City Guides

Key West, Florida: Your Guide

Matt Wilson
January 16, 2024

If you want to survive Key West without falling into the drunken tourist traps this guide is for you.  As someone who’s spent my entire life exploring the Florida Keys, here’s what I can offer…


For years only puddle jumpers could fly into Key West International Airport departing from Miami, but in recent years United, Delta, and American all fly directly into Key West on much larger planes. Jetblue has even begun to operate via Silver Airways.  

The photo opportunities flying into Key West are absolutely incredible.

Photo by Rob O'Neal

Budget conscious?

Grab a cheap flight to Fort Lauderdale on Spirit or Jetblue, or fly into Miami.  Then, rent a car and prepare for one of the most beautiful drives in the world.  Return the car in Key West--I don’t suggest driving on the island.

Pro-tip: Upgrade yourself to a convertible.  You will never forget cruising the Keys with the top down.  Neither will your mom…

Where to Stay

I have the least amount to offer regarding lodging as my family lives in Key West.  

My best suggestion is to find an Airbnb as close to Old Town as possible.  The island isn’t big but staying on the North part of the island can be disappointing.

After all, you didn’t come to Key West to stay at the Best Western or eat at Outback Steakhouse.

Renting a place in Old Town will really add to the charm and local feel of your trip.  

Where to Eat

As my grandmother, a 35 year Key West resident recently pointed out, you don’t stay in business in Key West unless your food is good.  

Competition is fierce, so expect excellent food wherever you go.  Cuban cuisine and seafood lead the way with choices like conch fritters, yellowtail snapper, and of course Cuban coffee.

My picks for top places to eat in Key West:

5 Brothers Deli: If you want authentic Cuban food, this is your hole in the wall.  Family owned for years, try the Cuban bread, cafe con leche, or a shot of bucci (cuban espresso).  For lunch go with the pork or grouper sandwich.

Blue Heaven: Want to eat where Hemingway refereed boxing matches?  Make your way to the up and coming neighborhood of Bahama Village.  I’d suggest having lunch after touring the Key West Lighthouse or Hemmingway’s Home.  Dinner time is packed at Blue Heaven because of the world famous backyard feel.  Expect 2+ hours wait if you arrive after 5pm.  

Salute: Owned by the same folks as Blue Heaven, this couple has expanded their humble empire.  Be sure to check out one of the only places in Key West where you can dine on the beach.  The food is excellent and it’s great people watching as all kinds of interesting people pass by on the boardwalk.

Chicos: This is local Tex-mex place and you’ll need to make your way outside of Old Town.  It’s worth the taxi ride, as the guacamole is some of the best I’ve ever had.  It has a great little garden where you can eat outside.  The owner is charming and everything on the menu is excellent.

Date and Thyme: (Healthy!)  Looking to keep your diet clean?  Look no further than Key West’s organic cafe, juice bar, and natural foods market.  Located at 829 Flemming Street, it’s the perfect place to detox before or after your big night out… and it’s just a few blocks from Old Town Fitness (featured below)

Duval Street / Nightlife

Duval Street Nightlife

Okay, here is where things get interesting. To be honest, staggering up and down Duvaul Street is your best way to find a party.  But let me give you the lay of the land…

Classics include The Hogsbreath Saloon with great live music (see their webcam!), Sloppy Joe’s where Hemmingway drank with his rum-running buddies, Rick’s is the the place to get down and dirty late night, and of course there is the cell-phone free nude bar Garden of Eden.

Here are a few of my quick picks for Best Bars in Key West:

Smallest Bar: Literally room for two bar stools.  Luckily congregating on the street with open containers seems to be perfectly legal.  Perfect to start off the night.  Ask the bartender where the best party that night is.

The Green Parrot: Key West’s local dive bar since 1890 is refreshingly not located on Duval Street.  Be sure to get a selfie with “Smirk” the famously creepy portrait on the wall who as they say “has seen it all.”    

Bull and Whistle: Sit on the second floor balcony and watch the people go by.  It has a Bourbon Street feel and yes on New Years’ Eve you can exchange beads for boobies.  

Tourist traps to avoid: The Hard Rock Cafe & Jimmy Buffett’s Margaritaville.

The Beach

Of course you came to Key West for the beach…but what is the Best Beach in Key West?  

My favorite off the beaten path spot is Fort Zachary Taylor.  Admission to this state park only costs a few dollars and it’s best seen by bike.  Arrive early in the morning and tour the Civil War Era Fort that was critical for fighting off pirates.

The beach is a little rocky but is one of the best places to see the sunset in all of Key West.  Directly next door is the US Naval Base that looks straight out of a Cold War movie, as Cuba is just 90 miles away.  It’s worth going to check out.

Smathers Beach

Admittedly, I haven’t spent much time at Smathers as it’s a little far from Old Town and much more touristy.  Here you will find kayak rentals, stand up paddleboard, catamarans, and just about anything you want to do.  

The sand is softer and is a solid way to spend the day.

Best Attractions in Key West

Southernmost Point

If you must take your typical tourist photo, continue past the Key West Lighthouse and wait in line to say you were exactly 90 miles from Cuba.  It’s my least favorite part of Key West, but I often peddle past on my bike on the way to 30 feet of shoreline called Dog Beach.

Mallory Square Sunset Celebration

I know this guide for how to stay off the beaten path in Key West, but Mallory Square is a sunset celebration like no other.  Go for the sword swallowers, high-wire acts, and fire juggling unicyclers.  Get a snack from my family friend Popcorn Joe and watch the entire show.

How to do more than just party: Top Activities in Key West

Rent a Bike

Key West has a lot to offer, so if you want to cover more ground, renting a bicycle is your best option.  Yes, you can rent a mo-ped but I prefer the less obnoxious, eco-friendly alternative.  Almost every single local has a beach cruiser with a basket in front.  


Opt for Deep Sea Fishing or Bone fishing in the backwaters. Either way, Key West is a fisherman’s dream.  I grew up fishing in the keys and think seeing these coral atolls by sea is one of the best ways to do it.  Go out for snapper, grouper, mahi-mahi, tuna, or catch-and-release sail fishing.


If you are going to spend money on one activity in Key West, I’d suggest a trip to North America’s only living coral reef. The Florida Reef is the third largest in the world behind the Great Barrier Reef of Australia and the Belize Barrier Reef where Under30Experiences snorkels! Go check out the countless shipwrecks, angelfish, pufferfish, and barracuda.  Yes, I’ve seen eels, sharks and dolphins.  

Note: The Florida Manatee or sea cow is an endangered species.  If you decide to rent a boat please key an eye out not to hit one of these gentle giants.

Old Town Fitness

Of course I need to show some love to my favorite old school backyard gym. You’ll quickly realize you aren’t at Planet Fitness anymore as it’s no shirt required and meatheads galore.  Try to flip the 500 pound tire, and be sure you have your tetanus shot before throwing around the rusty iron weights.  Every bouncer in Key West will be there-- it’s a great place to make local friends.  

Key West Ghost Tour

Finally, a trip to Key West would not be complete without hearing a little more history about this weird place.  “The Island of Bones” is host to a ton of haunted places, pirate burial grounds, and countless ghost stories.  Go with an open mind and remember-- don’t ever take a photo of Robert the Doll.

Matt Wilson
Matt Wilson is Co-founder of Under30Experiences and Author of The Millennial Travel Guidebook: Escape More, Spend Less, & Make Travel a Priority in Your Life. He is host of the Live Different Podcast, Millennial Travel Podcast, and formerly Co-founder of He is committed to helping people live more adventurous lives.


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