islamorada itinerary girl hoola hooping on the beach with palm trees in the background

Itinerary: What To Do In Islamorada, Florida

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As you all know, I recently had the immense pleasure of visiting the Postcard Inn Resort in Islamorada, Florida. It was such a wonderful trip full of exciting activities, stuffing my face with some seriously delicious seafood, and of course, relaxing time at the beach. I had such a wonderful time that I thought that it would be fun to put together an Islamorada itinerary for those of you who are hoping to visit.

From paddle boarding, to kayaking, to fishing, and many things in between, there’s no shortage of things to do when you’re in Islamorada. It’s known as the sport fishing capital of the world, which means that you’ll never have a dull moment while you’re there. My entire trip was filled with fun experiences and drool-worthy food. I want to share my Islamorada itinerary with you so that you can enjoy your trip there just as much as I did.

Breakfast

islamorada itinerary postcard inn ciao hound kitchen & bar

Head to either Ciao Hound or Starbucks to start your day, both of which are on-site. Ciao Hound is dog-friendly so you can have your four-legged friend with you while you dine, and Starbucks is an easy staple.

After Breakfast Activities

No Islamorada itinerary would be complete without some water activities. You can paddle board or kayak on the crystal-clear Atlantic waters. If you’re trying to stay dry, you can participate in beach activities like ping pong, corn hole, volleyball, or hoola hooping. 

You can take a “fish like a local” class so you can experience the best of what Islamorada has to offer. (And you can potentially bring your fresh catch back for a hook and cook meal at dinner!) If you’re trying to just chill out and relax, spend some time at the Kokomo Poolside Bar or take a nap in one of the cabanas.

Lunch

For lunch, head to Tiki Bar or Raw Bar. Tiki Bar has killer cocktails and some seriously fun island-inspired food, and Raw Bar is one of the few double-deck raw bars in the entire Florida Keys. Fresh seafood with ocean views? It really can’t get better than that.

After Lunch Activities

There are a ton of different things that you can do to fill out your Islamorada itinerary and kill time before you head to dinner. Sometimes, there are DJ pool parties on property so you can let loose a little bit. For a chiller vibe, you can head back to Kokomo Poolside Bar. Raw Bar also has a happy hour so you can grab a cocktail or two (or five).

Dinner

islamorada itinerary postcard inn nighttime

If you want to stay on-property, I highly recommend dining at Ciao Hound, which offers Italian food. You can also visit Amara Cay Resort’s Reelburger for your meal. (There’s a free shuttle offered between the two resorts.)

Hope you all enjoyed following along with my day in Islamorada itinerary! I had such an amazing time on this trip and I know that all of you will, too. If you end up heading to Islamorada or the Postcard Inn, tag me in your photos and let me know how much you love it!

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