The Best Things to Do in Key West Happen Before Noon and After Dark
The best things to do in Key West cluster at the edges of the day. Catch the Dry Tortugas ferry at 8 a.m., swim at Fort Zachary Taylor before the cruise crowd lands, and save Old Town for after the heat breaks. Midday on Duval Street is hot, loud, and mostly T-shirt shops. Here’s how I’d spend three days, and what I’d skip.
Key West Is Four Miles Long, So Plan Around Heat, Not Distance
Key West, Florida, sits at Mile Marker 0 of the Overseas Highway (US-1). It’s the last island in the Florida Keys and the county seat of Monroe County. The island runs roughly four miles long and two miles wide, so you can cover Old Town’s grid of Duval, Whitehead, and Caroline Streets on foot in an afternoon.
The drive from Miami International Airport is about 160 miles and takes 3.5 to 4 hours without traffic. Weekends add an hour at the single-lane chokepoints. Most of the route crosses open water, including the Seven Mile Bridge at Marathon. Flying into Key West International Airport (EYW) skips the drive but usually costs more. The official Florida Keys & Key West tourism board (fla-keys.com) posts the current events calendar.
Heat is the real constraint. From May through September, I treat 11 a.m. as the end of the walking day. That’s why I’d book one of the dreamy Airbnbs in the Florida Keys with a pool or deep shade, so you have somewhere cool to retreat when the afternoon sun hits.
Spend Your First Morning at Dry Tortugas National Park
Go to Dry Tortugas National Park first. It’s the best day trip from Key West, and it’s the one booking that fills up.
The park sits about 70 miles west of Key West in the Gulf of Mexico and belongs to the National Park Service (nps.gov/drto). Its centerpiece is Fort Jefferson, a 19th-century coastal fortress on Garden Key built from more than 16 million bricks.
The Army later used it as a prison, and Dr. Samuel Mudd, convicted in the Lincoln assassination conspiracy, served time there.
The ferry: my pick for a first visit
The Yankee Freedom catamaran (drytortugas.com) leaves from the Historic Seaport at 8 a.m. The crossing takes about 2 hours 15 minutes each way. Check-in opens around 7 a.m., so you’re up before sunrise. You get roughly four hours on the island, and the boat gets back to Key West around 5:30 p.m.
A ticket ran a little over $200 per adult when I last looked, with breakfast, lunch, and snorkel gear included. Park entry is a separate line item, so read the booking page closely.
Snorkel along the moat wall around the fort, where fish crowd the old brickwork. Then climb to the top of the fort for the view across the flats. Four hours feels short, and most people wish they had five.
The negative: the Gulf crossing can get rough. I’ve watched passengers spend the whole ride bent over a bag. Take a motion-sickness tablet an hour before boarding, and sit low and mid-boat.
The seaplane: faster, pricier, shorter
Key West Seaplane Adventures flies the same route in about 40 minutes. It costs considerably more per person, and the half-day option leaves little time on the sand. I’d choose it only if you get seasick or you truly have just a morning.
The Old Town Stops That Earn Their Admission (and Two That Don’t)
Old Town packs its history into a few blocks. Book these in the cooler hours, and you’ll finish before the worst heat.
Harry S. Truman Little White House
Start at 111 Front Street. Truman wintered here during his presidency, visiting 11 times by most counts. The guided tour runs about 45 minutes and rarely feels crowded. I rank it above the Hemingway house, mainly because I can hear the guide.
Ernest Hemingway Home and Museum
The Ernest Hemingway Home and Museum (907 Whitehead Street) is a Spanish Colonial house from 1851. Hemingway lived and wrote here in the 1930s. The polydactyl (six-toed) cats are descendants of his own, and roughly 60 roam the grounds.
Admission runs about $20. Go when it opens at 9 a.m., because tour groups pile in by late morning. If Hemingway doesn’t interest you, skip it. You’re paying a steep price for a 45-minute visit.
Key West Lighthouse and Keeper’s Quarters
The lighthouse sits across Whitehead Street from the Hemingway house. The climb is 88 steps, and the top gives you a clear view over Old Town’s tin roofs to the Gulf. Pair it with the museum below, which costs nothing extra.
Key West Cemetery
Entry is free. Walk the lanes at 8 a.m., before the heat settles, and look for the headstone of B.P. “Pearl” Roberts, which reads “I told you I was sick.” It’s the cheapest laugh on the island.
The two I’d skip
The line for the Southernmost Point buoy (South and Whitehead Streets) grows fast after 9 a.m. Show up at sunrise for a photo, or skip it. The marker notes the distance to Cuba as 90 miles, and that’s all you’ll get from it.
I’d also skip the narrated trolley and train tours. Old Town is small enough to walk, and a bike covers the rest.
Fort Zachary Taylor Beats Smathers for Swimming
Fort Zachary Taylor Historic State Park, run by Florida State Parks (floridastateparks.org), has the best swim beach in town. The water is clear, and shaded picnic areas back the shoreline. It also holds a Civil War-era fort, so you can pair a swim with a history stop.
Entry is a few dollars per vehicle, and less for walkers and cyclists. The shoreline is rocky coral rubble. Bring water shoes, or you’ll limp back to your towel.
