These are some of the best things to do in Key West, Florida if you only have 48 hours. Fortunately we felt like we’d made the most of our time without feeling like we were rushing from activity to activity. If you have a third day be sure to book a trip to Dry Tortugas National Park, accessed via a high speed boat. It’s fabulous.
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Our first impressions driving into Key West didn’t mix with my preconceptions of loud floral shirts, Cuban cigars and Hemingway. Instead we were treated to traffic jams, roosters and cats – and the odd view of turquoise blue water and tiny islands making up the Florida Keys.
Ditch the car when you arrive in Key West
First lesson – ditch the car and don’t plan to use it again until you leave Key West. The old town is immensely walkable and if that doesn’t appeal, then rent a bike or take a taxi. Bikes are an especially great way to get around.
Bring ear plugs and a lint brush
The roosters start crowing early – as in 1:30 AM early one day. A lint brush wouldn’t hurt either if you have a fondness for cats – as they’re everywhere. Hemingway’s house alone is still home to about three dozen of them – all named after famous people.
It’s a good life as a cat in Key West. Some of the cats in Hemingway’s house are the descendants of Snow White, the original cat
Book hotels in Key West well in advance
If it’s high season, book your hotels in Key West well ahead of time. We stayed at the Gardens Hotel – a lush oasis within walking distance of all the sights. It was mentioned in 1000 Places to See Before You Die.
We didn’t spend a lot of time in our room – opting to explore as much of Key West in the limited time we had. Although it’s got a reputation as a party town, that’s not what we’d come for. Still the rooms are well-appointed, the pool area lovely and there’s a great vibe to the place.
I’d also recommend The Perry Hotel Key West at the Stock Island Marina Village just outside of Key West. It’s got a fabulous aesthetic, a stunning pool and a fantastic restaurant – Matt’s Stock Island Kitchen & Bar.
Take a tour of Hemingway’s Home
Our guide brought him to life. Not only did we learn of Hemingway’s writing schedule – 700 words per day starting first thing in the morning, but we learned the stories behind the urinal disguised as a water fountain and the fights with wife #2 related to the building of the $20,000 pool.
Taste test Key Lime Pie
The Florida Keys are renowned for their Key Lime pie. Key West is no exception. I am in awe at the variety you find – from sickly sweet to perfectly balanced with the right amount of sweet and sour.
Be sure to visit Kermit’s Key Lime Shoppe and try Key Lime Pie on a stick. As you make your way through the shop you can sample key lime peanuts, cookies, jellybeans and more. You will have no problem finding a gift for your petsitter or dogsitter at home.
Visit the Key West Butterfly and Nature Conservancy
Near Hemingway’s house is the Key West Butterfly and Nature Conservancy. On a rainy day, it’s a particularly good place to visit. Everyone we saw on the rainy day that we visited sported a big smile – all happy to see so many butterflies and birds in one place.
Wander the back streets of Key West
Wander the back streets and discover the real charm of Key West. Tiny, beautiful homes in a rainbow of pastel colours, often festooned with gardens and planters make up the majority of the buildings in the old town. We wandered down to the pier, checked out the southernmost point in the continental US and eventually landed at the Little White House where Truman vacationed and worked.
Visit the southernmost point of the continental United States
Take a tour of Truman Little White House
We hadn’t planned to visit Truman Little White House but I am so glad we did. Years ago I’d read Truman by David McCullough so this President became far more real when I could see where he lived and worked. Boasting a modest interior by today’s standards, it cannot be photographed but life inside the house came alive with the stories told by yet another superb guide.
Go kayaking in the Florida Keys
In a previous blog, Florida Keys Kayaking near Key West, I recommended a half day kayaking trip – ideal for families and anyone looking for some soft adventure. Paddle through a mangrove tunnel, admire the wide variety of seabirds and iguanas (an invasive species), and ooh and aah over the price tag of the homes you paddle by.
Take a sunset cruise – one of the top things to do in Key West
One of my favourite things to do in Key West was the sunset cruise, especially the late afternoon/early evening wine and cheese cruise offered by Danger Charters. There are several companies offering similar tours but the concierge at the Gardens Hotel suggested we go with this company – as they don’t overload the boat.
I couldn’t believe how many people were crammed on some boats (see photo below). Some of them are loud party boats – whereas ours was not.
Check out Mallory Square at sunset
If you’re not a fan of cruises, then I’d recommend at a minimum walking down to Mallory Square to enjoy the sunset with all the other tourists in Key West. There is lots going on – with juggling acts, vendors hawking all manner of things including fresh coconut milk.
Be sure to find your spot on the seawall well before sunset to get the best view.
Dine in a neighbourhood restaurant
Key West is loaded with great restaurants. The ones I loved the best were those in a real neighbourhood and well off the main street. Some of the best ones with great reviews as of late 2019 – both in and outside the core include Bien, Little Pearl, Pepe’s, BlackFin Bistro and Onlywood.
If you have more than 48 hours
What I’ve described is what we were able to comfortably see in Key West in 48 hours. Of course there are more tours you can do, there’s shopping which we did none of and we didn’t ride a bike. I did do a trip to Dry Tortugas National Park on another trip and HIGHLY recommend it.
I wish we’d had time to do the gravestone tour – as I would have liked to see the gravestone with this epitaph – written in Spanish that translates as – At least I know where you’re sleeping tonight.
It was a great trip, but if I were to do it over again I would opt to fly to Key West to avoid the traffic. It’s a lovely little airport.
Further reading on things to do in Florida
- 14 Essential Stops on the Miami to Key West Drive
- Myakka State Park: A Haven for Nature Lovers
- A Stop at Bahia Honda State Park in the Florida Keys
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Thank you to Florida Keys Tourism for providing complimentary passes to museums and tours.