The Ultimate Key West Travel Guide: Best Things to Do, Where to Eat & Insider Tips
Looking for the best things to do in Key West? Whether you're planning a weekend getaway, a Florida Keys road trip, or a cruise stop, Key West offers colorful streets, incredible sunsets, fresh seafood, and a laid-back island vibe that's unlike anywhere else in the United States.
People think Key West is just Duval Street, the nightly sunset celebration, and a slice of key lime pie—but they're missing about 90% of what makes this island magical. If you're wondering whether Key West is worth visiting, the answer is an easy yes.
Drive the Overseas Highway at Least Once
One of the best parts of visiting Key West is actually getting there.
The Overseas Highway stretches about 113 miles from mainland Florida to Key West, crossing 42 bridges with ocean views almost the entire way. If you've never driven the famous Seven Mile Bridge, put it on your bucket list.
If it's your first visit, make the drive. Stop in Islamorada for lunch, Marathon for photos, and enjoy the journey because it truly becomes part of the vacation.
That said, once you've experienced it, flying is a great option. From Central Florida, Avelo Airlines offers inexpensive nonstop flights from Lakeland, making future trips much easier.
Why Key West Feels Different
One of the biggest surprises for first-time visitors is that Key West doesn't feel like Florida.
It feels like the Caribbean mixed with New Orleans and Old Havana, all wrapped into one colorful, quirky island.
Everyone is wearing flip-flops. Nobody seems to know what day it is—and honestly, nobody cares. Life slows down here, and that's exactly why people fall in love with it.
Even better? You get Caribbean-blue water without needing a passport.
Explore Duval Street
No visit is complete without walking Duval Street.
Stretching nearly a mile across the island, it's packed with restaurants, bars, local boutiques, art galleries, live music, Cuban coffee shops, and endless people watching.
Live music starts long before sunset, making it easy to spend an entire afternoon wandering from one venue to another.
Insider Tip: Grab a seat on the second-floor balcony at Bull & Whistle. It's one of the best places on the island to relax, enjoy the breeze, and watch the parade of humanity stroll down Duval Street.
Don't Miss the Sunset Celebration
Every evening, Mallory Square transforms into one giant celebration.
Street performers, musicians, local artists, and hundreds of visitors gather to watch the sun disappear into the Gulf. When it finally sets, everyone applauds—and after seeing it yourself, you'll understand why.
If you're looking for an even more memorable experience, consider:
A sunset cruise
Dinner on Sunset Key
A private boat charter
Each offers incredible views away from the crowds.
What to Eat in Key West
Fresh seafood is everywhere in Key West.
Be sure to try:
Stone crab (in season)
Lobster
Conch fritters
Cuban sandwiches
Key lime pie
Speaking of key lime pie—don't stop at one slice. Whether you prefer traditional, frozen, or chocolate-dipped, everyone has a favorite.
Waterfront dining is another highlight, especially if you can snag a reservation on Sunset Key.
Visit the Ernest Hemingway Home
The Ernest Hemingway Home is one of Key West's most famous attractions.
Yes, you'll see Hemingway's writing studio—but many visitors come just to meet the famous six-toed cats that still roam the property. They're descendants of Hemingway's original cats and have become celebrities in their own right.
Take the Southernmost Point Photo
Yes, there's a line.
Yes, everyone takes the picture.
And yes—it's worth doing.
If you want to avoid the longest wait, arrive early in the morning or later in the evening.
Pro Tip: Decide where everyone is standing before you reach the front of the line. You'll get your picture faster and keep the line moving for everyone else.
Hidden Gems in Key West
If you want to escape the crowds, don't miss these favorites:
Fort Zachary Taylor State Park
This is home to arguably the best beach in Key West, along with excellent snorkeling and fascinating Civil War history.
Key West Butterfly Conservatory
Small but unforgettable, this tropical glass habitat is filled with hundreds of butterflies and offers one of the most peaceful experiences on the island.
Sunset Key
Accessible only to resort guests or those with dining reservations, Sunset Key offers beautiful waterfront dining and one of the best sunset views in the Florida Keys.
Get Out on the Water
Key West isn't really a beach destination—it's a boating destination.
Some of the best experiences include:
Snorkeling trips
Sunset sails
Paddleboarding
Kayaking through mangroves
Catamaran cruises
Private boat rentals
Sandbar excursions
Sport fishing
The water is unbelievably clear, and it's common to spot dolphins, sea turtles, rays, and tropical fish.
Take a Day Trip to Dry Tortugas National Park
If you have extra time, don't miss Dry Tortugas National Park.
Located about 70 miles west of Key West, it's accessible only by ferry or seaplane and features crystal-clear water, incredible snorkeling, and historic Fort Jefferson.
If you're going to splurge on one experience, the seaplane is hard to beat.
Where to Stay in Key West
If you want nightlife within walking distance, consider staying near Duval Street.
Popular options include:
Hyatt Centric Key West
Ocean Key Resort & Spa
Looking for something quieter? Boutique inns and charming bed-and-breakfasts just a few blocks away offer a more relaxed experience while still keeping everything within easy walking distance.
For the ultimate luxury stay, Sunset Key is hard to top.
Is Key West Expensive?
Yes—but it doesn't have to break the bank.
Hotels are often the biggest expense, while many of the island's best experiences—walking Duval Street, watching the sunset, exploring historic neighborhoods, and people watching—cost little to nothing.
Staying slightly outside downtown can also help save money.
Samantha's Best Key West Tips
Visit between late fall and spring for the best weather.
Book hotels early—they fill quickly.
Rent bikes instead of driving.
Wear comfortable shoes or flip-flops.
Bring reef-safe sunscreen.
Get out on the water—it truly is the best way to experience Key West.
Is Key West Worth Visiting?
Absolutely.
Key West isn't famous because it has the biggest attractions. It's famous because it has one of the biggest personalities.
It's colorful, quirky, laid-back, and unforgettable. Whether you're road-tripping the Overseas Highway, exploring Duval Street, watching the sunset at Mallory Square, or spending the day on the water, Key West has a way of reminding you to slow down and simply enjoy where you are.
