Want somewhere that feels like the Caribbean but doesn’t need a passport? It’s right in our backyard: Key West. People think Key West is just Duval Street, a sunset celebration and maybe a slice of key lime pie, but they’re missing about 90% of what makes this island magical. It’s one of my favorite destinations in Florida, and I’m telling you right now, if you’ve never been, go.
Here’s how to get there, where to go beyond the crowds, where to watch the sunset, what to eat, the one photo everyone takes (and how not to be the person holding up the line), where to stay and whether Key West is worth it. So grab your flip-flops, because it’s five o’clock somewhere, and we’re headed to the end of the road.
Getting There: Drive the Overseas Highway at Least Once
Let’s start with one of the greatest road trips in America. U.S. Highway 1 stretches about 113 miles from mainland Florida all the way to Key West, across 42 bridges, with water surrounding you almost the entire drive. It’s one of those drives where you find yourself slowing down, not because of traffic, but because you can’t stop staring. If you’ve never driven across the Seven Mile Bridge, put it on your bucket list. Windows down, music up, it feels like you’re driving across the ocean.
I kept taking pictures and pictures and pictures, as if I’d never seen blue water like that before. When people ask me where they can go in the U.S. to get water as blue as the Caribbean, my answer is the Keys. It’s like being in the Caribbean while still being in the U.S. And when people ask me where they can go without a passport? The U.S.!
Stop in Islamorada for lunch, in Marathon for photos and maybe to feed some tarpon. The journey becomes part of the vacation.
But Maybe Only Drive It Once
Now, here’s the honest part. Key West is about a four-hour drive from Miami, and man, is it a drive. It just keeps going, and if traffic stops, it’s crazy. That drive might be one you only do once, like me. I’ve since been to Key West on a cruise ship, and my plan is to fly in next time. If I were to drive it again, I’d stop and stay on some of the other islands on the way down and on the way back.
If you live in Central Florida like I do, there’s a quick way to get there. Avelo Airlines has offered inexpensive nonstop flights from Lakeland, which is between Orlando and Tampa. If you’ve already done the drive, flying is well worth it, because that drive is brutal. But if you’ve never done it, it’s gorgeous, and you should stop along the way.
Good to know (checked October 2026): Avelo’s current route listings don’t show a Lakeland to Key West flight, so check schedules before you plan around it.
Why Key West Feels Different
Here’s what surprises first-time visitors: Key West doesn’t really feel like Florida. It feels like a mix of the Caribbean, New Orleans, Old Havana and a quirky artist colony, all wrapped into one. It has its own specific vibe, which is really cool.
It’s super laid-back. Everyone’s in flip-flops, shorts and T-shirts, sometimes half in a bathing suit, and nobody dresses up. The architecture is colorful, those crazy roosters wander the streets, and no one seems to know what day it is. Honestly, nobody cares. The pace slows down, and people walk instead of rush. It’s wonderfully weird, and that’s exactly why people fall in love with it. And because it’s still the U.S., nothing feels so different that you’re thinking, “This is weird, I don’t like this.” You’re just in the Caribbean without leaving home.
Duval Street
The most popular thing in Key West is, of course, Duval Street. It runs from one side of the island to the other, about a mile long, and while a couple of stretches in the middle are kind of meh, the two main sections are packed with restaurants, bars, boutiques, live music, ice cream shops, art galleries and enough people watching for an entire weekend. During the day, browse local art, grab a Cuban coffee and pop into hidden little courtyards.
The live music doesn’t only happen at night. It starts the minute the bars open their doors, which I think is so cool. It reminds me a lot of Nashville: as soon as you’re on Duval, you hear music coming from every direction, and you don’t know where to go. “Ooh, I like that music. No, I like that one!” It makes for a fun pub crawl, and you can start early, because as we get older, maybe we don’t stay out as late as we used to. You don’t have to drink to enjoy Duval, either. You can just wander and listen to the music.
My Favorite People-Watching Spot
Some of the best entertainment in Key West is grabbing a drink, sitting outside and watching the parade of humanity go by. You’ll see chickens, street performers, bachelorette and bachelor parties, retirees and people dressed like pirates, and somehow it all feels completely normal.
My favorite spot for this is the balcony on the second floor of the Bull. It overlooks Duval Street, the breeze is nice up there, and you can people watch for days. A lot of people miss it, because they don’t think to go upstairs, and many Key West bars don’t have outdoor seating at all, just because of the way they were built. Note: the second floor, not the third. The third floor does other things. That’s a whole other show!
Good to know (checked October 2026): the building is the Bull & Whistle, at 224 Duval Street. The second-floor balcony bar is the Whistle Bar. The third-floor rooftop, the Garden of Eden, is clothing-optional, and photos aren’t allowed there.
Outside Rick’s on Duval Street, Key West.
