An Extended Family Trip to the Florida Keys

31 January 2024

You may recall that one of my informal “resolutions” for 2023 was chronicling our trips on EFM within a month of returning home. I’m happy to say that I stuck to it, including for the Articles Club retreat, our road trip to Serenbe and Watercolor, weekend trips to the Biltmore and Beaufort, our anniversary weekend in Charleston, and a long weekend in Boone. It’s a resolution I’m carrying into 2024, so expect more prompt travelogues coming your way in the months to come :)

But before we kick off 2024 travel, there’s one trip from 2023 I have yet to chronicle: Thanksgiving week in the Florida Keys with my extended family. I’d love to share a few photos and details, if you’d like to see!

Like last year’s trip to Watercolor, this Thanksgiving trip was in honor of a major wedding anniversary for one of our parents – in this case, my parents’ 40th (albeit two years delayed!). They graciously paid for most of the trip, and once we jointly decided on the Florida Keys as our destination, they handed over the reins to John to plan the details.

This was an honor and something he was happy to do (travel planning is one of his hobbies!), but it was also intimidating! Though my family travels a well-worn groove to Maine each year, we haven’t done much other group travel. Within our numbers we have different accommodation, budget, and activities preferences, and so it was nerve-wracking for John to feel he was making decisions for a varied group, for a destination we’d never been to, and for an expensive (!) and milestone trip like this.

But of course, he did an amazing job. My expectations for the trip as a whole were exceeded and I think it’s safe to say everyone had a great time.

Where We Stayed in the Florida Keys:

After researching the many (many!) towns that make up the Florida Keys, we settled on Marathon for our home base. We were looking for cottage-style accommodations (versus hotel rooms), which limited our options. We ultimately decided on two side-by-side beach houses at Tranquility Bay in Marathon and were very pleased with the decision.

The beach houses each had a full kitchen, a dining room table, a living room area, three bedrooms, three bathrooms, and upper and lower porches. The upper porches had expansive views of the ocean and the lower porches had wide steps down to a grassy lawn that led to the beach and pool.

Getting to the Florida Keys:

Since we were joining up from various points in the country, getting to the Florida Keys was an adventure in itself. We opted to meet up in Fort Lauderdale on the Sunday before Thanksgiving before caravanning down to Marathon the next day. My sister and her family drove from Charlotte, and the rest of us flew into FLL from our respective home airports: Nashville, Raleigh, and Hartford.

We rented an SUV at the airport and got everyone to the Pelican Grand Beach Resort in Fort Lauderdale, where we were staying the night. We had plenty of time to eat lunch by the pool, wade in the waves on the wide beach, and have an outdoor dinner that night along the canal at Casa Sensei.

We chose the Pelican Grand because it had suites, which is always helpful for traveling with kids, and because it was right on the ocean with a pool and lazy river. We ate breakfast the next morning in their restaurant, which was convenient and yummy, but, you know, expensive :)

After breakfast we packed up and drove about an hour to Gator Park in the Florida Everglades – another National Park to check off our list!

We bought tickets (no reservations required) for an airboat tour of the Everglades and it was… perfect. And perfectly hilarious. Our boat captain was straight out of central casting – everything you could hope for in a gator guide. He had a deep, gravely voice, skin browned from years in the sun, and personal names for all the gators. He expertly guided us through the reedy channels and opened the throttle as we skimmed over the marsh grasses. We saw LOTS of gators, many swimming right next to the boat. Annie slept through the whole thing :)

Things to Do in the Florida Keys:

After the gator tour and a quick lunch, we drove the remaining 2.5 hours south to Marathon for our next four days in the Keys. We worked hard to create an itinerary that reflected everyone’s interests, and it paid off – we pretty much stuck to it!

After checking in on Monday around 5pm, we headed to dinner on-site at the Butterfly Cafe, Tranquility Bay’s nicer restaurant. We ate outside on the porch at a verrrrry long table, and it was delightful.

The next day (Tuesday) we spent the morning moving between the pool and the beach, where there was cornhole, a giant chessboard, and a volleyball net. We ate lunch on the beach, too, at TJ’s, the resort’s other (more casual) on-property restaurant.

This was a very relaxed day — Annie napped at the house in the afternoon, and the rest of us read, played games, visited the beach, chatted, and swam in the pool. Kim, John, and I even made it to Tranquility Bay’s gym, which was actually really fun to do together :)

For dinner we headed to Burdine’s Waterfront, a casual bar and grill at a marina where we had hush puppies, cheeseburgers, shrimp burgers, key lime pie, and delicious fries — and a gorgeous sunset! We finished the evening with a round of mini golf and games back at the house.

The next day (Wednesday) was our day trip to Key West! I was a little unsure of what to expect because, you know, Key West is known for being kooky, but it was a great day. We started by touring the West Martello Gardens and Fort. The botanical garden is on the site of a former Civil War fort; admission is free and it’s beautiful.

We then drove a short distance to the Truman Waterfront Park, home to the US Coast Guard cutter Ingham, now a floating maritime museum.

As many of you know, my Dad was an officer in the Coast Guard for most of my life, and even served on the Ingham briefly during the Mariel boatlift. It was incredibly cool and meaningful to get to tour it with my kids and to share this important part of our family’s life, and I can only imagine how special it was for my Dad to get to do it with all his grandkids.

After about an hour and a half on the ship, we walked over to Kaya Island Eats for a late lunch. Fish tacos under a shade canopy hit the spot.

