If you’re looking for the ultimate 2025 Key West travel guide, you’ve found it. As a local charter boat captain, I’ve lived on the island for quite a few years now, and I’ve learned what my guests are looking for and what they wish they’d known before coming down. Here’s a look at some of those locals’ insights, along with the basics of my lovely little tropical island home.
Read on for all your answers as to what makes Key West special, how it stacks up against the other Florida Keys, what you must see and do when you’re here, how to get here, and how to plan it all for an epic island getaway.
Never Been to Key West? Here's What to Expect
Key West is a small island located at the very southern tip of Florida, about 150 miles southwest of Miami. It’s connected to the mainland by the Overseas Highway (US Highway 1), which follows the Florida Keys island chain. The island is sandwiched at the intersection of the Atlantic Ocean, with the Gulf Stream, which pushes warm water up from the Caribbean, and the Gulf of Mexico, which has an identity crisis.
What Is Key West Famous For?
What isn’t Key West famous for is more the question! Geographically, Key West is famously the southernmost point in the continental US. There’s a photogenic marker in town for all your Instagramming needs. But there’s so much more to the place than that!
This island has more personalities and lives than most seaside towns. It was “discovered” by Juan Ponce de León in 1513, although the Calusa and Seminole tribes had long inhabited the area. It was settled after Spain’s cession of La Florida to the US in 1819.
The island went through many phases, first as a home for wreckers who came from the Bahamas, and later as a strategic military port. The US Navy still has a presence on the island. During the early 20th century, tourism became a thing, and people flocked to the island for its tropical appeal. President Harry S. Truman spent a lot of time here, as did celebrities like Ernest Hemingway and Tennessee Williams.
In the 1960s, Key West was in full swing and became an artists’ community. It was a haven for all sorts of people who liked its location: a place that feels more than a bit like the end of the road. A little-known singer/songwriter began belting out ballads about the place, and Jimmy Buffett’s Key West was born. People now flocked to the island not only for its tropical appeal but for a complete change of lifestyle, an escape from reality.
There are some bad things about Key West; it has grown busier and become a little more tourist-oriented over the years. But it’s still the special place that Hemingway and Buffett enjoyed. You can stroll down quiet lanes of colorful conch houses, sit at the bar and listen to local musicians, and enjoy the sun setting over the Gulf of Mexico.
Key West Versus the Florida Keys
The Florida Keys are a chain of islands that stretch from the tip of the Florida mainland southwest toward Mexico. Hundreds of little islands go out for about 150 miles. The largest islands of the chain are connected by the Overseas Highway (US Highway 1) and a whole bunch of bridges.
Key West is the largest city in the chain and is located at the end of the highway (the islands actually continue for another 70 or so miles west). Since it’s the primary town, many people assume that it’s the only destination. But once you visit, you’ll quickly realize that this is the tale of two distinct destinations. In a nutshell, the Keys are made up of quieter small towns, while Key West is a much busier tourist port.
The Florida Keys are essentially a rural, seaside area comprising small towns that were once sleepy fishing villages along the highway. These towns lack the party, counter-culture vibe that has made Key West famous, and instead lean into their beautiful natural environment and fantastic boating to draw in visitors.
Key West, on the other hand, is an all-in-one island vacation. There’s tourist-centric Duval Street with bars, clubs, and parties. There are dozens of great restaurants, resorts, and shopping, most within walking distance of Old Town. And you can find any sort of adventure you want, from scuba diving and sportfishing to parasailing, jet skiing, or kayaking.
What's the Conch Republic, and What's Up with the Key West Flag?
While visiting, you’re bound to notice that Key West is a city with a unique flag and a history to match it. The story goes like this: Back in 1982, at the height of the Florida/Miami Vice drug enforcement bonanza and the government’s “war on drugs,” the Feds set up a border checkpoint to search vehicles and hassle visitors driving into the Keys.
The tourism industry took a hit, and the Key West mayor was tired of the Feds not listening. To get their attention, he seceeded from the United States. For a few seconds, Key West was the capital of the newly created Conch Republic. It didn’t last, but it got the press (and the Feds) to pay attention. The mayor demanded foreign aid and surrendered quickly.
But that independent spirit certainly lives on, as does the Key West flag.
Best Time of Year to Visit Key West
Key West has distinct tourist seasons, and they aren’t necessarily based on Key West’s weather.
First off, weatherwise, Key West has a tropical environment, so its seasons are the wet and the dry. The wet season is essentially summer, characterized by humid air and afternoon thunderstorms. If you are here when it rains, don’t worry — there are plenty of things to do in Key West on a rainy day.
It’s also the time of year when tropical storms and hurricanes are a risk in this part of the world. The Atlantic hurricane season runs from June 1 to November 30, with its peak occurring during the second week of September. It’s usually not a problem, but be wary from mid-August to mid-October when most storms form.
