The Florida Keys are nothing short of amazing. In truth, we had low expectations given our close proximity and abundance of travel abroad, but, we were honestly blown away at just how beautiful Islamorada is!

If you’re planning a trip, this post covers all the best of Islamorada, where to stay, where to eat and 5 things you MUST do!




traveling blondie 5 things you must do in Islamorada florida

The Florida Keys is abundant with different locations to visit: Marathon, Big Pine Key, Key Largo and the famous Key West. Yet, Islamorada was our choice for this trip because of its relaxing vibe and close proximity to Miami.

Islamorada is a collection of islands that stretch about 20 miles, and, at some points, is just 150 feet (46m) wide. It was named by Spanish explorers who fell in love with the purple sky at sunset and named it “Isla Morado” = purple island. It also happens to be the sport fishing capital of the world, if you’re into that kind of thing.

While Key West is located approximately 3-4 hours (pending traffic) from Miami, Islamorada is just 1.5-2 hours from the Magic City. This makes it the PERFECT location for a night or two away or even just a day trip from Miami.


Normally, we stay in Airbnb’s when we travel to gain a more local perspective, but this trip warranted full service rest and relaxation. There are an abundance of affordable Airbnb’s in the keys, so I highly suggest you have a look before settling on a hotel, as most hotels are pricier due to the limited availability/abundance.

For $55 off your first AIRBNB booking, click HERE!


Traveling Blondie 5 Things You Must Do in Islamorada Florida Keys

We elected to stay at Cheeca Lodge & Spa after the countless amount of recommendations… and it did NOT disappoint. We elected to stay in the oceanfront room, which I HIGHLY recommend for a romantic vacation.

The balconies are screened in to prevent all those Florida bugs from creeping in and the views are just beautiful. Overall the hotel common areas and beach/location of hotel get 4 stars from me, while the room only receives 3 stars because they are in need of some updating.

Cheeca offers up EVERTHING, so much so, that you never have to actually leave the resort. They have 3 restaurants, a private beach, 3 pools, a fishing pier, fitness studio, tennis courts, tiki bars, a spa and SO much more. The perk that we loved is that the daily resort fee ($40) covers golfing (including clubs), tennis, paddle boards, kayaks, etc.


We ALMOST stayed at the Post Card Inn because it’s totally gorgeous (and looks more updated than Cheeca), but we elected not to because we called for 2 days straight and they didn’t even answer the phone (we’re all about customer service-it was a bad sign, right?). They also are located a bit further from everything in comparison to Cheeca Lodge and we’re all about walking everywhere.

I’m sure we will stay here at some point because the rooms are all renovated and it looks totally gorgeous! It’s a bit pricier than Cheeca, but looks to be worth it (if their customer service improves)!

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traveling blondie 5 things you must do in Islamorada Florida Keys

There is NO shortage of food in Islamorada. I was completely overwhelmed at the amount of restaurant recommendations that I received. We were only able to visit a few on the list, and I wasn’t that impressed with where we ate at, but we’ll surely be back to try more!


Islamorada Fish Company

traveling blondie 5 things you must do in Islamorada floridaOk, so I’m not going to lie, Islamorada Fish Company’s food wasn’t all that it was hyped up to be. The atmosphere was lovely, the service was friendly, but the fish sandwich was less than mediocre.

We have pretty high standards when it comes to fish sandwiches thanks to the Deck Down Under in Port Orange, Florida (currently drooling just thinking about it), and I imagined that the Islamorada Fish Company didn’t have to measure up 100%, but I’d give it a 40% in comparison. OUCH, I know.

That being said, you should go and order something else! The coconut shrimp was good and the key lime pie was wonderful!

*Note: we went on a Monday and still had to wait about 45 minutes (because we went an hour before sunset=peak hour). Fortunately, there’s a bar offering up adult beverages for you to sip as well as chairs for you to relax in nearby the water.


traveling blondie Islamorada Florida Keys Robbies Robbie’s (also pictured above) is the quintessential Florida Keys outdoor restaurant and shouldn’t be missed. It’s sprinkled with colorful decor all around and has an endless amount of souvenir stands for you to peruse.

Josh and I only ate a few apps here, as we came for a quick bite before our jet-ski tour (located at Robbie’s as well), so I cannot really give a fair judgement of the food.

It’s a popular place that came highly recommended, so you should at least just check it out for the atmosphere and a cocktail.

