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48 Hours In Key West, Florida

48 Hours in Key West, Florida

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.

Views of the Florida Keys en route to Key West

Views of the Florida Keys en route to Key West

We had only planned on 48 hours in Key West, Florida. Here’s what we did that allowed us to feel like we’d made the most of our time without feeling like we were rushing from activity to activity.

Roosters are king in Key West

Roosters are king 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, as 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

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

Booking Hotels in Key West

If it’s high season, book your accommodation well ahead of time. We stayed at the Gardens Hotel – a lush oasis within walking distance of all the sights. Mentioned in 1000 Places to See Before You Die, it was pleasant but not peaceful. The building directly across from our room was being torn down so the noise level beginning at 7 AM was most unwelcome. Hopefully that doesn’t last much longer.

Main floor common area - The Gardens Hotel

Main floor common area – The Gardens Hotel

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.

On the first day it rained off and on so we decided to make that our museum and exploring day.

Don’t miss the tour of Ernest Hemingway’s Home and Museum. I have been intrigued by the man since reading The Paris Wife last year. 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

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

Hemingway's pool

The pool his wife built at a cost of $20,000

Close to Hemingway’s house is the Six Toed Cat Cafe. (Many of the cats living at Hemingway’s home have six toes; most cats have five.) It is here we had our first piece of Key Lime pie on the trip. Watch out. It’s rich and one piece is plenty for two people.

Key Lime Pie from the Six Toed Cat Cafe

Key Lime Pie from the Six Toed Cat Cafe

Nearby is the Key West Butterfly and Nature Conservancy. On a rainy day, it’s a particularly good place to visit. Filled with people, I didn’t see a single soul without a big smile on their face, 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 in Key West

From there we wandered the back streets and discovered the real charm of Key West. Tiny, beautiful homes in a rainbow of 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 Key West

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

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

Mural in Key West

You feel part of this mural when you walk by

Trees get monster sized big in Key West

Watch what type of tree you plant in your backyard!

Abandoned building on the pier in Key West

Abandoned building on the pier

The quiet part of the pier - a world removed from the cruise ship dock - Key West

The quiet part of the pier – a world removed from the cruise ship dock

Birthplace of Pan American World Airways

Birthplace of Pan American World Airways

We hadn’t planned to visit The 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

You can easily spend a couple of days walking, visiting museums and taking long lunches.

Key West is equally well known for its water adventures. 

In a previous blog, Discovering the Florida Keys by Kayak, I recommended a half day kayaking trip – ideal for families and anyone looking for some soft adventure.

Kayaking near Key West

Kayaking near Key West

And equally fun is a wine and cheese sunset cruise. We enjoyed a late afternoon/early evening with 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).

A sunset sailing tour with Danger Charters

A sunset sailing tour with Danger Charters

That’s what we were able to comfortably do 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 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.

Key West is loaded with restaurants. What I particular liked was their location – often within a neighbourhood and well off the main street.

Neighbourhood restaurants in Key West

Neighbourhood restaurants

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.

Click on the photo to pin to your Pinterest board.

48 Hours in Key West, Florida

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

Leigh McAdam

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

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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