The Florida Keys are one of those hidden gems (well, not so hidden anymore) that definitely need to be in your future travel plans. The Keys are great for solo travelers, families, or group trips. Since I live in Florida, it’s a great weekend trip or even a day trip to the Upper Keys.
First, a few stats about the Florida Keys. In total, there are 800 keys (“Key” is derived from the Spanish Cayo, meaning a small island) that stretch over 180 miles, with 42 bridges connecting all the Florida Keys. The longest bridge is the Seven Mile Bridge, which is 35,716 feet long and is one of the longest segmental bridges in the world. In addition, located just a few miles offshore is the Florida Reef. It’s the only living coral reef system in the continental United States and is the 3rd largest barrier reef in the world behind the Great Barrier Reef in Australia and the Mesoamerican Barrier Reef System off the coasts of Mexico, Belize, Guatemala, and Honduras. Do you like to fish or better yet, eat them? Islamorada is known as the sportfishing capital of the world, which hosts the largest fishing fleet per square mile in the world!
There are a few ways to get to the Keys, but my favorite and most scenic is driving the 113-mile Overseas Highway, U.S. Route 1, through the Florida Keys south to Key West.
Keep in mind, holidays, Friday, and Sunday afternoons can test your patience as it’s a 2 lane road for most of the 113 miles. Bring your patience! In my opinion, it’s totally worth it!
Check out the Top 5 Scenic Routes for a Summer Road Trip for more details and the other 4 epic road trips!
First stop is a little off the beaten path, but worth it! Take Card Sound Road and stop by Alabama Jacks to grab a drink and try the gigantic conch fritters.
THE FIRST KEY IS KEY LARGO AND HERE’S A FEW OF MY FAVORITES:
- Mrs. Mac’s Kitchen – for lunch or dinner is old school with a very laid-back vibe. There are 2 locations, but I suggest the original. Keep in mind, they are closed on Sunday.
- Key Largo Fisheries Market– Great place with views of the marina and FRESH fish. You can shop for a meal in their fish market
- Shell World– HUGE shopping for souvenirs, but the store has home décor, a children’s section, lots of SHELLS (of course), and many more goodies to take home with you. Believe me, you are going to need time to shop!
- Caribbean Club– Great spot for live music in the evening under the stars. I was lucky enough to have a full moon on my visit.
ISLAMORADA – Sportfishing Capital of the World
Islamorada is a village encompassing 6 of the Florida Keys and known as the Sport Fishing Capital of the World!
If you are staying in Islamorada, there are a few properties I would recommend.
Additionally, Islamorada offers a wide range of charming short-term rentals, making it easy to find the perfect base for your tropical getaway.
Islander Resort, located right in the heart of Islamorada, offers a laid-back beachfront experience with spacious suites, two oceanfront pools, and easy access to water activities like snorkeling and paddleboarding.
Just a short drive away, the iconic Cheeca Lodge & Spa is perfect for those seeking upscale amenities, featuring a full-service spa, a private beach, a nine-hole golf course, and some of the best dining in the Keys. Speaking from experience, it’s a great property when visiting the Keys.
For a more boutique, marina-front vibe, Three Waters Resort & Marina sits bayside with stunning sunset views, modern rooms, and convenient boat slips. It’s ideal for travelers who want to explore the water by day and unwind in stylish comfort by night. Additionally, Islamorada offers a wide range of charming short-term rentals, making it easy to find the perfect base for your tropical getaway.
Favorite Dining Options
Morada Bay is a slice of heaven for lunch or dinner, sunset, or just the views! If you are in town in time for the golden hour, this is one of the best spots. (in my opinion, of course) The fish tacos are YUMMY! Additionally, Pierre’s, located next to Morada Bay, is a fine dining restaurant. If it looks familiar, the Netflix series Bloodline was filmed in Islamorada. My small family group decided after several tastings of key lime pie in the area that Pierre’s has the BEST! Tough job, but someone has to taste test key lime pie!
Lorelei is a great spot for drinks, dinner, plus live music, oh, the sunset too! The Key Lime Colada is delish, tastes like a Key Lime pie cocktail! You can’t miss it because there is a huge mermaid out front to greet you! 😉 You will know it when you see it.
