish and occasional PORTUGUESE MAN O' WAR washes, which are painful and are posted when present.
MOSQUITOES ARE SERIOUS FROM JUNE TO NOVEMBER and Monroe County has recorded locally transmitted DENGUE cases in recent years, which is unusual on American soil, so repellent is a health measure rather than a comfort one.
HURRICANE AWARENESS IS THE ONE NON-NEGOTIABLE, for the reasons at the top of this post: one road, phased evacuation, visitors first.
SCOOTER RENTALS CAUSE MOST VISITOR INJURIES HERE. Narrow streets, chickens, drunk pedestrians and inexperienced riders in flip flops: the hospital sees them constantly. A bicycle is the better choice.
The Key West Packing List
Subtropical heat and humidity year round, extreme sun, salt water, sudden rain and air conditioning turned down hard.
Our merino base layers are 100% Australian merino at 17.5 micron, and a long sleeve merino wool base layer for women is a less obvious choice for the tropics than it deserves to be: fine wool is the best sun cover there is because it keeps working wet, it carries sweat off the skin in humidity rather than holding it like cotton, and it resists the smell that salt, sunscreen and three days of heat produce in a synthetic shirt. It is also the layer you want on a boat at dawn and in a restaurant cooled to 68F.
A long sun hoodie and a wide brim UPF sun hat, which on this island are equipment and not accessories.
Insect repellent for June to November, when dengue makes it a health item, and a dry bag for the reef trip and the Dry Tortugas ferry, where spray soaks everything on an open deck.
A quick dry travel towel and a Marmot PreCip Eco rain jacket, which packs small and handles an afternoon squall.
Not linked and worth packing: SOMETHING ON YOUR FEET IN THE WATER, because Fort Zachary Taylor's entry is rock and urchins and fire coral are present, and our registry's only water-shoe entry has a contested product identity so we will not link it; REEF-CONSCIOUS SUNSCREEN with non-nanoparticle zinc oxide, noting that "reef safe" is not a regulated term anywhere, so read the ingredients; A REUSABLE WATER BOTTLE; AND ONE SMART-CASUAL OUTFIT, because Key West dressing up means a sundress and sandals and nothing more. The US is almost entirely card-based with tipping at 18 to 20 per cent.
Recommended Tours and Experiences
Essential Resources for Women in Key West
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.
THERE IS ONE ROAD OUT AND MONROE COUNTY EVACUATES VISITORS FIRST. US 1 is the only road off the Keys and is largely two lanes for over a hundred miles, so hurricane evacuation is PHASED and the FIRST PHASE IS FOR VISITORS, often a day or more before residents. A MANDATORY VISITOR EVACUATION IS AN ORDER, NOT ADVICE: hotels close and you must leave at once, while the road still moves. HURRICANE SEASON IS 1 JUNE TO 30 NOVEMBER, peaking mid-August to September; carry weather-inclusive travel insurance and keep flights flexible. HURRICANE IRMA STRUCK THE LOWER KEYS AS A CATEGORY 4 IN SEPTEMBER 2017. KEY WEST HAS ALMOST NO NATURAL BEACH: Smathers, Higgs and Fort Zachary Taylor are small and man-made, and the fort's is rocky underfoot with the clearest water. THE DRY TORTUGAS FERRY SELLS OUT MONTHS AHEAD and is cancelled for sea conditions, with no food or water on the island beyond what the boat carries. THE SUN AT 24 DEGREES NORTH, ON WHITE CORAL AND WATER WITH A COOLING BREEZE, IS THE MOST LIKELY THING TO HURT YOU. MOSQUITOES ARE SERIOUS JUNE TO NOVEMBER AND MONROE COUNTY HAS RECORDED LOCALLY TRANSMITTED DENGUE, so repellent is a health measure. SEA URCHINS, FIRE CORAL AND SCORPIONFISH are present on rocky entries and jellyfish and Portuguese man o' war wash in from May to September. SCOOTER RENTALS CAUSE MOST VISITOR INJURIES: take a bicycle instead. CRIME IS ALMOST ENTIRELY ALCOHOL-RELATED AND CONCENTRATED ON DUVAL STREET, where bars close at four in the morning. FANTASY FEST in late October is an adult costume carnival with widespread public nudity and fills the island completely.
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: Lower Keys Medical Center on Stock Island, about three miles from Old Town, is the only hospital in the Lower Keys and has a 24 hour emergency department; SERIOUS TRAUMA IS FLOWN TO MIAMI, which is the fact worth knowing on an island this remote. Dial 911 for police, ambulance or fire, and note that an emergency on the water goes through 911 to the UNITED STATES COAST GUARD, or VHF channel 16, rather than a land ambulance. 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 the US public health guidance, with the Florida Department of Health in Monroe County the authority for local dengue advisories and the National Hurricane Center for storm tracks
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 Key West and the Florida Keys visitor information, with Monroe County Emergency Management the authority for evacuation phases and orders
Takeaways
One road out, and visitors are evacuated first. Know that before June.
The beaches are poor. The reef, the lanes and the light are not.
Book the Dry Tortugas ferry months ahead.
Rent a bicycle, not a scooter, and never a car.
Solo women safety assessment: Key West is one of the easiest places in the United States to be a woman travelling alone. It is a small, flat, walkable island town of about 25,000 people with a long tradition of leaving everyone to their own business, Old Town's lanes are quiet and well used at almost any hour, and nothing about arriving by yourself stands out here. Crime is low and is overwhelmingly alcohol-related and concentrated on and immediately around Duval Street late at night, which is the honest caution: this is a town organised around drinking, the measures are generous, the bars close at four, and nearly every unpleasant incident involving a visitor begins there, so pace it, watch your own drink and walk back along Duval rather than through unlit lanes. 911 REACHES POLICE, AMBULANCE AND FIRE, an emergency on the water reaches the Coast Guard through 911 or VHF 16, and Lower Keys Medical Center on Stock Island is the only hospital in the Lower Keys, with serious trauma flown to Miami. THE TWO RISKS WORTH REAL PREPARATION ARE NOT CRIMINAL. The first is the sun, which at this latitude on white coral and water with a constant breeze burns people badly on their first day; long sleeves, a real hat and repeated sunscreen are equipment here. The second is the hurricane geometry, which is unique in America: one two-lane road for over a hundred miles means Monroe County evacuates visitors before residents, often more than a day ahead, so between June and November keep your flights flexible, carry insurance that covers weather disruption, and treat a visitor evacuation order as something to act on immediately rather than to weigh up.
Reading On
Key West is the end of a chain and almost everyone reaches it through South Florida, so the Miami packing list is the natural first half of the trip at 160 miles up the highway, and the Fort Lauderdale packing list covers the other common arrival airport and the hurricane planning that goes with it. Up the peninsula, the Orlando packing list covers the theme parks and the inland heat. For the same reef-and-island shape elsewhere in the library, the Kauai packing list and the Big Island packing list cover Pacific equivalents with better beaches and the same sun problem, and the New Orleans packing list shares the Gulf humidity and the drinking culture. For the country, the United States travel guide for women carries the transport, the health insurance question and the regions in full. For why fine wool is the best sun and sweat layer in the tropics, 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.
If the outer journey is calling you, the inner one usually is too. Explore SoulMap at romantrail.com/blogs/soulmap.
