1st Timer’s Guide to Key West: Everything You Need to Know
Heading to Key West for the first time? You’re in for a real treat! This island paradise is packed with beautiful beaches, delicious food, unique things to do, and a quirky, fun spirit that’s hard to describe.
From turquoise waters and spectacular sunsets to six-toed cats and free-roaming roosters, Key West is full of surprises.
Ready to plan your first trip to Key West? Buy some beachwear, book that tropical vacation villa, and get ready to brush up on your Key West knowledge — here’s a Key West travel guide for first timers!
First Visit: Best Things to Do in Key West
There’s no shortage of things to do in Key West, but if you don’t have a ton of time or are just looking for the best of the best, here are a few of the can’t-miss things to add to your itinerary.
Enjoy the Beaches and Watersports
Key West has gorgeous beaches, so you’ll definitely want to make time to visit them. And of course, this island is also famous for its watersports. From diving and snorkeling to kayaking and paddleboarding, there’s so much to do on the water in Key West.
If you’re up for an adventure, we highly recommend trying snorkeling. You can see a variety of sea creatures, including tropical fish, sea turtles, crustaceans, and more. There are several places to go snorkeling in Key West, from boat tours that take you to the coral reefs to beaches where you can snorkel right from the shore.
Take a Stroll Down Duval Street
Akin to Bourbon Street in New Orleans, Duval Street is where everything happens in Key West. Stretching from the Atlantic to the Gulf side of the island, Duval Street is lined with shops, restaurants, bars, museums, galleries, and so much more. It’s also where you’ll find famous bars like Sloppy Joe’s and Capt Tony’s Saloon.
No visit to Key West is complete without taking a stroll down Duval Street. And yes, you might see a rooster or two roaming around, a dog in a bar wearing sunglasses, or an Ernest Hemingway impersonator — it’s all part of the Duval Street charm!
Catch the Mallory Square Sunset Celebration
Another can’t-miss Key West experience, the Sunset Celebration in Mallory Square offers arguably the best sunset in the Florida Keys. Every night, rain or shine, people pack Mallory Square at sunset to watch the sun paint the sky over the water. And as the sun sets, you’ll enjoy live music, street performers, food vendors, and local artists.
Enjoy the Local Culinary Scene
Being surrounded by water gives Key West a huge advantage in the seafood department, and with so many different cultural influences on the island (Cuban, Spanish, French, and Bahamian — just to name a few), the culinary scene here is a foodie’s dream.
Indulge in fresh seafood, rich Cajun dishes, and some of the best Cuban sandwiches you’ll find outside of Havana. And of course, who could forget the Key lime pie? You’ll find this famous pie as a staple on every restaurant’s dessert menu, and as the star in bakeries and pie shops across the island. You’ll definitely want to dine out while visiting Key West; here are a few of our top restaurant recommendations to get you started.
First Time: Must-See Key West Attractions
From famous forts and historic homes to brightly colored buoys and butterfly gardens, there are so many big Key West attractions. If you have the chance to see them all, we highly recommend it, but if you can’t, here are a few must-sees.
Southernmost Point
The most popular spot to snap a selfie in all of Key West, the Southernmost Point is a large, brightly colored buoy overlooking the Atlantic Ocean that famously reads “90 Miles to Cuba” — marking the Southernmost point in the Continental United States. No Key West vacation is complete without a picture in front of the Southernmost Point.
Being as popular as it is, don’t be surprised to see long lines forming here, day or night. But don’t be discouraged; they tend to move quickly, and the photos are worth the wait.
Pro tip: visit first thing in the morning when the crowds are typically lighter, and the sunrise gives everything a nice glow.
Ernest Hemingway Home and Museum
Former home of the late literary icon Ernest Hemingway and his famous six-toed cats, the Ernest Hemingway Home and Museum is a must-see when visiting Key West. You’ll learn all about Hemingway’s life and written works, tour the historic home and gorgeous gardens, and of course, meet the famous felines that roam the grounds — descendants of Hemingway’s original six-toed cat, Snow White.
Key West Butterfly and Nature Conservatory
Once named “The Best Attraction” and “The Best Place to Take the Kids” in Key West, the Key West Butterfly and Nature Conservatory is another must-see, especially if you’re traveling with little ones and looking for kid-friendly things to do in Key West.
