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Heading to the Florida Keys and wondering how to make the most of one day in Key West? I’m here to help!
While I would always recommend spending more time in Key West, I completely appreciate it’s not always possible which is why I put together this 1-day itinerary.
Key West is like nowhere else in America. Firstly, the whole drive there is incredible. It’s one of the most scenic road trips in the US and Key West itself is just so unique.
Pastel conch houses, roosters wandering the streets, Cuban coffee windows, and a sunset that the whole town turns out to watch every single evening…
The best part? Old Town is tiny. You can do everything on foot, which means one day genuinely is enough to see the highlights.
This itinerary takes you on a loop from the waterfront to the Southernmost Point, then back up Duval Street in time for sunset at Mallory Square.
🚶 Getting around: You do not need a car for this itinerary. Every stop is within a few minutes walk of the last one.
✈️ How to get to Key West
Key West sits at the very end of the Florida Keys, and there are three ways to get there.
Fly straight into Key West (EYW). The island has its own airport with nonstop flights from around two dozen cities. It’s the fastest option by far, and the right one if you’re only coming for a weekend — but it’s noticeably pricier than flying into Miami, and a lot of the smaller routes only run in winter.
Fly to Miami and drive down. This is what I’d recommend if you have any time to spare at all. Miami has cheap flights from all over the US and internationally, and it sits right at the top of the Keys.
From Miami it’s about 160 miles down the Overseas Highway (US-1) and it’s truly a sensational road trip! You’ll cross 42 bridges on the way, including the famous Seven Mile Bridge.
Don’t think of that drive as the boring bit. It’s actually the exciting bit which is why it’s considered one of the best road trips to Key West in America, and there are so many stops that are worth your time.
👉 Click here to see the best car rental prices in Miami.
Take the bus. If you don’t want to drive, Greyhound runs Miami to Key West a few times a day. It takes about 4.5 hours and fares start around $26. It drops you at the airport on S Roosevelt Blvd, a short taxi ride from Old Town. It’s not glamorous, but it’s cheap and it works.
🛌 Where to stay in Key West
Let’s get the awkward bit out of the way first: Key West is expensive. It’s one of the priciest places to sleep in the whole of the US, and there’s no real budget scene the way there is in Miami.
Rates swing hugely by season too — February to April and the Christmas holidays are peak, while August to October is much cheaper (that’s also hurricane season, so take the insurance).
Where you want to be is Old Town — the historic grid around Duval Street and Whitehead Street. That’s where the conch houses, the bars, the restaurants and everything in this itinerary are.
Here are three I’d point you towards, one for each budget:
💲💲💲 Luxury — H2O Suites. An adults-only all-suite boutique hotel on Simonton Street, one block back from Duval towards the Atlantic side. You get the quiet without giving up the location, and some of the suites have their own private plunge pool. It’s a proper treat.
💲💲 Mid-range — Courtney’s Place Historic Cottages & Inns. A cluster of little cottages and rooms on Whitmarsh Lane, a quiet side street about a block and a half from Duval. There’s an outdoor pool, it’s genuinely charming, and it’s the best-value Old Town option I know of.
💲 Budget — Authors Key West Guesthouse. On White Street, on the calmer eastern edge of Old Town. It’s a 13-room guesthouse in a set of historic cottages, still an easy walk to Duval, the waterfront and Higgs Beach — and considerably kinder on the wallet than anything closer to the action.
💡 PRO TIP: Whatever your budget, book early. Key West is a small island with limited rooms.
The Ultimate Key West 1-Day Itinerary
Right, let’s get into it!
Key West is a small town and this whole itinerary is on foot. It’s a loop, so you’ll finish roughly where you started, at Mallory Square for sunset.
One honest warning before you set off: there are five paid museums on this route and you cannot do all of them in one day — you’d be looking at nearly $100 in tickets and no time to actually enjoy the town. Pick two that appeal to you, and walk past the rest. I’ll flag which ones I’d prioritise as we go.
📍 Stop 1: Mallory Square
Start your day in Mallory Square.
It’s the most famous spot in Key West, but you can keep it brief this morning as you’ll be back here at the end of the day for the sunset celebration, and that’s when it really comes alive.
For now, just get your bearings on the waterfront and carry on.
