Key West sits at the very end of US-1, closer to Havana than to Orlando, and it feels that way the moment you roll into town. Roosters wander the streets, conch fritters outnumber fast-food joints, and the whole island seems to operate on "island time" whether you're ready for it or not. Whether you're driving down the Overseas Highway yourself or booking one of the many Key West tours from Miami, this little island packs in enough history, water, food, and eccentricity to fill several days — or a very jam-packed one.
Here's a real rundown of what to do once you're there, plus the smartest ways to get there if you're staying in South Florida.
Wander Old Town and Duval Street (But Don't Stop There)
Duval Street gets all the postcard fame, and yes, you should walk it at least once — bar crawls, drag shows, key lime pie stands, and all. But the real charm of Key West lives a few blocks off the main drag, in the quiet lanes of Old Town lined with conch-style cottages, gingerbread trim, and hidden gardens.
- Mallory Square for the nightly Sunset Celebration, a decades-old street-performer tradition of jugglers, tightrope walkers, and cheering crowds as the sun drops into the Gulf.
- The Hemingway Home and Museum on Whitehead Street, home to Ernest Hemingway's six-toed cats and the pool he reportedly begged his wife to build.
- The Southernmost Point buoy, that red-and-black concrete marker everyone photographs — yes, the line is worth it, at least once.
Get on the Water
Key West without a boat is like Miami without a beach club — technically possible, but you're missing the point. The water here shifts from turquoise to deep sapphire blue depending on the depth, and there's a reason so many visitors plan their whole trip around it.
Snorkeling and Reef Trips
The Florida Reef Tract runs just offshore, and half-day snorkeling trips out to spots like Sand Key or the Eastern Dry Rocks put you right above coral heads, sea turtles, and schools of parrotfish in water often no deeper than 15 to 20 feet. Most snorkeling tours include gear, a guide, and a couple of hours in the water — plenty for beginners and kids.
Sunset Cruises
A sunset cruise out of Key West Bight is a different experience than the crowd at Mallory Square — quieter, breezier, usually with a drink in hand. Catamarans and old-school schooners head out most evenings, and some pair the cruise with live music or a champagne toast as the sky turns orange and pink over the Gulf.
Fishing Charters
Key West has been a fishing town since long before it was a party town. Half-day and full-day charters go after mahi-mahi, tarpon, and grouper, with backcountry flats trips available for anglers chasing bonefish in skinny water.
Day Trip to Dry Tortugas National Park
If you do one thing beyond the island itself, make it this. Key West tours to Dry Tortugas run about 70 miles west into the Gulf, either by high-speed ferry (roughly 2.5 hours each way) or by seaplane (about 40 minutes), landing you at one of the most remote and least-visited national parks in the country.
The centerpiece is Fort Jefferson, a massive 19th-century brick fortress that never finished being built, sitting on a tiny island surrounded by some of the clearest water in the Florida Keys. Snorkeling right off the fort's moat wall puts you among coral, sergeant majors, and the occasional nurse shark, and the beaches here are practically empty compared to anything back on the mainland.
Ferry trips typically include breakfast, lunch, snorkel gear, and a guided tour of the fort — figure on a full day out, roughly 8am to 5:30pm. It's not a cheap add-on, but for a lot of travelers it ends up being the single best day of their whole Florida trip.
Dig Into the Food and Drink Scene
Key West food culture blends Cuban, Caribbean, and old conch traditions into something you won't find anywhere else in Florida.
- Key lime pie — try it frozen and dipped in chocolate from a street vendor, or the classic version at a sit-down spot like Blue Heaven.
- Cuban sandwiches and café con leche from spots that have been slinging both since before the island got trendy.
- Conch fritters and fresh stone crab (in season, roughly mid-October through mid-May) at waterfront shacks around the harbor.
- Sloppy Joe's and Captain Tony's Saloon for a dose of Hemingway-era bar history along with your rum drink.
Explore the Island's Weirder Side
Key West has always attracted artists, drifters, and free spirits, and that history shows up in some genuinely odd attractions worth an hour of your time.
- The Key West Butterfly and Nature Conservatory, a glass-enclosed garden with hundreds of free-flying butterflies.
- The Key West Shipwreck Museum, which digs into the island's history as a wrecking town that once made it one of the richest cities per capita in America.