Smathers Beach on South Roosevelt Boulevard is longer and flatter, with imported sand. It suits a walk and people-watching, but I wouldn’t snorkel there.
Snorkeling Trips, Sunset Sails, and Other Key West Activities on the Water
The reef is the main reason to book a boat. The Florida Keys National Marine Sanctuary, managed by NOAA (floridakeys.noaa.gov), protects the only living barrier reef in the continental United States. Half-day snorkel trips leave from the Historic Seaport, and Sand Key, about seven miles offshore, is a common stop.
Certified divers can ask about the USS General Hoyt S. Vandenberg, a 500-plus-foot ship sunk as an artificial reef in 2009 roughly seven miles south of town. Beginners should skip it, since the wreck sits deep.
For sunset, I pick a small sailboat over a big party catamaran. Fewer passengers means better photos and less shouting over music.
The free alternative is Mallory Square, where the nightly sunset celebration brings street performers and, when cruise ships dock, a packed pier. I’d rather watch from Fort Zachary Taylor.
Things to Do in Key West When It’s Too Hot to Walk
Take the siesta seriously. I’m usually back at the hotel pool by 1 p.m., because the afternoon sun on Duval Street is no fun.
Two air-conditioned museums fill the gap well. The Mel Fisher Maritime Museum displays treasure from the Nuestra Senora de Atocha, a Spanish galleon that sank in 1622 and was found in 1985. The Key West Museum of Art & History occupies the 1891 Custom House and covers the island’s wrecking, cigar-making, and fishing past.
Where I Eat, and Where I Only Drink
Key lime pie is the obligatory order. Kermit’s Key West Key Lime Shoppe sells it on a stick dipped in chocolate, which is easy to eat while walking. Blue Heaven in Bahama Village serves a tall meringue version in a garden where chickens wander between the tables.
For a Cuban sandwich, try El Siboney (900 Catherine Street) or Sandy’s Cafe for coffee and a cheap sandwich. For seafood, I’d cross to Stock Island, Key West’s working-fishing neighbor, and eat at Hogfish Bar & Grill. It’s a short ride by bike or car.
Duval Street is for drinking, not dinner. Sloppy Joe’s (201 Duval Street) and Captain Tony’s Saloon (428 Greene Street) both trade on Hemingway lore, and the prices reflect it. Have one beer, soak up the history, and eat elsewhere. For live music, I’d rather walk to the Green Parrot Bar on Whitehead Street.
Skip the Rental Car, Keep the Bike
You don’t need a car in Key West. Old Town is flat and bikeable, parking is scarce, and many Old Town guesthouses charge a daily fee for it. Ask about parking before you book.
If you’re driving from Miami, make one stop: Bahia Honda State Park at Mile Marker 37 has the best sand beach in the Keys. It’s roughly 40 miles before Key West, so it breaks up the drive well.
Seasons, Crowds, and What a Cheaper Trip Looks Like
High season runs December through April, with the best weather and the highest prices. Summer is cheaper, but expect 90-degree highs and sticky humidity. Hurricane season runs June 1 through November 30 and peaks from August through October.
Fantasy Fest takes over the island in late October. It’s an adult-oriented costume festival, hotels fill early, and I’d skip it with kids.
A budget trip leans on free stops:
- Key West Cemetery
- Mallory Square at sunset
- Higgs Beach
- The Southernmost Point photo, at sunrise
- A walk through Bahama Village and Old Town’s gingerbread-trim houses
Quick Answers Before You Book the Ferry
How many days do you need to cover Key West?
Three days covers it. Give one full day to the Dry Tortugas, one to Old Town’s museums and beaches, and one to a reef snorkel or sunset sail. Two days works if you skip the museums. A long weekend beats a single night, because the drive or flight eats most of day one.
Is Key West worth the trip?
Yes, if you come for the water and the history rather than the bar scene. Dry Tortugas, the reef, and Fort Zachary Taylor justify the long drive alone. If your plan is Duval Street nightlife only, you’ll pay a premium for what a cheaper beach town offers.
What can you do in Key West with kids?
Kids do best with water and animals. Fort Zachary Taylor’s beach suits wading and snorkeling, the Hemingway Home’s six-toed cats hold attention, and the Dry Tortugas ferry includes snorkel gear. Skip Duval Street after dark and skip Fantasy Fest week in late October, which skews adult.
What can you do in Key West for free?
Walk the Key West Cemetery, photograph the Southernmost Point buoy, watch sunset at Mallory Square, and swim at Higgs Beach. Walking Bahama Village and Old Town’s gingerbread-trim houses costs nothing either. Paid parking is the sneaky expense, so leave the car at your hotel and walk or bike.
Do you need a car in Key West?
No. Old Town is walkable and bikeable, and parking is scarce and often priced per day. Bring a car only if you’re driving from Miami anyway, then park it at your lodging and leave it there. Use a bike or the local city buses for Smathers Beach and farther stops.
Lock In the Dry Tortugas Ferry Before You Book Anything Else
Pick your dates, then reserve the Yankee Freedom ferry on the operator’s site (drytortugas.com). Plan the rest of your trip around that 7 a.m. check-in. Most other stops on this list are easy to add a day or two out. Pack water shoes, leave the car at the hotel, and go early.
