Islamorada Florida Keys Family Travel Guide (Florida Beaches Tour #3)

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Islamorada Florida Keys is a vacation destination I’d always wanted to visit. It seemed as if it was a little more laidback and lesser known than most of the other Florida Keys and Key West. I was right and you know I’m all about beach seclusion!  So consider this your personal family travel guide to Islamorada Florida.  It also happens to be part #3 in our Florida beaches series.  If you missed them, catch up on the beans I spilled about the 7 things to do in West Palm Beach and Miami Beach with kids!

young girl in water kissing snout of dolphin and caribbean blue two story Florida Keys cottage

Islamorada Florida Keys Guide

If you’ve been keeping up with us lately, then you know that we set out to compare the sand and surf of several beaches along the east coast of Florida – all the way to Key West.  At this point, we’ve made it to Islamorada Florida Keys.  I can’t wait to share how adorable Islamorada, Florida really is.  I’ll share all about it with the experiences that we enjoyed as a family. Thank You to The Florida Keys & Key West Visitors Bureau and the brands below for hosting us.  As always, my opinions are my own.

Family Travel Guide to Islamorada Florida Keys - aerial of Islamorada

An Islamorada welcome

When we drove past Key Largo and into Islamorada, Florida, it was as if we entered a small beach town with a natural habitat that just happened to be surrounded by water on both sides. I immediately fell in love with the laidback vibe of this fishing village that had everything we needed (and nothing more) in close proximity with one Publix grocery store, a handful of attractions, many diving and fishing shops, low-key resorts and restaurants.  The following are the Islamorada points of interest that we visited:

World Wide Sportsman by Bass Pro Shops 

When my husband mentioned that there was a Bass Pro Shop in Islamorada, I may have rolled my eyes.  Don’t get me wrong, I enjoy walking through the gorgeous Bass Pro Shops when we visit large cities, but I couldn’t picture one of those huge stores that are normally full of hunting gear on a Florida Keys island.  What I didn’t realize was that it was a smaller store and it was all about sportfishing.

The property was so beautiful and wowed us immediately as we pulled in the parking lot. We were beckoned by the Bayside Marina and Boardwalk out back before we entered the store.  The store was gorgeous and even included a massive boat display to represent Ernest Hemingway’s fishing boat (if you didn’t know, Hemingway loved fishing the Florida Keys and his house is in Key West).

What a beautiful place!

If you visit Islamorada in the Florida Keys, make this one of your first stops.  You won’t be disappointed!

Family Travel Guide to Islamorada Florida Keys - Bayside Marina & Boardwalk at World Wide Sportsman

Theater Of The Sea 

Family owned and operated since 1946, Theater of the Sea is also the world’s second oldest marine mammal facility.  Not only are there opportunities to swim with bottlenose dolphins, sharks, and sea lions, you can also interact with stingrays and learn about sea turtles, birds, fish, sharks, alligators and marine invertebrates.

This marine facility is unlike anything we’d seen before with its tropical gardens and three-acre lagoons.  We enjoyed the dolphin, sea lion, parrot and guided marine life shows, the bottomless boat ride around the dolphin lagoon, and then the private lagoon-side beach where you can snorkel, sunbathe, or just relax.  Then we were privileged to swim with two Atlantic bottlenose dolphins for about an hour in a natural, salt-water lagoon.

It was incredible!

Family Travel Guide to Islamorada Florida Keys - Sea Lion Kiss at Theater of the Sea
Family Travel Guide to Islamorada Florida Keys - Swim with dolphins at Theater of the Sea

Marker 88 Restaurant & Beach

We had no idea how much Marker 88 was going to be a part of our Islamorada vacation!  Our experience with this waterfront property started when we arrived for dinner on our first evening in the tiny fishing village.  The food, service and the views were outstanding.  We dined inside but many opted for the quaint outdoor dining tables with umbrellas and tiki hut bar.

Of all the Islamorada restaurants, we know that we found a jewel with its true Florida Keys vibe and a must-stop spot since 1967.  We enjoyed steaks and sweet potato fries but they also offer some of the Keys’ freshest seafood.  After dinner, we enjoyed taking pictures of the sunset and walking along their boat dock (where several had arrived by boat).

Just to the side of the outdoor dining area, we were delighted to find an adorable natural beach.  When the manager graciously came out to make sure our dinner was pleasing, he was incredibly friendly and we chatted about his history with the restaurant and he told us we were welcome to return the next day to the Marker 88 beach.

The next day was Sunday morning when we arrived and noticed a sign that mentioned a five-dollar charge for the beach.  However, we were the only ones there and enjoyed sunbathing and snorkeling to ourselves with the option of lunch choices right next to us at the restaurant.

Family Travel Guide to Islamorada Florida Keys - Outdoor dining at Marker 88 Restaurant
Family Travel Guide to Islamorada Florida Keys - Marker 88 Beach
Family Travel Guide to Islamorada Florida Keys - Snorkeling in the bay at Marker 88 beach

Islander Bayside Townhomes 

There are only a handful of Islamorada resorts to choose from, nestled along the ocean or the bay and the one located at mile marker 81 captured our hearts.  This small community of townhomes on the bay was like a home away from home with its fully-equipped gourmet kitchen that had top-of-the-line stainless steel appliances and granite counter tops.  We enjoyed many meals in the comfortable seating areas, private balcony and front porch.

