What possessed us parents to take the kids to Key West for a part of Spring Break? I can’t really say, other than it’s an area neither one of us had been to in Florida and well, we are always up for a random adventure so Key West (Hemingway! Jimmy Buffett! Pirates! Shipwrecks! Key lime pie!) sounded like it could be fun. And like all our family vacations, it was a trip to remember.
GETTING THERE
We road-tripped down from Palm Beach in a giant red truck that we ended up getting more intimately acquainted with then we would have imagined. More on that later. However, you can also fly into Key West via Silver Airways (they have a cute pink flamingo logo, but a not-so-cute customer service operation) or on one of the bigger jet airlines (these routes can be seasonal and depending on where you’re coming from, typically involve a stop somewhere.)
WHERE TO STAY
We had initially wanted to stay at Hyatt Centric Key West or one of the Hyatt Residence Clubs in Key West, particularly the Beach Club, which as the name suggests has residence-like accommodations that are perfect for families. But these were all sold-out since we were booking within two weeks of the trip.
If you prefer smaller hotels or just traveling with your partner, Kimpton Hotels has several small properties throughout Key West that are small on space but big on personality and cuteness. These really feel more like staying in a B&B rather than a hotel.
(Good to know: Both Hyatt Hotels are part of the Hyatt Privé program which means you’ll get extra benefits during your stay when you book through a Privé advisor like myself! Here’s more about what I do as a travel advisor. Email me with your dates and rates if you’re ready to book!)
However, the next best for families option and one I’ve actually dreamed about visiting for a while was Sunset Key Cottages, an exclusive property on its own island with a range of accommodations from studio cottages to full residences. We opted for a two-bedroom cottage with a garden view. Yes, it was pricey but it came with a $500 resort credit as well as 25 percent off the room rate.
WHAT TO KNOW ABOUT SUNSET KEY COTTAGES
This is probably the best place to stay in Key West, in terms of luxury and space. It’s accessible only by boat, which runs every 30 minutes, so you have to be ok with boats if you want to stay here. (The ride is 11 minutes from the main marina in Key West and Mallory Square and it’s a breeze!)
The grounds are absolutely charming with cottages dotted all over the island and a main cottage that houses The Latitudes restaurant, a small fitness center, library and lounge. There’s a pool area that’s great for young children and an edge of the island has been carved out as a beach, although it is a little hard and rocky to walk on.
Our cottage had plenty of space with two bedrooms, two bathrooms, two porches and a little kitchen where you can make your own meals. But a real highlight here is that every morning they drop off pastries, juice, yogurt and water for everyone to have. Pulling the bag inside every morning to see what was inside was a real highlight of this stay for our kids.
The pool was within steps of our cottage and it’s great for younger kids, but for the adults, there is no adults-only or quiet pool. The bar and food options are just so-so.
The Latitudes restaurant, however, is a stand-out and is indeed one of the best restaurants in Key West. It’s open to everyone, not just hotel guests, so reservations book up fairly quickly. However if you go early enough you can usually get a great table, especially if you are staying on the property. Be sure to time your meal to the sunset which is absolutely spectacular from Sunset Key.
We didn’t have enough time to try the spa but I did get a run in on the fitness center treadmill. I wanted to run around the island, even though it’s very tiny, but I was told that the residents who own houses on the island aren’t exactly fond of guests running through the streets. Hmm.
All in all, this is a special place not just for Key West but for Florida too, largely because of its exclusivity and location. Watching the rain over the water from the front porch of our cottage with my coffee in hand was a moment I savored immensely. But with cottages regularly upwards of $1,000 a night, it does seem like a very high price to pay for a family vacation in Key West.
If I had to do it all over again, I would have opted for a more family-friendly resort in the middle of the Keys so that we would have had more access to kid-friendly water sports and activities. Then we could have day-tripped to Key West to spend the day there seeing the town and doing activities.
Speaking of activities…
WHAT TO DO WITH KIDS IN KEY WEST
Key West has a bit of a debaucherous side to it, especially on Duval Street where the shops are a little bit pirate, a little bit drag queen, a little bit Doctor Feelgood. But Key West has an incredible history to see, starting with the Ernest Hemingway museum.
My kids are too young to have read Hemingway but they got a kick out wandering around the old house and keeping track of all the cats in the house. (Important Note: The place only takes cash.) I’d also recommend a stop into the Hellings Curry Museum, for a quick history session with one of the friendly docents about Key West’s beginnings.
Here’s a short list of the other things we saw/ate:
The Key West Butterfly & Nature Conservatory: This was so sweet. You can walk through a little greenhouse filled with butterflies. (Must be cool with butterflies landing on your shoulder.)
Ghosts and Gravestones Ghost Tour: Definitely do the night tour, although it’s not that scary. My tween and I were ready to be freaked out by Key West’s most terrible ghosts but it was tame. Except for the Robert the doll story. Eek.
Southernmost Point : This is the giant buoy you always see on the news during hurricane coverage. Lol. There’s always a line for the photo op but if you don’t mind randos in the background of your photo you can take a quickie here.
Rent a Gas Golf Cart: These are so popular in Key West, we had to do it. We rented from HydroThunder and it was $170 for 3 hours for up to 6 passengers.
Hit Up the Random Arcade: There’s a super small arcade on the 2nd floor of the building near the dock where we waited for the boat to go back to Sunset Key. The cruise ships dock near here too, just FYI.
Pop into Moon Dog Cafe: This was right near the Hemingway Home and it was delicious food and rather sweet cocktails. Also, someone’s wiggly tooth started bleeding and caused a commotion involving a lot of tears and napkins and giggles from his older sisters but eventually he calmed down upon learning that dessert would probably feel good for his wiggly tooth. 🙂
Eat Key Lime Anything: We stopped into Kermit’s Key West Lime Shoppe on Duval Street for our key lime fix, although you can get key lime anything everywhere here.
2 THINGS WE DIDN’T DO (and are bummed about)
Since this was a bit of a last-minute trip to Key West right after Easter, we didn’t have enough time to book the Dry Tortugas National Park which is something we plan on coming back to do another time. Dry Tortugas has some insanely cool history, but it is an entire day excursion so just plan for that.
We did however book some water sports including parasailing but we got rained out because well, Florida.
LEAVING KEY WEST
After 2 days and 3 nights we were on our way to Orlando. But because of the rain, Silver delayed our flight about 4 times then cancelled it entirely. So we drove in Big Red, our rental truck, 8 hours up to Orlando. I’ve already blacked out that experience but I remember a stop at McDonald’s, a lot of rain and somewhere near Fort Lauderdale, thanking God that I had packed some random party pack jars of play-doh for my kids to use. Of course, as always I thanked Steve Jobs for inventing the iPad.
BOTTOM LINE
While I always recommend you take the trip, keep in mind Key West itself isn’t exactly the Florida beach vacation you may have in mind. If a resort style is more your speed, look about an hour north of Key West proper for Hawk’s Cay or Isla Bella for family-friendly resorts where you can make a day trip out of visiting Key West but still have all the resort comforts you need.
Need help planning your trip to Key West? Start filling out your trip wish list here and I’ll be in touch!
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