🗿 Stop 2: Key West Historic Memorial Sculpture Garden
A couple of minutes’ walk from Mallory Square, on Wall Street, you’ll find the Key West Historic Memorial Sculpture Garden.
There are 36 bronze busts here of the people who shaped the island — wreckers, writers, politicians and businesspeople.
Under each one there’s a biography explaining who they were and what they did, and it’s a lovely quick introduction to how strange and specific Key West’s history actually is.
It’s free and open daily, and ten minutes here will set up the rest of your day nicely.
💡 Fun fact: Almost everyone will tell you Mallory Square is named after Stephen Mallory, the Confederate Navy Secretary. It isn’t! A local historian tracked down the original 1961 document and it turns out the square was named for the Mallory Steamship Line, the shipping family whose boats connected Key West to New York and Texas.
🚢 Stop 3: Key West Shipwreck Treasure Museum
Keep walking along Wall Street and you’ll find the Key West Shipwreck Treasure Museum right on the corner at Whitehead Street.
Key West made its fortune from shipwrecks.
In the 1800s this was the richest city per capita in the entire US, and the money came from “wrecking” — salvaging cargo from ships that came to grief on the reef.
The museum tells that story with costumed actors, and it’s genuinely interactive rather than a room full of labels.
It’s a great one with kids, but adults enjoy it too.
The building is a full-scale recreation of Asa Tift’s 1856 wrecking warehouse (not the original, despite what you’ll read elsewhere), and it has a 65-foot lookout tower you can climb for views over the harbour.
Tickets are around $19 for adults and $9.66 for children, and it’s open daily 9am–5pm with last entry at 4.30pm.
If museums aren’t your thing, walk by, take a photo of the tower and keep going.
🛍️ Stop 4: Clinton Square Market
Your next stop will be Clinton Square Market, on Front Street.
It’s a big brick building that started life as a US Navy depot and storehouse, built between 1856 and 1861.
The Coast Guard took it over in 1939, and today it’s an air-conditioned indoor market full of little shops.
It’s a good spot for souvenirs that aren’t the usual tat, and there’s a Cuban Coffee Queen inside.
⚓ Stop 5: Mel Fisher Maritime Museum
Keep walking a minute’s walk to Greene Street where you’ll find the Mel Fisher Maritime Museum.
This is the other shipwreck museum but it’s completely different as it’s a proper, traditional museum.
Mel Fisher spent 16 years searching for the Spanish galleon Nuestra Señora de Atocha, which sank in 1622, and finally found it in 1985 with hundreds of millions of dollars of gold, silver and emeralds aboard. A lot of that treasure is in this building.
Adult tickets are $17.50 and children $8.50. It opens at 10am with last admission at 4pm.
Honestly? If you only do one of the two shipwreck museums, do the Shipwreck Treasure Museum for the fun and this one for the substance. If neither appeals, the building itself is a nice historic one, so pause for a photo and walk on.
From here, head down Front Street for a couple of minutes towards the Truman Little White House.
🏛️ Stop 6: Harry S. Truman Little White House
This is one of my favourite stops in Key West, and if you’re only paying for one museum today, I’d make it this one.
Built in 1890 as naval officers’ quarters, the house became President Truman’s winter White House.
He first came down in November 1946 and returned 11 times, spending 175 days here altogether — working, fishing, playing poker and famously walking around in extremely loud shirts.
Truman wasn’t the only big name to stay.
Thomas Edison lived here in 1918 while developing depth charges for the Navy during WWI, and Eisenhower used it in 1955–56, including while recovering from his heart attack.
The house is preserved almost exactly as Truman left it, right down to the poker table.
Entry is by guided tour only and the guides are brilliant — this is a place where the stories make the visit.
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⛪ Stop 7: Cornish Memorial A.M.E. Zion Church
Walk about 15 minutes to the Cornish Memorial A.M.E. Zion Church on Whitehead Street.
It’s a striking all-white timber church and one of the oldest African American congregations in Florida.
It’s a quick stop but well worth it if you enjoy architecture.
🍽️ Lunch: Blue Heaven
📍 729 Thomas St, Key West, FL 33040
Blue Heaven is one of the best-loved restaurants in Key West and it’s tucked away in Bahama Village, two blocks off Duval — which means plenty of visitors miss it entirely. Don’t be one of them.
