4-Day Florida Keys Trip Itinerary & Travel Guide 2023

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.

What Are The Florida Keys Known For?

The Florida Keys are known for their lush tropical landscape and crystal clear water, making this the perfect destination for a tropical vacation with plenty of water activities. The beautiful beaches and peaceful atmosphere of the Keys make it an ideal place to relax away from busy city life. 

For those with an adventurous spirit, the Keys offer endless activities to keep you entertained. Fishing is a popular pastime here, whether you’re searching for big game or simply enjoying a leisurely afternoon on the water.

Scuba diving and snorkeling are also popular activities here, as the shallow coral reefs provide a vibrant underwater playground filled with colorful fish, turtles, and more. Boating is another must-do activity, whether you’re taking part in deep-sea fishing or simply exploring the bays and coves around each island. 

The Keys are also home to unique cultural experiences that can’t be found anywhere else in Florida.

Key West is known for being one of America’s most unique cities, with its unique ‘conch culture’ that dates back centuries. The streets of Key West are filled with art galleries and independent shops selling handmade crafts –and perfect souvenirs to remind you of your time spent in paradise!

For music lovers, there are plenty of live music venues all over Key West where you can enjoy local musicians playing blues, jazz, country rock – even steel drum music!

The Florida Keys truly have something for everyone!

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.)

Day 1 & 2: Marathon

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!

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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.

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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.

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Day 3 & 4: Islamorada

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 is the Best Month to Visit the Florida Keys?

For those looking to get the best out of their Florida Keys vacation, it is a good idea to plan ahead and visit during the optimal time of year.

The best time to visit the Florida Keys is usually between November and April. This period, known as the dry season, typically has low humidity levels and temperatures in the 80s. Rainfall is also much less likely during this time, making it ideal for outdoor activities such as snorkeling and fishing. Additionally, you’ll avoid the summer hurricane season by scheduling your trip during this part of the year.

December through February tends to be a bit cooler than other months and is not as inviting for swimming and sunbathing at the beach, although I still loved my visit in January!

I’d also recommend checking out festivals and events you might be interested in attending during your trip. For example, you can schedule your vacation during the Lobster Mini-Season or Fantasy Fest.

No matter when you decide to visit The Florida Keys, each season has something unique to offer travelers!

Best Foods to Try in the Florida Keys

The Florida Keys offer some of the most delicious and unique food in the United States. There are a variety of dishes to try, including classic Floridian favorites, local seafood specialties, and exciting new culinary trends.

Here are some of the best foods to try in the Florida Keys:

Key West Conch Fritters – This classic seafood dish is made with freshly-harvested conch meat that is ground into a paste, then deep-fried in a light batter. The crunchy outside and soft inside make for an irresistible snack! Try them with a side of remoulade sauce for a truly unique experience. I recommend checking out The Conch Shack, if you’re in the area!

Grouper Reuben Sandwich – This signature sandwich consists of fresh grouper filet, sauerkraut, Swiss cheese and Thousand Island dressing served on marbled rye bread. Enjoy it as an afternoon snack or lunchtime meal – either way, it’s sure to satisfy! “Off The Hook” Grill serves a great one!

Stone Crab Claws – Stone crabs are wild-caught from local waters and their sweet claws are especially prized for their delicate texture. Stone crab claws can be boiled or grilled and served with lemon butter or garlic butter sauces. If you’re looking for a place to try this amazing dish, check out Conch Republic Seafood Company.

Key Lime Pie – No trip to the Florida Keys would be complete without sampling famous Key lime pie. The tart flavor comes from freshly squeezed limes which are combined with sweetened condensed milk (or egg yolks) before being poured into graham cracker crusts. A dollop of whipped cream makes this dessert even more enjoyable! Almost every restaurant serves Key Lime Pie and, in my opinion, you should sample one from every place!

These are just some of the amazing foods you can find while visiting the Florida Keys – there’s something delicious to suit every taste! 

How Many Days Do You Need in the Florida Keys?

When it comes to planning a trip to the Florida Keys, there are many factors to consider. One of the most important questions is how many days do you need to fully experience everything that this beautiful destination has to offer?

While it may be tempting to try and squeeze in a quick weekend getaway, it’s important to remember that the Florida Keys are best enjoyed when you allow yourself more time.

I recommend staying in the Florida Keys for at least four days. This allows for enough time for exploring all that this charming island chain has to offer, from its stunning white sand beaches and vibrant coral reefs to its picturesque marinas and quaint fishing villages. 

It also gives you ample opportunity for relaxation, with plenty of chances for lounging on the beach or taking sunset cruises aboard luxury yachts. With four full days in the Florida Keys, you can truly experience the best of what this tropical paradise has to offer.

For those looking for an even longer visit, a week-long trip spent in the Florida Keys will give you even more opportunities for exploration.

With a few extra days, you can take a leisurely tour of Key West’s historic sites or spend more time snorkeling or diving amongst some of the world’s most spectacular marine life. You might even choose to go fishing with one of Key West’s experienced guides or take an eco-tour through Everglades National Park – just two hours away from Key West by car.

Alternatively, adding a few extra days offers up even more time for simply relaxing on sandy beaches and soaking up some sunshine – something that never seems like enough when visiting such a stunning coastal destination!

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.

FAQ: Florida Keys Travel Tips