Key West with a Kid: What We Loved, What We’d Skip, and What I’d Do Differently Next Time

If you’ve been following along, you know we had to pivot our spring break plans this year. What started as one trip turned into Key West, Florida, and honestly, it ended up being one of those trips you don’t forget.

Not perfect. Not cheap. But full of memories.

And isn’t that kind of the goal? key west with a kid

Day 1: Late Arrival and a Slow Start

We got in late Friday and kept it simple. Dinner at our resort, Margaritaville Beach House Key West, and I will say this, the food was surprisingly good. After a travel day, that is all you really need.

We spent a little time at the pool, soaked in that warm Florida air, and called it early.

Day 2: Walking Into Old Town and Why You Should Too

Saturday morning started with breakfast at the resort, which quickly became our daily routine. Convenient, good, and yes, a little pricey. But welcome to Key West.

We decided to walk to Old Town instead of Ubering, and I am so glad we did.

The beach walk alone was worth it. Along the way we stopped at the African Cemetery at Higgs Beach and took a quiet moment to pay our respects. We continued on to the pier where we spotted a baby nurse shark just cruising along like he owned the place.

We passed gardens, historic churches, and more charm than I could take in at once. I have a thing for old churches and history, so I was a very happy camper.

We walked past the Ernest Hemingway Home, but skipped going in because my 9 year old would have been bored senseless, minus the six toed cats.

The rest of the day was shopping. Lots and lots of shops.

That evening we had dinner at La Trattoria Old Town. I thought it would be like the one in Naples, and I was wrong. The food was still good, but the Naples location is in a league all its own.

We walked a bit more that night and then called it because my feet were done.

Day 3: Boat Day, Sandbars, and a Lesson Learned

We headed to the marina for a 5 hour excursion booked through Sunset Watersports. The plan was kayaking and a sandbar stop. The weather was iffy at first, but it turned into a really nice day on the water.

The crew made the experience. They were incredible with my son and even let him help, which made his entire day. The captain was just okay, but the crew more than made up for it.

We did not get as much time kayaking through the mangroves as I expected, but it was still beautiful to see. The sandbar was relaxing once you adjusted to the water temperature, and the lunch they provided was actually really good. They also had unlimited sodas, juice, beer, and wine.

All in all, it was a great trip, but next time I would book a private charter even though our group was only 28 people.

When we got back, we grabbed an Uber, took cold showers, more on that in a minute, and got ready for dinner.

Dinner that night was at Dorada, and I am so glad I booked it. My husband said it might be the best steak he has ever had, and we have eaten some incredible meals around the world. That says a lot.

Day 4: History, Wildlife, and That Key West Sunset

We were originally planning to go snorkeling, but after talking with the captain the day before, we decided to skip it. The wind and storms had shifted everything, and visibility would not have been great.

Fun fact, Key West is home to part of the Florida Reef, which is the third largest living coral reef system in the world. It stretches over 350 miles and is filled with marine life, but conditions have to be just right to really enjoy it.

Instead, we pivoted to a slower day.

We visited the Key West Aquarium. It is small, but I appreciated seeing the rescued sea turtles and the other marine life up close.

From there we walked to Fort Zachary Taylor Historic State Park, which ended up being one of my favorite stops. Built in the 1800s, it played a role in both the Civil War and the Spanish American War. Between the history and the ocean views, it was absolutely worth the visit.

We spent the afternoon at Mallory Square for the sunset celebration. Street performers, music, people gathering together, and then that sunset.

It is one of those moments where everything just slows down for a minute.

Dinner that night was lackluster, so we will just leave it at that.

Where We Stayed: Margaritaville Beach House Key West

Let’s talk about the resort.

The pros were the staff, the welcome, the onsite restaurant, the daily cookies, and the free shuttle to Old Town. The shuttle runs every hour on the hour from the resort and picks up every half hour from downtown, which was incredibly convenient.

The cons were hard to ignore.

Three full days with no hot water. We had to have the smoke detectors removed because they were blinking nonstop. The AC ran constantly trying to keep up. And the beds were so firm I have honestly slept on softer floors.

The room itself was nice and spacious, but comfort matters.

The first day we were told it was a power issue. The second day it was a part being ordered. The third day, as we were checking out, we were told it should be fixed. We still took a cold shower that morning.

To their credit, they refunded our resort fees, but I will be reaching out to corporate. Had we been told upfront, we would have made a different decision.

I know many people love this resort, but unfortunately, this was our experience.

Things to Know Before Visiting Key West with Kids

If you are planning a Key West family vacation, here are a few things I wish I knew ahead of time.

Everything is farther than it looks. Walking is one of the best ways to explore, but those quick walks turn into miles very quickly, so wear comfortable shoes.

Food is expensive. Every meal felt like a bit of a splurge, especially at dinner. Worth it in many cases, but definitely something to plan for.

Weather matters more than you think. Wind and storms can completely change water activities, so having flexible plans helps a lot.

And make reservations. Key West is busy, especially during spring break, and the best restaurants fill up fast.

Final Thoughts on Key West

We had three full days, and I am pretty sure we did not even scratch the surface of what Key West has to offer.

It is not the cheapest trip we have taken, especially when it comes to food, but it was filled with memories we will not forget.

And honestly, when we are not navigating everyday mom life, we are usually planning our next beach escape.

And this one will be hard to top. 🌴✨