My dining favorite is the Square Grouper. If you wonder about the name, be sure to look around the restaurant for clues. 😉 I’ll be honest since they don’t take reservations… You may have to wait for hours to have dinner. No, I’m not kidding. It’s worth the wait, but be prepared.
What to Do in the Florida Keys: Off-the-Beaten-Path Experiences
Welcome to your fishing paradise! Islamorada, known as the Sport-fishing Capital of the World, is a must-visit even if you’re just a beginner like me. The Bass Pro Shops location here is a hub for all things fishing, offering easy access to fishing charters that depart right from the area, as well as from other spots throughout the Keys. Robbie’s is another hot spot for fishing charters. Whether you’re after a quick adventure or planning to reel in something big, you’ll find no shortage of options. Just a tip: if you’re prone to seasickness, be sure to take motion sickness medication a few hours before heading out-especially if you’re venturing into the Gulf.
If you need your shopping fix, Wild Lily Boutique is a great place to find clothing, shoes, and accessories. One of my favorite necklaces is from the shop. Locally made, too. I love shopping local!
A fun photo stop is located at Mile Marker 86 at the Rain Barrel Artisans Village in Islamorada, Florida, on the Overseas Highway. The giant lobster’s name is Betsy & she’s made of fiberglass and measures 30 feet tall and 40 feet wide. Great place for a selfie with Betsy!
A great option to stay out of the sun or rain is the Diving Museum. Great artifacts and interesting history.
Attention Nature, Outdoor Enthusiasts & Adventurists!
Turtle Hospital – If you’re interested in nature, especially turtles, this is a fun spot to visit, located in Marathon, FL.
Bahia Honda State Park, Big Pine Key– Activities include camping, bird watching, boating, fishing, kayaking, hiking, picnicking, snorkeling, shelling, stargazing, swimming, scuba diving, and much more! $8 per vehicle for a day trip. Plan ahead! Due to the park’s popularity, it may close when its day-use areas reach maximum capacity.
Seven Mile Bridge– connects Knight’s Key in Marathon in the Middle Keys to Little Duck Key in the Lower Keys. Among the longest bridges in existence when it was built, it is part of the Overseas Highway. There are two bridges in this location. The modern bridge is open to vehicle traffic, while the older one is only open to pedestrians and cyclists. Recently, after a $44 million restoration, the bridge has been open to pedestrians. I recently experienced it myself, and it’s an excellent spot for sunrises and sunsets, perfect for walking, running, biking, or simply taking photos and enjoying the 360-degree views of the water. The century-old 2.2-mile bridge is just phase one of a 30-year $77 million plan to restore and maintain the iconic structure. Flagler would be proud!
Located on the north side of the Seven-Mile Bridge in Marathon, Florida, is the modern luxury property known as Isla Belle Beach Resort. I haven’t stayed overnight here, but I spent time in the area, and the property is definitely on my list!
Pigeon Key is a 5-acre island located beneath the Old Seven Mile Bridge near Marathon. Originally known as “Cayo Paloma” on Spanish charts, it earned its name from the white-crowned pigeons that once roosted there. The island gained prominence in the early 1900s as a base camp for over 400 workers constructing Henry Flagler’s ambitious Overseas Railroad, which connected Miami to Key West. Today, Pigeon Key is a National Historic District accessible by walking or biking the restored 2.2-mile section of the Old Seven Mile Bridge, or by taking a passenger train from the Pigeon Key Visitor Center at 1090 Overseas Highway. The island offers guided historical tours, opportunities for snorkeling, fishing off the pier, birdwatching, and picnicking in shaded areas. Admission fees vary, with options for guided tours or self-guided exploration.
Of course, these are just a few of my personal favorites in the Florida Keys! Yes, Key West needs a blog all to itself!
If you need more travel planning advice, I’m here to help. Send me an email or direct message on any of my social media channels @travelcharlee
If you are interested in more Florida gems, take a peek at Florida’s Best Kept Luxury Secrets!