If you’re dreaming of a weekend with sunshine, island vibes, and just the right mix of chill and adventure, Key West is calling your name.
You can explore history, hang with tropical animals, eat your weight in seafood, and dance your way into the night, all without ever needing a jacket.
Whether you’re here for the views or the wildlife, this weekend itinerary has you totally covered.
We’ve also included a ‘bonus section’ at the end of the itinerary that you are definitely going to want to see if you want to guarantee that you leave with some life long memories.
1. Fort Zachary Taylor Historic State Park
Fort Zachary Taylor Historic State Park is located at the southern tip of Key West and it’s home to a real Civil War-era fort built in the 1800s.
It’s known for having the largest collection of Civil War cannons in the U.S., plus you can actually walk through the old brick corridors and peek into the cannon rooms.
The park also has one of the best beaches in Key West, with clear blue water, rocky coral areas for snorkeling, and shady picnic spots under Australian pines.
It’s just $6 per vehicle (up to eight people) to get in, and you can spend the whole day swimming, exploring the fort, or catching the sunset from the seawall—it’s a local favorite for a reason.
2. Southernmost Point of the Continental USA
Just a 5-minute drive from the fort, you’ll find one of Key West’s most famous photo ops—the giant red, black, and yellow buoy that marks the Southernmost Point of the Continental USA.
It’s about 90 miles from Cuba, and the sign actually says that, which makes it one of the most photographed spots in all of Florida.
There’s usually a line (especially around sunset), but it moves fast and the ocean views while you wait are pretty amazing.
You won’t spend long here, but it’s one of those “you were really in Key West” moments you’ve gotta check off your list.
Please note: At the time of writing, Key West’s Southernmost Point buoy was removed on September 4, 2025, for a year-long restoration project. During this period, a replica buoy has been installed nearby at the southern end of Duval Street (1499 Duval St.) for photo opportunities.
3. The Key West Butterfly and Nature Conservatory
Just a short walk from the buoy, you’ll step into a totally different world at The Key West Butterfly and Nature Conservatory and yes, it’s just as magical as it sounds.
This glass-enclosed tropical paradise is home to over 50 species of butterflies, plus flamingos, tiny birds, and even a few turtles cruising around.
It’s warm, steamy, and packed with flowers, so don’t be surprised if a butterfly lands right on your shoulder while you wander through.
The visit usually takes about 30 minutes to an hour, but it’s pure joy from start to finish and honestly, it’s the most peaceful place in all of Key West.
4. Truman Little White House
Just when you think Key West couldn’t get any more interesting, the Truman Little White House adds a presidential twist to your trip.
This cute white building tucked away in the historic Old Town was President Harry S. Truman’s winter getaway, and he spent 175 days here during his time in office.
You can take a guided tour through the rooms where he lived and worked, complete with original furniture, vintage phones, and even his famous “The Buck Stops Here” sign on the desk.
It feels like a history lesson, as well as a time capsule, and it’s way cooler than you’d expect a presidential museum to be.
5. Sunset Celebration at Mallory Square
After soaking up some presidential history, head straight to the water for the one thing you have to do in Key West, the Sunset Celebration at Mallory Square.
Every evening, about an hour before sunset, this spot turns into a full-on street party with food carts, magicians, musicians, and even cats jumping through fiery hoops.
Crowds gather along the seawall to watch the sun dip below the ocean, and the sky seriously puts on a show with crazy-good colors.
It’s loud, fun, totally chaotic in the best way, and the perfect way to wrap up a day in Key West.
6. Key West Historic Seaport
Another must-do is taking a stroll over to the Key West Historic Seaport, where the boardwalk is lined with sailboats, seafood joints, and salty sea air.
This place has been around since the 1800s and now features a mix of restaurants, bars, shops, and marina views that stretch forever.
You can hop on a sunset cruise or grab conch fritters at Conch Republic Seafood Company which is a local favorite with big portions and even bigger vibes.
It’s the kind of spot where you can wander aimlessly, snack constantly, and still feel like you’re doing something worth writing home about.
7. The Hemingway Home and Museum
Next, swing by The Hemingway Home and Museum, which is located just a few blocks from the seaport.
This was the actual house where Ernest Hemingway lived in the 1930s, and those six-toed cats lounging around the garden are all descendants of his original pet, Snow White.
You’ll walk through rooms filled with his typewriters, trophies, and stories about his wild life in Key West, Cuba, and beyond.
Even if you’ve never read a word of Hemingway, the house is super cool, the guides are full of juicy stories, and the cats basically run the place.
8. Duval Street Nightlife
After a day of cats, cannons, and sunsets, Duval Street is where the party really kicks in.
This legendary strip stretches from the Gulf to the Atlantic and is packed with bars, live music, frozen drinks, and people having the time of their lives.
You can catch live music at Tiki House, dance at Irish Kevin’s, or sip a mojito at The Green Parrot, one of the oldest bars in Key West.
It’s loud, a little wild, and totally unforgettable—basically, if Key West had a heartbeat, it would be thumping right down Duval Street.
Bonus Section!
In this bonus section, we wanted to highlight some of the top things to do that aren’t on this itinerary.
You should definitely consider adding these to your trip if you have enough time.
They are all memorable activities that you’ll be talking about for a long time to come.
Get Out On The Water
If you’re in Key West, we highly recommend you get out on the water to experience some nature in this beautiful part of Florida.
Here are some highly rated recommended activities for getting out on the water in Key West:
- Shark and Wildlife Viewing Adventure in Key West
- All-Inclusive Sandbar Safari with Dolphin Playground Encounter
- Key West Mangrove Kayak Eco Tour
Walking Tours
A walking tour is a great way to familiarize yourself with Key West.
There are different walking tours for different themes and you can do anything from a food & culture tour to a haunted pub crawl.
Here are some top-rated walking tours you can do:
Trip to Dry Tortugas National Park
If you want to give Dry Tortugas National Park a visit then this is the easiest way to visit (with breakfast and lunch included):
Related Posts