The dry season occurs when the humidity drops during the winter and spring. There’s less chance for rain, and it’s not so muggy.
The dry season corresponds to Key West’s peak tourist season, since winter is when most people are escaping from colder climates. But the island is also a popular destination during school holidays in the summer.
The quietest time to visit Key West is during late summer, after schools are back in session and before winter crowds come down. Unfortunately, this also corresponds to the peak of hurricane season, so you’ll want to make plans carefully and check out cancellation policies and things like that.
In the end, the best time to visit might depend on what sort of activities you want to enjoy. For example, the best time of year to visit the sandbar isn’t necessarily the best time to go on long walks around town, and it might not coincide with big events like Fantasy Fest or the Key West Southernmost Air Spectacular airshow.
Getting to Key West
There are only three ways on and off Key West (it’s an island, after all!).
- Fly into Key West International, our tiny island airport
- Come by boat (if you don’t have your own, plenty of cruises call on Key West, and there’s also a high-speed ferry).
- Drive in on the Overseas Highway
Here’s a closer look at the details of all three options.
Flying Into Key West International
Key West has a small airport right on the island, so it’s pretty easy to get here without a car. EWY is not a big airport, so you’ll likely need to take a connecting flight to get here on a commuter airline. Still, there’s an impressive array of direct flights from all over the East Coast thanks to American, Delta, United, Breeze, JetBlue, and even low-cost carriers Spirit and Allegiant.
Keep in mind that air service is seasonal here, and there will be fewer flights during the off-season.
As is nearly always the case when flying into smaller airports, ticket prices are much higher to get to Key West than if you flew into a major hub airport. If you find a deal, it might make sense to fly into Miami International (MIA) or Fort Lauderdale-Hollywood International (FLL). This means a long drive, and you must rent a car. Keep reading for details on the drive.
Ferries and Cruises to Key West
Being an island, the traditional way to arrive is by boat! If you own a boat, sailing into Key West is a bucket list item for some. For the rest of us, we’ll have to make do with the ferry or a cruise.
The Key West Express high-speed ferry connects Key West with Marco Island and Fort Myers Beach, both on the west coast of the peninsula. Round-trip fares are generally between $150 and $200 per person. You can save a little money by purchasing advanced tickets.
The ferry operates as a day trip, so it departs the West Coast in the morning, gives you all day on the island, and then leaves Key West in the evening.
Many cruise lines stop in Key West, particularly those sailing the Western Caribbean. Nearly all the major lines stop here: Celebrity, Carnival, Virgin, Holland America, Royal Caribbean, Margaritaville, and Norwegian. Keep in mind that Key West is only a port of call along the way — all of these cruises depart from somewhere else, usually Miami, Fort Lauderdale, Tampa, or Port Canaveral.
If arriving by cruise ship, you’ll only get a few hours on the island. If coming by the ferry, you can choose to stay for the afternoon or grab a hotel to unwind for a few days on island time.
Driving the Overseas Highway
While arriving by sea or air provides convenience and more time on island, driving in is an epic adventure in itself. How many other islands can you drive to?
The Overseas Highway is the present-day incarnation of the Overseas Railroad, first opened by Henry Flagler in 1912 and hailed at the time as the Eighth Wonder of the World. The route required 42 bridges to connect mainland Florida with Key West via many of the other Florida Keys.
The railroad was destroyed in a monumental Category 5 hurricane on Labor Day, 1935. But it was rebuilt as a road and has been going strong ever since. Along the route, you’ll see a few old rail bridges that modern highway spans have replaced. The longest bridge section is aptly named the Seven Mile Bridge — you’ll never guess how long it is!
Distances and locations on US 1 are measured in Mile Markers. When you get to Key Largo, you are at about MM 107. The mile markers count down until you get to MM 0 in Old Town, Key West.
Leaving from Miami, it’s roughly 160 miles to get all the way to Key West. Because much of the route through the Keys is a narrow, two-lane highway that goes through towns, it’s not a fast trip. Without any stops, plan for it to take at least four hours.
But most visitors to the Keys do stop. There are pull-offs where you can take pictures and enjoy palm trees framing clear blue water views. A road trip lets you find the best beaches in the Keys along the way, if you know where to look. The towns along the road — Key Largo, Tavernier, Islamorada, Marathon, Big Pine Key — offer their own attractions, including hotels, resorts, restaurants, dive shops, fishing charters, cafes, bars, … well, you get the picture. It’s going to take you way more than four hours to get here, and it’s a pretty epic road trip to drive from Fort Lauderdale to Key West.
Is Key West Walkable? Getting Around the Island
Key West is a small island, but it’s not that small. Around Old Town (the area around the harbor and Duval Street), parking can be a problem in Key West. When the town is busy, there are simply more cars than there are spaces. Still, you can usually find a spot if you head a few blocks off Duval or use one of the city garages. Either way, you’ll wind up doing plenty of walking.