Stroll through the gardens filled with beautiful butterflies, birds, and flowers, browse the insect exhibits, and visit the learning center to learn about the butterfly lifecycle and see some cute caterpillars. There’s also a gift shop and gallery filled with butterfly art, souvenirs, and gifts.
Fort Zachary Taylor Historic State Park
A mix of natural beauty, fascinating history, and water recreation, Fort Zachary Taylor Historic State Park has it all. Tour the fort and learn all about its functions during the Civil War and Spanish-American War. And if you happen to be visiting during the third weekend of the month, you may even get to see live reenactments.
The beaches and green spaces surrounding the fort are perfect for sunbathing or going for a stroll. And as an added bonus, the water’s rocky outcroppings make an excellent snorkeling spot. The park also features a cafe, beach rentals, and plenty of showers and restrooms, making it a great place to spend the day.
Where to Stay in Key West
Where you stay in Key West can shape your entire trip, especially on a first visit. The island may be small, but each area offers a completely different experience—from lively, walkable streets to quieter, more residential pockets.
Every Key West neighborhood comes with its own unique charm. If you want to be in the middle of the action, Old Town puts you steps from Duval Street, historic homes, restaurants, and nightlife. It’s the most iconic (and busiest) part of the island.
For a more laid-back, local feel, areas like Midtown or New Town offer more space, easier parking, and a slower pace—ideal if you’re planning to explore beyond the main tourist spots.
Book your stay with Vacation Homes of Key West and enjoy a quiet, fully furnished space with plenty of room for the whole family, and special perks like private pools, hot tubs, and more. You’ll never have to wait for a seat at the breakfast table or fight for a pool chair again!
Best Time to Visit Key West
With year-round sunshine and warm water, there’s really never a bad time to visit Key West! But if you want to make the absolute most out of your trip, we recommend visiting around winter or spring.
December through May tends to have the best weather, with less heat, humidity, and rain, and it’s outside of hurricane season. Although major storms are still rare, if you’re worried about last-minute cancellations due to weather, winter and spring have the least chance of that happening.
Of course, spring and winter are also the most popular, so if you want to avoid crowds or find deals on accommodations, you may prefer to visit in summer or fall. Each season has its upside.
Key West Travel Tips for First Timers
First-time trips to Key West are all about timing, location, and knowing a few local tips that can make your stay smoother, easier, and more enjoyable.
Bring Sun Protection
The UV index in the Florida Keys is high, and when you’re out in the sun all day on the beach, in a boat, or while sightseeing, that exposure can add up. We recommend bringing hats, sunglasses, reef-safe sunscreen, and maybe a few long-sleeve sunshirts. Find more Key West packing tips here.
Explore Hidden Gems
Sure, the big attractions are fun and definitely worth your time, but Key West is also full of hidden gems and unique things to do, like haunted pubs, pirate ships, and scandalous dessert restaurants. And don’t be afraid to ask around for recommendations; most locals love to tell you about their favorite dive bar or secret spot.
Take the Trolley
If you want to go sightseeing and save your feet, the Old Town Trolley offers a great way to get around. You can hop-on/hop-off at over a dozen top spots around Key West, including the popular Old Town Key West area, Hemingway House, Key West Lighthouse, and more.
Try All the Key Lime Pies
Key lime pies are the pride and joy of Key West, and nearly every restaurant, bakery, and pie shop has put its own spin on the recipe. From chocolate-covered to meringue-topped and everything in between, everywhere you go will claim to have the best slice.
We highly recommend conducting your own research and trying them all! And if you’re not sure where to start, here’s our list of must-try Key lime pies.
Don’t Let a Little Rain Get in the Way
Rain happens in Key West, after all, you’re in the tropics. But just because it’s raining doesn’t mean you’re doomed to be stuck in your vacation rental all day. There are lots of things to do in Key West when it’s raining, so just grab an umbrella and go enjoy your day!
Take a Road Trip
If you’re visiting by car, consider taking a day trip to explore nearby Stock Island and the other Florida Keys. The Overseas Highway offers amazing views and plenty of fun places to stop and explore.
Make the Most of Your First Time in Key West
We know you’re going to love Key West; there’s just nowhere else in the world like it. Even all the other Florida Keys islands, each unique in its own way, don’t come close to matching the beauty and energy of the “Conch Republic.”
Want to make the most out of your first time in Key West? Book your stay with VHKW and enjoy fully furnished vacation homes with premium amenities like pools and hot tubs, all within walking distance of top Key West attractions.
