Ah, the Florida Keys, the legend of Buffet songs, and the promise of a lazy day. Sun and sand and clear waters tease our imagination when we think of the Keys.
Our family felt the temptation of this spit of land at the base of Florida, and by the lure of cheap and convenient tropical vibes in early November. Catching a very affordable ticket to Miami courtesy of Spirit Airlines, we said goodbye to the uninspiring Virginia winter skies and headed to the Keys for a long weekend.
Our first stop out of Miami was Biscayne National Park. Yet after a few days of adventure and movement there, we made our way out of town and down the Keys.
This wasn’t our first trip to the Keys. Over thriteen years ago, Mr. Family Trip and I did a similar trip, all the way down to Key West, while I was pregnant with our first.
At the time, we thought our vacation in Key West was enjoyable, but it didn’t really resonate much. Maybe it’s not the place to go while pregnant. The culture there focused primarily on outdoor bars, drinking, parties, and a loud adult atmosphere starting at early hours and ending at earlier hours. It may be different now, of course, but we couldn’t shake that experience and ultimately decided given that and its distance from Miami, we would opt for a different Key this trip.
We eventually landed in Islamorada for a family vacation in the Florida Keys.
Since I made a pledge to always be honest on this website, I have to admit that while a family trip is never anything to regret, this vacation was a tad disappointing.
Setting airfare aside, the prices for food and services in Islamorada surpassed some of the international destinations we’ve visited, with less quality upon delivery.Â
We also found ourselves frustrated with amenities, or lack thereof, and the lack of things to do that felt both appropriate and affordable for a family of four. While our intention was to lay on the beach and relax, maybe swim, and definitely get a pina colada or two from the poolside bar, we didn’t find much of this readily available.
If you’ve spent any time in the Keys, you know there aren’t many real beaches. The resort beaches are manmade and, if not kept up by hauling sand in by truckloads, they disappear. This isn’t the place to wade into the ocean from soft, sandy beachfront ramps.
The pools at the resorts we tried weren’t anti-kid, but they weren’t large and our kids were either very bored very quickly or in the splash space of adults trying to drink, sun, and converse.
Restaurants were overpriced and underwhelming for the most part if we could even find ones that seemed kid-friendly.
All being said, we still loved being together in the sun. We managed to find some ways to enjoy the trip and were glad we tried this again, this time in a different phase of life.
But I also seriously questioned whether the Keys are for families in our stage of life at all. The parties we encountered, while of all ages, were more of the “spring break” variety – there with friends and partners to throw down, drink heavily, play loud music at the pool, and let loose. God love them, but we’re just not there right now as we’re hauling our teenager and tween around with us.
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Maybe we picked the wrong Key, or maybe the wrong time of year? And it wasn’t a hopeless trip, of course. So if you decide to take advantage of the kind of cheap airline tickets we did and head to the Florida Keys with the kids, here’s my best advice…
Pick your island carefully – traffic in the Keys can get intense! Miami Airport to Key West is 3.5 hours without traffic, but you can pretty much count on traffic. Getting just from Islamorada to Key West can take over two hours.
Dry Tortugas National Park is quite a haul. For us, it was simply too much for a long weekend adventure.
Use bikes. The Keys are flat, and there is a nice sidewalk even along the main thoroughfare. Find some bikes and use those to get around. You beat the traffic and have a lot of fun doing it!
Where to Stay in Islamorada (with Kids)
Given how hard resorts were to find that met our criteria, we ended up at The Bayside Villas by Islander Resort. (The only Airbnb we found had us too far up the Keys, in Key Largo.) But we wanted a kitchen and, hopefully, a beach.
The Bayside Villas gave us a small pool right outside our front door. And while it promised a beach, it didn’t really have one. The little sandy area had dwindled to basically a small patch and was overgrown enough to be rendered inaccessible.
We did enjoy the amount of space we got at the “Villa”, although it was desperately in need of some care and maintenance and the furniture was noticeably uncomfortable. However, we had a Villa with a porch that overlooked the water, and that was the most amazing place to have coffee in the mornings.
There was also a little marina area for boats to dock. While we never saw a boat there, we did see some manatees in the warmer waters and that was magical.
Another plus of the Bayside Villas was the access to the Islander Resort across the street. The Islander is the sister property and has a large beach area, bikes to take out (for free), a large area for basketball and beach volleyball (which our kids loved), and two pools complete with poolside bar service and food.