Tarpon fish feeding is also EXTREMELY popular at Robbie’s. You’ll see a school of more than 100 tarpon that come and hang out nearby all day to be fed by tourists. Although we didn’t personally partake, our table was set within sight of the feeding and it was fun to watch them jump out of the water for food. Admission to the dock is $2.25 per person and each bucket of fish feed is $4.00 (5-8 fish per bucket).

Green Turtle Inn

traveling blondie Islamorada Florida Keys green turtle inn breakfast If you love breakfast as much as I do (especially after a night of drinking), then you CANNOT miss the Green Turtle Inn. Aside from the portions being large enough to feed a small village, the Green Turtle cooks up some incredible eats.

Open since 1947, and featured on the famous Food Network show “Diners, Drive Ins and Dives” in 2016, the Green Turtle Inn is a timeless icon in Islamorada and shouldn’t be missed, even if it’s just to stop by for their famous Turtle Chowder.

The Keys Benedict (with blue crab) was mouthwateringly delicious and Josh’s Captain’s French Toast with toasted coconut and bananas was the best carb coma he’s eaten himself into in months.

I also LOVE the small town feel to this restaurant. It reminded me a lot of a diner in Brooklyn, Michigan where I grew up (shout-out to Papa’s Place!). The service is great as well! Green Turtle Inn was the best food we ate the entire weekend and the only place I’d return to for eats on the next trip! 

LoriLei Restaurant & Cabana Bar

traveling blondie Lorelei restaurant Florida Keys Lorelei Restaurant has to be the best atmosphere we experienced during our dining adventures in Islamorada.

The outdoor seating is steps from the ocean, they have live music, and the food/service is descent. There were even a magician putting on a show for kids when we left (although he was slightly creepy-the keys is just weird, go and let me know if you feel the same).

We sat at the tiki bar and enjoyed the sunset and our dinner. The fish sandwich was mediocre, but the coconut shrimp and key lime pie were great! We also loved that it was conveniently walkable from Cheeca Lodge (us city folk love to walk everywhere). I would return for a drink and app here at sunset, but not for the food.


Be prepared to feel overwhelmed… I honestly am just writing this list, but they’re worth looking into. I’ve bolded the ones I plan to go to on our next adventure to Islamorada.

A Few Restaurants to stop on the way to/from Islamorada

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traveling blondie 5 things you must do in Islamorada Florida Keys


You CANNOT come to the keys and NOT revel in a sunrise or a sunset! Our hotel faced east, so the sunrises were STUNNING, but all the restaurants we ate at faced west, giving us some beautiful sunsets.

The keys are so thin that it’s such a great place to capture both sunrises and sunsets! DON’T miss them! You can check out this article for the best places in other ares of the keys to catch them as well!

Note: If you’re going to a restaurant and planning to catch the sunset, go EARLY-like 1 hour+ before sunset, because, guess what? Everyone else wants to do the same thing that you do and there are only a handful of restaurants on the water with great views.


traveling blondie 5 things you must do in Islamorada Florida Keys

You cannot come to the keys and not get out on the water. Whether it be on a boat, a paddle board or just swimming in the beautiful blue ocean.

If you can charter or bring your own boat, then that should be your #1 choice. Otherwise, there’s Robbie’s Jet Ski Rental! 

We took a 2 hour jet ski tour for $199 per jet ski (we shared so the other person could film). The tour is guided and there were about 5 other jet skis in our group. The guide did a GREAT job of taking us all around the area, through the mangroves and we even snorkeled for 30 minutes.

Note: If you’re planning to head to Robbie’s and eat lunch prior to your jet ski adventure, GO EARLY-like 1.5 hours. This restaurant is super busy and we didn’t have enough time to eat our food prior to the tour (I was literally stuffing it in my mouth while the guide was giving safety instructions).


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Anne’s Beach is named after local environmentalist, Anne Eaton, who passed away in 1992. She was best known for her attempts at preserving the keys and campaigning against over-development.

The beach is located at mile marker 73.5 and is free to visit (woo hoo!). Pack a beach bag, grab some beers, put on some screen and relax and soak in all the Florida Keys have to offer! Note that parking is limited, although there is a lot nearby with just a short walk.


Sadly, our tour didn’t go out to Alligator Reef Lighthouse, as it’s located about 4 miles offshore. This was a big disappointment for us because it looks incredibly beautiful out there! It’s also arguably one of the best diving and snorkeling spots in all of the Florida keys…now you know why I’m disappointed 😉

My amazing friends at The Adventure Encounters filmed an INCREDIBLE video that will give you all the information you need about this incredible little slice of heaven (below)! Forewarning: you’ll want to book a trip and go here as soon as you finish this video! You can also follow their adventures on Instagram @theadventureencounters as well!

