Key Largo to Islamorada: Ultimate Travel Guide For the Upper Keys

If you’re planning a trip to the Florida Keys, you may have heard of Key Largo and Islamorada. These are the two main towns in what is commonly known as the “Upper Keys”. The Upper Keys is one of the most popular areas to visit, and for good reason!

As a Florida native, I grew up visiting the Keys and even got married here! I’ve traveled throughout the Keys many times and love sharing about them. If you’re considering visiting the Keys, I highly recommend including Key Largo and Islamorada in your itinerary.

In this guide, I cover everything you need to know about visiting the Upper Keys, from Key Largo to Islamorada! This includes where to stay, things to do, and how to get between the two towns.

So whether you only have a few days or a few weeks in Florida, this guide will help show you why the Upper Keys should be on your bucket list!

Note: This post contains affiliate links. If you click an affiliate link or book through an affiliate program, I receive a small commission at no cost to you! 

Key Largo to Islamorada: Everything You Need to Know About the Upper Keys and Traveling Between the Two

How Far Apart are Key Largo and Islamorada

The distance from Key Largo to Islamorada is approximately 17 miles. If you’re driving, the journey should take between 20 and 30 minutes to get between the two, barring any major traffic delays.

It’s important to note that the road from Key Largo to Islamorada is mostly two lanes per side. Although the speed limit ranges from 35 to 55 mph, it’s common for things to move a bit slow, especially on weekends.

The Overseas Highway is the only road that runs from Key Largo to Key West, so traffic jams and accidents can back things up quickly! I recommend giving yourself plenty of “fluff” time if you have a major event (like a wedding!).

Note: Most restaurants and hotels in the Florida Keys designate their locations by referring to their Mile Marker! For example, Islamorada Fish Company is located at Mile Marker 81.5. Key Largo starts around Mile Marker 107, and Key West ends with the famous Mile Marker 0!

How to Get From Key Largo to Islamorada

If you’re wondering how to get between Key Largo and Islamorada, you have a few options! First, you’ll need to get into the Florida Keys, which requires some driving from nearby parts of Florida (or flying into Key West!).

The most popular option for out-of-towners is to fly into Fort Lauderdale International Airport (FLL) or Miami International Airport (MIA). From there, you’ll need to make the drive into the Keys. Leaving from Fort Lauderdale, it will take about 1.5 – 2 hours. From Miami, it should take 1 – 1.5 hours. However, rush hour in Miami might add to these times!

If you’re looking for more information about getting from Miami to Key Largo, check out my complete Miami to Key Largo road trip guide.

Once you’ve arrived in Key Largo, it’s easy to make the journey to Islamorada. The best option is to rent a car while in Fort Lauderdale or Miami, as you’ll definitely benefit from having your own vehicle in the Keys!

However, if you find yourself in Key Largo and need to get to Islamorada without a car, there are still options.

You can take a Greyhound or a Flixbus, which run 2-3 times a day and are extremely reasonably priced (~$8-$10).

Another option is to take an Uber, Lyft, or taxi. These will vary in cost for this route, with rideshares tending to be cheaper.

Lastly, you can book private a tour that includes transportation between the two!

Best Time to Visit Key Largo and Islamorada

The good news about the Florida Keys is there’s really no “bad” time to visit! Different seasons bring different pros and cons, which I’ll give a summary of below!

Winter (November – February): A very popular time to visit the Florida Keys due to the mild “winter” temperatures. Think average highs in the upper 70s! This is high season in Key Largo and Islamorada, so expect increased prices at hotels, more crowds, and longer wait times at restaurants.

Spring (March – May): My personal favorite time to visit the Keys, spring is the perfect shoulder season! Temperatures start to warm up, and rain chances are low. There might be spring break crowds in Key West, but otherwise, this is a great season to visit.

Summer (June – August): If you are planning to visit Key Largo and Islamorada in the summer, be prepared for the heat and humidity. In the Keys, prices are typically lower in the summer, so it can be a good time to visit if you don’t mind the soaring temps! Also, don’t forget to consider hurricane season!

