I think we can all agree that three-day weekends are simply the best. What could possibly put one over the top? A three-day weekend trip to Key West, of course! But to make it epic, you’ll need the perfect Key West itinerary — put together by an insider, someone who knows what makes this island tick.
Well, dear reader, here it is — my ultimate guide to visiting Key West for a weekend.
Capt Zak's Ultimate Key West 3 Day Itinerary
Is three days enough to visit Key West? The answer depends on how much you want to see and do, of course. Every trip to Key West, whether you’ve done it once or a dozen times, takes on its own shape. Will you spend your time diving the reef or boating out to the sandbars? Will you be landlocked due to rainy weather or hunting air conditioning to hide from the August sun? Will you remember day one at all or be responsible for what happens on day two?
All of these troubles and concerns can be alleviated with a good plan. So, if you’re coming to Key West for a weekend, here’s an itinerary to keep you out of too much trouble.
Day 1 in Key West — Slow Down to Island Time
So you walk off the plane at EWY. Where do you go? What do you do? Do you have to walk to town? Where’s the bar? What country are you even in?
Calm down. First step: grab a Key West pink cab and head into town. There’s always a line of them parked at the airport, ready to give confused visitors a ride. And they’re knowledgeable enough to get you into town without getting too lost. Why are they pink? No one knows, but it’s Key West. We roll with it and don’t ask pressing questions about the taxi’s gender identity here. Also, you’re in the Conch Republic. Thankfully, there’s never a line at customs.
Hopefully, you’ve lined up a place to crash for the weekend. My recommendation: The Saint Hotel in Old Town, right on Eaton Street. It’s a few steps from Duval, and the place is beautiful. After checking in, check out the Key West happy hour specials at the Burgundy Bar inside the hotel. It’s dark and seedy and luxurious; try the octopus special and a few espresso martinis.
Time to move on! Willy T’s is just across the street, and there’s probably some live music. It’s a tradition to staple your dollar bill on the wall or ceiling. Or floor. We don’t judge.
Happy hour is probably winding down by now, and if the sun is getting low in the sky, head to Mallory Square, widely considered the best place in Key West to watch the sunset. It’s home to the world-famous sunset celebration. Amble your way to the end of the island and enjoy the view as the sun sets over the Gulf of Mexico. Snap some selfies and then head back to your hotel.
Wait, don’t go straight back to the hotel! What are you, 85 years old? And even if you are (we don’t judge), you’re in Key West! Hit up two or twenty more hot spots on Duval on your way home (again, no judgment!). If you haven’t done the landmarks, Captain Tony’s and Sloppy Joe’s are right there.
Stop by Walgreens on Duval to grab a couple of bottles of water. Then, head back to your room and regenerate for the next day. Day 2 in Key West is going to be a big one!
Day 2 in Key West — Hittin' the Water and Makin' the Most of It
Rise and shine; day two is here! Grab breakfast at Sandy’s Cafe, which has the absolute best breakfast sandwich on the island. Lots of coffee will help clear your head from those twenty bars you hit on the way home last night.
Time to switch it up and change islands. Get a cab or ride share and head over to Oceans Edge on Stock Island. It sounds far, but it’s only about ten minutes away. Hop aboard my boat, the Casual Monday, and I’ll take you on the best sandbar excursion — or wherever you want to excursion to. Snorkeling, mangrove eco-tours, dolphin watching, whatever — we can do it, it’s your charter. Just say the word.
Once we get back to land, you’ll probably be ready for a late lunch. Hog Fish Grill is right around the corner. It’s the sort of seedy Keys seafood place you dream about. Grab some grub, then head back to your hotel for a shower and to get ready for the night on the town.
Another night on the town, you ask? Did you already do that? Well, I’ve got some surprises for you. If you’ve got time, take it easy with a few art galleries, a museum, or some souvenir shopping on Duval.
For dinner, check out Lola’s Bistro on Simonton. It’s an incredible spot and consistently ranks #1 on Captain Zak’s Guide to the Best Restaurants in Key West, but you have to show up for the 6:00 seating, and it’s cash only. God only knows what they’re making; the menu is verbal, so go with an open mind! After dinner, how about making a pit stop the next block up at Bobby’s Monkey Bar for some late night karaoke?
Day 3 in Key West — Last Call
Day 3 has arrived. It’s always sad to start heading home, but make the most of your last few hours on the island. Head to la Grignote for a glass of bubbles and some honey cake. Their Benedict is killer, and it’s the perfect spot for some people watching from the balcony. This is what Key West is all about.
After the boating and late nights, a massage probably sounds pretty good, doesn’t it? Ocean Key Spa is the place to go, and it should properly zen you out for the flight back home. Then, it will be time to pack your bags and check out of the hotel.
The airport in Key West is small, so TSA is usually a breeze. Except when it isn’t, know what I mean? There’s a lot of construction at the airport, too, so there’s not a lot of space to stand around and wait right now. But there is a cocktail bar called Last Call, and that’s where I would go while I wait for boarding to be called.
How Many Days in Key West Is Enough?
Let’s face it, three days is not enough time to truly embrace the island lifestyle that is Key West. But we can’t all live on the island full-time, and three days is better than no days. So…
If you’ve got a weekend to spare
and need to taste the island air,
head to Key Weston a double-dog dare
and wear some flair
watch out for the bear
with nary a care!
Ok, so poetry isn’t my strong suit, but driving the boat is. Call today to book your Day 2 Key West adventure of sandbar hopping, snorkeling, or just cruising because you haven’t seen Key West until you’ve seen it from the water.
