I love Key West! I love the vibe of the island, I love all that there is to do, I love the people, about the only thing that I don’t like is getting there. You say that the drive there is beautiful. I agree, it is beautiful, but please don’t be one of those people poking around, going five miles under the speed limit. Then when they get to the passing lane, they speed up to 80 until it’s back down to one lane, then it’s back to five miles under the speed limit. It’s the damndest thing, it happens every time. Anyway, on to three perfect days in Key West.
Actually, this is “It would’ve been three perfect days in Key West but I couldn’t go diving because I was still recovering from a broken foot, so it was just three really really great days in Key West”. But that was a bit too long of a headline.
You’ll want to find the perfect hotel to stay in while you spend your three perfect days. Find a list of hotels here.
Unless you’re flying into Key West early in the morning, these three days don’t include travel days. Key West is about four hours from Miami, so you pretty much waste a day traveling if you’re flying into one of the Miami airports. If you’re traveling from somewhere other than Homestead, you’ll do good to get to Key West, check into your hotel and spend the night relaxing.
Cheat Sheet
Day 1 Walking and Exploring
903 Duval Street, Key West, Florida
938 Whitehead Street, Key West, Florida
907 Whitehead Street, Key West, Florida
Fort Zachary Taylor Historic State Park
Southernmost Point, Key West, Florida
1316 Duval Street, Key West, Florida
Day one of three days in Key West has a lot of walking in it so make sure that you bring plenty of water, good walking shoes, and you can cut out attractions as you see fit.
Key West Butterfly and Nature Conservatory
The number of butterflies in here is amazing! You learn all about butterflies with a butterfly primer in an outer room and then move into the butterfly room. Very tropically landscaped with butterflies and birds flying throughout. There are even two Pink Flamingos, Rhett and Scarlett, who’ll entertain you with their antics. Once you’re done, no rush, you end up in, you guessed it, the gift shop. But you already knew that because that’s where you started.
The Southernmost Point
Yeah, everybody who has been to Key West has their picture in front of The Southernmost Point sign on their Facebook page. What they don’t show you is the line that you have to wait in to get that pic, in the heat, with no shade. It’s on the way to the next attraction so you can stop, wait, and post it to your Facebook/Insta account, or not.
Fort Zachary Taylor State Park
Named after Zachary “Old Rough and Ready” Taylor, Fort Taylor was built in 1845 and held “active duty” status through 1947. When it was built it was three stories high and completely surrounded by water. Through the years it has been updated to suit the needs of the military. Today it’s only one story, but it still holds the largest cache of Civil War-era seacoast cannons.
But Wait, There’s More…
There’s more than just a fort, there’s also a beach area and nature trails. Bring your fishing gear and impress your family with how resourceful you are as you catch fish, clean it, and cook it on the convenient grills in the picnic area. After you’re done eating, wait the “mom required” 30 minutes and snorkel right off the beach. Don’t have snorkeling gear? Don’t worry they’ll rent it to you right there. After you’ve spent your day touring, fishing, and snorkeling, relax in one of the beach chairs that you rented when you returned the snorkel gear and enjoy a fantastic sunset.
Earnest Hemingway Home and Museum
Full of history, the house is well preserved with plenty of pictures. Get a guide or do the self-guided tour thing. Either way you’ll enjoy exploring the grounds and learning the history of Earnest Hemingway. He wrote about 70% of his books in this very house. One of the things that you’ll learn there is that ole Ern was a cat person and there are still descendants of his famous six-toed cats living at the house.
Key West Lighthouse and Keepers Quarters
Go ahead, climb to the top of the lighthouse and get a bird’s eye view of the island. Key West is a notoriously hard island to navigate a boat around. And you’ll find that out when you tour the keeper’s quarters and explore the history of lighthouses on the island.
Viva Saloon
What a better way to end the day than on the patio enjoying fresh seafood and a cold drink or two. Live music plays throughout the day. This is a great place to unwind, and the prices are reasonable.
Day 2 Sailing, Snorkeling, and Kayaking
Day two of three days in key west is on the water. If you bring sunscreen, make sure that it’s biodegradable.
Danger Charters Cruise
Cool name, but it’s not dangerous. That guy sitting across from you? He’s not a pirate, he’s just a hipster.
This is a fun trip, and you can do a morning trip, afternoon trip (which stays out for the sunset) or bring out the sailor in you and spring for the full day trip.
Leave from the Margaritaville Resort and Marina and set sail to Key West National Wildlife Refuge. Once the crew drops anchor it’s time to get your snorkel gear and jump into the water. Under water you’ll see some of the more than 600 tropical colored marine wildlife species, including sting rays among the coral reefs.
Once everybody gets back on board it’s time for snacks, or lunch and drinks (oh yeah!). You can eat and socialize while you head to your next destination, the mangroves. Mangroves are essentially forests of shrubs and small trees that grow in the salt water. Once you’re there, everybody gets in their kayaks and the crew will guide you around the tree/shrub island and tell you about their formation.
Finally, enjoy the relaxing trip back to the marina as you mingle and enjoy the complimentary drinks.
Schooner Wharf Bar
After a day on the water head on over to the Schooner Wharf Bar. Cold drinks, great food, fun crowd, and live bands. Do yourself a favor and sit by the water so you can watch the fishing boats bring their catch in.
Day Three Biking and Exploring the Island
Day Three, the final day of three days on Key West is an exploring the island day.
Sunrise to Sunset
Wake up early and join the crowd (yes, there is a crowd) for the sunrise at the Edward B. Knight Pier. While you’re there, there’s a great bike/running path along the seawall that starts at Higgs Beach and goes to the airport.
Rent a bike or scooter and explore the island. Bike to Duval Street and pick up your souvenirs, T- shirts, and Fine Art. Cruise up and down the side streets and be amazed at how tight they pack their houses, then get even more amazed at how adverse they are to grass and actually landscape every inch of their yard.
Bike on over to Fort East Martello Museum and explore another Civil War era fort. Or go to the poor man’s West Martello Tower, which is the twin to East Martello. It’s not as intact and it’s free. It’s run by Key West Garden Club and funded on donations so don’t be a total tightwad, donate a couple of bucks.
Or let the adventurer in you out. Check out Fury’s Parasailing. Get awed when you’re floating above the crystal-clear waters that surround Key West. Get really awed when you see dolphins and sharks in the water and you realize how close that they swim to shore!
Commotion on the Ocean Sunset Sail
Find it on TripAdvisor as Key West Sunset Cruise with Fury Water Adventures. You might get lucky and get the appropriately named Captain Morgan. Be sure to ask him to do the Captain Morgan pose for you, he loves that.
Beer, wine, margaritas, and champagne flow continuously as a band plays on the main deck. Enjoy the sounds of 80s bar music floating in the background and laugh at the 20 other boats who don’t have music. Be prepared, because when the sun sets, it’s spectacular!
Once you get back to shore there’s still plenty of time to hit up one of the great restaurants on Duval Street. Go ahead and enjoy yourself, you’re going back to real life tomorrow.
Not enough for you? Well, wander over to our Ultimate Guide to Key West then.
Okay, you’ve read about and now you want to get to Key West as fast as you can. Find out how to get the cheapest airfares here.
