You’ve booked your Key West vacation; you go online and, wow! There’s so much to do, where do you begin? Here, you begin here with our handy Key West vacation checklist.
Included in our list are excursions and places to visit that have that definitive “island vibe”. What is island vibe you ask, well, you’ll feel it once you arrive in the Keys. Tropical islands surrounded by turquoise water, tiki bars on the edge of the water, and skies lighting up beautiful yellows and oranges as the sun sets all add to the vibe.
Visit Truman’s Little White House on Your Key West Vacation
Harry Truman loved Key West so much he practically moved the White House there. He spent 175 days there between 1946 and 1952. Originally constructed as Officers Quarters in 1890, not only was the house used for visiting dignitaries, five other presidents spent time here.
Now it’s a museum with guided tours of the house and grounds. They also host events throughout the year including an Easter Egg Roll, and Fourth of July cookouts. Or, for a cool $600, you can spring for the VIP White Glove Tour. Invite up to five of your friends and get exclusive behind the scenes upgrades like a photo op at Truman’s desk, as well as a ride in his Limo.
The Southernmost Point Buoy
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Might as well get this one out of the way. People love to get their pics in front of this thing so much, there’s a line there most of the day. The buoy usually is at the corner of Whitehead Street and South Street. But currently it’s at the end of Duval Street by the Southernmost Point House due to construction on Whitehead/South Streets. Pro Tip – Get there early morning not only do you avoid the line, but you also get better light.
Key West Lighthouse and Keeper’s Quarters
Climb the 88 stairs to the top of the lighthouse for fantastic views of Key West and the gin-colored waters surrounding it. The lighthouse opened in 1848 and operated until 1969; it set an unheard-of precedence at the time as the first keeper was a woman.
Today you can climb to the top of the lighthouse and walk on the catwalk around the top. Down on the ground the Keeper’s Quarters have been rehabbed into what it was like to live there in the 1800s (except for the added AC). If you like it enough, you can rent the venue for your wedding or any other big happening.
Stop By the Ernest Hemmingway Home on Your Key West Vacation
Famous author Ernest Hemmingway loved Key West, and it seemed to be pretty good for him as he wrote some of his most famous books while he lived there. Now his house is a museum. They have rehabbed the house, and his office is pretty much the same way it was when he wrote in it. Guided tours are available every day, on your tour you’ll learn how Ernest lived, worked, partied, and fished. You’ll even be able to see the descendants of his six-toed cats.
Fort Zachery Taylor Historic Fort and Spectacular Beach
The fort is from the mid-1800s and currently houses the most civil war era canons in the U.S. At one time it was three stories but unfortunately over time, it got cut down to the single story that stands now. You can take a self-guided tour, or if you time it right, there is a ranger-led tour once a day.
After you’ve had your fill of history, take a hike on one of the nature trails that crisscross the park. When you’re done with that, there’s a fantastic beach waiting for you to sit back and relax. You can snorkel, swim, raft, or fish from the shore. If you don’t want to lug beach chairs, rafts, or snorkel gear from the hotel, that’s alright, they rent them at the Chickee Hut.
Hit up Duval Street
Duval Street is the heart of Key West. It’s filled with colorful people, and unique restaurants, bars, art galleries, and shops. Daytime is fun on Duval Street, but it really comes alive at night.
There are historic bars, fine dining restaurants, cigar bars, drag show bars and cabarets to fit whatever mood that you’re in. If you can’t decide where to go, just pull up a chair on the patio at Carolines and people watch.
The Shipwreck Museum
Long before Key West was a vacation destination, it was filled with “Shipwreckers”. Men who would go out in the worst storms and salvage people and ships that would run up onto the many shallow reefs scattered about the Florida Keys.
The Shipwreck Museum is a recreation of a 19th century shipwrecker warehouse, complete with an old captain regaling tales of the life of the wreckers (but I don’t think that he’s really from 1850). After you’ve toured the warehouse and seen the treasures that were found on the Issac Allerton wreck, the richest shipwreck in Key West’s history, be sure to climb the lookout tower. What was once used as a way to spot shipwrecks on the horizon now is a way to get spectacular views of Key West and the surrounding waters.
Visit Key West Butterfly and Nature Conservatory on Your Key West Vacation
You open your eyes and you’re in a tropical forest, hundreds of butterflies and exotic birds are flying through the air, some even landing on you. A creek meanders through the tropical trees; there are turtles in the water. Standing in the water are two pink flamingos named Rhett and Scarlett. Am I dreaming? Am I in heaven you wonder. Suddenly one of the flamingos lets out an annoying squawk (probably Rhett, that loudmouth). Oh, that’s right, you’re at the Key West Butterfly and Nature Conservatory.
You’ll start off with a short video where you’ll learn about the different stages that butterflies go through, from birth to their adulthood. Once inside the massive greenhouse, you’ll view multiple species of butterflies in their habitat. This really is a relaxing and fun afternoon that you shouldn’t miss when you’re in Key West.
Mallory Square Sunset Celebration
To say that Key West takes their sunsets seriously is an understatement. Live bands, stunt performers, and local artists show up every night and celebrate the sunset.
Just a hint, things begin happening up to two hours before sunset. Be sure to get to Mallory Square at least one night on your Key West Vacation and join visitors from all over the world to celebrate the sunset!
Take a Sunset Cruise
There’s no shortage of ways to watch the sunset in Key West. Big, filled charter boats, small intimate sailboats for two, catamarans with a band playing as the sunsets, dinner sunset cruises, and even schooner cruises.
Whatever your mood is for the night, these and more are all available to help you enjoy the sunset on the water. So, whether you want to have a romantic sunset with just you and your spouse, or party till the sun goes down, and then some, you are in luck.
The sunset cruises that we like are the Commotion on the Ocean, a Fury charter, and the Key West Sunset Sip and Sail.