Again, the beach here isn’t really swimmable. However, having access to the large area with lounge chairs (and that view) was fantastic!
Sidenote: The Islander does not allow outside food or beverages anywhere, including at the beach. But the service is slow (it’s a big beach) and the drinks are really expensive. We found those two things limited how much time we ended up spending here.
Family Fun Activities in Islamorada
Our favorite adventure was kayaking out of and then enjoying Robbie’s of Islamorada. This marina/restaurant had all of the Florida Keys feelings we’d been hoping for. Particularly fun was watching the folks who paid to feed the large tarpon fish (see our Instagram story for more).
We didn’t eat at Robbie’s because of the time of day, but the service was friendly and the kayak rental was easy.
Sidenote: Indian Key pops up on all the lists as a great thing to do as a family; however, it is only accessible by kayak. And during our days in Islamorada, no one would rent kayaks to a family intending to paddle out there because the conditions were too dangerous.
There are more excursions available, of course. We just decided not to do them because, again, of the cost compared to the perceived value.
But here are some popular options:
- Theater of the Sea
- History of Diving Museum
- Snorkeling (we had just snorkeled a few days earlier)
- Scuba diving
- Fishing
- Sailing
Still determined to find a beach (missing our Wrightsville Beach days, I am sure), we popped over to Anne’s Beach.
While this seems to appear on nearly every single list of “top things to do in the Florida Keys,” there is a critical piece of information I never saw shared –
If you go to Anne’s Beach while the tide is in THERE IS NO BEACH. This area is highly susceptible to tides. So if you want to hit it when there is actually a beach, you need to check the tide charts.
We didn’t know this, so we had only a spit of sand to sit on. The kids still enjoyed getting wet and splashing around, but we were all a little disappointed.
In general, we found ourselves unsure of how best to enjoy the sun and be outside with the unique challenges each activity, resort, and excursion offered. Our teenager ended up reading quite a bit inside, and to be honest, we found we put on football and watched sports on the uncomfortable couch more often than we normally would simply due to lack of enthusiasm for the options.
Where to Eat in Islamorada
Of course, prior to even leaving on this trip. we had promised the kids some famous key lime pie. We elected to stop at Midway Cafe and were not disappointed. I loved this little spot!
The outdoor picnic tables combined with the lush vegetation and seriously fluffy pie were perfect. This was definitely the best thing we ate while down in the Keys.
For other dining options, again, we weren’t particularly excited by any of the menus we saw when viewed with prices. We did ultimately walk over to the Islamorada Fish House since the location was so great for us. The sunset view was lovely – the restaurant perched out over the water. It was also memorable to partake in the (free) feeding of the fish! While the service was great, the food was lackluster and overpriced. This was definitely a spot for appetizers and a cocktail, but I wouldn’t pay for dinner there again.
There are international destinations that are tropical in nature, not much more expensive to get to, and then cheaper and far more impressive once the traveler arrives. Costa Rica (where I traveled for 10 days years ago), Guatemala, and Puerto Rico (where I’ve now been twice) pop into mind immediately. But I am sure there are more. The Florida Keys benefit from convenience and comfort for Americans, which is why we chose it, but I am not sure we’re interested in a third trip.
Of course, we don’t regret our trip to the Florida Keys with our kids at all. I think the biggest takeaway was that Mr. Family Trip and I were shocked at the price tags being slapped onto everything while there didn’t seem to be any pride or investment in the quality of what was provided to the customer.
Well over five million visitors come to the Florida Keys every year and 74% of them are Americans who live in the lower 48 states. Those tourists (like us) spend around $2.4 billion a year on lodging, food & beverage, excursions, transportation, and shopping. Maybe given all the business, the Florida Keys don’t have to do much? Demand has obviously driven prices up. The question is: what drives that demand, and is it merited?
The Florida Keys have a heavy tourism economy, even after Irma destroyed so much of the infrastructure. The story of the Florida Keys is one of recovery and strength, too. In 2017, the Hurricane slammed into the area and destroyed homes, took lives, and left many financially ruined. What exists now is a testament to the resilience of what we can do as humans.
Yet it also feels it is still struggling to come into its own, to determine what to do with the demand and the desires of millions of tourists.
The Florida Keys have so much amazing potential.