- Fort Zachary Taylor Historic State Park, which has the best beach on the island along with Civil War-era ramparts to explore.
Getting to Key West: Tours vs. Driving Yourself
The drive down the Overseas Highway is famous for good reason — 42 bridges, including the Seven Mile Bridge, with open ocean on both sides. But it's also a 3.5 to 4 hour drive one-way from Miami, longer with traffic, and parking in Key West can be tight and pricey.
That's why a lot of visitors staying in South Florida opt for organized Key West tours from Miami instead. These typically run as full-day trips, picking up early (think 6:30 to 7:30am), handling the drive both ways, and building in stops or guided time on the island before heading back that evening. It's a long day — usually 12 to 14 hours round trip — but it means no driving, no parking hassle, and someone else worrying about the logistics.
Travelers based farther north have similar options with Key West tours from Fort Lauderdale, which follow the same idea but with an even earlier pickup given the extra driving distance. Some tours also offer overnight packages, splitting the trip across two days so you're not doing eight-plus hours of driving crammed around a single day of sightseeing.
For those who'd rather explore at their own pace, renting a car and staying one or two nights in Key West lets you catch both the sunset celebration and an early-morning start on the water before the day-trippers arrive. Either approach works — it really comes down to how much time you've got and whether you want to drive.
Best Time of Year to Visit
Key West is a year-round destination, but conditions do shift with the seasons. Winter and early spring (December through April) bring the driest weather, cooler temperatures, and the biggest crowds, especially around holidays. Summer is hot and humid with the best water visibility for snorkeling, plus the wild energy of Hemingway Days in July. Hurricane season runs June through November, with September and October carrying the highest storm risk — worth keeping an eye on if you're booking a Dry Tortugas trip or sunset cruise during that window, since weather can affect boat schedules.
Planning Your Key West Trip
Realistically, Key West rewards at least two full days — one for the island itself, one for the water. If you're tackling it as a single day trip from Miami or Fort Lauderdale, prioritize: Mallory Square at sunset, a walk through Old Town, and either a snorkel trip or a couple of hours at Fort Zachary Taylor beach. If you can swing an overnight or a dedicated trip, add Dry Tortugas to the list — it's the kind of place that's hard to describe accurately until you're standing on that beach looking back at a 150-year-old fort.
However you get there — behind the wheel, on a guided tour, or hopping a ferry into the Gulf — Key West has a way of slowing you down. Give it the time it deserves, and it'll give you one of the best stretches of your whole Florida trip.
Watch: 3 Key West streets locals love (not Mallory)
Frequently Asked Questions
What is the best time of year to visit Key West?
The best months are April, May, and late October through November, when temperatures hover around 80°F with lower humidity and fewer crowds than peak winter season (December-March). Hurricane season runs June through November, so travel insurance is wise if visiting in late summer or fall.
How many days do you need in Key West to see the main sights?
Three full days is ideal for first-timers: one for Old Town and Duval Street, one for a snorkeling or sunset sailing tour, and one for water sports or a day trip to the Dry Tortugas. Two days works for a quick visit hitting Mallory Square, the Hemingway House, and a sunset cruise.
What is the best sunset cruise or tour in Key West?
A 2-hour catamaran sunset sail with complimentary drinks (typically $55-$85 per person) is the most popular option and usually departs from the Historic Seaport around 90 minutes before sunset. Book at least a few days ahead in high season (December-March) since sailings sell out.
Is it worth taking a day trip to the Dry Tortugas National Park?
Yes, especially for snorkeling around Fort Jefferson's moat wall and reefs; the fast ferry runs a full-day trip (about 7-8 hours round trip) for roughly $200-$220 per adult, including breakfast, lunch, snorkel gear, and a guided fort tour. Seaplane options cut travel time but cost more, around $400-$700 depending on half- or full-day.
How much does snorkeling or diving cost in Key West, and what's included?
Half-day reef snorkeling trips to the only living coral barrier reef in the continental US typically run $45-$75 per person and include gear, a guide, and 2-3 stops; scuba trips for certified divers average $90-$150 for a two-tank dive. Many operators also offer combo trips pairing snorkeling with dolphin watching for an extra $20-$30.
