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The Best Things To Do In Key West If You Have 48 Hours

The Best Things to do in Key West if You Have 48 Hours

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.

Views of the Florida Keys en route to Key West

Views of the Florida Keys en route to Key West

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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.

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

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.

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

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.

Main floor common area - The Gardens Hotel

Main floor common area – The Gardens Hotel

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

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 in Key West

Lush gardens surround Hemingway’s house in Key West

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 petsitter or dogsitter 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.

Lots of photography opportunities at the Butterfly Gardens in Key West

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 in Key West

Nature and technology collide in Key West

Visit the southernmost point of the continental United States

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

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 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.

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

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.

Kayaking quiet channels near Key West

Kayaking quiet channels near Key West

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. 

A sunset sailing tour with Danger Charters

A sunset sailing tour with Danger Charters

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.

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 late 2019 – both in and outside the core include Bien, Little Pearl, Pepe’s, BlackFin Bistro and Onlywood.

Neighbourhood restaurants in Key West

Neighbourhood restaurants in Key West

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

Click on the photo to bookmark to your Pinterest boards.

The best things to do in Key West if you have 48 hours

Thank you to Florida Keys Tourism for providing complimentary passes to museums and tours.

 

Leigh McAdam is a Calgary based writer, author, photographer and social media enthusiast with over 57,000 followers. Her blog: HikeBikeTravel is frequently cited as one of the top travel and outdoor adventure blogs in Canada.

Author of Discover Canada: 100 Inspiring Outdoor Adventures
Co-author of 125 Nature Hot Spots in Alberta

This Post Has 25 Comments
  1. 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.

  2. 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.

  3. 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.

  4. 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.

  5. 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.

  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. 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!

  8. 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.

  9. 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!

  10. 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!

  11. 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?

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