Things to do in Key West: Duval Street, sunset, and the drive

Key West is the destination, not a stop along the way

Of all the Florida Keys, Key West is the one with a real identity of its own: a compact, walkable town at the far end of the Overseas Highway, with a downtown core built for wandering rather than driving through. Islamorada and Marathon sit along the same route and are worth a brief stop if the timing works, but neither is a reason on its own to make the trip. Key West is.

The island’s reputation rests on a handful of things that hold up: Duval Street’s mix of bars, restaurants, and galleries; the nightly sunset gathering at Mallory Square; the Ernest Hemingway House; and the Southernmost Point buoy, a short walk from downtown and about 90 miles from Cuba. None of it is flashy, and none of it needs to be oversold. What it does need is an honest account of how long it takes to get there, because that single number changes how the whole day should be planned.

The drive: what 160 miles actually means

Key West sits at the end of US-1, about 160 miles (257 km) from Miami by road. The stretch that gets the attention is the 113 miles and 42 bridges between Key Largo and Key West, known as the Overseas Highway, including the Seven Mile Bridge near Marathon. In practical terms, that’s 3.5 to 4 hours of driving each way without stops, assuming clear traffic — and traffic on this two-lane road is rarely guaranteed, especially on weekends and holidays.

That math rules out a “quick” round trip. A drive down and back in the same day means 7 to 8 hours behind the wheel or on a coach, on top of however long is spent in Key West itself. Guided day trips from Miami handle this by starting early, often before sunrise, and returning late; they’re a reasonable way to see Key West without renting a car or arranging an overnight stay, but they are a long day, not a relaxed one. Anyone renting a car and driving independently should build in the same expectation: this is a full day of travel wrapped around a few hours in town, and rushing it defeats the purpose. Details on how the drive compares to a guided coach trip are in the guide to driving versus a bus tour to Key West.

The honest alternative is a night in Key West. Splitting the drive across two days, or simply staying over, turns a rushed round trip into an actual visit — time for dinner on Duval Street, the sunset at Mallory Square without a bus waiting, and a slower morning before the drive back. It costs more and takes more planning, but it changes what the destination actually delivers.

Duval Street and downtown

Duval Street runs about a mile from the Gulf side of the island to the Atlantic side and functions as Key West’s main artery — bars, seafood restaurants, T-shirt shops, and galleries packed close together. It’s loud in the evening and considerably quieter in the morning, when the same street works better for breakfast and a walk before the day’s heat sets in.

The side streets off Duval hold most of the town’s quieter character: shaded lanes of conch-style houses, small galleries, and cafés without the crowd. Old Town Key West rewards walking without much of a plan, and most of the sights below are within 15 to 20 minutes on foot of each other.

Mallory Square and the sunset gathering

Every evening, weather permitting, crowds gather at Mallory Square on the Gulf side of downtown for a informal sunset celebration — street performers, food carts, and a genuine crowd watching the sun go down over the water. It’s free, it doesn’t require a reservation, and it gets tight in the last half hour before sunset, so arriving with some time to spare makes for a better view. It’s one of the few things in Key West that costs nothing and rarely disappoints, though it’s worth knowing it’s a crowd event, not a quiet moment alone with the horizon.

The Ernest Hemingway House

A few blocks south of Duval Street, the Ernest Hemingway House is a paid house-museum tour of the writer’s former Key West home, built around his years living and writing on the island in the 1930s. The garden’s population of six-toed cats, descendants of Hemingway’s own, is as much a draw for some visitors as the house itself. It suits anyone with an interest in Hemingway, in the island’s literary history, or in a well-preserved 19th-century house — it’s a slower, more deliberate stop than most of what’s on Duval Street, and worth budgeting 45 minutes to an hour for.

The Southernmost Point and the walk south

At the corner of Whitehead and South streets sits the Southernmost Point buoy, a concrete marker painted like a giant buoy and one of the most photographed spots in the Keys. It marks the southernmost point accessible to the public in the continental United States — not, technically, the island’s absolute southernmost point, which sits inside a nearby restricted naval property. The buoy is roughly 90 miles from Cuba, a fact repeated often enough locally that it’s worth stating plainly rather than treating as a surprise. Lines for a photo can run long at peak times of day; early morning or later afternoon avoids the worst of it.

Beyond downtown: water, wildlife, and side trips

Key West’s setting is as much water as land, and much of what’s worth doing sits just offshore. Boat tours and sunset cruises leave from the harbor regularly; snorkeling trips head out toward the reef; and kayak eco-tours cover the mangrove backcountry north of town. For anyone weighing how to spend a half-day beyond downtown, the Key West boat tours and cruises guide and the Key West snorkeling and diving guide both cover the options in more detail.

Travelers who want to reach the Dry Tortugas — a separate national park about 70 miles further west, reachable only by ferry, seaplane, or private boat, never by road — should plan that as its own day rather than adding it onto a Key West day trip; it needs a full day on its own and advance booking.

