At the very tip of Florida a small archipelago called the Florida Keys stretches out into the abyss where the Gulf of Mexico meets the Atlantic Ocean. At the end of this stretch lies Key West… a small island where the sun is always hot, the drinks are always cold, and the beach is always beautiful. In Key West, you’re always on island time!
Whether you’re visiting Key West with your honey, your favorite bachelorette, or your rowdy family, you’re going to love the laid back beach town vibe Key West emotes, with its unique conch-style houses, beautiful coral reefs, and sandy beaches. You might just have to indulge in a classic Key West Rum Runner if you’re feeling a little extra frisky!
Below we have detailed out favorite places to grab a bite, the best happy hour sports in town, and all the most adventurous ways to spend your day exploring Key West.
GOOD EATS
Blue Heaven
If you’re looking for an oasis in the middle of a bustling paradise, Blue Heaven is the groovy restaurant and bar you’re looking for. Not only will you LOVE the food, but live music makes your dining experience dinner and a show. Vibe check? Cool vibes only!
Sloppy Joe’s
Looking for some long lasting fun while you enjoy a good meal? Sloppy Joe’s features live music and a dance floor to boot— this restaurant is a little slice of Nashville down in the tip of Florida.
Seaside Cafe at the Mansion
Whether you’re planning on eating or drinking, you cannot go wrong at the Seaside Cafe. The food is delicious and the mojitos are refreshing… what more could you want?! An amazing view? The ocean is just a stone’s throw away. Such a lovely cafe with a delightfully fun atmosphere!
Mattheessen’s
There’s no such thing as a cookie that’s too big, and Mattheessen’s proves this with their amazing half-pound cookies. Your self-control will not be able to resist stopping in one of their two locations… both are on Duval street, so you can’t miss it! If cookies don’t tempt you, they also sell fudge, macaroons, key lime pie, and ice cream. It’s Florida, so no matter how cold it is elsewhere, it’s always ice cream weather in Key West.
Margaritaville
Can you go to Key West and not stop into Margaritaville for a drink? Channel your inner Jimmy Buffet and order yourself a margarita— or two piña coladas… one for each hand! We enjoyed all our food there as well!
SO MUCH TO DO, SO LITTLE TIME
Key West Butterfly and Nature Conservatory
There’s something breathtaking about the ethereal beauty of a butterfly. At the Key West Butterfly and Nature Conservatory, you will feel like a Disney princess come to life as you wander through the lush, tropical garden with hundreds of butterflies.
SouthernMost Point
The large landmark buoy is a hallmark visit during any Key West trip. If you are this far south in the country, you must visit the southernmost point in the continental United States!
FYI: Depending on the time of year, you may wait in line for this photo.
Dry Tortuga National Park
Every day the Yankee Freedom departs from Key West at 7:30 am and heads out to Fort Jefferson in the Dry Tortugas National Park. It takes just over two hours to reach the island from Key West.
Once there, you will be able to swim, lounge on the beach, walk around and through the fort, take a guided tour, and snorkel (snorkeling gear included in the cost ticket). The water is crystal clear and truly perfect for snorkeling. If you keep an eye out while walking the perimeter of the fort, you may find some beautiful pieces of sea glass as well— a charming memento of a gorgeous place. Adventurers spend five to six hours on the island, so the trip lasts about ten hours in total.
As a note: While we actually have not taken this cruise, we have sailed down to Fort Jefferson in the Dry Tortugas from our hometown in Fort Myers, FL. We would see the Yankee Freedom arrive and depart every day throughout our stay, and we are well versed in all the beauty waiting to be discovered on this small island. The starkly clear water, beautiful snorkeling, and immense calm of endless blue are incredible and certainly worth taking the day to see!
High Stakes Charters
If you’ve never been deep sea fishing, Key West is the place to do it, and High Stakes Charters is the group to do it with! Whether you’re in Key West for a family vacation or a bachelor party, this is an amazing time for all ages. Any boat day is a good day, but a boat day offshore fishing is one you’ll never forget!
Mallory Square
At the north end of Duval street, the road ends and you will find Mallory Square. This is THE spot to watch the sunset in Key West. A couple hours before sunset, a sunset celebration commences. This daily ritual includes a wide array of performers and vendors that entertain while others wait for the sun to go down. Live music and a stunt show of sorts are almost guaranteed.
Fort Zachary Taylor Historic State Park
The perfect combination of historic fortitude meets beautiful Florida beaches lies at the Fort Zachary Taylor Historic State Park. There’s something to do for everyone in the family! History buffs can wander throughout the fort, while outdoor enthusiasts have a wide array of activities to choose from: biking, fishing, bird-watching, hiking, paddling, scuba diving, snorkeling, and swimming. At the end of the day, this is also a beautiful spot to watch the sunset.
THE HAPPIEST HOURS
If you enjoy a cold, refreshing beverage of choice, you will have endless options to choose from. These are a few that we found with some above average happy hour specials. Enjoy!
Pepe’s Cafe
The only thing better than a fresh-squeezed margarita is a $6 fresh squeezed margarita. Pepe’s Cafe also does half off oysters for their happy hour. Their breakfast spread is also notoriously delicious!
Happy Hour: 4-6 p.m.
First Flight Island Restaurant & Brewery
First Flight Island Restaurant & Brewery has some historical roots as it is housed in the birthplace of Pan American World Airways… Pan-Am’s first tickets were sold out of this very building in 1927! These days, you can enjoy half off their house drafts as well as some finger-lickin’ plates.
Happy Hour: 4-6 p.m.
Hank’s Hair of the Dog Saloon
What’s better than one happy hour? TWO! Hank’s Hair of the Dog Saloon has a brunch happy hour to help get the party started. You can indulge in some two-for-one mimosa’s or perhaps kick your hangover to the curb with a couple bloody mary’s. Afternoon happy hour is pretty standard, but they have live music playing throughout the afternoon and into the evening.
Happy Hour: 11am-2pm & 4pm to 7pm
The Roost
The understated vintage charm of The Roost will leave you feeling glad you wandered a bit from the touristy chaos of duval street. This specialty cocktail bar is guaranteed to deliver something a step above the rest.
Happy Hour: 3-6 pm
Bonus Round
If you are driving down to Key West, stop by Robbie’s to feed the tarpon!! These massive fish will leap out of the water to eat bait fish right out of your hand. The experience is exhilarating and just a little frightening.
Robbie’s is on Islamorada (about halfway down the Florida Keys archipelago), so it makes for a perfect mid-drive pit stop!
We hope you have the best time enjoying your relaxing Key West vacation. From Duval Street to the Dry Tortugas, so many adventures await (don’t forget to pack your sunscreen)! A Rum Runner is the official drink of Key West, so be sure to try at least one while you’re there… cheers!
written by Hannah
Hannah has learned the hard way to be careful what you wish for— sometimes happily ever after lands you with a husband and puppy… in the Midwest. Despite leaving Florida to move to Wisconsin, Hannah maintains her bossy big sister role with regular phone calls to keep up with all the little sister shenanigans. Notoriously chatty with her patients as well, Hannah stays busy as a physical therapist, but loves spending weekends exploring newfound hikes.
