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  • Writer's pictureHannah Shuman

Which Florida Key is the Best? (And Which YOU Should Add to your Road Trip Itinerary!)

Updated: Mar 11, 2021

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Which Florida Key is the Best

Wow! How to choose just one of the Florida Keys as the best?! This is still one of my favorite destinations within the continental U.S. Dotting along the Southern coast of Florida, the Florida Keys are a water wonderland made up of 1,700 islands. You are surrounded by turquoise water, so you instantly feel like you are transported to the Caribbean. With all different kind of vibes, you can rest assured you will find something for you! From big family get togethers, tropical weddings and romantic weekend getaways, or bachelorette parties and boys fishing trip, The Florida Keys has it all! While I DO have my opinion which is the best, I will leave it to you to decide which you should add to your next road trip!


When to go to The Florida Keys:

Florida really is a year-round destination. With temps averaging mid – 70’s, you will enjoy a tropical climate during most of the year. When deciding the best time for you, there are a few things to consider. While summertime brings plenty of sunshine, there are almost always afternoon thunderstorms. Plus, hurricane season runs from June to November and while it isn’t likely you will get hit with a huge storm, just make sure you have a flexible booking during those months. With so much rain, mosquitos are also a big nuisance in the wet season. Winter is the dry season so definitely less rain and bugs to worry about, but the water will be pretty cold and might not be ideal for a swim. (I have gone swimming in Florida year-round, so it really depends on your cold tolerance!) May and October usually give you the best weather in Florida!

Other key things to factor in are holidays and special seasons. Accommodation prices rise significantly during holidays like Christmas and New Year’s. The regular lobster season in the Florida Keys is always August 6 through March 31. The two-day mini lobster season is the last consecutive Wednesday and Thursday in July. Make sure to verify dates and regulations with Florida Fish and Wildlife. Be sure to book early for mini season as it is one of the first dates to get booked each year!


Getting to The Florida Keys:

We are going to start the journey to The Keys in Miami. (Check out alllll there is to do in Miami and stay a few days!) You can fly into Miami International Airport from basically any corner of the planet. Here you can rent a car and start your trek down the coast. Make your way through the city of Homestead and stock up on any last-minute road trip supplies and fuel. All of the Keys are connected by one loooong road, so you won’t have to worry too much about getting lost. Once you get out on to U.S. Route 1, you are basically in the Keys!

The first main key you come to is Key Largo and then there are 30 more inhabited islands before you reach the tip of the keys, Key West. If you drove straight from Key Largo to Key West it would take you about 4 hours, but an even better option is to choose a few stops along the way! But 30 possible keys are a lot! So, let’s narrow it down to the best keys to visit and explore things to do along the way!


Stop #1: Key Largo

Good For: Dive Enthusiasts

Epic Florida Keys Road Trip: Key Largo

Our first stop gives you a nice “mini” road trip as it is only about an hour out of Miami. BUT you still get beautiful views driving in over miles of bridges. Key Largo is the largest key but not necessarily the busiest. This quiet residential area has more to do in the water than on land. Still, there are quite a few gorgeous resorts and holiday homes here. This is also where you will find the only All-Inclusive in The Keys. The Bungalows is an adult-only luxury escape that will blow any expectations out of the water!

Divers will love this stop with over 23 artificial reefs sunk over the last 20 years. The coral reefs dotting the Keys are a crucial part of the ecosystems within Florida so coral restoration projects can be found throughout the Keys! Even if you aren’t a diver, you can still take advantage of the underwater wonders at John Pennekamp Coral Reef State Park. This was the first underwater national park! This park is the home to the Christ of the Abyss statue, a larger-than-life statue of Christ set in about 25 feet of water making it super easy to snorkel, too! Just remember if you do snorkel or dive, DON’T touch the coral (you will kill it ☹) and never take anything but pictures 😊

Christ of the Abyss
Christ of the Abyss

Stop # 2: Islamorada

Good For: Fisherman

Epic Florida Keys Road Trip: Islamorada

This place is literally called “The Sport Fishing Capital of the World”. Fishermen unite. You have found your paradise. Honestly as much as I love being on the water, I have never been into fishing. I have been plenty of times growing up along the Manatee River and Gulf of Mexico but it’s just not for me. Boating on the other hand, tons of fun! So evennnnn if you don’t like fishing, don’t just pass up Islamorada. There are a TON of hidden surprises here to visit, even if it’s just for a pit stop!

First thing’s first though. We have to take care of our fishing and boating enthusiasts! If this is the place for you, there are so many GORGEOUS waterfront family holiday villas here! If you own a boat, many have boat slips making them absolutely perfect for that early morning start time! My recommendation? Something with a pool. There is nothing better than having a dip in the pool after a long day of salt water!

