Things to do in Islamorada

The Florida Keys is our happy place. I’ve been going since high school and now living in South Florida the fact that we can see the US-1 sea foam median (IFYKYK) in less than 1.5 hours is a dream. It’s also the first trip we took together as a couple.

I was debating whether to include all of the Florida Keys in this post or break it out by Key. Each key has it’s own personality so to start with the one that matches mine the most - ISLAMORADA!

Situated as a ‘halfway’ marker to Key West, this Key shouldn’t be overlooked if you are making the drive all the way down. It gives you the perfect evolution of getting toasty in the sun to the tiki bar (with live music, of course). It has the true paradise vacation vibes mixed with a taste of the local culture.

Below is a compilation of our favorite places in Islamorada from our own experiences - whether it was for a romantic weekend, a couples weekend, weddings, a quick stop on the way to the Keys, etc.

FYI - I’m keeping it simple so it’s easy to copy/paste as you build out your itinerary (I also included a custom map at the bottom for your reference). Cheers to getting away in paradise!

  • Robbie’s Marina *great place to go kayaking, paddle boarding, and feed tarpon

  • Lorelei Restaurant & Cabana Bar *best sunset and live music

  • Pierre’s at Morada Bay *if you’re a Bloodline fan, it’s a must + very romantic date night

  • Chef Michael’s *delicious food options and great for date nights

  • Cheeca Lodge *premier fishing resort with a classy tiki bar

  • Amara Cay *beautiful trendy rooms and resort area with a poolside tiki bar

  • Sandbar by Wahoo’s *the namesake of the beer Sandbar Sunday - find yourself a boat and go out!

  • Square Grouper *good food and ambiance

  • Islamorada Fish Company *great for a casual lunch

  • Bass Pro Shops *grab yourself a PFG or sun hat

  • Hog Heaven dive bar on water *great for sports 

  • Postcard Inn Holiday Isle *great outdoor tiki bar and live music 

  • Marker 88 *great spot for lunch or dinner on your way down if driving 

  • Islamorada Beer Company *a local spot with craft beers, liquor and the best merchandise

  • Florida Keys Brewery *hidden gem with fun outdoor area

  • The Blonde Giraffe Key Lime Pie Factory *great key lime pie and cute outside area

  • Cafe Moka *great coffee and pastries

  • Bob’s Bunz *get there early, cinnamon buns sell out

  • Midway Coffee & Bar *great for a quick breakfast or coffee run





Embed Block
Add an embed URL or code. Learn more
Previous
Previous

Staycation in Miami Beach

Next
Next

Intro: Have a Soleil Day