Fall (September – November): Fall is another great time to visit, as hurricane season comes to a close and temperatures start to go down. I recommend visiting in October and November, after hurricane season and before the winter crowds arrive!

For more information on this topic, make sure to check out my blog post for a full review of the Best Time to Visit the Florida Keys!

Is Islamorada Better Than Key Largo?

A tough question that really comes down to personal preference! When I visit the Keys, I typically stay in Islamorada, for a few reasons. Most importantly, Islamorada holds a special place in my heart since it’s where I got married!

In general, there’s a little bit more to do in Islamorada. Islamorada is home to two different incredible breweries, Florida Keys Brewing Company and Islamorada Brewery & Distillery. Islamorada also has a little more variety when it comes to restaurants. Places like Chef Michael’s and Pierre’s are incredible spots that cater more towards “fine dining”.

Islamorada also has the famous Robbie’s, a restaurant, a souvenir shop, and a marina all packed into one! This is arguably one of the most famous places to stop in the Florida Keys, where you can hand-feed tarpon off the dock! More on this later.

From an underwater perspective, you won’t be disappointed with the snorkeling in Key Largo or the snorkeling in Islamorada. There are plenty of places to check out, from the Christ of the Abyss Statue to the Alligator Reef Lighthouse.

However, Islamorada does have the incredible “Islamorada Sandbar”, where you can relax in shallow water and party the day away!

Key Largo Guide

Now that we’ve covered how to get between Key Largo and Islamorada, let’s dive into the details of both towns, starting with Key Largo.

Key Largo is the first Key as you make the drive into the Florida Keys from South Florida. Key Largo spans 33 miles, making it the largest Key in the Florida Keys. Although it’s large, Key Largo has a very sleepy and local vibe.

Things to Do in Key Largo

Key Largo is the self-proclaimed dive capital of the world, so most of the activities here center around the water. There are tons of incredible places to snorkel in Key Largo, like the Christ of the Abyss Statue and Grecian Rocks.

You can rent a boat yourself (if you have experience) or go on an organized snorkel tour to visit these iconic spots!

There are also plenty of scuba diving sites if you are certified. Some of the most popular spots include Molasses Reef and the USS Spiegel Grove (a shipwreck!)

Another iconic thing to do in Key Largo is to swim with dolphins. There are a few different places to swim and interact with dolphins in the Florida Keys.

I personally recommend Dolphins Plus, as they are committed to protecting their dolphins and giving back to the community. They do not perform dolphin “shows” and instead focus on educating their visitors about these incredible creatures.

Lastly, one of the top things to do in Key Largo at night is to watch the sunset! I highly recommend going on a Key Largo sunset cruise during your time here. They are different options around town, like a glass-bottom boat tour or a Crusin’ Tiki Hut!

However, if you are focused on free things to do in Key Largo, you can still see epic sunsets from shore!

Where to Stay in Key Largo

Key Largo has a variety of hotels and vacation rentals to choose from! From boutique bed and breakfasts to luxury resorts, there’s something for everyone (and every budget!) in Key Largo. Here are my top recommendations, in order from least expensive to most expensive.

Coconut Palm Inn: A tropical hideaway located on the bayside! Recipient of Travel and Leisure’s annual “40 Secret Hideaways” in the world. The property puts off “Family Beach House” vibes and captures the true essence of the Florida Keys.

Kona Kai Resort: A budget-friendly resort nestled into the bayside! Perfect for those looking to escape the crowds. There are only 13 bungalows on the property, plus a pool, gallery, and more! You can read my full review of this property here.

Playa Largo: An Autograph Resort collection hotel, Playa Largo feels more like a “hotel” than the others, but that doesn’t mean it isn’t gorgeous. The property is incredible, with a luxurious pool, beach bar, and plenty of activities to keep you busy. I recommend checking out their Sol By the Sea restaurant where you can dine in the water!