If you don’t have your own boat, don’t worry! There are plenty of boat rentals and fishing charters for all levels that will take you out to the best spots. If you are just here for the boating fun, you can’t miss the sand bar, just a mile off-shore Mile Marker 84. There will usually be a ton of boats out there so you can’t miss it! Sometimes the sand bar is so exposed you can set up a beach chair and enjoy the day! Another great option is the historic lighthouse at Alligator Reef.

Alligator Reef

If you are just passing through Islamorada, you still MUST stop at Robbie’s and feed the tarpon! It is definitely not for the faint of heart because tarpon are VERY large fish, and they are not shy! Still, one of the most iconic stops in The Keys so you have to check it out! If you are a history buff, make a pit stop and see the History of Diving Museum where you will find all kinds of relics including a 16th century iron treasure chest! Islamorada is also full of cute restaurants, bars, and shops so it is definitely worth a stop!


Stop # 3: Marathon

Good For: Beach Lovers

Epic Florida Keys Road Trip: Marathon

Marathon is about 2 hours from Miami making us about to the halfway point! This is your stop if you are looking for a unique beach vacation! Most people don’t think of the Keys when they think of Florida Beach Destinations but SURPRISE! This stop has some of the most beautiful scenery without having to go out on a boat!

Sombrero Beach is one of the few sandy beaches found in the Keys! This is a great place to bring the kids to go snorkeling and also has another historic lighthouse just offshore! Another can’t miss spot is Bahia Honda State Park! I mean wow! This one takes the cake for some of the most “Caribbean-esk” views throughout all of The Keys. Crystal clear turquoise waters and bright white sand. This is a no-brainer to add to the itinerary!

Plan a great stay here at one of the cute beach spa resorts so you can take advantage of your time in the sun! Wanting to swim with dolphins? This is your stop! Many of the resorts have all kinds of amenities including restaurants, spa services, animal encounters and eco-tours!

As you are leaving Marathon, you are crossing the Seven-Mile Bridge! This was once one of the longest bridges in the U.S. and gives especially spectacular views. Remnants of the old bridge still connect to Pigeon Key but have been damaged through the years by hurricanes. This bridge was the reason anyone was even able to get to Key West!


Stop #4: Key West

Good For: Party Goers

Epic Florida Keys Road Trip: Key West

What can I say? Key West is DEFINITELY (in my opinion) the BEST Key! With so much to see and do, you could easily spend a whole week just wandering the palm lined streets. The main drag in Key West is Duval St. Start in the main port and work your way through the dive bars and saloons filled with remarkably interesting characters from pirates to Jimmy Buffet cover bands. You will definitely feel lost in Margaritaville after one bar crawl… Don’t worry, bars aren’t the only thing around here. Take a guided snorkel or dive tour to explore the 3rd largest coral reef in the world! If you are really down for an adventure, grab the ferry to the Dry Tortugas National Park. While there is an old fort there that is cool to see, bring your snorkel gear and get in the water! Unbelievably untouched and pretty much as remote as you can get in the continental U.S.! Don’t forget to grab a slice of Key Lime Pie to finish your day!

While accommodations right on Duval are pretty steep, they are well worth the cost for the convenience of being able to stumble home from the bars. If you want a luxury experience steps from Duval, I would recommend Sunset Key Cottages. Parking is impossible so make sure it is included in your stay! If you are on a budget, just prepare for expensive cab rides or a lot of walking. Biking is another easy way to get around as long as you aren’t under the influence! (Yes, you can still get a DUI on a bike!) Overall, Key West is relatively walkable and there are iconic spots all over the island. Besides Duval St., make sure to see the Southern Most Point, Earnest Hemingway’s Home, Smather’s Beach, Fort Zachary Taylor State Park, and Mallory Square at sunset!

Key West is good for all walks of life from families to couples. It has such a rich culture and a very “old-Florida” vibe. Life here is very easy-going and you are on island time. Enjoy the rum and the sea breeze and get lost in paradise!

Epic Florida Keys Road Trip Itinerary

If you can’t decide on just one, you could also string them together in one epic road trip!

Epic Florida Keys Road Trip Itinerary:

Epic Florida Keys Road Trip Itinerary

Day 1: Fly into Miami International Airport (MIA)

· Plan to spend the night and enjoy some of the Miami nightlife!

Day 2-3: Key Largo

· Hit the road early and plan to spend the day at John Pennekamp Coral Reef State Park snorkeling down to see the Christ of the Abyss

· Spend the next day on guided dive or snorkel tour of the World’s 3rd Largest Coral Reef

Day 4-6: Key West

· Skip all the way down to Key West to see where the party is at

· Catch a ferry out to Dry Tortuga to snorkel the untouched reefs

· Do a bar crawl along Duval St. stopping for tropical drinks and Key Lime pie

Day 7-8: Marathon

· Spend one night in Marathon exploring the beaches of The Keys – Bahia Honda State Park and Sombrero Beach

Day 9-10: Islamorada

· End your trip with some relaxation on the water, hit the sand bars for a boat day or explore the depths as you chase the monsters of the deep

· Head back to Miami to make the journey back home


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