It all started with a group text that read: “Family beach trip???” followed by the classic thumbs-up emoji from Dad and total silence from everyone else. A week later, we were arguing about which snacks to bring, who was not sharing a room with the snorer, and whether Aunt Cheryl’s parrot counts as a carry-on.
And so began our chaotic, sun-drenched, coconut-scented Florida Keys vacation.
Step 1: Herding Cats, a.k.a. Traveling to the Florida Keys
First things first: getting your family to Florida is no small feat. Between delayed flights, forgotten toothbrushes, and someone insisting on wearing Crocs to the airport (Dad), the journey to paradise starts with a test of patience.
But once we landed and got that first blast of ocean air, even our most dramatic teen went quiet (briefly). There’s just something about the turquoise water and palm-lined streets that says, “Shh, you’re on vacation now.”
We rented a minivan that somehow smelled like both Febreze and hot dogs, cranked up the road trip playlist, and officially began travelling to Florida Keys like the loud, sunblock-smothered squad we were born to be.
Pro tip: stop at the first roadside smoothie shack you see. Not only will you get something cold and delicious, but the photo op with your awkwardly named drink (ours was “Funky Flamingo Surprise”) is prime social media gold.
Step 2: Vacation Goals vs. Vacation Reality
We had big dreams for our vacation in Florida Keys. Kayaking. Snorkeling. Beach yoga at sunrise. Making those matching t-shirts that scream “WE LOVE FAMILY TIME.”
Here’s what we actually did:
- Had a group meltdown over SPF levels.
- Lost Uncle Bob during a jet ski rental fiasco (found him at a tiki bar).
- Attempted one yoga session before collectively choosing naps.
- Took exactly one photo where no one was blinking.
Still, it was perfect in that beautiful, chaotic way only family vacations Florida beaches can be.
Unexpected twist: Our youngest cousin found a hermit crab and named it “Shell-don,” and now he has his own Instagram account with more followers than half of us. He even got a tiny beach hat.
Step 3: The Food, Glorious Food
We learned quickly that a full family is a happy family. And nothing unites a group like the smell of grilled seafood and key lime pie.
Highlights included:
- A Cuban sandwich that made three grown adults cry (happy tears).
- Fresh conch fritters that were suspiciously addictive.
- Watching Grandma challenge a bartender to a mojito taste-off (she won).
Pro tip: If you’re on a family beach florida vacations mission, go heavy on the food stops. Local diners, roadside food shacks, sunset pier dinners, you can’t go wrong.
Try letting each person pick one place to eat. It avoids endless debates and adds surprise variety to your vacation dining (although expect someone to choose a place with animatronic fish).
Step 4: The Great Key West Escapade
Ah yes, the infamous family trip to Key West. We packed everyone into the minivan, drove south, and within 30 minutes someone needed Dramamine, someone else needed a bathroom, and the Bluetooth only played sea shanties.
But Key West delivered.
Between the pastel buildings, roosters casually strolling the streets, and sunsets that looked filtered in real life, it was one of the trip’s biggest wins. We took a boat tour (two people got mildly seasick, it’s fine), tried to take artsy photos by the Southernmost Point, and debated whether or not to get matching henna tattoos (we didn’t—but barely).
If you’re planning a key west family vacation, just accept that the plan will go sideways. But also that sideways might be better than the itinerary ever could’ve predicted.
Step 5: Sandcastles and Philosophical Debates
Somewhere between beachside naps and watching the littlest cousin declare himself “Lord of the Crabs,” we realized something: this chaotic crew? Pretty amazing.
We had hours-long beach hangs with spontaneous shell-collecting competitions and deep convos about whether dolphins are just wet dogs. Every sunset turned into an Instagram photo shoot, complete with filters and passive-aggressive caption debates.
If you’re looking for ideas for family vacations in Key West Florida, it’s this: less structure, more sunscreen, and an openness to whatever weird magic the Keys decide to throw your way.
Best discovery of the trip? A secret beach spot only locals seemed to know about. We found it thanks to a friendly stranger at a kayak rental place. Proof that sometimes, talking to strangers is a good idea.
Step 6: Takeaways, Tan Lines, and Truce Talks
By the end of the week, we were sun-kissed, slightly sand-covered, and emotionally hydrated. There were moments of tension (someone accidentally deleted the group photo), unexpected joys (like beach karaoke night), and so many memories that we needed three group chats just to share them all.
Yes, there were sibling squabbles. Yes, Grandma made us all wear matching flamingo hats for dinner. Yes, Dad made a playlist called “Keys to Our Hearts” and played it every single day.
But would we do it again? Absolutely.
Because a Florida Keys vacation isn’t just about beaches or sunsets. It’s about family inside jokes, questionable tan lines, and bonding over the universal horror of shared hotel bathrooms.
So next time you’re dreaming of that perfect Florida Keys vacation, remember: it doesn’t need to be Pinterest-perfect. Just bring your people, your snacks, and a willingness to laugh when things go sideways.
One Last Tip Before You Go
If you’re still debating when to book or how to get there without mortgaging your sanity, pro-tip: sites like My Exclusive Deals are lowkey lifesavers when it comes to flight savings. The more you save getting there, the more you can splurge on key lime everything once you arrive.
Sunburns fade. Memories last. Book the trip.
(But maybe leave Aunt Cheryl’s parrot at home.)