You eat outdoors in a courtyard under the trees, with roosters and cats wandering between the tables.
The building has had a wild past: it’s been a gambling hall and a boxing ring where Hemingway is said to have refereed fights.
The food is Caribbean-meets-Floridian, and this is the place to have your first slice of Key lime pie — theirs comes with a ludicrous tower of meringue. The banana pancakes are also famous, if you’d rather do this as a late breakfast.
💡 PRO TIP: The lunch kitchen closes at 2.30pm and they don’t take reservations for breakfast or lunch, so aim to arrive by 1.30pm at the latest. There’s almost always a queue — it moves, but factor it in.
🐈 Stop 8: The Ernest Hemingway Home and Museum
You can’t do a Key West itinerary without the Ernest Hemingway Home and Museum. It’s the most famous landmark on the island, and for good reason.
Hemingway was born in Illinois but lived here through the 1930s, and this is where he wrote some of his best work.
He’d already published The Sun Also Rises by the time he arrived; he went on to win the Pulitzer Prize in 1953 for The Old Man and the Sea and the Nobel Prize in Literature the following year.
The house itself is gorgeous, and the interiors have been left much as they were.
A guided tour is included in your ticket — they run every 15 minutes and take about 20–30 minutes, and I’d definitely take one.
Also, you’ll get to see the cats. Yes, real cats! Nearly 60 of them live on the grounds, and around half have extra toes. The line started with a white six-toed cat called Snow White, given to Hemingway by a ship’s captain.
🔦 Stop 9: Key West Lighthouse
The Key West Lighthouse is directly across the street from the Hemingway House, which makes it an easy pairing.
Key West’s first lighthouse went up in 1825, but it was destroyed by the Great Havana Hurricane of 1846.
The tower you see today was built in 1847 and it’s just over 90 feet tall. It was deactivated in 1989 and is now a museum run by the Key West Art & Historical Society.
You can visit the tower and the keeper’s quarters, and the views from the top over the whole island are fantastic — you’ll look straight down onto Hemingway’s garden and pool.
There are 88 steps to climb, so it’s a short but steep effort.
It’s open daily.
🌴 Stop 10: Southernmost Point
From the lighthouse, walk down Whitehead Street to the Southernmost Point Buoy.
As the name suggests, this marks the southernmost point of the continental USA — and it’s Key West’s most photographed spot. If you only take one picture on this trip, it’ll be here.
You should expect to stand in line here as it gets busy.
⚠️ Check before you go: The buoy has been temporarily moved while the seawall at its usual corner is rebuilt. It’s currently standing at 1400 Duval St, next to the Southernmost Beach Café, and the city is aiming to have it back in its original spot by the end of 2026.
While you’re here, walk past the Southernmost House hotel — a beautiful Victorian mansion — and if you want a coffee with your feet nearly in the sea, the Southernmost Beach Café has those oversized chairs everyone photographs.
🍹 Stop 11: Duval Street
Once you’re done, head back up on Duval Street, Key West’s most famous street.
There is genuinely nowhere else like Duval. It’s a mile of bars, restaurants and shops where a Texan saloon sits next to an Irish pub next to a Caribbean rum bar, and it somehow all works.
Walk up from the southern end. A few things worth looking out for on the way:
- The Bull & Whistle Bar (224 Duval) — three floors, each with its own personality. The Bull is open-air with live music, The Whistle has the balcony, and the Garden of Eden on the roof is clothing-optional. Yes, really.
- The Strand Theater (527 Duval) — a gorgeous 1918 cinema facade with a colourful marquee. Fair warning: it’s been a Walgreens inside for decades. Photograph the outside and move on.
- Captain Tony’s Saloon (428 Greene St, just off Duval) — this was the original Sloppy Joe’s, where Hemingway drank, until the bar moved down to 201 Duval in 1938 over a $1-a-week rent increase. It’s all hanging barstools, business cards and stories.
Stop somewhere for a drink before you head back to Mallory Square.
⚠️ One thing to know: you’ll hear a lot of people say Key West is an open-container town. It isn’t, technically — city ordinance prohibits drinking alcohol in public streets and sidewalks. In practice, bars hand out plastic go-cups and enforcement on Duval is famously relaxed, but it’s a custom rather than a legal right.