If you’re staying at a resort in Old Town, you can walk nearly everywhere you want to go. Pink cabs are easy to find, and you can also get a ride share with Uber or Lyft. Many visitors like to rent bikes or golf carts for their stay, which gives them some mobility and eliminates the parking problem.
If you’re staying in New Town (the east side of the island) or on any of the other Keys, it’s best to have your own car so you can explore at will. Some of the hotels, including the Perry Hotel on Stock Island, have shuttles to get you to and from Duval.
Where to Stay in Key West
There’s no shortage of places to stay in Key West. From the poshest luxury digs to old school ma-and-pa motels, this island provides anything you might like.
Where to Stay, Key West Hotels vs Airbnb
Key West has no shortage of hotels and resorts, but if you’d like the privacy of an Airbnb rental, we’ve got those too.
Several condo/rental communities are operated a little like resorts, but they’re set up like rental homes with full kitchens and more privacy. These can be a great option if you’re coming to the island with a bigger group.
Best Hotels and Resorts in Key West
When shopping for hotels on the island, make sure to think about what you really want from it. Do you want your Key West hotel to be right on the beach? Or do you need it to be a pet-friendly hotel? Do you want a romantic couples vibe, or is a kid-friendly place with a big pool in your future?
Location is an equally important consideration. If you want to be within walking distance of Duval Street, you need to be in Old Town. Parking is a pain down there, so if that’s where you want to spend your time, you’d best find a place nearby. If you stay in New Town or on the next island over (Stock Island), you’ll need a car to get to most places, but some resorts have a shuttle, as well.
Best Places to Eat in Key West
You will not go hungry in Key West because this little island has a spot for everyone. From bars with great happy hours to late-night restaurant bites, Key West dishes out great food all day long.
Trying Local Key West Foods
Key West is all about seafood, which makes sense since we’re out here in the middle of the ocean.
Lobster is probably the island’s most popular seafood, but remember that Key West lobster is not like its northern cousins. Our “bugs,” as the locals say, don’t have claws. These are Caribbean spiny lobsters, and the meat is a little less sweet than the cold-water critters from up north.
Other crustaceans you’ll want to try on the island include stone crab claws and Key West pink shrimp.
Conch (pronounced “konk”) is a giant sea snail that’s made famous by our Conch Republic flag. It was plentiful in these waters, but the early settlers ate most of them. They’re protected here now, but you can still find conch fritters, conch chowder, and cracked conch on the menus at many restaurants.
Of course, there are plenty of fish in the sea, too. The most popular fish to eat down here is mahi-mahi, locally called dolphin. Hogfish, lionfish, wahoo, snapper, and grouper are also popular, locally caught options.
No Keys meal is complete without a slice of authentic Key Lime pie. In case you are wondering, Key Limes are special — they are smaller, tarter, less green, and more yellow than typical limes.
Best Places to Eat in Key West — Local-Restaurant Experiences
The quintessential Florida Keys dining experience is open-air, on a dock right on the water, with classy plastic chairs and a roll of paper towels on the table to use as napkins. The salt shakers are invariably caked up from the humidity, unless the proprietor puts raw rice in to keep them from clumping. So it follows that the best places to eat on the water in Key West will be around the harbor or near the beach. There are also all the great boat-up bar destinations around the Lower Keys, but don’t worry, you can drive to them too!
Sunset is a big part of Key West life, and if you’re looking for a special night out, you can’t beat finding a place to eat dinner and watch the sunset at the same time. There aren’t many places where you can pull it off, so those that have the best view will also require advanced reservations!
Key West Itineraries
With so much to see, do, eat, and drink, you might be wondering how many days you need to do Key West justice. Is three days enough to visit Key West? The answer depends a lot on how much you want to see and do, but generally, most people can spend a lovely long weekend soaking it all in. Sure, there’s plenty more to explore — I mean, heck, you could easily spend a few weeks and still not do everything!
If you’re combining Key West with a trip to the rest of the Florida Keys, you might want a longer trip since your time in each place is more limited. But many people spend just a few hours on the island, just driving down for the afternoon from their resorts in Key Largo, Islamorada, or Marathon.
Key West's Must-See List and Things to Do in Key West
Coming from off-island, it can be a little daunting to figure out which Key West tours are the best and which ones you should give a pass. It’s an island full of unique things to do, but there are a couple of things you should know going in. Here’s a look at the must-see and must-do attractions in Key West.
Bar Crawling and Browsing on Duval Street
The party scene on Duval is as varied as it is inebriating. Key West is home to several famous bars, including Sloppy Joe’s, Green Parrot, and Captain Tony’s Saloon. Some were made famous by the likes of Hemingway or Buffett, while others got that way by swinging their own way (like, for instance, the Garden of Eden, Key West’s clothing-optional bar).
