Everything worth knowing before you land

Before you plan anything, it helps to understand where Key West actually is. It sits at the end of a chain of islands stretching about a hundred miles from the Florida mainland, and it's closer to Havana — around 90 miles — than it is to Miami. That remoteness isn't a detail. It explains almost everything else about the place: the pace, the architecture, the food, and why the water looks the way it does.

The island itself is small — roughly two miles by four. Old Town, where almost everything you've read about is, occupies maybe a quarter of that. You can walk from the Southernmost Point to the Historic Seaport in about thirty-five minutes, and most visitors never go much beyond those bounds. That's not a criticism; there's genuinely enough in those four square miles to fill a week. But it's worth knowing that the island continues in both directions, and the parts beyond Old Town are where locals actually spend their weekends.

Key West has water on both sides, which matters more than it sounds. The Atlantic is on the south and east; the Gulf of Mexico is on the north and west. Between them sits some of the shallowest, most fish-rich backcountry in the United States. The practical consequence is that the wind direction, not the wind speed, decides what's worth doing on any given day. A brisk northerly can leave the backcountry flat as glass while the reef is rough; reverse the wind and it flips entirely. If you take one thing from this guide, take that — because it's why we'll sometimes suggest a different activity than the one you asked for.

The island also has a history that shapes its personality. It was a wrecking port in the nineteenth century, a cigar-manufacturing town after that, a Navy base, and a place where artists and writers — Hemingway and Tennessee Williams among them — came to be left alone. It has been, at various points, the richest city per capita in Florida and a place people fled to. That mix produced a town that is genuinely tolerant, mildly eccentric, and unimpressed by wealth in a way that's unusual for a resort destination.

Practically, this means three things. First, don't try to do everything — you'll enjoy it more if you pick two or three water days and let the rest of the trip be wandering. Second, plan around the wind rather than a rigid schedule. And third, accept that the best parts of Key West are the slow ones: an hour on a sandbar, a long lunch, the walk down to the water before dinner.

There are two ways to arrive: fly, or drive the Overseas Highway. Both are worth considering, and which is right depends on how much time you have.

Flying is straightforward. Key West International (EYW) is a small airport about ten minutes from Old Town, with direct services from several East Coast hubs plus Miami and Atlanta. Fares are higher than flying into a major city, and the aircraft are often regional jets or turboprops, so luggage allowances can be tighter than you're used to. The alternative is to fly into Miami or Fort Lauderdale and drive — which takes three to four hours from Miami and around four and a half from Fort Lauderdale.

Driving is the more memorable option. The Overseas Highway — US Route 1 — runs the length of the island chain over more than forty bridges, with the Seven Mile Bridge as the centrepiece. It is genuinely one of the great drives in the United States. Break it up: stop at Key Largo for lunch, pull over at Bahia Honda State Park, and allow a full day rather than rushing it. Note that the drive in and out of the island can be slow on Sunday afternoons and holiday weekends.

By ferry, there's a passenger service from Fort Myers that takes around three and a half hours and arrives at the Historic Seaport. It's a pleasant alternative if you'd rather not drive and don't want to fly.

Here's the thing most first-time visitors get wrong: renting a car in Key West is usually a mistake. Old Town is dense, the streets are narrow and one-way, and parking is genuinely scarce and often expensive. A car you don't use will cost you more in parking than it does in rental. The only reason to have one is if you're planning to drive up the Keys — and if that's the plan, a Jeep is a far better choice than a sedan.

Walk. This is the real answer for Old Town. Everything — Duval, Mallory Square, the Historic Seaport, the museums, the restaurants — is within a comfortable walk of everything else. Wear shoes you can walk in.

Bicycle. The island is flat and the bike paths are decent. It's the fastest way to get between Old Town and the beaches on the south side, and the cheapest. Rentals are plentiful and usually run by the day or week.

Golf cart. The most popular option with visitors, and the most fun, with caveats. A cart is easy to drive, holds four to eight people, and lets you park in spaces a car can't use. But it's slow, there is no weather protection, and you should check before booking whether carts are permitted on the specific roads you're planning to use — rules vary by street and by operator. For getting around Old Town and the immediate surrounds, it's ideal.

Moped or scooter. Cheap, quick and easy to park. Only worth it if you're a confident rider — the traffic in Old Town is slow but unpredictable, and the roads are shared with pedestrians, carts and bicycles.

Jeep or car. The one vehicle that justifies its cost, but only if you're heading up the Keys. A Jeep lets you reach Bahia Honda, Big Pine, the Lower Keys and the quieter beaches that are twenty to forty minutes away — the parts of the chain most visitors never see. If you're staying strictly in Old Town, skip it.