While we considered taking a photo with the famous Southernmost Point Buoy, the line was insane – so we hopped back in the car for the hourlong drive back to Marathon, which all of the kids took as an opportunity to nap. Once home, some of us went in the pool and we made tacos for dinner at the house.

The next day was Thursday – Thanksgiving! And what an unusual Thanksgiving it was :) We watched a bit of the parade in the morning, then set off for a kayak adventure through the mangroves of Boot Key (we booked our rentals through Key Kayak).

It was incredible! We saw dolphins, leaping manta rays, and manatees so close we could touch them (!!!) while on our two-hour tour. (For those wondering, I had Annie and June in one tandem kayak and John and Shep were in the other, while the rest of the fam took either tandems or singles.)

We headed back to the house to rinse off or hop in the pool while some of the grown-ups got Thanksgiving dinner ready. We had opted to order a meal from Publix catering, and while we were all pleasantly surprised at the quality and tastiness, it was more challenging than we expected to get everything warm and on the table at once. (Little things like not having tin foil tripped us up!) But we did it, and we were more than thankful to get to celebrate together :)

We closed out the day by catching the sunset from Seven-Mile Bridge, a Florida Keys classic if there ever was one, and with a performance by the kids of their original song about my parents – set to the tune of “Wouldn’t It Be Nice” by the Beach Boys, which was their wedding song. John’s credited on the liner notes as a co-lyricist :)

On our last full day in the Keys we had yet another very special adventure: a dolphin encounter at the Dolphin Research Center! Needless to say, the kids were incredibly excited about this and I don’t blame them: this was something I desperately wanted to do when I was their age. (As an aside, granting my kids a wish that went unfulfilled in my child is an interesting experience: there’s joy and delight in doing it, yes, but it can also bring up worries about “spoiling” them or whether they’ll truly appreciate what they’re being given. But I DIGRESS.)

For both our kids and the kids inside us, this was a delightful excursion. We got to get in the water with the dolphins, touch them, lead them in skills, hold hoops for them to swim to, watch them leap out of the water, and learn more about the center and the research and rehabilitation they do. Very, very cool. We had lunch at Island Fish Co (good, but not my favorite), then headed back to Tranquility Bay for naps and more dips in the pool. Our last meal was a spaghetti dinner in the cottage – easy!

We packed up on Saturday morning and went our separate ways – some flying and some driving.

Though I wouldn’t want to spend Thanksgiving in the Keys, or even at a destination, every year, it was a fun adventure to do it this year. We squeezed in many memorable moments in celebration of a very wonderful anniversary, and I’m grateful we could be together. (And grateful to my parents for making it happen, in more ways than one!)

If you have any questions, I’m happy to answer them in the comments! Thanks for letting me share, friends!

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January 31, 2024 9:12 pm

1. The picture of John and Shep on the bridge. Framer!!
2. Would love to read more about granting wishes for your kids! I think about this often. I have never been to Disney World, for example, and often wished to go as a kid, but now it’s a weird point of pride for me as an adult. Should we take Foster, if he shows an interest, and fulfill my childhood wish? Should we skip it because holy moly it’s expensive and I did fine without it? Fascinating thoughts!
3. Annie in the last photo. AMAZING.

February 1, 2024 5:35 am

Your dad in that last photo — beaming with joy! What a wonderful trip! Thank you for taking us along for the ride.

February 1, 2024 7:19 am

Annie’s face in that last photo is priceless. What a fun adventure and great job on the itinerary!

February 1, 2024 8:56 am

What a great trip! I hadn’t been to the Florida Keys until a few weeks ago when I went to Key West for a college friend’s (very tame) bachelorette party. We had great time! I had wondered what the rest of the Keys might be like, so your trip gives me a great glimpse! Also, hi and happy anniversary to your mom (my CWM merch booth buddy : ).

Kelly Strawberry
February 1, 2024 11:33 am

Oh my goodness! As I was reading through this post, I was beaming with excitement! My in-laws had a waterfront home in Marathon for the past decade. We’ve made so many trips I’ve lost count. Burdine’s – a favorite! Kayaking the mangroves – another favorite! I had no clue you all were going, but if you ever do go back, I have many more Keys recommendations for next time! Truly one of my favorite vacation spots. :)

February 1, 2024 12:03 pm

A friend and I visited Fort Lauderdale from Atlanta over a long holiday weekend last year, and on a whim, we decided to drive down to the Keys and back to FLL. She’d never been! What fun we had tooling around and hitting the state park beaches on all the islands! The highlight of our trip, though – and I’m sorry it looks like you missed it – was visiting the Key Lime Pie Factory. It felt like it was going to be really campy and touristy, and it kind of was a little bit, but we were surprised and delighted by their semi-secret serenity garden! It is a hidden gem, to be sure! Completely picturesque and charming! If you’re ever traveling the Overseas Highway again, definitely make a stop. It’s lovely!

February 1, 2024 12:35 pm

What a fun recap! My brother-in-law is stationed at USCG Station Islamorada in the Keys and while it has seemed daunting to get there to visit him with our 1.5 year old, this post has my wheels turning. My husband was a USCG officer for 6 years and would be over the moon to show our daughter the Ingham. Might have to make it happen this year!

February 2, 2024 1:51 pm

Love it! The Keys are so much fun. Truly more like a Caribbean island than anything else. This looked like a great trip!

February 2, 2024 3:29 pm

I’m lobbying for a guest post from John about trip planning! Where does he even start? It seems so overwhelming!

February 8, 2024 4:35 am

I love that your family tried something new for this special occasion! I am all for family trips. Can you please share where your awesome hat is from?