There are so many bars along Duval that attempting a bar crawl here may be dangerous to your health. It’s best to go in with a plan. As Newman said, “Pace yourself, you’ll be doing this all day for very little money.”
And if you’re looking to enjoy Key West sober, don’t worry — that’s totally possible and equally fun! Skip the bars, stick to the good eats, and read on for the other activities. You don’t have to drink on Duval — the entire street is lined with art galleries, curio and curiosity shops, t-shirt shops trying to swindle you, and a tasty mix of fudge, ice cream, and Key Lime pie stands.
Historical Places and Town Tours
Being one of the oldest towns in Florida, Key West has a ton of history packed within its 4.2 square miles.
One of the best ways to see the sights is to explore the island on a walking tour. There’s also the uber-popular Conch Train tour, which you will invariably see cruising back and forth around the island. It’s a hop-on, hop-off tour that runs all around the town all the time.
Here are just a few of the most popular historic sites and local hot spots around the island:
- Fort Zachary Taylor State Park (Civil War fort)
- Hemingway House and Museum
- Key West Lighthouse
- Truman Annex and the Little White House Museum
- Southernmost point buoy
- Key West Historic Seaport and Harbor Walk
- Butterfly Garden and Nature Conservancy
- Various distillaries and breweries
Sunset Celebration at Mallory Square
Every evening, nearly everyone on the island wanders their way to the west side of the island to watch the sun set over the Gulf. The open area on the docks known as Mallory Square has become ground zero for the famous Key West sunset celebration.
It’s a crowded scene, but the views of the sunset, sailboats slipping by, and performance artists doing their thing are a singular Key West experience that shouldn’t be missed.
If the crowded pier works your introvert nerves, consider booking a private sunset cruise for your group.
Natural Beauty of the Florida Keys
No matter what you come to Key West to do, you must spend some time out in nature, enjoying the Florida Keys away from town. The Keys are best enjoyed by watercraft, and it’s the perfect spot for a bit of kayaking or paddleboarding.
Many of the Keys are covered in mangrove trees, which provide habitats for countless species of birds and fish. The shallow waters and sandbars around the islands are also home to Florida manatees, playful dolphins, and curious sea turtles.
The Keys are fringed by the only living coral reef found in the continental US. For the most part, the best reefs are located offshore and are only accessible on a boat tour. There are a few spots where you can try your hand at snorkeling from shore, but the most Key West reef fish and other sea critters will be seen on the bigger reefs several miles from land.
Fun Things on the Water — Fishing, Diving, or Snorkeling the Coral Reefs in Key West, Florida
If you live for water sports, you will love the Florida Keys. Key West is one of the best places to take a boat ride thanks to the wide variety of things to do and see. For example, one day you could head offshore and go snorkeling or diving on the reef. The next day might be too windy out there, so you decided to head into the backcountry — the winding creeks and mangrove islands on the bayside of the islands. It’s out there where you’ll see a lot of the incredible Keys wildlife, from birds to dolphins and everything in between.
If you don’t want to get wet but still want to see the reefs, there are many different Florida Keys boat tours to check out. Many people enjoy the glass-bottom boat tours, which take you out to the reef and allow you to see the coral and fish through underwater viewing windows. And many first-timers enjoy snorkeling in Key West, even if you’re not a strong swimmer. The art of snorkeling lies in relaxing on the surface and just enjoying the view. While it is possible to try snorkeling from the beach, the best views are found offshore.
If fishing is your game, you’ll want to hook up with a guide while you’re in town. There are three main types of fishing in the Florida Keys: offshore (deep-sea), nearshore or reef bottom fishing, and backcountry flats fishing. Each requires its own techniques and equipment, from different kinds of boats to specialized rods and reels. You can go on private or shared fishing charters, and you can find specialized charters for things like spearfishing or lobstering. If all that’s a bit much for you, there are also places in Key West where you can fish from shore.
Boat Charters and Sandbar Tours
You don’t have to go diving, snorkeling, or fishing to have a good time on a boat. Keys’ locals live on the water, and down here, a trusty old fiberglass boat is more useful than a fancy new SUV. It gets you to your favorite activities, restaurants, and even the best beaches in Key West.
Sandbar hopping is a popular pastime down here. You see, most Key West, Florida beaches that you find along the highway are less than spectacular. Many of the best ones at resorts are man-made! The islands are made up of mangroves, with tree-lined shores and few sandy patches. But in the backcountry, natural sandbars form. They’re perfect for spending the day on the water, floating with a beer, and just relaxing in a very Keysy way.
Even if you’re considering renting a boat when you get here, you still need to navigate safely through the backcountry to get to the best sandbars. That’s why most people opt to hop on one of our sandbar charters or private boat tours.
