Girls’ Trip to the Florida Keys

Note: This trip occurred in February, pre-COVID-19.

While we were in Ohio seeing family and friends at Christmas, one of my friends mentioned taking a girls’ trip to the Florida Keys for her 40th birthday. Our other girlfriend was going to be six months cancer free at about the same time, so it seemed like we had plenty to celebrate!

Between work and kids and life, we only had a long weekend available, plus we were sneaking in our stay at my friend’s sister’s second home on Marathon Key. Their parents were headed down to spend a week at the house, and her sister was generously letting us pop in for a few days between her renters and her parents.

If you’re looking for a place to stay in the Keys, I would highly recommend renting their place! It’s in a great location, it’s a beautiful and very large home with multiple rooms and amenities, and there’s both a private pool/hot tub as well as public water access right in their backyard. I had taken the red eye from Seattle to Fort Lauderdale so I was also enamored with the gigantic second story back porch overlooking it all where I took an amazing hammock nap our first afternoon. Check it out!

We managed to squeeze a lot in during our short trip: relaxing at the house, working out on the water, enjoying wildlife, visiting Key West, taking a charter boat to the Everglades, and walking the beach. Every single day we tried to go parasailing, but it was too windy– we’ll have to save that activity for next time!

I have to admit, I’m not much of a beach person– I don’t love hot weather, and I can only take laying around in the sun, even with a good book, for so long before I’m itching for something to do. Give me cool hikes through the mountains any day of the week. However, this trip was incredible–the weather was beautiful (70s and windy/sunny), we had a perfect balance of relaxation and activities, and more than anything I felt renewed being able to catch up with two very dear friends that I don’t see nearly enough anymore. Here are a few highlights from the trip!

Feeding the Tarpon

My friend’s sister recommended we split up our drive from Fort Lauderdale to Marathon Key by stopping to feed the tarpon at Robbie’s on Islamorada. We purchased a bucket of small fish, signed our lives away (no feeding the pelicans, no feeding the manatees, etc.), headed to the dock, and began dangling the fish out over the water, scared to death the giant tarpon would grab our hands along with the food!

The anxiety builds as you watch the tarpon swimming back and forth under you, waiting for one to suddenly burst up through the water to grab your fish. The tarpon weren’t the only problem — there were pelicans EVERYWHERE and they became extremely aggressive, trying to steal fish from the buckets when you were least expecting it. The workers kept shouting for people to hold their buckets up in the air and walking around the docks, gently pushing the pelicans back into the water. We had one terrifying moment where a pelican charged Tanika, beaking her in the back of the leg, reaching around my hunched over frame, and stealing the fish I was holding in my hand before I even knew what had happened!

We could only take a couple rounds of this before handing the remains of our bucket to some little kids who were having a blast, our nerves completely frayed.

The saving grace of the experience was a gigantic manatee that kept popping up in the area where we were dangling our fish, looking for a bite. If I’ve ever been that close to a manatee, I don’t remember it — what an incredible creature!

Kayaking / Paddleboarding

In addition to having the water right behind the house where we were staying, there were kayaks and paddleboards available for our use! Our second morning we dragged them down to the beach out back and launched them into the canal so we could explore the surrounding area.

It was Tanika’s first time paddleboarding and the perfect place to do it–there weren’t any boats around and the water was fairly calm. We ended our activities with a soak in the hot tub — not a bad way to spend a morning!

Visiting Key West

We spent one afternoon and evening exploring Key West, which was only an hour drive from where we were staying. Thankfully we were there early enough in the year and early enough in the day to avoid the crowds and parties, which really weren’t of interest to us.

We found free parking only a few blocks away from the 1847 Key West Lighthouse and I was surprised to learn that neither of my friends had ever been in a lighthouse before! I feel like we climb every lighthouse we encounter when we travel!

We had great views of the surrounding area but only a short time to explore — we had arrived only 30 minutes before they were closing for the day. The employee was very kind and gave us the ‘local discount’ since we were having such an abbreviated visit. Well worth the stop on a clear day!

My friends humored my bibliophile sensibilities and joined me for a docent-led tour of the Ernest Hemingway House and Museum. The house and grounds are beautiful — we were not surprised to see that they were setting up for a wedding reception in the main yard! — and I enjoyed hearing about Hemingway’s time living in the Keys.

Of course my favorite part was seeing all of the friendly six-toed cats!

We walked all over downtown Key West, and I loved the architecture, palm trees and flowers, chickens/roosters, and overall vibe. I could see the appeal of the island life!

My favorite moment of the day was popping into Judy Blume’s bookstore, Books & Books, and finding her there dusting the shelves! We were all completely starstruck and had to nudge one another to talk to her and ask if she would autograph our purchases. She was absolutely charming — she recommended books for Candis and Tanika’s children, she introduced me to her first adult novel, and she insisted we pose for a picture together. Favorite moment of the trip!

From trying the Papa Doble at Captain Tony’s — the original Sloppy Joe’s Bar — to eating conch fritters to enjoying a drag show to indulging at a late-night dessert bar — Key West was everything I hoped it would be and more!

Taking a Boat Ride to the Everglades

Candis found a pontoon boat tour that would take groups out to the Everglades and then to a sandbar for snorkeling. When we arrived for our tour, we discovered we were the only people who had booked and that the day was a little too windy for snorkling–the water wasn’t clear and unless you were proficient, you were likely going to be swept around by the water too much for general enjoyment.

Instead, our captain offered to take us out on his smaller boat for a more intimate and personal tour. The three of us climbed in the front and he took us to some amazing neighborhoods full of mansions, to his local marina where we got up close and personal with some more manatees, and then out to the Everglades to explore among the mangroves.

He was full of local knowledge — I felt like we were on a guided tour rather than just a chartered ride. We ended our tour by the sandbar and dipped into the water for a moment — he was right that it was a little too cool and choppy to be relaxing, and I was glad we took his recommendation for how to spend our time on his ship!

Walking Sombrero Beach

Our final morning we packed, grabbed some breakfast, and made a quick drive over to Sombrero Beach for a final walk along the water before we needed to hit the road for Fort Lauderdale. It was early and it felt like we had the place all to ourselves!

What a wonderful weekend away with my girls — can’t wait to do it again!

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