florida keys
Islamorada
the Trip We Take Every Year
Slow days on the water, three generations under one roof, and the house in the Keys we still talk about.
There are a few places our family goes back to without ever really deciding to. The Keys are one of them.
We live in Fort Lauderdale, and the Keys are an easy, exciting spot for us to get away. It's a couple of hours down US-1 with everyone in the car, no airport, no packing for a flight, and that alone makes traveling with little kids and our dog feel seamless. We go twice a year, sometimes more, and land somewhere between Key Largo and Marathon in whatever rental house has room for all of us. My parents, my aunt, the kids, the dog. I think the reason we keep going back isn't anything you'd put on a list. It's the slow days on the water. Grilling while the kids are still in the pool. Swimming together at that hour when the light goes soft and nobody wants to be the one to say it's time to come in. Those are the memories I have from growing up, and the Keys are where we've been able to give the same ones to our kids without getting on a plane.
Last October at Mahi Key
Last fall we booked Mahi Key in Islamorada through Latitude Key for a long weekend, and it turned into one of our favorite trips we've taken as a family. It was three generations this time, my husband and me, our two kids, my parents, my aunt, and the dog, and somehow it never felt crowded.
The house sits right on the water with its own little stretch of sand, a pool, and a dock, and honestly that was the whole trip. The views from the bedrooms are absolutely beautiful, overlooking the bright blue hues of the water. We cooked most of our meals and ate outside while the kids went back and forth between the sand and the pool until someone got hungry. My son fished off the dock with his grandpa in the mornings, we kayaked every single day, sometimes twice, and by evening everyone had drifted onto the porch, a little sunburned and in no hurry to do anything about it.
I take a lot of photos on these trips, and we've rented a lot of homes in the Keys. It's important to us to have a clean, beautiful home because it's always in the background of our family photos, and that was another reason I loved Mahi Key and so many of the homes Latitude Key has to offer.
We're also lucky that my sister, Kristen, comes on almost every one of these trips, and she happens to be a professional photographer. It means our family photos from the Keys look the way the trip actually felt, which I don't take for granted.
What we actually do. We keep it simple down there. Over the years we've settled into the same few things every trip, partly because they're easy and relaxing with little kids, but mostly because they've turned into our traditions. The kids know what's coming, and they look forward to it all year.
Robbie's. Every trip, without fail. The kids feed the tarpon off the dock and spend the entire time scanning the water for sharks, which is a little chaotic and exactly why they love it.
Grandpa's boat. My dad brings the boat down, so we get out on the water for at least a day, a slow ride out to a sandbar and lunch on the boat. Nothing fancy, and the kids talk about it for weeks.
Kayaks. Mahi Key had them at the house, and they got used constantly. If your rental has kayaks and paddle boards, that alone will fill an afternoon with kids.
Grilling. We pack a cooler from home and grill most nights. It's easier with little ones, and dinner at the house with the water right there beats most restaurants anyway.
I get asked about rentals in the Keys a lot, so here is what I'd tell a friend. Mahi Key was clean, new, and updated, with a nice pool and a real beach. The Latitude Key team was easy to reach the whole time, which matters more than you'd think when you have three generations and a dog in one house. And the little things made a difference: there were bikes and toys for the kids already there, which meant less to pack and more to do.
If you're going with little kids
A few things I've learned over the years:
Book a house, not a hotel. Especially with more than one family. The pool and the dock do the entertaining.
Enjoy the calm mornings before the sun rises. It’s absolutely beautiful. And of course the colors of the sunsets are stunning.
Plan one outing a day, at most. Robbie's, the boat, a lunch out. Then go back to the house.
Ask about kayaks, bikes, and kid gear before you book. It changes the trip.
Go in the fall. The water is still warm, the crowds are gone, and long weekends are perfect for it.
We'll be back this year. We always are.
💌
Jenn from The Mom Society™
Read more about why we go back to the same places every year in The Family Tradition That Started With One Trip.