Things to Do in Key West, Florida

You feel part of this mural when you walk by
You feel part of this mural when you walk by

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.

Views of the Florida Keys en route to Key West
Views of the Florida Keys on route to Key West

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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.

Bikes are a great way to get around Key West
Bikes are a great way to get around Key West

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.

Roosters are king in Key West
Roosters are king in Key West

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 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.

Main floor common area - The Gardens Hotel
Main floor common area – The Gardens Hotel

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 reading The 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.

Hemingway's House & Museum - notice the cats sleeping on the master bed
Hemingway’s House & Museum – notice the cats sleeping on the master bed
Lush gardens surround Hemingway's house
Lush gardens surround Hemingway’s house
The pool Hemingway's wife built at a cost of $20,000
The pool Hemingway’s wife built at a cost of $20,000

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.

You have to try Key Lime pie while in Key West
You have to try Key Lime pie while in Key West

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.

Lots of photography opportunities at the Butterfly Gardens
Lots of photography opportunities at the Butterfly Gardens 

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.

A public beach within walking distance of Old Town Key West
A public beach within walking distance of Old Town 
Looking out to sea near the southernmost point of the continental US
Looking out to sea near the southernmost point of the continental US
Nature and technology collide
Nature and technology collide

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.

The southernmost point in the continental US - open to the public
The southernmost point in the continental US – open to the public
Colourful houses can be seen all through old town Key West
Colourful houses can be seen all through old town Key West
Lots of flowers add to the appeal of the little houses
Lots of flowers add to the appeal of the little houses
You feel part of this mural when you walk by
You feel part of this mural when you walk by
Watch what type of tree you plant in your backyard!
Watch what type of tree you plant in your backyard!
Abandoned building on the pier
Abandoned building on the pier
The quiet part of the pier - a world removed from the cruise ship dock
The quiet part of the pier – a world removed from the cruise ship dock
Birthplace of Pan American World Airways
Key West is the birthplace of Pan American World Airways

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 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.

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. 

Truman used The Little White House as a vacation home and as a functioning White House
Truman used The Little White House as a vacation home and as a functioning White House

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.

Kayaking quiet channels near Key West
Kayaking quiet channels

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. 

A sunset sailing tour with Danger Charters
A sunset sailing tour with Danger Charters

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.

Lots of vendors at Mallory Square at sunset
Mallory Square is full of vendors at sunset

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.

Neighbourhood restaurants
Neighbourhood restaurants in town

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.

There are beautiful white sand beaches – with interesting shells
There are beautiful white sand beaches – with interesting shells in Dry Tortugas National Park

Location map of things to do in Key West, Florida

                                                         

Further reading on things to do in Florida

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Top things to do in Key West, Florida

 

  1. I’ve been reading and re-reading these, as we are headed there soon for about the same amount of time. Can I assume from this that you can take pictures in the Hemmingway house?

  2. What an action packed 48 hours this was. I love this since that’s usually our time frame for many cities. It’s great that you were able to do many varied activities and sightseeing. We’ve toyed around with the idea of Key West and your visit is inspiring. Beautiful photos!

  3. Great tips on Key West. I went there a couple of summers ago. I’d love to go to the Truman House. I think there’s a lot more to do in Key West than people realize. Love your photos too!

  4. I visited the Keys in Nov 2014. Although I didnt get as far as key West I loved the area. I expected it just to be beaches and sea but I was thrilled to find lots of nature and national park area.

    I hope to get back to this area again, it was a wonderful trip.

  5. Sounds like the kind of place I could spend a week in quite easily. Haven’t been to Florida in almost 30 years – maybe it’s time for a return visit. Great pics, and a real ‘take me there’ post. Love it!

  6. Love Key West! Thanks for sharing your experience! We went a bit further and did the Fort Jefferson camping experience which was fabulous, so this is definitely something I would recommend if you have more than 48 hours next time.

    So glad you had such a great time!

  7. To be honest, Key West wasn’t somewhere I ever particularly wanted to visit. But now, after reading your post, I’m inspired to stroll through the Old Town in the morning. Before taking part in some adventure sports in the afternoon.

    1. @Matthew Florida is not my first choice for a vacation but John’s Mom goes every winter so we wanted to check in on her this year – and so bookended the trip with a visit to her and through Key West and kayaking in the middle.I think Key West is well worth seeing – I just found the drive long and rather uninspiring to get there.

  8. It sounds like you had a lovely stay and packed quite a bit into 48 hours! We have only been to Key West on a cruise stop and it was so hot and crowded that we didn’t see anything. I would love to go back and have the time to explore.

    1. @Lisa We packed a ton in 48 hours but that was ok. I really enjoyed walking through all of the old town and the museums are so worth visiting. I don’t think I’d want to see the city on a cruise boat stop – though that may just be me.

  9. 1 a.m. really is too early for those roosters! 🙁 I’ve often thought about visiting Key West and other places in the Keys. My cousins lived there for a long time, but I never quite made it to see them. Visiting Hemingway’s House has been on my list for quite a while, but I didn’t know about some of the other highlights you mentioned. Birthplace of PanAm? Cool! Afraid I’m not a big cat fan, but I’m sure I could deal with them just fine. Love your photos, as always.

  10. WoW you for sure did a lot in 48 hours. I have been to Key West about 20 years ago. I still remember the sunsets which were amazing. Your post makes me want to go back.

  11. I absolutely LOVED this post, Leigh!!! You know I’ve been waiting patiently 🙂 I would love to see Hemingway’s place and the Little White House. How come you can’t take photos?? Is there super secret squirrel stuff in there? That photo you framed with the birds on the post and the microwave tower and satellite is brilliant. Loved the southern most point pic…I would so dig standing there and realizing that Cuba is only 90 miles away! Now, a couple things because you know this is one of my bucket list places. I’m highly allergic to cats. Two, I am not an early morning person and a rooster or other noises that would walk me prior to when I wanted to get up would likely make me quite grumpy. Do they have hotel properties down there that possibly would ensure some quiet. I know I can look it up but I want to know from you directly first hand. This was soooooo much fun for me to read and thank you! 🙂

    1. @Mike I think there are some resort type hotels down near the water where I did’t see any roosters – or cats. And anywhere outside of old town Key West, though lacking in the same charm, would most assuredly have little in the way of rooster noise.

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