Fun story about the Lighthouse: In 1825, the 86 foot USS Alligator sank in shallow water and, to prevent this ship from being salvaged by pirates, it was blown into pieces! This helped to lay the foundation for the incredible coral reef that now exists there with over 500 pieces of marine life!


Josh and I are die hard beer lovers. If I didn’t control my carb intake, I’d literally be 50 pounds overweight from IPA consumption. If you’re as big of beer lovers as we are, than a visit to Islamorada is NOT complete without having a brew (or two, or three) at the Florida Keys Brewing Company!

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Do the words microbrewery, tasting room and beer garden get you as excited as I get when I hear them?! If they do, then you don’t want to miss this little gem. We are suckers for microbrews and the FKBC is the first microbrewery in the region.

Pro Tip: Pay this place a visit before heading to dinner…its the perfect time to catch a buzz, enjoy the music and artwork, play games and sip on some delicious local beer.

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traveling blondie 5 things you must do in Islamorada Florida Keys

  1. If you’re on a budget, you can save a TON of money by staying on a Sunday, Monday or Tuesday. Our rooms were HALF the price compared to Friday and Saturday.
  2. You won’t really feel like you’re in the keys until you get to Islamorada, in my personal opinion. Key Largo just doesn’t have they keys-ey feel to it.
  3. Book directly with the hotel websites, especially if you’re a Florida resident (they always have discounts).
  4. Enjoy the drive but, if you’re planning to come in on Friday evening and leave on a Sunday, be prepared for TRAFFIC! The road in/out of the keys is a one-lane road (occasionally opening up to two lanes for short periods of time). The speed limit is slow and, if you go during peak weekend times, be prepared to add more time in your itinerary for travel.

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Things To Do in Miami in June

There are a few places that you won’t want to miss nearby Islamorada, including my home city of Miami, of course 😉

Robert is Here Fruit Stand

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If you happen to fly into Miami or are driving down from another part of Florida, then you cannot pass by Homestead without visiting Robert is Here Fruit Stand (location)!

Although this family-owned market is only currently open (as of September 2020) for drive through ordering, it’s still a MUST visit! Picture a local market overflowing with exotic fruits, veggies and groceries and one of the best milkshake menus around!

Don’t miss this place, even if for a quick drive through, you won’t be disappointed!

John Pennekamp State Park

Located in Key Largo (the first of the Florida Keys), John Pennekamp makes for a great day trip from Miami or Islamorada (if you have the spare time). It’s actually the first undersea park and “covers 178 nautical square miles of coral reefs, seagrass beds, and mangrove swamps.”

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It’s basically a divers, snorkelers and paddle boarders/kayakers playground! Don’t miss it if you have the additional time! Did I mention that you can rent boats and also join one of their glass bottom boat tours?! Are you ready to go yet?


traveling blondie things to do in Islamorada Florida Keys miami

If you’re flying in to go to the keys, then you’re most likely flying into Miami, MY CITY! I’m VERY biased, but this city has SO much more to offer than just partying (although if you want to just do that too, I totally understand as well). I’ve written countless articles on how the best things to do in this great city, if you want to check them out!

Key West

traveling blondie things to do in Florida Keys key west

This is an obvious MUST visit if you’ve never been. I’ve personally been three times and didn’t care for it much each time, but we’re planning to return and give it another go sooner than later. I have yet to visit Dry Tortugas National Park, which looks INCREDIBLE!

One tip I have to give you if you go, is you MUST eat key lime pie (and breakfast/brunch) at Blue Heaven Restaurant, trust me, you wont be disappointed!

Also, a sunset at Mallory Square is a definite must, although super touristy, as well as a photo at the Southernmost point in the USA-pictured here with my Mom and sis 7 years ago (oh how time goes so fast)!

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Traveling Blondie 5 Things You Must Do in Islamorada Florida Keys

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  1. LOVE THIS!!! Great tips and info and THANK YOU for sharing our video to the Alligator Reef Lighthouse!!! This is seriously so amazing of you guys!! THANK YOU!!! Lookong forward to reading more!!! 👏👏👏👏

  2. Thank you guys SO much for giving us the honor to feature your video on the blog! Much love XOXO

  3. Islamorada brewing was actually the first in the region. My son is a brewer there.

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