Do you like tropical breezes? How about warm, sunny days? Sand between your toes? If you answered yes to these questions (and if you answered no, get your pulse checked, bud!) then we have the place for you! And that place is called Islamorada in the Florida Keys! Certainty you are familiar with Key West – but did you know that is only one of nearly 1,700 islands in the Florida Keys archipelago? Follow along with us as we explore how to spend a fabulous weekend in this lesser-known gem.

Islamorada is a mere hour and a half drive from Miami but a world away – Islamorada will automatically lower your blood pressure and force you to stop and smell the suntan lotion. You can lounge the days away or fill them with adventure on the high seas!

Friday:
Check in to the Drop Anchor Resort and Marina and check out of reality for a few days. This pastel paradise is both the perfect jumping-off point for your island adventures and your ticket to relaxation. With 10 different rooms, this newly renovated property offers everything you need including a pool, not one but TWO boat ramps, kayaks, and paddleboards for aqua adventures and hammocks for relaxing. Where will you get your frosty beverages you ask? Well, a bar is currently in the works – wish granted! One of the most unique things about Drop Anchor is that you can actually rent out the entire property for a large event like a milestone birthday, family reunion or wedding!

Drop Anchor Resort is uniquely located for anything you want to do in Islamorada including kayaking out to the sandbar for some day drinking, diving the only coral reef in the continental US, grabbing a fishing charter for some of the best fishing in the Florida Keys (Islamorada is actually known as the sport-fishing capital of the world!) or just disconnecting from the world for a little while in one of the property’s many palm framed hammocks.

Once you have explored the property, head over to the Islamorada Beer Company & Distillery to get your weekend started off right! This brewery opened it’s doors in October 2014 and began distilling their own rum, gin, and vodka in 2017. Do a free tasting on the distillery side and then try out the Lavender Lemonade Drink. After that switch over to one of (or ALL) this spot’s 17 delicious beers on tap- our favorites were the No Wake Zone Coconut Key Lime Ale and the Islamorada Ale. Oh, also check out their delicious hard waters. We guarantee it’s like nothing you’ve tasted before! Perfect for drinking the whole afternoon away. Everything in this brewery emulates their tagline “Island State of Mind” – from the striking teal and yellow building, to the laid back island music, to the fruity flavors that run through their beers and spirits – you will immediately feel relaxed with an IBC drink in hand. And while you are partaking in these lovely libations make sure to snag some of their gourmet popcorn in cool flavors like Buffalo Ranch and Chocolate Peanut Butter (YUM!!).

When you are ready for a more substantial meal call the FreeBee Shuttle and head down the street to Morada Bay. It’s not called FreeBee for nothing; it’s seriously free and seriously fun! All you have to do is download the app and follow along. There are some restrictions on where they go, but we loved our ride! Morada Bay is a beautifully situated eatery and the perfect spot for sunset. We recommend coming a little early to get all those jaw-dropping golden hour photos. The food and drinks here are great (if a little pricey) and the fish tacos are a must! Oh and we almost forgot, any Bloodline fans out there? Then Morada Bay will definitely look familiar! Pro Tip: Order the Key Lime pie. It is THE BEST we’ve ever had. And trust us, we’ve had a lot. Excuse us, while we drool in the corner.

Saturday:
Do yourself a favor and have breakfast at the Green Turtle Inn – and if you don’t get the shrimp and grits we cannot be friends anymore you are missing out. This smokey, bacony, creamy bowl of goodness was possibly the best s&g’s we have ever had! Ever! In our whole lives! Oh, the sticky bun was also great too! 

Now that you are nice and full it’s time to be entertained! Head to a very popular attraction in Islamorada and spend a few hours at the Theater of The Sea! This marine wildlife rehabilitation center is adorable and really well thought out. They have continuous rounds of shows and events which help you (and those kiddos) stay entertained. We loved the dolphin show for its cool tricks and the sea loin show had the perfect amount of cheesiness! You can also take photos with parrots and other exotic birds and there is even a little area where you can snorkel with parrotfish and other sea life! If you want to get closer, they have numerous options for dolphin and sea lion encounters where you can learn more about them and even swim with them in private pools. 

