Our trip to the Florida Keys to honor my dad was perfect. And it was a beautiful mixture of many things at once. 

It was moving. It was celebratory. It was emotional. It was significant. It was dark. It was light. And yet, it was also really fun — just how my dad would have hoped it would be. Throughout our three nights in the Keys, we often told each other that my dad must have been so happy to be looking down on us all together doing all the things he would have wanted to be doing with us too.

(If you haven’t read my post about my dad, here it is: “Remembering my dad.”)

Celebrating my dad in the Florida Keys

When my dad, Larry Pinder, passed at the end of last year, we knew right away that we wanted to honor him by spreading his ashes in the Florida Keys. There was really no question. Although, clearly, the middle of winter during a pandemic, when Dave, Brady and I were still living across the country in California and preparing to move, was not the right time. But last week was a much better time to come together and make it happen. And we are so glad we made it happen just as we did.

Why the Keys, you ask? My immediate family spent a week almost every summer for nearly 20 years in a row going to Islamorada in the Florida Keys every late July or August. We stayed at the same couple of places, we went to the same few restaurants, we did the same fishing and boating trips. And it was very special.

As a kid, I wanted us to go to new places every year and was never pumped about repeating the Keys. But looking back now, I love that we had that routine, that tradition and that special place that we could go back to over and over to enjoy. And this is something Dave and I have talked about creating for our little family moving forward in some way too.

Before this trip, I hadn’t been to the Keys in several years. Although I went to two bachelorette parties in Key West in the last 10 years or so, that’s just not the same. The rest of the Keys are a lot different than Key West. And Islamorada was always our low-key fishing-village Key of choice.

The last time we went to Islamorada as a family of four was probably in 2007 or 2008. As my brother, Matthew, and I got older and had regular jobs and lives, it was never as easy to put that trip together. But now I’m wishing we had tried a little harder to go even one or two more times.

(Here’s my dress, and here are my sandals.)

During this trip, we stayed at a VRBO in Key Largo, just a few minutes from Islamorada. And while we were there, we visited many of the major stops that we would have done in family trips of the past. But this time, we also had Dave, we had my brother’s wife, Stephanie, and we had Brady with us too. It was great to show them places we had gone before, and it was great to all see some new places together as well.

And as the combination theme of this trip continued: We honored our old memories, but we absolutely made some new ones. We were in the moment having fun, but we were also remembering why we were there.

Spreading my dad’s ashes in the Atlantic Ocean

On our first full day in the Keys, we rented a boat in Islamorada, and went out on it for our official “memorial service” for my dad. The wind was blowing and the seas were really rough, so we didn’t make it out to Alligator Light, a landmark about five miles out off the coast of Islamorada that we always visited by boat in year’s past. But we could see Alligator Light in the far distance, so at least there was that.

Even though all six of us were on the boat that day, Matthew, my mom and I did a private tribute to my dad toward the middle of our boat outing, once we found a calm enough spot to stop for a bit. I pressed play on a special playlist I had made specifically for this day, with some of my dad’s favorite songs and songs that we felt were significant and meaningful for us during this time. (And if you’re a Spotify user, you can actually see the playlist I made for my dad here.)

Then, we each spent some quiet time speaking to my dad as we took turns pouring his ashes into the blue-green waters and watching them quickly get swept away in the current. It was beautiful. But it was sad. And it felt like a million emotions rushing out of me during those moments. We said goodbye to my dad, we hugged, we sat in silence for a bit, and we felt all the feelings — our first time coming together to grieve him since he left us in November 2020.

Yet, after we spread his ashes and had that big release, I felt this very somber sense of peace come over me, which I was not expecting and can’t describe. I’ve never really dealt with major loss in my life and this has been my first experience. And because of the timing of my dad passing, and then our move across the country and COVID restrictions, I do think that much of my real processing was a bit delayed and drawn out.

But this event, this memorial and this time provided a chance for a cathartic release for me. In fact, even throughout the first half of the boat ride, as we were heading away from the coast and the waves were rough, I sat silently, in the front of the boat going through so many emotions as water splashed onto my face and the wind blew my hair. I actually felt so good, yet also so sad at the same time.

Coming back to the Keys and doing something that I had never done except with my dad as the captain of our boat (Matthew drove the boat this time), felt bizarre. Every time Matthew slowed the motor down to say something, I truly kept thinking I would hear my dad’s voice — because that’s the only voice I’ve ever known to hear out in the Atlantic over choppy water coming from the captain’s seat — pointing out landmarks and leading the way into the unknown.

Once we spread his ashes, we all toasted to my dad, and then we pulled up to a sandbar, anchored our boat and got off to hang out. It couldn’t have been a more casual, more informal or more fitting “reception” as a way to honor him. 

(World’s squintiest pictures, but still worth sharing. And here’s my bathing suit.)

From there, we decided to leave the choppy waters and we cruised around the harbor side of the water. And Matthew even stopped the boat to show Brady how to fish for a little bit. They didn’t catch anything, but Brady was so happy to have tried. My dad always wanted to introduce Brady to fishing, and while he may not have been able to do it himself, this was the next best thing.

Our adventure out in the water that day was my favorite time of the whole trip. I replayed so many memories from my childhood, I sorted through so many feelings, and I soaked up the natural, beautiful and intense conditions of the deep blue-green ocean. An ocean that is vast, powerful, inviting and captivating, and the ocean that my dad’s remains now call home forever.