The Sunset Celebration (and Better Ways to See It)
Every evening, there’s a sunset celebration at Mallory Square. If you’ve never experienced it, hundreds of people gather to say goodbye to the sun. The sunset is literally an event: street performers come out and juggle fire, musicians play and artists sell handmade crafts. Then everyone collectively turns toward the water, the sun disappears, and the crowd applauds. Yes, people actually clap for the sunset, and after you see it, you’ll understand why. It’s hard to find parking, so Uber in or walk from wherever you’re staying.
There are other great ways to see the sunset, too:
A private boat. I did a private sunset cruise, and it wasn’t a big, massive yacht, just a regular powerboat with open seating in the bow and more in the back. We had a captain, and he parked us with what felt like millions of other boats. It was beautiful. We watched for the green flash at the very end, as the sun disappears behind the water, but unfortunately, we didn’t see it. I’m still on the hunt for that elusive green flash.
Sunset Key. This private island across from Key West is absolutely gorgeous, and you can definitely see the sunset from there, with dinner completely outdoors. You can’t go over unless you’re staying at the hotel on the island or you have a dinner reservation, so book ahead.
Good to know (checked October 2026): Sunset Key’s restaurant is Latitudes, and non-guests can dine there with a confirmed reservation.
What to Eat in Key West
You can’t leave Key West without trying fresh seafood. The whole island is surrounded by water and everyone’s fishing, so it’s all about the seafood. Look for:
Stone crab, when it’s in season
Lobster (there are some great lobster rolls around)
Conch fritters
Cuban sandwiches
And, of course, key lime pie
Now, here’s the debate: frozen, traditional or chocolate-dipped? Everyone has an opinion, so I recommend trying more than one. Key lime pie is really good there. Everyone loves Kermit’s, and you can’t go wrong with key lime pie anywhere. Key West also does waterfront dining exceptionally well, and Sunset Key is stunning, with phenomenal food.
Key lime pie: don’t stop at one slice.
The Ernest Hemingway Home
Ernest Hemingway lived in Key West throughout the 1930s, and his home became one of the island’s biggest attractions. The house gives you an incredible glimpse into his life, and yes, you can still see the writing studio where he created some of his famous works.
But what people remember most is the cats. Descendants of Hemingway’s original six-toed cat still roam the property today, and many of them still have six toes. They’re celebrities in their own right. It makes me laugh that people go there to see the cats. I’m sorry, I can’t get over it.
The Southernmost Point Photo
Let’s be honest: you’re taking the picture. Everyone does. The buoy sits on a rounded street corner right at the water, because you can’t go any farther south. It gets so crowded that it stops traffic, and I’m sure people almost get run over. Recently it was moved so the area could be refurbished, and my guess is they’re making it a little safer for everyone.
There will be a line. I’ve ridden a bike there a couple of times and also taken an Uber, and you can walk, because it’s not super far. Go early in the morning or later in the evening if you don’t want to wait as long.
My Rant: Know Your Spots Before You Get There
I actually prep the people in front of me and behind me in line, which is kind of funny. If you’re going to stand in this line, don’t be the group that gets up there and says, “Oh, Tom, go stand over there. Samantha, you come over here. Sarah, you go there. Jen, oh, you over there.” No. Know where you’re standing before you get to the front, because you’re holding up the rest of the line. When Jim looks at that picture after you get home and asks why Jen is standing by Dave, nobody cares! Know your spots, and the line moves much faster.
This goes for Disney character photos, too. When my travel agency goes to Disney, at the very first picture I say, “Okay, get into your spots. Everyone remember where you’re standing, because this is where we’ll stand for every picture.” Then, at every character after that, I say, “Assume your positions!” Everyone goes straight to their spot (“I’m next to Carrie and Jessica, I’m good to go”), smile, done, and we’re out. Don’t rearrange everybody like it’s a Christmas card. Get your picture taken and move on. Sorry, that was my rant for the day.
Good to know (checked October 2026): the Southernmost Point buoy closed for a seawall and plaza renovation in 2025, and a replica buoy was set up a short walk away at the end of Duval Street in the meantime. The city expected the work to finish around late summer 2026, so check whether the original spot has reopened before you go.
Hidden Gems in Key West
Fort Zachary Taylor Historic State Park
Locals love it, and it’s really pretty. It’s home to arguably the best beach in Key West, with excellent snorkeling, clear water and fascinating Civil War history.
Here’s what you need to know: Key West is not a beach city. Not at all. There are little beaches at most of the hotels, but if you’re going to Key West for beaches, you’ve missed it. The good beaches are on Florida’s west coast. But if you have to go to the beach, go to Fort Zachary Taylor. That beach is great.
