How to Find Adventure in The Florida Keys + 3-Day Itinerary

The Florida Keys are a string of islands located right under the peninsula of Florida, about 120 miles off of the coast. There are five “keys” total; Key Largo, Islamorada, Marathon, Big Pine and Lower Keys, and Key West.

Why is Key West so special? Not only is it beautiful, but Key West is extremely unique. With neighborhoods that resemble the southern states and cities like Charleston and Savannah, and free-roaming chickens, Key West is sure to inspire.

If you live in Florida, this is a must- see place, that is most likely within driving distance. If you do not live in Florida, a quick trip is still possible. Keep reading to find out more about what this place has to offer and how YOU can find adventure in The Keys…or scroll to the bottom for a 3-day Key West itinerary.

How to get there

For local Floridians living in Orlando and below, you can make a drive to Key West in about 6 hours. The drive is completely worth it, too. Most of the drive consists of crossing bridges with a beautiful view of the blue waters below. If you are within driving distance, I highly encourage making the drive at least once.

For those of you who do not live in Florida or within a reasonable driving distance, you have a few options:

1. Fly into Miami International and rent a car- You can always find cheap flights into Miami, and find a budget rental for the weekend. Fair warning, driving in Miami is terrifying. Traffic is crazy at all times, and the driving can get *intense*.
2. Fly into Fort Myers regional and take the Key West Express– The Key West Express is a ferry boat that takes you from Fort Myers to Key West in 3.5-4 hours depending on the weather. Complete with a full bar and galley, this ferry is notorious for seeing its passengers experience the results of sea-sickness and over drinking…that being said, everyone should experience it at least once. At $175 round trip, this may be a cheaper option than the latter.
3. Fly directly into the Key West airport- As you can imagine, this is going to be the most expensive option, as the Key West airport is extremely small. This may be a better option for those who don’t want to deal with a car or ferry. Once in Key West, there are many options for transportation, including golf carts and bikes. The island is only 7 square miles, so it is fairly easy to get from place to place walking.

Places to stay

If you want to go all the way down to Key West, be aware that finding a good, decently priced place to stay can be tricky. Key West is a very popular location for bachelorette parties, spring break, you name it. There are many luxury options in Key West, but if you are looking for somewhere low cost, check out local Airbnbs. You can find a variety of options, including stays on sailboats.

If you want to save, a cheaper option may be to stay in one of the upper keys, and make a day trip down to Key West. The further North you go, the lower the price will be. Some keys also offer camping, if you’re someone who likes to rough it in the wild. One place to consider for this, is the Bahia Honda State Park. This area is relatively close to Key West, but offers options for low cost camping.

Things to do

No matter what you like to do, there is something for you in the Keys. Some of my favorite activities include sunset sailboat rides, lounging on the beach, and touring downtown. Below are some exciting activities to do in Key West:

1. Sunset Sailboat Ride– One of my favorite things I’ve done in Key West is the sunset sail with Classic Harbor Line. For $96, you can take a 2 hour sail with complimentary wine and charcuterie. Nothing better than the wind in your hair as you sip your 6th glass of wine and converse with strangers!
2. Hemingway House- Key West is famous for being the winter destination for Ernest Hemingway, a famous American novelist. You can still visit (and even stay in!) the Hemingway House at the tip of the island.
3. Snorkeling- If you love to see wildlife up close, snorkeling is one of the best ways to do this, especially in the Keys. Surrounded by many atolls and reefs, you’re sure to see some amazing sights on this excursion. Check out Fury Cat, this highly rated company offers a 3 hour snorkeling excursion for around $50, equipment provided.
4. Walk around the island- I am a firm believer that one of the best things you can do in a new place is to simply walk around and explore for yourself. Key West has many different, beautiful neighborhoods to explore. Even at only 7 square miles, you’re bound to find something exciting. Like Mallory Square, for instance. This Square is often booming with live entertainment, music, and people. Enjoy the warm ocean mist as you sip a cocktail and watch a man balance a ladder on his nose!
5. Dry Tortugas National Park- This is one of the hidden gems of the Keys. 70 miles off of the coast of Key West, and only accessible by boat or seaplane, Dry Tortugas is full of beauty and history. This National Park houses a 19th century fort and is surrounded by tons of marine life. In full transparency- it can be costly to make the journey to this island- roughly $200 to take a ferry and even more to charter a boat or take a seaplane. Definitely worth a visit if it’s in your budget, however.

Places to eat

If you’re a foodie like me, you’ll appreciate the options in Key West…and if you love seafood (sorry, I don’t get it), you’re in luck! Key West has some of the freshest seafood around. The Conch Republic is the place to go if this is what you’re seeking.

Some of my personal favorites include a Cuban restaurant in Mallory Square called El Meson De Pepe’s Restaurant and Bar. If you check this out, you’ll not only be in the center of the fun of Mallory Square, but you’ll enjoy a festive vibe in the restaurant itself. Be sure to sit outside to enjoy a coastal breeze as you dine. I would highly recommend the Pan con Bistec (a delicious steak!!).

You’ll want to check out Hemingway’s favorite spot, Sloppy Joe’s, for a drink, or perhaps the Funky Rooster for a quick breakfast. The point is- there are plenty of options for all meals and all cravings in Key West, and sometimes the best spots can be found by exploring on your own.

3- Day Itinerary

Check out my 3-day itinerary for The Florida Keys, and get out there & see some sights!