Spending time as a family in the Keys

I am so grateful and thankful for my family, which is not a big family at all. We do not see each other all together as often as we should, and we are spread out in three states. But when it matters, we are there for each other. We all had a great time together during this trip — soaking up all the moments. And Brady is such a fan of having a few extra audience members around to applaud all his tricks and antics. (Not sure where he gets this … me. He gets it from me.)

And, in addition to having all that quality time together as a small group, my cousin, Karen, and her husband, John, drove down from the East Coast of Florida to join us to hang out and pay tribute to my dad as well during this trip. We all had dinner together one night, then Karen and John joined us for a visit to Theater of the Sea and lunch in Islamorada the next day too. 

(I set up my phone on a self-timer for some of these blurry group shots. I think those are the best kind of group shots. We took this one before we went to dinner on the first night. Here’s a similar version to my dress.)

Visiting the Theater of the Sea in Islamorada

Let’s talk about sea life!

The Theater of the Sea is a place we went many, many times during Keys trips growing up. And I didn’t expect to be wowed by it this time, now that it’s been maybe 20 years or more since I’d last been. But this time, we had Brady and Stephanie and Karen and John in tow. And even though it was super hot, we had a fabulous time here. We saw a sea lion show, a bird show, we went on a bottom-less boat ride, we saw alligators, crocodiles, sea turtles, and we watched an absolutely amazing dolphin show.

Our entire group was so enthralled with the dolphin show, because there was a dolphin trainer who got into the water with the dolphins and did all sorts of crazy tricks with them. She was so good. The dolphins were so good. I don’t think I had ever seen anything like it before, actually. It was also set to music, and the whole experience was awesome.

I know people can be strange about zoos and aquariums. But Theater of the Sea is known for rehabbing animals and providing a home for sea life creatures that need care. They use friendly husbandry training with all the animals too — a quality place, and a family-owned one as well.

It was really hot that day, but well worth a visit. And if you ever go to Islamorada, you need to catch the dolphin show here for sure. You can also swim with dolphins, but we didn’t do that. I’ve never actually done that before and am totally fine watching the dolphins from afar.

Visiting all of our favorite Keys spots and finding new ones too

Our trip was three nights long, and we did one big activity every day, then went back to our VRBO to nap, shower and chill, before a few activities at night. We went out to a delicious dinner every single night, and I ate so much good seafood. I had a lot of mahi mahi (the star of the show in the Keys), shrimp, tuna and a lot of cheesecake too, because big desserts are a vacation essential. I also had key lime pie once, because that’s also a Keys staple, but it’s not quite as good as cheesecake, in my humble opinion.

(Another blurry self-timer snap on a dock, before we went out to dinner on our last night. Here’s a similar version to my dress.)

For some landmarks: We ate at Bayside Grille, Sol by the Sea and The Green Turtle Inn for dinner. We ate at Wahoo’s for lunch, and we got take-out lunch from City Hall Cafe. All were really good.

We also went to Shell World, a huge shell store, where Brady got a stuffed marlin toy. And we went to Bass Pro Shops, where I bought a hat. Both places are ones that we always swung by on family trips of the past.

We found that not a lot has changed in Islamorada over the years, because all of these places looked exactly the same. It was actually really comforting to see that.

Brady was a total champion on this trip. He does great on the airplane having been a traveler since before we could even speak, but we weren’t sure how he would do on a long car drive. And we were pleasantly surprised that he has no problem doing long car rides, as long as he can talk the entire time to someone.

He also loved the VRBO (there were seashell decorations everywhere and he kept sorting the shells), he loved the boat, and he was a complete trooper when it came to staying up past his normal bedtime each night at dinner.

We’re pretty strict with his bedtime at home and on trips, but figured we’d let it slide a bit on this significant trip, and it was totally fine. Brady happily sat at the restaurants with some tiny headphones watching his shows on Dave’s phone and eating whatever we gave him to eat. It gave us adults a chance to chat about whatever we wanted, eat our food and connect. And it’s not something we usually do, but it sure worked like a charm for this trip.

Closing thoughts on our Keys trip

This trip was a big undertaking. The Keys are not the easiest accessible place to visit. And that being said, making this trip happen required a lot of travel for us. We flew down to my mom’s house in Southwest Florida. We stayed the night there and left Rudy with my mom’s dog for a dog-sitter to come and stay with them for three nights. We rented a big SUV to accommodate our group, we drove across the state of Florida, and we picked up Matthew and Stephanie from the Miami airport. We coordinated schedules, time off, logistics and so many other things. And it was worth every bit of effort, and I’d do it again in a second. 

I truly came away with a little bit of peace in my heart for my dad. I introduced Dave and Brady to the beauty that is the Florida Keys. And I made some new memories with my family too. I’m absolutely grateful that we could do this trip. 

Thank you for reading this post, my friends. Have a wonderful rest of the week!

Other posts you may like …

• Remembering my dad
• All about our adults-only Jamaica beach trip
• What I’ve learned from traveling with a baby across the country multiple times

Questions of the day

When was the last time you had a moving experience that was cathartic for you?

Have you ever been to the Florida Keys?

Is there a destination that you’ve visited many times over the years?