Key West, FL – Summary of Experience

You step out of the airport into a colorful catwalk in Miami and the air is already sticky in May. We’d just come from Norman, OK – where a rare stretch of rain accompanied a somber occasion amongst family – and we welcomed the warmth. At first. By the time we took a shuttle from the airport to a small rental company called Fox and stood in the humid heat for about 1.5 hours before getting a car we were ready to hop into the nearest ocean. But we had a 4 hour drive to Key West so we opted for air conditioning.

We had no issues with our Fox rental – but apparently we’re the anomaly. A quick yelp search revealed some shocking experiences people had with this cheap car rental company. If you opt to go with them, expect looooong wait times and audit all the paperwork, do your research, and take lots of pictures of the car. We were reading horror stories of people getting charged fees for random things 5-6 months down the line. We haven’t received any additional bills yet (insert nervous lol) but will update here if we do.

– About Fox Retal

At the rental company, we got to know a couple who had decided on Fox rental on the whim. We told them about some of the reviews we were reading and advised them to book through Enterprise. They did, and once we got our car we drove them over to the dealership. I only mention this because Sam and I have been working on building relationships with the strangers around us. Building human connection – which is ultimately a major driving force in our lives.

We drove through the Florida Keys at sunset. The two-lane road that leads you over the collection of islands wasn’t as impressive as I imagined! Most of the way there the freeway is flanked with trees and shabby buildings (and one amazing Italian restaurant we stopped at) but the occasional panoramas of the oceans as you cross a high bridges helps immerse you into your environment.

Kimpton Key West
Winslow’s Bungalows

Read more below about our stay at this luxury hotel.

We arrived at our resort at 9:30pm – about 30 minutes before the front desk intended to close. The staff here was wonderful – they called once at 7pm to ensure we were still en route and assured us if we arrived after 10pm, they could share the night manager’s number with us and they would come let us into our room. The first room we received was small and very cramped feeling with no windows. It did have a little deck that was very cute but the view from it was of the parking lot lol. It felt more like a boujee hostel than a boutique or luxury resort. We asked the front desk if there was any flexibility for our booking and they were able to accommodate our request! This was huge for me because I usually don’t complain or share my concerns – I typically take what I get and that’s that. But learning to speak up and just ask was able to provide me with the boutique feeling I’d hoped to get from this hotel.

I’m obviously super pleased with the staff and their nimble adjustment but I will leave that note here – that there’s a potential if you book that your room it just a small master bedroom in one of the buildings. If we were going to book here again I would request a room with a little front yard (that’s what we had) or an upstairs room (some of the rooms we saw upstairs looked great!).
The location of the hotel was superb – we were in walking distance of Duval street which is like a little main street with a whole lot of restaurants, bars, and beach shops.

Kimpton Key West, Winslows Bungalows
Overall Rating

Rating: 3.5 out of 5.

We loved our stay in Key West and the Winslow Bungalows provided the perfect boutique experience. The only detractor for me is the price we paid versus the value – this is also just a Key West thing as it is just a pricey place to visit but for the off-chance of getting a cramped room and no real good sunset or sunrise views it missed the mark on some of the things that are really important to us. I think for a 5 star rating I would need to see a significant decrease in price or a more generous inclusion of amenities (for example, you could buy drinks at the pool but for 8ish ounces you were down $10). Stay here if price isn’t an issue, you’re looking for a convenient and centralized location, you like hanging out at the pool for the peaceful experience, and you love plants. There’s hella plants here and they. are. incredible.

We spent most of our days really vacationing. You know, not planning too much, taking our time lounging, etc. We got coffee from Cuban Coffee Queen every morning (read more about that here!), walked Duval street, swam and lounged at the pool and ate really good food. We were in awe of the amount of greenery in Key West and enjoyed looking at the diverse plant life growing out of people’s yards and spilling into the streets. There’s also a ton of wild chickens running amuck and I loved seeing those guys!

Fury Water Adventures

On our third day in Key West we signed up for an Ultimate Adventure packaged from a water sport company called Fury which was incredibly fun. We rode Jet Skis, parasailed, got lugged around on a banana boat, played around on a inflatable “water park”, and tried snorkeling for the first time (read more here!). The whole package was only about $160 per person which is a steal considering we jet skii(iiid?) in Santorini, Greece for like $500, and this one came with an open bar at the end and free (although subpar) lunch offered. If you’re in Key West, you have to do this. It’s perfect for all age groups and especially if you haven’t experienced some of these activities – it’s a great introduction to each of them.

Beaches in Key West

We anticipated finding a beach would be fairly easily in Key West but the end of Duval Street where we spent most of our time was all docks and piers! We ended up going to a beach in Fort Zachary Taylor State Park. We saw a beautiful sunset here and took a dip in the ocean. Later on in the trip we drove around and came upon a few other beaches but lucked out with some stormy weather lol.

By our fourth day there we were nursing some gnarly sunburns with dollops of aloe lol. The Fury boat offered complimentary sunscreen (thick, thick sunscreen – like applying clay to your skin) and although we reapplied several times, our fragile Portland skin succumbed to that sweet, ruthless Floridian sun. CVS was just a block away from our hotel and was perfect for aloe, sunscreen, snacks and cheap wine.
As we recovered in our hotel, Sam had to take care of some work issues that came up so I took the opportunity to visit the Hemingway museum – one attraction she was 0% interested in seeing.

The Ernest Hemingway Home & Museum

As a writer and fan of Hemingway’s first book The Sun Also Rises, I was excited to visit this museum – although to be fair, I was uncertain of what to expect.
Cats. Expect cats.

Apparently, a sailor gifted Hemingway a 6-toed cat and its been spawning off six-toed cats ever since. During my visit there I spied at least a dozen cats and one, I’m fairly certain, had six toes (see first image above!). There was also a replica of an artifact gifted to Hemingway from Picaso (of a cat). And there were portraits of his many wives in the kitchen, which in retrospect was probably kind of a tasteless placement. But that’s it. Besides it being a beautiful house it wasn’t particularly awe-inspiring, and I guess I wouldn’t expect a Hemingway home to be. If you don’t have time to fit this one in your Key West itinerary, I wouldn’t lose sleep over it. Unless you love cats. Definitely stop here for cats.


All in our, our experience in Key West was wonderful. As the southernmost part of the US and its relative closeness to Cuba, there are some wonderfully exotic influences here and the architecture was absolutely stunning. This trip did exactly for us what we were looking for – lots of good food and drinks, a little bit of adventure and a whole lot of relaxed vacationing. It was the perfect unwind from a long stretch of stressful months at work all leading up to an emotional pinnacle with my family.

What’s been your favorite Key West experience? What are you most excited to see in your upcoming trip?

We’re also starting to crush on Florida – any other beautiful cities worth exploring? We want to hear from you!

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