Guided ways to see the island without a car

For visitors arriving without a rental car, or who’d rather not deal with downtown parking, a hop-on trolley-style tour covers the island’s layout quickly:

a narrated trolley tour around Key West’s neighborhoods and historic sites

For those coming from Miami without their own transportation, a full guided round trip handles the drive and a chunk of the day in town:

a small-group day trip from Miami covering the drive and time in Key West

Travelers who want the day trip plus a stop in the water on the way can combine the drive with reef snorkeling:

a Miami day trip that pairs the Key West drive with a snorkeling stop

For a quieter, paddle-based look at the island’s backcountry, a guided kayak trip through the mangroves is a different pace entirely from Duval Street:

a guided kayak eco-tour through Key West’s mangrove backcountry

How Key West compares to the rest of the Keys

Key West is the anchor destination of the Florida Keys, but it isn’t interchangeable with the stops along the way. Key Largo, about an hour from Miami, is built around a short reef-snorkeling excursion at John Pennekamp Coral Reef State Park — a half-day trip, not a full-day commitment. The things to do in Key Largo guide covers that shorter format in detail, and the Key West versus Key Largo comparison lays out which fits which kind of day.

Islamorada and Marathon, further along the highway, are worth a stop for lunch or a quick look at the Seven Mile Bridge, but they don’t carry the same weight as a planned destination on their own. For anyone building a longer Keys itinerary rather than a single day trip, the Miami to Key West road trip itinerary spreads the drive and the stops across more than one day.

Stop	Typical time from Miami	Best treated as
Key Largo	~1 hour	Half-day reef and snorkeling excursion
Islamorada	~1.5 hours	Brief stop along the drive
Marathon	~2 hours	Brief stop, Seven Mile Bridge view
Key West	~3.5–4 hours	Full day trip, better as an overnight stay

Planning notes before booking anything

A day trip to Key West works best with realistic expectations set in advance, whether driving independently or booking a guided tour. A few points worth checking ahead of time:

What to check	Why it matters
Departure time	Early starts (often before sunrise) are normal for one-day round trips
Return time	Late evening returns are common; confirm before booking evening plans in Miami
Traffic on US-1	The two-lane highway backs up on weekends and holidays; build in buffer time
Hemingway House tickets	A paid, timed entry; check current hours and price on the official site or your booking confirmation
Weather	Hurricane season runs June 1 to November 30, with a peak from August through October; check forecasts before locking in a date

Prices for tours change with season and demand, so treat any figure as a starting point and confirm the current rate on the booking page before paying. The same goes for hours at the Hemingway House and any seasonal changes to the Mallory Square schedule.

Frequently asked questions about visiting Key West

How far is Key West from Miami, really?

About 160 miles (257 km) door to door, including 113 miles and 42 bridges on the Overseas Highway from Key Largo to Key West. Expect 3.5 to 4 hours of driving each way without stops, more with weekend traffic.

Can you do Key West as a day trip from Miami?

Yes, guided day trips by coach run from Miami and cover the drive both ways plus a few hours in town. It’s a long day: roughly 7 to 8 hours of round-trip travel for maybe 4 to 5 hours on the island, so an overnight stay changes the experience considerably.

What is there to do on Duval Street?

Duval Street is Key West’s main strip, running from the Gulf side to the Atlantic side, lined with bars, restaurants, galleries, and shops. It’s the natural starting point for exploring downtown on foot.

Where do people watch the sunset in Key West?

Mallory Square, on the Gulf side of downtown, hosts a nightly sunset gathering with street performers and vendors. It’s free to attend and gets crowded in the final 30 minutes before sunset.

Is the Hemingway House worth visiting?

It’s a paid house-museum tour of the writer’s former home, known for its six-toed cats and garden. It suits visitors with an interest in Hemingway or Key West’s literary history rather than a quick photo stop.

How far is Key West from Cuba?

About 90 miles across open water. The Southernmost Point buoy near the corner of Whitehead and South streets marks the spot and is a popular photo stop, though it isn’t technically the island’s southernmost point (that’s on a nearby restricted naval base).

Should I stop in Islamorada or Marathon on the way?

Both sit along the Overseas Highway between Miami and Key West and work well as brief stops to break up the drive. Treat them as waypoints rather than destinations if Key West is the main goal for the day.

Is Key West different from Key Largo for a day trip?

Key Largo is a short excursion focused on reef snorkeling and diving, under an hour from Miami. Key West is a much longer commitment centered on the town itself, so the two suit different kinds of days out. More on Hemingway’s time on the island is in the Hemingway in Key West story, and more on the buoy itself is in the Southernmost Point and mile marker zero piece. For a fuller comparison of the day-trip options from Miami, see the Key West day trip from Miami guide and the ghost tours and history guide for evening options once the sun goes down.