Famous for its link to Ernest Hemingway, colourful, quirky houses, fantastic sunsets, along with an interesting history – cue President Truman’s Little White House, Key West offers the visitor plenty to see and do, even over just a few days. Described are some of the top things to do in Key West, the southernmost city in the contiguous United States with an off-beat vibe and some very good Key Lime pie.
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. But if you’re willing to explore and you have two to three days you can experience the best Key West has to offer.
If you have the time or inclination, be sure to book a trip to Dry Tortugas National Park, accessed via a high speed boat. It’s fabulous for its history, swimming, and white sand beaches.
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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 for your time in Key West
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.
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 theGardens 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 recommendThe Perry Hotel Key Westat 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.
Tour Hemingway’s Home in Key West
Don’t miss the tour of Ernest Hemingway’s Home and Museum. I have been intrigued by the man since readingThe Paris Wife.
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 pet sitter or dog sitter 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.
There’s a small greenhouse filled with exotic birds, two flamingos, 50 – 60 species of butterflies and tropical plants. You could do the visit in twenty minutes, but the birds will keep you entertained so allot 30 -40 minutes.
It’s open 365 days a year from 9 AM – 5 PM. Kids are very much welcome but strollers are not in the Conservancy. Admission is in the $13 to $14 range depending on how old you are. Kids three and under are free.
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 in Key West
Apparently there can be long line-ups to visit the southernmost point in the continental US but if you time it right, you should be able to wander right up and get your picture taken.
It’s interesting to see the waves breaking over the top of this marker in storm footage.
Take a tour of Truman Little White House
We hadn’t planned to visit Harry S. Truman Little White House but I am so glad we did. Years ago I’d readTruman by David McCulloughso 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.
This was the winter White House for 175 days of Truman’s presidency from 1946 to 1952 Other Presidents have used the Little White House too – in much the same way Camp David was used. John Kennedy, William Taft, and Dwight Eisenhower all spent time here.
This historic building served as the winter White House for President Truman beginning in 1946. He spent 175 days of his presidency here, and documents issued from the Little White House read “the White House, US Naval Station, Key West, Florida.”
Tours are offered every 20 minutes beginning at 9:30 AM and finishing at 4:30 PM, with the last entry at 4 PM. It is open 365 days a year. Tickets are $23.44 per adult and $10.21 for kids 4 to 12. Under four are free. Military personnel get a break on the adult price. The VIP White Glove experience is $645 for up to 6 people.
Kayak in the Florida Keys near Key Wes
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 my favourite things to do in Key West
One of my favourite things to do in Key West was yo go out on a sunset cruise. I especially enjoyed 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 in Key West
If you’re not a fan of sunset cruises, but you love a good sunset, then I’d recommend walking down to Mallory Square, located on the waterfront in the Old Town area of Key West.
There is a daily sunset celebration that draws hundreds of people beginning two hours before the sun sets. This is THE place to go to enjoy the sunset.
It’s one of the most popular things to do in Key West, so be sure to arrive well before sunset and stake out a good spot on the seawall so you get a good view.
The Mallory Square area is vibrant with lots going on including juggling acts, clowns, and vendors hawking all manner of things including fresh coconut milk. Look for arts and crafts for sale, and check out the street vendors. The people watching is darned good too.
Mallory Square looks out to the Gulf of Mexico so the views are sublime especially when the brilliant oranges and reds light up the sky as the sun goes down.
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 2023 – both in and outside the core include Cafe Marquesa, Garbo’s Grill, Little Pearl, Blue Heaven, Azur, and The Lobster Shack.
If you have more than 48 hours in Key West
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.
Location map of things to do in Key West, Florida
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
- Kayaking in Florida on the Turner River
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