Family Traditions and Hidden Gems: Our Ultimate Florida Keys Vacation Guide

Family Traditions and Hidden Gems: Our Ultimate Florida Keys Vacation Guide

Wow! It’s been a minute since I put some thoughts to paper. We just wrapped up our annual Keys vacation with the girls, and there’s something so liberating about leaving the world behind for a week and becoming one with the ocean. Our family has vacationed in the Florida Keys for over 30 years, and I have some of the fondest memories of summers there as a child. I always dreamed that one day I could do the same with my girls.

Our family Keys traditions started before I was born. Once my parents had us, it became an annual ritual to pack up and head to the Keys for a week or two every summer. When my parents separated, my dad carried out the Keys trips from then on. The key to our Keys trips included my uncle, Jim. He was an essential part of our trips and held the title of “Donkey Boy” – the one who dropped/pulled up the anchor or was thrown in every time we got to a ledge to check for lobster. He had a spirit that was unmatched, and I’ve never met anyone like him in the world. When I think of him, I think of his “Frosty Drinks” – a celebratory frozen mudslide after a long successful day on the water. He taught me to “fish like a girl,” meaning to do my best to outfish the boys every chance I got. Sadly, he passed away unexpectedly a few weeks after Seth and I were married, so my girls never got the chance to experience his passion for life and the humor he carried into every room.

Once I grew up and had a family of my own, our Keys traditions became traditions with friends instead of family. We had the opportunity to spend some time in the Keys with my dad when he made plans for his annual trip this year. I think this trip was healing for both of our souls. Our relationship has evolved over the years with many bumps along the way. The best part about spending this week with him was reminiscing about my childhood while watching my girls enjoy some of the experiences I loved so much as a kid. Our slogan for the trip was, “we reminisced on a lot of memories and created lots of new ones.” We even enjoyed a few “Frosty Drinks” in memory of Uncle Jim.

When we’re not lobstering and fishing, we’re often enjoying the many attractions and dining experiences. So enough sappy reminiscing, let’s move on to the real reason for this post. Here are some of our favorite places to go in the Keys!


Robbie’s of Islamorada – Robbie’s Marina of Islamorada is the place to stop, either on your trip down to the lower Keys or heading back up the Overseas Highway to head home. Robbie’s is best known for hand-feeding massive tarpon, but we love it for the eclectic artists’ small shops set up around the property. The waterfront deck is the best place to devour fresh seafood or enjoy craft beers and cocktails. It’s not a Keys trip without a visit to Robbie’s. Robbie’s of Islamorada

Theatre of the Sea – Theatre of the Sea was established in 1946 by the McKenney family. It is home to natural saltwater lagoons that originally were a rock quarry for the Henry Flagler railroad. Some of the main attractions include a bottomless boat ride and marine life shows scattered throughout the park. If you’re looking for more adventure, you can book an experience to swim with dolphins, meet a sea lion, or swim with sharks and rays. Theatre of the Sea is perfect when you need a break from long boat days. General Admission - Theater of the Sea

Aquarium Encounters Florida Keys – If you watched our stories this past week, you probably saw several videos of us feeding animals and playing in touch tanks. One of my favorite places to bring the girls is the Aquarium Encounters of the Florida Keys. The aquarium houses two large tanks for hands-on experiences. The snorkel lagoon encounter allows visitors to experience snorkeling on a reef. The Big Shark Bay experience allows visitors to feed friendly nurse sharks from the surface. Throughout the park, there are feeding stations where you can purchase food cups to feed turtles, lobsters, stingrays, tarpon, and more. Touch tanks include the isopod touch tank, stingray tanks, nursery tank, and the tide pool touch tank. Finish your trip by digging for shark’s teeth in the sandbox and enjoying a cold beverage or ice cream overlooking Vaca Cut. Marathon Marine Park | About Florida Keys Aquarium Encounters

Dolphin Research Center – The Dolphin Research Center was founded as a nonprofit organization in 1984 as a dolphin conservation and research facility. Their general admission package allows you to view and learn more about the bottlenose dolphins and California sea lions that call the Dolphin Research Center home. The center also features a Sprayground where the kids can cool off under water blasts and misters. The Dolphin Research Center is another great place to swim with dolphins with a number of different encounter options. Dolphin Research Center

The Turtle Hospital – The Turtle Hospital opened in 1986 as a rehabilitation and release center for injured turtles. They host a 90-minute guided educational program. It is currently a working hospital. The Turtle Hospital. Rescue, Rehab, Release.

The Ernest Hemingway Home and Museum – Ernest Hemingway, the popular writer, relocated to Key West through Havana, Cuba in 1928. He was best known for his poems, short stories, and novels. The Hemingway House was not only home to Ernest Hemingway but also to polydactyl (six-toed) cats. There are approximately 60 Hemingway cat residents currently on site. The museum is open daily for guided tours. The Hemingway Home & Museum


Hog Heaven Waterfront Bar and Grill – Located on gorgeous waterfront property in Islamorada. Enjoy hog-licious drinks while overlooking the water.

Herbie’s Bar and Chowder House – One of my personal favorites is this small hole-in-the-wall place with three entrances for different experiences. Herbie’s is one of the oldest restaurants in Florida. Enjoy fresh seafood or a number of different craft beers they have on draft.

Square Grouper Bar and Grill – For a fresh and innovative dining experience, Square Grouper has the ambiance and cuisine. If you’re going for cocktails, the third-floor sunset lounge is 21+ and open for happy hour.

Kiki’s Sandbar and Grill – Kiki’s features waterfront dining on Little Torch Key. Dine upstairs in the main dining room or enjoy the beachfront tiki bar and seating with outdoor games. They have a wide range of cocktails, with my personal favorite being the key lime mojito. Their live entertainment allows you to enjoy music and dining with the best view.

Wahoo’s Bar and Grill – Wahoo’s is located right above Whale Harbor Marina. Overlook the marina while enjoying waterfront dining.

Blue Heaven – Located in Key West, Blue Heaven offers the perfect outdoor seating experience with canopies of tropical foliage. Cats and chickens roam the patio.

F-ing Bagels – F-ing Bagels is in Islamorada and a small coffee/bagel shop with a lot of personality. I highly recommend the jalapeño cheddar bagel if you’re into something that packs a punch.

Sweet Savannah’s Bakery and Gifts – Sweet Savannah’s is an eclectic bakery and gift shop. Their signature baked goods include cupcakes and cookies. Enjoy ice cream and floats as well! The Key Lime cookies are to die for.

Duval Street Bar Crawl: If you travel to the Florida Keys, you can’t leave without experiencing the Key West Duval Street Bar Crawl. Here are some of the best bars to stop at:

  • Fat Tuesday’s
  • Sloppy Joe’s
  • The Bull & Whistle Bar
  • Rick’s
  • Captain Tony’s Saloon
  • Hog’s Breath Saloon
  • Durty Harry’s
  • Smallest Bar
  • Irish Kevin’s
  • Flying Monkey Saloon
  • Caroline’s
  • Backyard Bar
  • Mango’s

There are so many places to go and things to see in the Florida Keys. I could go on forever. If we missed one of the many hidden gems, leave us a comment and let us know where we should check out next!

Pictured: Our last fishing trip with Uncle Jim. 



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