Switching Gears at Opal Key Resort
On the 2nd, we packed up and made the hop across town to our second home base: Opal Key Resort. Now, “across town” in Key West is all of two miles, but when you’re traveling with kids and suitcases in the Florida heat, an Uber is absolutely the right call. No regrets there.
Opal Key sits right on the cruise port at Mallory Square, which meant a completely different vibe from the quieter Reach Resort we’d left behind. This was the bustling heart of Key West — street performers, tourists milling about, and the energy that comes with being at the island’s main hub. The good news? It was summertime, which meant cruise traffic was minimal. We only had one ship come in on our last day there, and honestly, the relative quiet was a gift.
The resort itself was lovely. The pool was beautiful, and we definitely took advantage of it. After the more secluded feel of our first few days, it was nice to be in the thick of things, checking out Mallory Square and scoping out options for water activities.
But there was something else we were tracking besides jet ski rentals.
When a Tropical Storm Crashes Your Vacation
Here’s the thing about traveling to the Keys in summer: hurricane season is very much a reality. We’d been watching Tropical Storm Diane (I’m pretty sure it was Diane) develop as we were packing to head down, hoping it would turn, hoping it wouldn’t amount to much.
It didn’t turn.
Days three and four at Opal Key became our hurricane days. There was flooding, there was wind, there was a lot of rain. But I want to be honest here — it wasn’t catastrophic. The storm hit far enough offshore that we caught the outer bands rather than the brunt of it. We were up high enough that the flooding didn’t affect us directly, and while we spent more time in our room than planned, we made the best of it.
Mark and Noah actually grabbed the bikes on the second storm day and rode back toward The Reach to check out the flooding and storm surge. They reported back on impressive water levels and, surprisingly, a bunch of kite surfers who were absolutely living their best lives in those conditions. There’s always someone who sees a storm and thinks “perfect wind.”
We went out when we could, stayed in when we couldn’t, and reminded ourselves that flexibility is part of the adventure.
Comedy break
Amid the tropical storm we needed to get out of the room and life seemed to be continuing as normal in the little town so hubs and I opted for a quick date night. He spotted a comedy club a block from our hotel that had a show that night. Given it was spur of the moment without a reservation, we were at the mercy of the doorman. After a about 10 min, he found us two seats at the bar wall at the back. Did’t matter to us, we were just happy to be out of the house.
The show was pretty good. Local talent and one headliner. We had a few good laughs and then had to sprint home amid the downpour. At least the rain was a warm one.
Snorkeling, Kayaking, and Hurricane Holes
By the 5th, the skies had cleared and we were itching to get back on the water. We booked a combo snorkel and kayak tour with a different outfit this time — Danger Charters.
Now, here’s some real talk: snorkeling two days after a hurricane pushes through is not ideal. The water was churned up, visibility was poor, and we didn’t see a whole lot beneath the surface. But you know what? It didn’t matter. The sun was shining, the boat was beautiful, and we were finally out there again.
The real highlight was the kayaking portion. We paddled around some of the outer mangrove islands, picking up little critters along the way and exploring at our own pace. Our guide taught us about “hurricane holes” — sheltered spots among the mangroves where boaters would tuck their vessels to ride out storms. Given what we’d just experienced, it felt especially relevant.
After we got back, we did what any self-respecting hammock enthusiasts would do: we grabbed our hammocks and headed back to Fort Zachary Taylor for some quality relaxation time. Sometimes the best part of a trip is simply swaying in the breeze.
The Jet Ski Highlight
Okay, I have to be honest — I don’t remember exactly which day we did the jet ski tour. The hurricane kind of scrambled our mental timeline. But whenever it happened, it was hands-down the highlight of the entire trip.
We rented through Fury again (they’d been great for our snorkel trip in part one but there is also another in the same area, Sebago), and this time we got a guided jet ski tour. Here’s what made it special: Noah, at 14, was old enough to drive his own jet ski whith me on it.
