There’s something about arriving in Key West that makes you want to immediately slow down. Maybe it’s the salt air, or the way the palm trees seem to sway with absolutely no urgency. Whatever it is, we leaned into it hard on this trip—and honestly, it was exactly what we needed.
Getting There: The Drive Down
We flew into Fort Lauderdale and picked up a rental car, though we did something a little unconventional: we booked two one-way rentals instead of a round trip. We knew once we got to Key West, we wouldn’t need a car. The island is small enough that bikes and the occasional Uber would get us everywhere we wanted to go.
The drive from Fort Lauderdale to Key West is long—we’re talking around four hours without stops—but it’s genuinely one of the most scenic drives in the country. We took our time, pulling off at a couple of state parks along the way, stopping to stretch our legs and soak in views of that impossibly blue water on both sides of the highway. If you’re making this drive, don’t rush it. The journey really is part of the experience.
Home Base: The Reach Key West
We checked into The Reach Key West, a Hilton property on the southern side of the island. It’s not in the heart of the beachy tourist areas, but the hotel itself has its own beach and a beautiful pool, which turned out to be perfect for us. That first evening, we just wandered around the property, let the kids splash in the pool, and watched the sunset paint the sky in shades of pink and orange. Not a bad way to start a vacation.
One thing I’ll say about The Reach—the sunsets from their little beach are absolutely stunning. We made a point to catch them whenever we could.
Fort Taylor and Getting Caught in the Rain
The next morning, we picked up rental bikes and headed out to Fort Zachary Taylor State Park. This became our go-to spot for the trip. The beach there is gorgeous, and more importantly for us, there are plenty of trees perfect for hanging hammocks.
So that’s exactly what we did. Mark took the kids into the water to play and snorkel while I claimed a shady spot, strung up my hammock, and read my book. We’d brought a backpack cooler (a purchase that proved worth every penny) stocked with snacks and drinks, so we were set for the day.
Well, mostly set.
About three-quarters of the way through our beach day, we noticed the sky darkening on the horizon. Florida summer storms don’t mess around, so we quickly packed up and started biking back toward the hotel. We almost made it.
The heavens opened up about three-quarters of the way back, and I mean opened up. We were absolutely drenched within seconds. But here’s the thing about summer rain in Key West—it’s warm. We were already in bathing suits, already salty from the ocean. So we just kept pedaling, wiping water from our eyes and laughing at the absurdity of it all. People on porches thought we were hysterical, and honestly? They weren’t wrong. It’s one of my favorite memories from the trip.
We headed back to the room to dry off and get ready for dinner and headed back out to Blue heaven where we had our first taste of Key West Key Lime Pie!
We sat on the back patio despite the drizzle and were treated to live music and roosters as we enjoyed our food. The food was good tho not entirely memorable (which, in itself is a good thing)
A Birthday Snorkel Adventure
July 31st was Lia’s birthday, so she got to call the shots for the day. Her choice? A snorkel trip out to one of the outer reefs with Fury , one of the bigger tour operators in Key West. (Sebago was another option along with Barefoot Billys )
We headed out to a lighthouse reef, and while the surf was rougher than we’d experienced on other snorkeling trips, it was still manageable. The water was a bit choppy—more floaty, if that makes sense—but the reef life was incredible. Leah was thrilled, which was really all that mattered.
Afterward, we discovered that our hotel gave us access to the pool at Casa Marina, The Reach’s sister property. Their pool was bigger than ours, and given that it was hot as heck outside (seriously, the only way to stay cool was to stay in the water), we spent most of the afternoon there.
For dinner, Lia chose Louie’s Backyard at the Southermost Hotel for pizza on the water. We grabbed key lime pie on the walk back—because you can’t celebrate a birthday in Key West without key lime pie—and sang happy birthday on the beach as the sun went down. Perfect end to a perfect day.
Exploring the Grid
August 1st was our designated exploration day. We got back on the bikes and just started working the grid, riding up and down the streets of Key West with no real agenda.
We stopped for a coconut and smoothie but then happened upon a park that had coconuts on the ground. The boy decided it would be fun to try to open the coconut
We traversed along the water, found a splash pad to cool off in (it was HOT!) and made our way back to Fort Taylor, but this time we parked the bikes and actually went inside the fort itself.
The path around the fort was beautiful. Typically our trips are big hiking trips with lots of camping. We decided that this trips version of hiking was biking around the island. Again, we just meandered as we went, not really following a path and not always knowing where we were exactly.
If we saw something cool, we stopped and checked in out. This led us to explore the fort more thoroughly as well as the Florida Keys Eco Discovery Center
On our way out of the park, we stopped by RamsHead for dinner in a beautiful open air setting that had elements of aviation decor (which seemed to be favored decor on the island)
After dinner we meandered our way back home for one one last sunset and pool time on this side of the island. In the morning we’d pack up and head across the island to the second half of our trip.
Stay tuned for part 2 - more water sports and a hurricane!
Tips & Info
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Skip the rental car in Key West. Seriously, bikes are the way to go. The island is small, parking is a nightmare, and biking lets you actually see everything. Uber works fine for longer distances or late nights.
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Consider one-way car rentals. If you’re flying into Fort Lauderdale or Miami, rent a car just for the drive down, then drop it off. It’s liberating not having a car sitting in a lot for a week.
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Fort Zachary Taylor State Park is a must. Great beach, great snorkeling, and plenty of trees for hammocks. Bring your own gear and snacks and make a day of it.
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Invest in a backpack cooler. Being able to carry food and drinks with you on bike adventures is a game-changer, especially in the summer heat.
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Budget for eating out. We kept breakfast simple with cereal, milk, and yogurt in a cooler with ice, but lunch and dinner out every day adds up fast. Key West isn’t cheap, so plan accordingly.
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Embrace the rain. Summer storms are inevitable. If you’re already in a bathing suit, getting caught in a warm downpour is honestly kind of fun. Just roll with it.
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Check for sister property perks. Our hotel gave us access to Casa Marina’s pool, which was a nice bonus. Always worth asking what amenities might be included.
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Book snorkel trips in advance for special occasions. Fury and other operators can fill up, especially during peak summer season. If it’s a birthday or special day, don’t leave it to chance.