🌅 Stop 12: Sunset Celebration at Mallory Square
This is the moment the whole day has been building to.
Every single evening, the town gathers at Mallory Square to watch the sun go down.
It grew out of informal gatherings on the pier in the late 1960s and became a proper institution in 1984, when the performers organised themselves into the Key West Cultural Preservation Society.
It has run nightly ever since.
Things start around two hours before sunset, and sunset itself varies a lot: roughly 5.40pm in December, around 8.20pm in July. Check the date before you plan your afternoon around it.
Get there early enough to grab a spot along the edge.
If it’s already packed by the time you arrive, head towards the bars on the right-hand side — it’s usually a bit less crowded there.
Failing that, buy a drink at one of the waterfront bars and take a table; they’re not cheap, but you get a seat and the view.
The sunset is beautiful — the colours over the water are ridiculous — but honestly, the crowd is half the show. Jugglers, tightrope walkers, a man who does a routine with cats, musicians. It’s a proper carnival.
Alternative: you can watch the sunset from the water instead on a sunset cruise. You lose the Mallory Square atmosphere, but seeing it from a catamaran with a drink in hand is hard to beat.
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🎉 Stop 13: Duval Street at night
Once the sun’s gone, walk back to Duval — it’s a completely different street after dark.
The music gets louder, the bars fill up and the whole place shifts up a gear.
Wander up and down, get a drink, dance a bit (in a bar or in the street, this is Key West, nobody minds), and enjoy the fact that you’ve seen an entire island in a day.
You’ll be hungry by now, so grab something to eat while you’re there — Duval and the streets either side of it are full of options at all hours.
Optional extras if you have more time or want to switch things up
This itinerary is designed so you can see all the highlights on foot in a single day.
But Key West has a lot going on in the water, and those activities need a bigger chunk of time — so it comes down to what you want to prioritise.
If you can only add one thing, make it a boat trip. Here’s what I’d consider:
Dolphin watch and snorkel eco tour. A 3-hour cruise out to see wild dolphins with snorkelling included and all the equipment provided. Great with kids. Bring a waterproof case for your phone.
SNUBA. A hybrid of snorkelling and scuba that you don’t find in many places. You don’t need a PADI certification, just the ability to swim — you wear a mask and breathe through a long air line from the boat, so you can stay under far longer than snorkelling without lugging tanks around.
Sailing cruise. If you’d rather stay dry, a sailing trip gives you gorgeous views back at Key West and Fort Zachary Taylor.
Parasailing. For the adventurous. Up you go for genuinely thrilling views over the island and the reef.
Fort Zachary Taylor Historic State Park. Key West’s best swimming beach plus a Civil War fort, about a 15-minute walk beyond Old Town through Truman Annex. Entry is $6 per vehicle or $2.50 on foot, open 8am until sundown. Bring water shoes, the beach is rocky. Budget 2–3 hours if you’re going to do it properly.
Ghost tour. Key West is one of the most haunted places in the US, and the Ghosts & Gravestones trolley tour is the best of the bunch. It’s about an hour, from roughly $37, boarding at 501 Front Street. Reservations are required and it’s rated PG-13, so it’s not one for small children.
🗺️ Map of this Key West 1-Day Itinerary
A few practical tips
- Wear good shoes that you can walk with. You’ll be walking a fair bit and while you obviously don’t need hiking shoes, you still need to wear footwear you like and are comfortable.
- Pick two or three paid attractions, not five. Doing all of them would cost close to $100 a head and leave you no time to enjoy the streets.
- Start early — ideally by 9am — so you’re not rushing the afternoon museums, which mostly close at 5pm.
- Check what time sunset is on your date and work backwards from there.
- Bring sun cream, a hat and water. There’s very little shade on Whitehead Street and it is relentlessly hot from June to September.
- The best months to visit are March to May and November to early December. August to October is cheapest but it’s peak hurricane season, so get travel insurance.
Is one day in Key West enough?
One day is enough to see the highlights, and because Old Town is so compact you’ll come away feeling like you’ve genuinely experienced the place rather than skimmed it.
That said, if you can stay two nights, do. It means you can add a boat trip or Fort Zachary Taylor without cutting anything, you get a second sunset, and you’ll have a much less frantic morning at the museums.
But if one day is what you’ve got — one day in Key West is a very good day indeed.
