You can thank the Beach Boys for my trip to the Florida Keys, specifically Islamorada & Key West. As a kid, my parents would pack up the kids in the car and force us to go to Pennsylvania to visit family. As we made the drive to visit “The Diner” (yes, there were Greeks in my family through marriage…and yes, there were diners) we’d listen to the Beach Boys and I’d imagine heading to the Florida Keys instead of boring, quiet, cold, snowy Pennsylvania. I only wish that back then we were headed to the warmth and that I had these Florida Key Travel Tips. I think I would have enjoyed myself so much more.

Florida Keys Travel Tips

I finally made it to the keys as an adult. While they are no Nice or Cannes, the keys are fun AND beautiful AND much closer. They don’t require a passport either.

Islamorada was cute. It was significantly quieter than Key West. While there’s not that much to do nightlife wise in Islamorada, there’s plenty to do during the daytime. We rented bikes from the resort and did quite a lot of riding. I recommend you bring a hat. The Florida heat is unforgiving and a hat & some sunscreen will protect you from wrinkles and skin cancer. We did plenty of swimming. The water in Islamorada was very calm and I was pleased to see fish swimming with me (if there are no fish swimming in your water, perhaps you should not swim there either). There were some decent restaurants, nothing out of this world, but nothing horrid either.

Once you get bored of the calm of Islamorada, head to Key West, it is quite a lively town. The architecture and homes are decorated in pastel colors and carved wood work. There are chickens running all over the place. You’ll see mama chicken trying to protect her chicks from the chicken catcher quite often. They arrived in Key West with the Cubans who came over in the late 1800’s. They used a special breed that was crossed with a Filipino breed known for its aggressiveness and used them in cockfights. Cockfighting was outlawed in the 70’s, and the chickens & their mates were put out on the streets. I found them to be quite charming. There are tons of restaurants, stores, and clubs for you to visit. If you head to Key West, I’d recommend you rent a hotel. You won’t want to go home once the party gets started. And BTW – if you are a homophobe, I’ve got two suggestions for you: skip Key West or get over it. It’s kinda late now to be so damn bigoted. There’s a very large, very active LGBT community in Key West. They keep the party going and if you’re lucky, you’ll be invited.

What to do in the Florida Keys?

Go Island Hopping – heck, there are 1700 islands in the Florida Keys, some of them are quite small, but you can still pick some of the major ones and check out each one.
Fishing – For this check out Islamorada, it is considered to be the “sportfishing capital of the world”. You can also check out Key West and Marathon.
Diving – Key Largo is home to the 3rd largest & only living coral reef in the continental United States.
Kayaking – Lots of spots to do this. Some are better than others. Make sure to bring a water proof camera. You’ll see tons of marine life.
Party like you’re back in college – The party scene in Key West is awesome. People drink on the street, music blares, and people have a grand old time. You’ll want to check out Duval Street. If you happen to be a homophobe, get over it. Key West has a rather large LBGT community & they keep the party going on and fabulous.
Check out Nature – Schedule a trip to Dry Tortugas National Park. Just $5 gets you in for 7 days. You can sail, go camping, kayaking, fishing…
Meet Chucky – Yup, if you head to East Martello Tower you can meet the doll that inspired the character of Chucky.
Key West Lighthouse – Work on those buns of steel as you head up 88 steps to get a lovely view of the city.
Hemingway House – This was one of my favorite spots. The home is gorgeous and you can really see how Hemingway’s life is reflected in his writing.
Fort Zachary Taylor Historic State Park – One of the least crowded spots in Key West, and one of the prettiest. You can check out the remains of the fort walls, take pictures of gorgeous butterflies, and swim in the best beack in Key West.
Dolphin Watching – Stay out of the water parks (dolphins and other marine life is not meant to be enclosed for your enjoyment). Instead, grab one of the cruises and check out dolphins in their natural environment. Besides, the pictures will be way better.

Where to Stay in the Florida Keys

I picked the Pines & Palms Resort because it had kitchens and because it was situated sort of in the middle of the keys. This was in the days before Airbnb, but it was nice overall. There were a few snafus, but nothing the staff did not handle. The kitchens worked perfectly and the rooms were clean. What I most enjoyed about the place was the nature. It was right on the water, which meant I could “hunt” for sea life on a daily basis. There was also a resident Egret who made his way over whenever we were using the grill. He was kinda fun. Here’s a breakdown of the amenities:

Heated Swimming Pool – fine, except it seemed at the times locals (or maybe an employee’s family, or maybe a guest’s family) were sneaking in. This included a baby in diapers. We let management know, which meant no pool while they cleaned it (and no pool after, I was kinda grossed out).
Complimentary wireless – worked well enough for us to run our internet business
Free Boat Dockage – no boat, didn’t use
Fishing and Swimming Piers – This was great, the water was warm, calm, and a pleasure to swim in
Sandy Sunning Beach with lounge chairs
Pool Bar – there really wasn’t a pool bar. At least not on a daily basis. Could be because the resort was pretty quiet when we were there
Barbecue Grills delivered to your room upon request – took full advantage of this.
Kitchens – in every room ours worked great and had all the basics
Kayaks and Bikes – used them both and had a great time doing so

How to Get to the Florida Keys

Planes: Fly to Miami. From there, you can grab a commuter plane to either Marathon Bay or Key West International.
Car: Hop on the US 1 from Miami. It’s a pretty nice ride unless you hit traffic.
Bus: Greyhound offers bus trips to the Keys with stops in Big Pine Key, Key West, and Marathon.
Ferry: There are various choices that will take you from Fort Myers to Key West. The trips take about 3 hours.

***In case you’re wondering about the poor little guy, he must have gotten hit by a car or something. We found him already decomposing on the road and I could not resist taking a picture. I thought he was an interesting subject.

Should you go to the Florida Keys?

Sure, why not. It’s way less expensive than heading to say France or even the Islands in the Caribbean. It can be a good vacay for a family (if you stay in Islamorada), or if you like to walk on the wild side (Key West).