Florida Keys Trip Itinerary & Travel Guide 2022

Our Florida Keys trip itinerary and travel guide covers everything you need to know — things to do, where to stay, packing and more!

Can you believe I’ve lived in the United States my entire life and I had never been to Florida except during a layover? I’ve always thought I needed to leave the United States in order to find the white-sand beaches and warm water that I crave on a regular basis. Florida never really crossed my mind until I was invited by the Florida Keys Tourism Development Council a few weeks ago for an eco-adventure trip.

Oddly enough, I happened to visit during some of the coldest weather that The Florida Keys has seen in a long time, but I did get to enjoy a couple of days of sunshine (so I do have a pretty good idea of what it’s like the other 362 days of the year in The Keys).

I wasn’t just excited to see the beaches and swim in balmy ocean water in January, but The Florida Keys is home to some of the most adventurous water sports — including flying over the water with a Jetpack. After I saw this on my trip to Aruba, I couldn’t wait to try it.

Most of my trip to the southernmost part of the United States was spent in Marathon and Islamorada — both of which have plenty of things to do for an entire vacation. As much as I would have loved to see all of The Keys, I was surprised at how much there is to occupy your time on just these two islands. If you are planning a trip this way, I highly recommend setting up camp in either place and exploring from there.
 

Florida Keys Trip Itinerary & Travel Guide

 

By viewing the map below, you can get an idea of where Marathon and Islamorada are located. (The Lower Keys are not included in this map.)

 

Best Things to Do in Marathon, Florida Keys

Marathon is situated in the Middle Keys and stretches about ten miles long. It’s composed of Knight’s Key, Boot Key, Key Vaca, Fat Deer Key, Long Point Key, Crawl Key and Grassy Key.

 

Snorkel Tour to Sombrero Reef

We took a boat tour to Sombrero Reef with Hall’s Diving Center and spent the day snorkeling with friendly fish. The captain and first mate were a fun crew who were obviously passionate about the ocean and its creatures.

 

Wakeboarding at Keys Cable

This was truly a unique experience. Imagine getting pulled across a lake on a wakeboard by an overhead cable. I’ve tried wakeboarding behind a boat once or twice, but you always have to trust the person who’s driving the boat to stay at a steady speed.

Wakeboarding at Keys Cable made it so much easier because you have an expert who is pulling you along with a remote, who knows exactly what speed to go and can even teach you to go over jumps. You can take your practice here and apply it to other water sports (or snow sports) back at home. It’s the perfect time to take your practice to the next level. If you are wondering whether it’s a good workout, I was sore for over a week!

Read more: 25 Best Honeymoon Destinations In The World (And Where To Stay)

 

Turtle Hospital

I’m so happy I was able to spend some time at the Turtle Hospital in Marathon. It’s heartwarming to see an organization who cares so much about these sea creatures. We watched a turtle surgery where they removed tumors and met dozens of turtles who were in rehab from boating mishaps and water pollution. Once the turtles have completely recovered, they make sure to release them in the same spot where they were found.

Read more: The Best Travel Cameras (And How To Choose One)

 

Where to Stay in Marathon, Florida Keys

Tranquility Bay is a recently-renovated resort that offers beach house rentals as well as sixteen new luxury guestrooms. It’s very tastefully decorated, has a swimming pool, beach volleyball court, tiki bar and award-winning restaurant right on the property. On my first night here, I went to watch the sunset at the beach and found a playful dolphin jumping around right near the shore. I’m told it’s a common occurrence here.

Hawks Cay Resort is another great option on Duck Key in Marathon. Their customer reviews are excellent — especially from couples looking for a quiet getaway.

Read more: The Best Carry-On Luggage (For Every Budget!)

 

Best Things to Do in Islamorada

Islamorada is known as the “Village of Islands” and it consists of Tea Table Key, Lower Matecumbe Key, Upper Matecumbe Key, Windley Key and Plantation Key.

 

Tiki Jet Jetpack Adventure

Trying Jetpack for the first time was beyond hilarious. The owner of Tiki Jet in Islamorada is highly entertaining and makes you feel safe every step of the way. I really thought it would be an easier sport, but I found myself trying too hard and that’s exactly what you don’t want to do.

If you are with a group of friends or on a family vacation in The Keys, you absolutely have to try Jetpack. You will be laughing the entire time and it will undoubtedly get your adrenaline pumping.

 

Where to Stay in Islamorada

I was stunned from the first moment I walked into Cheeca Lodge and Spa. This hotel sits on a long, perfectly-groomed beach and is home to the longest pier in The Keys. They offer seventeen different room types, a snorkeling lagoon, kayaks and several restaurants on the property.

I have never seen a more luxurious soaking tub than the one I found sitting on my huge, private balcony. They also offer adult-only bungalows for happy couples looking for a little peace and quiet.

 

What to Pack for a Trip to the Florida Keys

For packing tips, visit our guide on How to Pack for Carry-On Only,  Packing Guide for World Travelers and our Carry-On Packing List.