With all the comforts of home and luxurious touches at our private beach cottage, we didn’t want to leave!

I personally spent most of my time in the swimming pool or the master bedroom’s balcony with a view of the Florida Bay.  There were 14 boat slips as well at Islander Bayside, so it was fun to watch boating families come in after a day of fun on the gulf.

Guide to Islamorada Florida Keys - Islander resort
Family Travel Guide to Islamorada Florida Keys - Islamorada resort pool
Family Travel Guide to Islamorada Florida Keys - Islamorada resorts boat slip

Islamorada Beaches 

I wanted to provide information for those who stay at an Islamorada resort without private beach access.  Believe it or not, public access to these Florida beaches is limited.  One of the most popular Islamorada beaches on the oceanside was Anne’s Beach, but unfortunately, the erosion and damage caused by Hurricane Irma have it closed permanently for safety reasons.

Our plan was to visit Founders Park, located directly behind the Islamorada Chamber of Commerce & Visitors Center, so we rode through the parking lot to check it out.  What we found was a beautifully maintained park with a mini beach on the bay that was hidden among the palms and mangroves.  There was clear, shallow water on this beach which would be perfect for small kids, relaxing, snorkeling and kayaking.  Nearby are public restrooms, a playground, and two Olympic-sized pools as well.

We never actually spent time at Founders Park beach. We opted for the complete seclusion of Marker 88’s mini beach as mentioned above, but Founders Park looked like a very lovely place to spend the day.  I also met a local that mentioned a very small spot of sand located along a mangrove channel (creek).  We never found the time to search for this, but the parks and recreation site list it at mile marker 81.5.

Watch video HERE

Which activity do YOU want to experience in Islamorada Florida Keys?

a view of Islamorada Florida Keys water and girl snorkeling


Places to visit in Islamorada Florida Keys

Islander Bayside Townhomes: 81450 Overseas Hwy, Islamorada, FL

Theater of The Sea: 84271 Overseas Highway, Islamorada, FL

Marker 88 Restaurant: 88000 Overseas Highway, Islamorada, FL

World Wide Sportsman: 81576 Overseas Hwy, Islamorada, FL

Founders Park: 86800 Overseas Highway Islamorada, FL

For more Islamorada Florida Keys information, visit The Florida Keys & Key West


Published on HuffPost, Okefenokee Living Magazine, and more, Shan is a Family Travel Journalist with a passion for helping women lose the overwhelm of planning family-friendly trips in the south. She shares travel reviews & insider secrets that Women REALLY want to know about Georgia, Florida, & the Carolinas vacations.

☕️ It’s THE REAL DEAL around here ☕️



  1. ShootingStarsMag
    August 16, 2018 / 7:37 am

    That townhome is beautiful – and I love that it has a pool! I’d LOVE to swim with those dolphins too.


  2. Cara Palmer
    August 16, 2018 / 7:38 am

    Looks like a beautiful place, I’ll have to add it to my bucket list.

  3. lanell
    August 16, 2018 / 7:45 am

    Looks like a fabulous place to visit. I must put this on my list to visit.

  4. Kristin Cook
    August 16, 2018 / 3:26 pm

    That looks like an incredible adventure! I’ve never been that far south in FL but I would love to go!

  5. April at LoveOurRealLife
    August 16, 2018 / 5:54 pm

    Beautiful! My husband and I had considered a trip to the Keys, but didn’t think it would be very kid – friendly. I’ll definitely put his on my list of places to consider vacationing!

  6. Cassie
    August 17, 2018 / 11:55 am

    How beautiful! This is a great guide. Looks like an amazing time 🙂

  7. Christina Beauchamp
    August 19, 2018 / 8:08 am

    I’ll have to add this to our bucket list. It look so amazing!

  8. Wendy Tomlinson
    September 5, 2018 / 12:46 pm

    I love this post. I’ve been to Florida quite a few times but never the Keys and I really want to do this on my next trip.

  9. Megan Jones
    September 6, 2018 / 8:15 pm

    What a great blog tour of Islamorada. The Keys are one of my favorite places to visit but somehow I always seem to spend my time on the Dive Boats and Key West. Apparently, I wish missing out on a lot of fun by not spending more time in Islamorada. I’ll have to change that next time I’m visiting.

    • Shan
      September 7, 2018 / 1:08 pm

      Thanks, Megan. I had no idea that Islamorada was so incredible either! We loved it so much. Definitely a lesser-known treasure in the Florida Keys.

      love much,

  10. Danny
    October 22, 2018 / 12:44 pm

    Hello from Key Largo Meagan. I’ve been living in key largo for 15 years and even i dream of moving to islandmorada. Isalnadmorada has access to the best fishing and water fun in the world. great article Meagan

  11. Piper
    May 7, 2019 / 5:37 pm

    Wow!!! just an amazing place Islamorada. I wish I could go there!

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