The Key West Butterfly and Nature Conservatory
I wouldn’t even call this one hidden, because a lot of people go, but it’s so much fun. It’s small and quick, and hundreds of butterflies surround you inside a tropical glass habitat. It’s peaceful, beautiful and surprisingly relaxing.
Sunset Key
I keep mentioning it because it’s so great. Go to this private island for dinner or stay there.
Get Out on the Water
This is what I really want you to understand about Key West: it’s not a beach town. Wipe that from your brain. It’s a water town. You want to get on a boat and go somewhere. There are so many ways to do it:
Take a snorkeling boat. There are tons of them.
Go on a sunset sail.
Try paddleboarding.
Rent a kayak and paddle through the mangroves.
Book a catamaran. They’ll pull up to a sandbar and let you get out.
Rent a little tiki hut boat and take your friends out for drinks on the water, which is super fun.
Rent a yacht. I’ve done it a bazillion times, and it’s one of my favorite things to do there.
Or rent a regular boat if you don’t want to spend yacht money. I’ve done that too.
Once, when we rented a boat, we went to a deserted island. Oh my gosh. There was a swing in the trees, the water came right up, and it was absolutely beautiful. So rent a boat and ask them to take you to the little islands, because the water is unreal. You’ll see tropical fish, rays, sea turtles and dolphins. I’ve seen dolphins constantly.
Key West is also one of the sport fishing capitals of the world, for tarpon, mahi-mahi and more, and there’s a lobster season every July if that’s your thing.
Good to know (checked October 2026): Florida’s two-day spiny lobster sport season (mini-season) falls on the last Wednesday and Thursday of July; in 2026, it was July 29 and 30. Monroe County, which includes Key West, has a lower bag limit than the rest of the state and bans night diving during the mini-season, so check the FWC rules.
Day Trip: Dry Tortugas National Park
This one is on my list, and I’m dying to do it. Dry Tortugas National Park is about 70 miles west of Key West, out in the ocean, so you can’t drive there. Most visitors arrive by ferry or seaplane. It’s home to Fort Jefferson, one of America’s largest coastal forts, plus crystal-clear water, outstanding snorkeling and very few crowds. The seaplane is the fastest way to go, and it costs the most. But if I were going to splurge on anything, it would 100% be the seaplane. (The Dry Tortugas also made my list of 15 hidden gems in the USA.)
Where to Stay in Key West
People always ask whether they should stay right on Duval Street. Honestly, there aren’t many hotels on Duval. It’s mostly bed-and-breakfasts, in the cutest little houses. Oh my gosh, they’re so stinking cute, and I’d definitely try one. There are only a few hotels downtown.
Near the action: the Hyatt and Ocean Key Resort & Spa are right near the main part of Duval Street, a very short walk if you want to be part of the nightlife. Both are very nice and right on the water, and you can watch the cruise ships come in and out from either one.
Quieter: stay a few blocks away. There are tons of boutique inns and bed-and-breakfasts within walking distance, and I highly suggest staying in town to enjoy the experience.
The splurge: Sunset Key, that private island I keep mentioning.
The first time I stayed in Key West, we stayed pretty far outside of town. The price was much better, of course, but it wasn’t easy to get to and from the main part of the city.
Good to know (checked October 2026): the Hyatt by Duval Street is the Hyatt Centric Key West Resort & Spa. The hotel on Sunset Key is Sunset Key Cottages.
Photo-op fun at 211 Duval Street.
Is Key West Expensive?
The short answer: yes, of course. It’s super popular, and hotels are pricier than in much of Florida, because there aren’t many of them. Parking is limited, and restaurants add up quickly. But you don’t have to spend a fortune to walk the island, watch the sunset, visit the beach, explore the historic neighborhoods and people watch on Duval. Some of the best experiences cost very little, and the Hemingway Home isn’t going to cost you a massive fortune. It really comes down to where you stay, and you can save money by staying outside of town.
My Quick Insider Tips
Go between late fall and spring for the nicest weather. It gets extremely hot and humid in summer, like everywhere else in Florida.
Book hotels early.
Wear comfortable shoes or flip-flops.
Bring reef-safe sunscreen.
Rent bikes instead of driving. We’ve had the best time biking, and you can bike all of Key West. Golf cart rentals look like a lot of fun, but you’ll be hunting for a parking space everywhere you go. With a bike, there are tons of bike racks.
Is Key West Worth Visiting?
Absolutely. I love Key West. One of my ultimate goals is to own a place down there, because it has the coolest vibe: between the chill and the fun, everyone’s just there for a good time. It’s not worth it because it has the biggest attractions. It’s worth it because it has the best personality. It’s quirky and relaxed, and somehow it reminds you to slow down.
Want to hear me talk through all of it? Watch the episode. And if you’re planning a trip to Key West, whether you’re driving, flying in or arriving on a cruise, my team at Fabulous Adventures Travel and I would love to help get you there.