After all that learning and entertainment you are probably hungry, right? RIGHT? Well, good news – we know just the place for you to fill up! Do not miss M.E.A.T. – Meat Eatery and Taproom. Featured on the Food Network’s Diners, Drive-ins & Dives, this gem tucked away in a nondescript strip mall will blow you away! When they bring their still crackling chicharrones to your table with house-made chimichurri aioli, you will understand their cult following. And if those aren’t your style, try the meaty wings, truffle fries or smoked fish dip. But make sure that you save room for the main event – the meat! Their burgers are amazing – our favorite was the pimento cheese and bacon filled “Juicy Lucy”. Voted Best Burger in Florida 2014 and 2015! Don’t forget to wash it all down with a house-made (boozy) shake or their variety of craft draft beers.

Then head over to the awesome Florida Keys Brewing Company, to wet your whistle. This brewery was opened by Craig (a Canadian) and his wife Cheryl (a Keys gal), check out the FKBC logo for a little nod to this union. This brightly decorated brewery will instantly make you happy – almost as much as their delicious beers. Their Iguana Bait is a fabulously crushable  beer. Get one and take it out to their beautiful beer garden full of great seating. You could also stay in their exclusive, 2 bedroom B&B (Bed & Beer, obvi) upstairs!

Grab a pack of beers to go because you have a boat to catch! Captain Jeff of Blacktip Charters can pick you up right from the Drop Anchor for a dolphin cruise. We spotted dolphins, a shark, lots of birds and even a crocodile – but the best part was a flying stingray. Did you know they jump out of the water sometimes and seem to “fly”? Well, we didn’t and when we saw them we may or may not have screamed like little schoolgirls with excitement! You can also bring some of your own jams for the ride. We were partial to “Under the Sea” (Little Mermaid) and “I’m on a Boat” (The Lonely Island). After a ride around the bay, have Captain Jeff drop you off at Lorelei’s in time for their famous sunsets. Grab a drink (we recommend the Key Lime Colada) and a sea-facing seat and wait for the magic moment!

Sunday:
Start the day off with a hearty breakfast at Mangrove Mike’s – the cinnamon crumb cake french toast is pretty incredible. Make sure to check out the art and oddities store that is connected to the restaurant. They have some fun stuff in there! Or, if timing is of the essence head to the Midway Cafe for a yummy breakfast sandwich to go!

Next head to Robbie’s of Islamorada for a chance to feed their famous tarpon. For about $10 you can get a bucket of fish and head to the docks where the tarpon are plentiful. You can dangle a fish over the side of the dock and watch the tarpon jump to grab it right from you for a perfect picture opportunity– don’t worry – it doesn’t hurt! Make sure to check out the many vendors at Robbie’s including book dealers, sign makers, and other bits and bobs!

After feeding the tarpon, head north one key for more fun on the water by renting jet skis with JSK Watersports! These Yamaha VX Deluxe jet skis are second to none – they have both reverse AND neutral settings, rearview mirrors and… wait for it….. step ladders on the back in case you fall off your jet skis! Not that that happened to any of us or anything… Brad from JSK offers a few different jet skis tours including 30 and 60 minute “free rides” that will take you out to the sand bar for some relaxation and sunbathing. But if you have the time the true highlight of your jet ski day will be the 2 hour Eco Tour. Brad will provide you will all the snorkel gear needed and will take you and up to 8 of your closest friends out to the Hen and Chickens Reef to take in the beautiful underwater world of the Florida Keys before heading to the aforementioned sandbar. After that travel through the mangrove tunnels to the infamous toilet seat channel (only in the Keys!). All trips are lead by an experienced guide who takes pictures of your group, keeps track of time and ensures the safety of everyone! JSK’s unique location means that they have both Bayside and Oceanside access so on super windy days you have more sheltered options. We promise you that a ride on Brad’s jet skis will be one of the highlights of your trip to Islamorada!

As you can tell, we had an amazing time in Islamorada. And whether your goal is to get your adrenaline fix on jet skis, catch the next record-breaking marlin or just unplug completely from the world under a swaying palm tree – Drop Anchor Resort in Islamorada is the perfect place to do absolutely everything or absolutely nothing!