The Ultimate Key West Travel Guide: Where to Stay, Eat, Ride, and What I’d Do Again
Planning a trip to Key West? Here’s everything I wish someone had told me before we visited, including where to stay, where to eat, what was worth the money, and a few surprises along the way.
There are very few places in the United States that feel completely different from everywhere else, and Key West is one of them.
It has Caribbean vibes, historic homes, quirky bars, chickens wandering the streets, turquoise water, incredible sunsets, and enough personality to keep you entertained for days.
We spent several days exploring the island on foot, by bike, and by jet ski, and if I went back tomorrow, there are plenty of things I’d do exactly the same.
Where We Stayed
We stayed at Casa Marina, A Curio Collection by Hilton, on the southern end of Key West.
Its sister property, The Reach Key West, is located right next door, and together they have some of the nicest natural beach frontage on the island, something that’s actually fairly rare in Key West.
One of the biggest advantages of staying here was the location.
It was only about a 7 to 10 minute walk to the Southernmost Point and the beginning of Duval Street, but just far enough away that evenings were much quieter than staying directly in the middle of downtown.
Would I stay here again?
Absolutely.
The rooms were comfortable, the grounds were beautiful, and the location made it easy to walk almost everywhere we wanted to go.
The only downside?
The food at Casa Marina was just okay.
Fortunately, that’s easy to solve.
Walk next door.
Don’t Miss Four Marlins- Restaurant inside sister property to Casa Marina
Located inside The Reach, Four Marlins ended up being one of our favorite restaurants during the trip.
The food was noticeably better than Casa Marina’s restaurants, the atmosphere was relaxed, and the oceanfront setting made it an easy recommendation.
If I stayed at Casa Marina again, I’d simply plan on eating several meals next door.
Walking Duval Street
From Casa Marina, we walked to the Southernmost Point and then continued onto Duval Street.
If you’ve never been, imagine a cleaner, more tropical version of Bourbon Street in New Orleans.
You’ll find:
bars
live music
souvenir shops
cigar stores
restaurants
drag shows
plenty of people watching
You’ll also quickly notice that Key West doesn’t take itself too seriously.
It’s fun.
It’s colorful.
It’s quirky.
If nightlife isn’t really your thing, don’t worry.
The farther you wander from Duval Street, the more you’ll discover the quieter residential neighborhoods that honestly became some of my favorite parts of Key West.
Rent Bikes
If I could recommend one activity besides simply walking, it would be renting bikes.
Instead of joining an organized tour, we rented bicycles and explored the island using Google Maps.
By the end of the day, we’d ridden somewhere around 15 miles.
That gave us the freedom to stop whenever we spotted an interesting house, marina, or quiet neighborhood.
One of my favorite discoveries was how different the island feels away from Duval Street.
You’ll quickly realize there’s a tourist Key West…
…and a local Key West.
Both are worth seeing.
One warning though.
Crossing A1A on bicycles can feel like playing Frogger.
Is the Jet Ski Tour Worth It?
For us?
Absolutely.
The guided tour circles the island in about two hours and gives you a completely different perspective of Key West.
Just know what you’re signing up for.
You’ll get wet.
You’ll be climbing on and off the jet ski.
You’ll hit waves.
And there are stretches where you’re running close to 50 mph.
If you enjoy adventure, you’ll probably love it.
If rough water, back problems, or speed aren’t your thing, I’d skip it.
Where We Ate
One of my favorite parts of every trip is trying local restaurants.
These are the places we’d absolutely recommend.
Bel Mare, My Favorite Dinner
If I had to choose one restaurant to recommend, it would be Bel Mare.
Located near the Historic Seaport, it offered the best combination of food, atmosphere, and service that we experienced during our stay.
The seafood was outstanding, the service was excellent, and the entire evening felt special without feeling overly formal.
If you’re planning one nice dinner while you’re in Key West, this would be my choice.
Reservations are recommended.
915
This may have been the most charming restaurant we visited.
Located inside a beautifully restored Victorian home on Duval Street, 915 feels tucked away from the crowds even though it’s right in the middle of everything.
There are only a handful of tables on the sidewalk, a few on the wraparound porch, and just a couple inside the historic home itself.
It’s quiet, romantic, and feels completely different from the lively atmosphere just outside.
If you’re looking for a memorable dinner in one of Key West’s most beautiful historic buildings, don’t miss 915.
Reservations are highly recommended.
Four Marlins
Great food.
Beautiful ocean views.
An easy recommendation whether you’re staying at Casa Marina or not.
A&B Lobster House
Located at the marina, A&B Lobster House is another excellent seafood restaurant.
The marina views are beautiful, especially around sunset.
While I personally preferred Bel Mare, A&B is still a wonderful choice if you’re looking for an upscale dinner.
Latitudes
If you’ve researched Key West at all, you’ve probably heard about Latitudes.
To get there, you’ll take a ferry from near Mallory Square over to Sunset Key.
The food was very good.
The sunset was incredible.
This is one restaurant you’ll definitely want to reserve well before your trip.
Louie’s Backyard
Multiple people recommended Louie’s Backyard to us.
Unfortunately, we never managed to get a reservation.
Next trip.
Visit the Historic Neighborhoods
One of the things that surprised me most about Key West was how beautiful the residential neighborhoods are.
Some of our favorite moments came while simply riding bikes through streets lined with colorful cottages, tropical landscaping, and historic homes.
We also enjoyed riding past Harry S. Truman’s Little White House and exploring the marina areas where fishing boats, sailboats, and enormous yachts all share the same waterfront.
Sometimes slowing down and wandering ends up being the best attraction.
Marina Life
The marina has its own personality.
Restaurants overlook fishing boats unloading their daily catch while luxury yachts quietly come and go.
People sit outside in flip-flops, cover-ups, and sunglasses enjoying cold drinks while watching the harbor.
If you’re expecting gourmet food everywhere, you might be disappointed.
If you’re looking for atmosphere, you’ll love it.
The Airport
Key West International Airport might be one of the easiest airports we’ve ever used.
It’s small.
Security was fast.
TSA PreCheck made it even quicker.
And the airport is only about five minutes from Casa Marina by Uber.
Ironically, getting from the airport to our hotel was faster than driving across town to dinner.
One travel tip we learned before arriving concerns checked luggage.
Because of the airport’s shorter runway, airlines sometimes have stricter baggage limits. At the time of our trip, Delta passengers were limited to one checked bag, while American allowed two. Policies can change, so it’s worth checking your airline before you pack.
Honestly, though, you don’t need much.
What to Pack
Don’t overpack.
Seriously.
Key West is one of the most casual destinations you’ll ever visit.
Most days you’ll wear:
shorts
sundresses
swimsuits
cover-ups
sandals
workout clothes
You’ll dress up a little for restaurants like Bel Mare or 915, but there’s absolutely no reason to haul around a giant suitcase.
A carry-on is plenty for most trips.
Final Thoughts
Would I go back?
Without question.
I’d stay at Casa Marina again.
I’d eat at Bel Mare again.
I’d make another reservation at 915.
I’d rent bikes on day one.
And I’d still carve out time to simply wander the neighborhoods with no agenda.
Key West isn’t about checking attractions off a list.
It’s about slowing down, enjoying the island’s quirky personality, watching the sunset, and letting yourself settle into “island time.”
If that’s the kind of vacation you’re looking for, I think you’ll love it as much as we did.