The Best Travel Guide to Key West To Plan Your Perfect Vacation
Key West, known as the Southernmost City, is so vibrant and full of energy! I’m obsessed with the culture in Key West! The streets are palm lined with gingerbread mansions and tin-roofed conch houses. Ernest Hemingway, Tennessee Williams, Elizabeth Bishop, Robert Frost, and Jimmy Buffett are a few of the famous people who lived and discovered solace and inspiration in the island city.
The Bahamian and Cuban heritage in large part was inspired by Bahamian wreckers, commercial fishermen, spongers, and Cuban cigar makers. Boasting some of the world’s most spectacular sunsets, Key West attracts people worldwide to embrace the festive lifestyle and explore the island’s one-of-a-kind art scene, nightlife, culinary offerings, and historic attractions.
I was so intrigued by how many ‘keys’ there were on our drive from Miami to Key West! In total, there are over 1700 islands in the archipelago. However, most of them are very small and few of these are populated. Only 43 of the islands are connected by bridges. In total, there are 42 bridges connecting the islands but the Seven Mile Bridge is still the longest.
Because there are so many islands within the Florida Keys they are often divided into several different groups. These groups are the Upper Keys, the Middle Keys, the Lower Keys, and the Outlying Islands. The Upper Keys are those located the farthest north and closest to Florida’s mainland and the groups extend out from there. The city of Key West is located in the Lower Keys. The Outer Keys consist of islands that are accessible by boat. You can learn more about The Florida Keys here!
From getting to and from, where to stay, where to eat, and what to do, our travel guide will help you plan the perfect vacation!
Pack your bags for an amazing vacation to The Florida Keys! Check out our Travel Guide below!
Key West is a three-hour scenic drive from Miami, a ferry ride from Fort Myers, and accessible by commercial airlines. This eight-square-mile island is nestled between the Atlantic Ocean and the Gulf of Mexico, among turquoise waters, towering palm trees, and sandy beaches.
If you prefer to explore, you can get a rental car or use Turo if you’re only in need of a car for a day or two. There are classic pink taxis that line up outside the airport as well.
As far as public transportation, there are pretty cabs, tour trains, trolleys, park-n-ride, and the bus.
Where To Stay
You have so many options for places to stay in Key West. From waterfront resorts, bed and breakfasts, home rentals, or hotels on Duval Street right in the middle of the action. You can try the Casa Marina Waldorf Astoria Resort or Pier House on the water or something like the haunted and historic LaConcha to be on Duval!
Where To Eat
OH MY gosh, the food in Key West is dynamite. My first recommendation is to eat key lime pie wherever you go. Just do it. Get your fill. It’s worth every calorie and most everywhere either makes their own homemade key lime pie or they buy it from Kermit’s. Bonus, Kermit’s serves food (even breakfast) so you can grab a bite there too! Everything is delicious so bring your appetite. The chocolate-covered key lime pie on a stick wasn’t my thing but give it a try yourself to see if it’s for you. My friend Ali loved it!
I’d recommend trying conch since you’re in the Conch Republic. Conch Republic Seafood is famous for its conch chowder, cracked conch, and stuffed shrimp. They have a large open-air seating area with a great view of the water. I also recommend grabbing a lobster roll because those suckers are hard to find unless you live somewhere like Maine or The Hamptons.
Obviously, Sloppy Joe’s is famous in Key West so stopping by there is a must for some people. If you’re looking for a nontourist spot, some other great food options are Eaton Street Seafood Market, 5 Brothers, Cuban Coffee Queen, The Lobster Shack, DJ’s Clam Shack, 2 Cents, Santiagos Bodega, and so many more! For a good dessert, head to Better Than Sex or Blue Heaven. If you want to get super local, there are a few good food trucks/holes-in-the-wall recommendations we have. You’re going to want to try Garbos Grill, Amigos, and Bad Boy Burrito (BBB was also on DDD)! A few nontourist bars to go to that have great live music are the Green Parrot, Hogsbreath, and The Porch.
What To Do
The spirited streets of Key West are dotted with unique shops, world-famous restaurants, and quaint cottages. The island doubles as a charming retreat for relaxation, learning, and adventure by day and transforms into an eccentric playground by night. The Key Lime Festival, Hemingway Days, Parrot Heads In Paradise and Fantasy Fest present a variety of entertainment options for everyone.
Well for starters, you’re surrounded by water so water activities are a must. You can head out on a sunset cruise with companies like Floridays. I recommend Floridays if you prefer a relaxing sunset sail. There were around 20 people on the boat and drinks were provided. The other companies I saw on the water had packed boats with 100+ people so make sure to ask before you book and pick one that works for you.
If you’re going in the summer, it’s going to be hot so I recommend heading for the water. I love being on a boat on the ocean. Speaking of summer, it’s the perfect time to snorkel because it’s so calm and clear. The water is so smooth, there’s no wake, which means everything on the bottom has settled so it’s better for viewing! If you’re visiting during the winter months, sailing is perfect because it’s much more windy! You can even take a boat to Dry Tortugas National Park to check out Fort Jefferson on Garden Key.
My husband always asks about golf so I feel like that is worth mentioning. If you’re traveling with your boo and he doesn’t want to go fishing while you’re at the spa, believe it or not, there is golf available!
If you want to hit the most popular tourist spots head to The Southern Most Point and Mile O (literally where the highway starts and ends)! Duval Street is super popular for all the shops and restaurants. You can do the Duval Crawl if you want to check out the bar scene! Head to Old Town and to the marina area while you’re out walking around. Front Street is also a good spot to explore! Be on the lookout for the locals, aka the many roosters that inhabit the island! You can hear and see them everywhere! Mallory Square is perfect to catch a great sunset and of course, The Hemmingway House and The Butterfly Garden are both great options.
If you’re into cool stuff and history pop into The Treasure Chest! They have a real treasure from the Atocia shipwreck. I’ve been wearing this necklace for 7 years and before that, my grandmother used to wear it every day. She gave it to me before she passed and the only backstory I got was that it was a treasure from a shipwreck. I’ve always wanted to know more but never knew where to look. So as fate has it, I walked into this store and saw another coin like the one I was wearing and flipped out! As it turns out, I’m wearing a piece of history. A 400-year-old coin was found at the bottom of the ocean. It makes this necklace so much more special now that I know its history.
When To Go
Surrounded by cooling waters, Key West boasts a warm, tropical climate with summer temperatures averaging 83 degrees. Comfortable winters average a balmy 73 degrees, making the island a premier travel destination year-round.
What To Wear
Dress for warm weather because it’s HOT and sometimes humid. Key West definitely has touristy areas so the style is very eclectic but you can find most people in shorts, tank tops, light dresses, and shorts. Flip flops are a must but make sure you’re wearing comfortable shoes when you’re out exploring because you’ll be on a boat or out walking around on most days. As a person that wears black a lot, I’d suggest brightening up your wardrobe while you’re there to beat the heat. You’re also going to want to snag a hat and some sunscreen to protect yourself from the sun.
I hope you have so much fun on your trip to Key West! Remember to tag us on social with #VGBSQUAD or #TRAVELGOLD so we can share the love!