Mark paired up with Lia, and I rode with Noah. I drove for a bit to get us started, but then we switched, and that kid took over with the biggest grin I’ve ever seen. He’d driven jet skis on lakes before, but this was the open water around Key West. For a teenager, it was absolute heaven.
Watching him navigate the waves, confident and capable, while the Keys stretched out around us — that’s the kind of moment that makes all the planning and expense worth it.
Eats
Since we were in hotels, we were eating out for dinner every night. We didn’t really plan where, we just walked until something looked good. Some were worth a second try, like El Meson de Pepe. Holy cow was their food good. First night we ate inside, second we sat on the patio ouside and listend to the live Cuban music. Hot and sweaty but perfect.
A few other favorites were First Flight which had a very aeronautic themed vibe. They had vintage TWA flight decor through out the entire restaurant. Ramshead Southermost was one we hit while out bike riding around. We’d just come back from the beach on the bikes and it was threating to storm again so we pulled off here for eats.
Blue Heaven was also a highlight. Walking on their back patio was like walking thru a jungle. Very Key West vibes with live music, a slight breeze, strong drinks, and good food. Oh, and the biggest piece of key lime pie to date.
We did skip one of the staples - Margaritaville. It was packed and we’d been there before in the past. It was worth trying some of the other amazing options.
There is one last place that I wish I could find the name of. It’s a literal hole in a wall in a neighborhood not that far from The Reach that had the most amazing cuban! We orderd two to go and rode over to the beach to enjoy. I cannot for the life of me find the name though.
The Journey North
On our last day, we had to head back to Fort Lauderdale for an early flight. Mark grabbed a rental car from the airport, and we decided to turn the drive into its own adventure. Why rush when the Keys give you so many reasons to stop?
We bridge jumped off Sugarloaf Key — always a thrill. We stopped at Islamorada for tarpon feeding and grabbed lunch while we were there. And because we’re us, we made a stop at Bahia Honda State Park (Pentacamp area) for more hammock time, where we got to meet some Cassiopeia jellyfish — those upside-down jellies that just chill on the sandy bottom like living decorations.
By the time we rolled into Fort Lauderdale, we were tired, sun-soaked, and ready for home. The flight back was uneventful, which is exactly what you want from a flight back.
The Honest Truth About Key West in Summer
Here’s where I get real with you: Key West in the summertime is tough. It’s hot. It’s humid. Air conditioning isn’t everywhere, and unless you’re spending all your time in or on the water, you’re going to be uncomfortable.
We also agreed, as a family, that two weeks was too long. We could have done with two or three fewer days and not felt like we missed anything. Key West is charming, but it’s small. There aren’t a ton of beaches, and the ones that exist you can see pretty quickly. Biking around was the right call, but the water activities — two snorkel trips, the jet ski tour — added up fast. Combined with eating out every night, this trip ended up more expensive than we’d planned.
Would I go back? Absolutely. Would I go in summer again? Probably not. And would I book two weeks? Definitely not.
But those jet ski grins, the mangrove kayaking, the hammock time at Fort Taylor, the bridge jumping on the way home — those memories are worth every sweaty, stormy, over-budget moment.
Tips & Info
- Best time to visit: Winter or early spring. Summer means heat, humidity, and hurricane risk.
- How long to stay: 3-4 days is plenty for Key West itself. Any longer and you’ll be stretching for activities.
- Getting around: Rent bikes. It’s the best way to explore the island and way more practical than a car.
- Water activities: Book through Fury for reliable snorkel and jet ski tours. For combo trips (snorkel + kayak), shop around for outfits that offer packages.
- Hurricane season: Runs June through November. Have a flexible itinerary and travel insurance, and keep an eye on forecasts.
- The drive back: Don’t rush through the Keys. Stops at Bahia Honda, Islamorada, and Sugarloaf Key are worth building into your return trip.
- Budget tip: Water activities and dining out will be your biggest expenses. Plan accordingly and maybe pack some snacks.
- For families: If you have teens, the jet ski tours where they can drive are absolutely worth it. Lifelong memory material.