The Bungalows: The definition of true luxury! One of the only all-inclusive resorts in the Keys. The property has two pools and two beaches, cabanas, snorkel gear, yoga classes, and more! Expect to pay a pretty penny for this incredible resort.

Make sure to check out my full guide to the Best Hotels in Key Largo here!

Islamorada Guide

Islamorada is not technically a “Key” but a village made of six different keys: Plantation Key, Windley Key, Upper Matecumbe Key, Lower Matecumbe Key, and the offshore islands of Indian Key and Lignumvitae Key.

If you are driving from Miami, Islamorada is the second major village you will hit, right after Key Largo! Islamorada spans from approximately Mile Marker 90 to 72.

Things to Do in Islamorada

Similar to Key Largo, many of the top things to do in Islamorada revolve around the ocean!

My favorite place to snorkel in Islamorada is Alligator Reef Lighthouse. Unfortunately, it’s a little challenging to get to without your own vessel, but some snorkel tours do visit here.

Located about 4 nautical miles offshore, the lighthouse is over 150 years old and sits in beautiful, clear, turquoise water. You can snorkel underneath and around the lighthouse, and you’ll encounter some of the most incredible coral and wildlife!

Another exciting water-based activity is to go jet skiing! Renting jet skis is one of my favorite things to do in the Keys, and Islamorada is the perfect place for it! 

We typically rent with A1A Watersports in Islamorada! They offer daily jet ski tours starting at $129 for one hour or $200 for two hours. They also have boat rentals here.

As already mentioned, another top thing to do in Islamorada is visit Robbie’s of Islamorada. Here, you can eat at their delicious restaurant (get a Bloody Mary!) or go on a backcountry kayaking tour.

However, the most popular thing to do at Robbie’s is feed the tarpon! On a normal day, there are typically over 100 tarpons around the docks of Robbie’s. You can buy a bucket of fish and watch them leap out of the water while feeding them – just watch your fingers!

Last but not least, Islamorada has some incredible restaurants and bars to choose from. I always visit one of the two breweries in Islamorada during my time there, for great beer and even better vibes!

In addition, there are not one but TWO restaurants in Islamorada that have been featured on Diners, Drive-Ins, and Dives! For more details, make sure to check out my guide to the Best Restaurants in Islamorada.

Where to Stay in Islamorada

Islamorada is home to some of the best resorts in all of the Florida Keys. From affordable beachside cottages to five-star resorts, there is something for everyone here.

Islander Resort: Mid-tier resort that is truly a slice of paradise! With over 114 rooms and suites, it’s perfect for those looking for more amenities on site, like bicycles, beach games, a poolside bar, and more!

Postcard Inn: Very similar to Islander, Postcard Inn offers reasonable prices with lots of onsite activities, including the famous Tiki Bar, home of the rum runner! Also has a little ocean lagoon for kayaking, paddle boarding, etc.

The Caribbean Resort: I might be a little biased since I got married here, but in my opinion, this is the most beautiful resort in the Florida Keys. With 22 unique Caribbean-style homes, a gorgeous zero-entry pool, and marina and fishing pier, you will not regret staying here! Check out my full review of the property here.

Cheeca Lodge & Spa: Located just down the road from the Caribbean Resort, Cheeca Lodge has a gorgeous property and stellar rooms. It’s also one of the only resorts in the entire Florida Keys that has a golf course on the property.

Make sure to check out my full guide to the Best Hotels in Islamorada here!

Final Thoughts

I hope you now feel prepared for your journey to the Upper Keys! From Key Largo to Islamorada, the Upper Keys are truly my favorite area of the Florida Keys and the perfect destination for all types of travelers.

There’s so much to do here, from snorkeling at John Pennekamp and Alligator Reef Lighthouse to eating incredible seafood and drinking local beer. Make sure to include the Upper Keys in your Florida Keys itinerary!