Taxis and rideshare. Available and reliable for short hops, particularly at night or if you're staying outside the historic district. There are also electric shuttles running fixed routes through Old Town.

Parking. If you do have a vehicle, know that free parking in Old Town is rare and metered spaces are enforced. Many accommodations include a space; if yours doesn't, ask before you arrive. The Park and Ride on the north side of the island is a reasonable fallback.

In most places, sunset is something you notice. In Key West it's an event with a schedule, a venue and an audience. Mallory Square, on the waterfront at the north end of Duval, hosts a nightly gathering that's been happening for decades — street performers, artists, food vendors, and a few hundred people watching the sun go down over the Gulf. It's free, it's a bit chaotic, and it's worth doing once.

The performers set up an hour or two before sunset and pack up shortly after. Arrive around ninety minutes early to get a spot near the railing and to see the acts. The fire-eaters and tightrope walkers are the ones that draw the crowds; the musicians scattered along the square are often better. Bring cash for tips — the performers work for them.

If crowds aren't your thing, there are quieter options. The Southernmost Point area gets busy at sunset but the beach at Fort Zachary Taylor State Park is calmer and, we'd argue, a better view — you're looking west over open water rather than across the harbour. There's a small entry fee and it closes at sunset.

On the sunset cruise question: yes, it's worth it, with one caveat. A sunset cruise puts you on the water as the light goes, which is genuinely different from watching from land — and most departures include drinks. The caveat is that you're sharing the view with everyone else on the boat, and the boats are often full. If that's fine, book it. If you'd rather have the horizon to yourselves, a private charter costs more but changes the experience completely.

One practical point: sunset time varies by more than two hours across the year — roughly 5:45pm in midwinter and 8:15pm in midsummer. Whatever you're planning, check the actual sunset time for your date, and aim to be in position ninety minutes before it. The best light isn't at sunset; it's in the hour leading up to it.

There's more here than boats, and if you're on the island for more than a couple of days you'll want it. The town is dense with history, and a surprising amount of it is genuinely interesting rather than merely old.

The essentials are straightforward, but a few things are specific to this place:

Reef-safe sunscreen. This is not optional in spirit or in practice — several operators require it, and the marine sanctuary rules restrict certain ingredients. Bring it rather than buying it here, where it's marked up considerably.

Sunglasses with a strap. The glare off the water is intense and a strap stops them going overboard, which happens constantly.

A dry bag. Small, cheap, and the difference between a working phone and a dead one. Even on a boat, spray gets everywhere.

Shoes you can walk in. Old Town is a walking town and the streets are uneven. Non-slip soles are worth having on boats.

A light rain layer. Summer storms are short but sudden, and in winter the wind can make an evening cruise colder than you'd expect.

Cash. You'll want it for tips — captains, mates, guides and the performers at Mallory Square all work for them. Many places take cards, but tips and small vendors are still a cash business.

Leave behind: heavy luggage, formal clothes and anything you'd be devastated to get wet or sandy. Nobody dresses up much here, and the island rewards travelling light.

Standard US practice applies: fifteen to twenty percent in restaurants. On boats, the mate works for tips and fifteen to twenty percent of the trip cost is the usual expectation. If you had a good captain, tipping them directly is appreciated.

Key West is expensive by Florida standards and everyone who lives here knows it. Accommodation is the big one, particularly in high season. Food and drink on Duval are priced for visitors. Water activities vary enormously — a group snorkel trip costs a fraction of a private charter, and both are legitimate ways to spend a day.

Places to save: eat lunch out rather than dinner, buy drinks at a liquor store for the boat rather than at a bar, take your own cooler on a sandbar trip if it's permitted, and book direct for simple rentals where there's no advantage to an intermediary. If you're doing three or more water days, combining them into one booking usually costs less than arranging each separately.

The sun is the main hazard, and it's stronger here than most visitors expect even when it's overcast. Reapply sunscreen throughout the day, particularly after swimming.

If you're prone to seasickness, take medication before you board, not after you feel unwell — by then it's too late to help. The offshore trips are the ones that catch people out; the backcountry and reef are usually calm.

There's a hospital on the island with an emergency department, and a number of urgent care clinics. Standard travel insurance is sensible, and it becomes genuinely important if you're visiting during hurricane season.

Old Town is largely flat and walkable, but many pavements are uneven, some buildings are historic with steps at the entrance, and not everywhere is wheelchair accessible. On the water, accessibility varies a great deal by boat — catamarans are generally easiest for boarding, smaller skiffs the hardest. If anyone in your party has mobility requirements, tell us when you book and we'll match you to an operator who can accommodate them rather than finding out at the dock.