The Ultimate Travel Guide to the Florida Keys: My Personal Journey to Paradise
When it comes to luxury beach vacations, the Florida Keys offer an alluring blend of pristine white sand beaches, turquoise waters, and top-tier resorts. Spanning 202 miles and known for its laid-back atmosphere and incredible seafood, the Florida Keys are a tropical paradise for those seeking an unforgettable getaway.
How to Start Your Florida Keys Adventure?
My First Stop in Miami
We flew into Miami, arriving late, and stayed at the MIA Airport Marriott for the night. While not a luxury experience, the friendly service and Titanium perks (like a free breakfast) made it a pleasant start to our Florida adventure.
What are the best luxury resorts in the Florida Keys?
Key Largo: My Favorite Luxury Resort
Stay at Bakers Cay: My Experience
The next morning, we headed to Bakers Cay, a Hilton Curio Collection resort in Key Largo. This lush tropical oasis felt like a hidden jungle paradise with its two distinct beaches—one sunny and one shaded. While the sand was more coral-like than soft, the clear waters, abundance of beach chairs, and excellent beachfront dining made up for it.
The Ultimate Beachside Cocktail
The highlight? A frozen coconut mojito that set a new standard for beachside cocktails. The resort also offered lovely rooms overlooking the water, ideal for a wedding reception on the sand. Service was great and the staff were very friendly.
Playa Largo: A Luxurious Stay
we went to stay at Playa Largo, a Marriott Autograph collection. This was another beautiful beach resort, not as lush, but just as nice, they’ve perfected the luxury vacation vibe. The pool area here was gorgeous, really felt like we were on a tropical vacation. They had live music playing, drink service, and nice comfy lounge chairs. The beach, just on the other side of the fence was really nice too. Soft, white sand, clear water. We could see interesting fish swimming by, and starfish too! They had floating cabanas, added a unique touch, and a sunset ceremony each night to celebrate the end of another beautiful day. The room was large, bright and had nice furniture. The meeting space would be great for a corporate meeting, but for a wedding, I liked Bakers Cay better, But I liked the accommodations at Playa Largo better.
Dining at Snooks Bayside
We had dinner at a nearby restaurant called Snooks Bayside. Nice beachy atmosphere, live music, incredible sunset and the food was great.
I wish we would’ve had time to check out the Bungalows Key Largo, one of the few All-Inclusive adults only beach resorts in the area. It was recently rated in the Top 10 for Resorts in the Florida Keys, and looks really great. With its inclusive luxury experience and tropical ambiance, it's definitely on our list for next time.
Exploring the Florida Keys by Boat
My Key Largo Princess Glass-Bottom Tour
We went on the Key Largo Princess glass bottom boat tour of the John Pennekamp Coral Reef State Park and the Key Largo National Marine Sanctuary. It was a 45 min ride out to the reef. We stayed for about 20 min, then came back. Unfortunately, we didn’t see much besides coral and a few parrotfish. It’s a nice way to see underwater when the water is too chilly to go snorkeling, or you just don’t want to get wet. The staff were knowledgeable and very friendly. The weather was nice & sunny, so it was enjoyable just to be on the boat. Afterwards, we had lunch at Skippers Dockside, right on the water.
Best Shopping and Dining in Islamorada
For the afternoon, we drove into Islamorada to do some shopping (since there is basically none, only Shell World- which is gigantic, in Key Largo). Islamorada had a few shops to choose from, one of which I really liked, Drift Island, very simple, classy clothes. We found a cute beach bar, called Papa Joes on the side of the road and had a drink overlooking the turquoise water. It was fun to watch the boats and enjoy the sunshine.
Little Palm Island Resort & Spa
Moving on to Little Palm Island Resort & Spa, a 5-star adults only resort, and the only private island resort in the U.S. Truly feels like being somewhere in the British West Indies; pure luxury and total relaxation- no phones, no TVs, no distractions. This is a total escape from reality that everyone should experience at some point in their life.
Key West: My Experience
Our journey continued to Key West, known for its breathtaking scenic drive along the Overseas Highway. The turquoise waters and boats lining the coast made the drive as enjoyable as the destination itself.
Staying at Margaritaville Beach House
In Key West, we stayed at the Margaritaville Beach House, a tropical resort inspired by Jimmy Buffett. The rooms are cute, with shiplap and hand painted murals done by local artists, rooms are kitschy but cute. We were greeted with a margarita (what else?!) and the service was very personalized. However, some details fell short of the luxury promised by the price. It’s a 10-15 min drive into downtown Key West. They have a shuttle, but it fills up quickly at busy times, so we ended up having to take a Lyft.
Exploring Mallory Square and Local Bars
Being my first time in the Keys, I wanted to check out the touristy areas, so we started with Mallory Square at sunset. Lots of art booths were set up and street performers doing their thing. The sunset was amazing, every shade of orange, which made for spectacular pictures, especially with the boats going by. It was fun to walk up/down the streets, people-watch, shop and bar hop. We ended up at a great place called Surly Siren Saloon, a newer bar with excellent live music and the best burger I’ve had in ages. The owner (Cris) ended up serving us, and we had a great time. It was our favorite bar…if you go to Key West, you’ve gotta go to this place! Can’t go to Key West without getting some key lime pie, so we walked (didn’t realize how far it was!) to the most highly rated place, Blue Heaven. I must say, it was delicious, and definitely big enough to share!
My Key West Dolphin Sunset Cruise with Honest Eco
The next day we took a Dolphin Sunset Cruise with Honest Eco, and what an amazing time we had! The weather was perfect, the catamaran was lots of fun and the crew (Hadden & Dan) were very knowledgeable. Honest Eco serves up fresh fruit and veggies/hummus rather than your traditional booze cruise. They’re geared toward teaching us about the dolphins, in a small group setting. And best of all, we saw dolphins! There were three of them that came right up to the boat and played around us for about 15 minutes. Such a great experience I will treasure forever.
The next day we drove back to Miami. Did I mention how slow the 2-lane highway is? It took us over 4 hours to get there, but we enjoyed the view. We spent the afternoon shopping and had dinner at Greenstreet Cafe in Coconut Grove, good food and a cute little area. It’s fun to sit outside and people-watch. Next stop, 1 Hotel South Beach, such a beautiful property, the best beachfront hotel in South Beach, in my opinion. It whispers comfy elegance the minute you walk into the lobby, with Restoration Hardware-type sofas that you sink into, truly a luxury beach hotel. The rooms are huge (700 sq ft) and very comfortable, with a separate seating area. The pool was superb with nice cushy lounge chairs overlooking South Beach. For dinner we found a cute little Cuban restaurant called Havana 1957. I had the best garlic shrimp entrée and mojito, that I think I’ve ever had. It was all so delicious! I recommend going to the Lincoln location, it’s better…we tried the Ocean Dr for more mojitos later in the evening and they weren’t nearly as good.
Conclusion:
Now it’s time to go back home, but the memories of the Florida Keys will stay with me forever. The weather was perfect, the experiences unforgettable, and every moment spent exploring this tropical paradise was absolutely worth it. From the serene beaches to the delicious local cuisine, this trip truly exceeded all my expectations.
If you're dreaming of a luxury beach getaway full of unforgettable experiences and crystal-clear waters, the Florida Keys might just be your perfect paradise. No passport needed, just the promise of relaxation and adventure.
I’d love to help you plan your own dream vacation. Reach out to me at www.luxurybeachtravel.com, and let’s curate an itinerary tailored to your unique needs and desires. Trust me, this is a journey you won’t want to miss!
FAQs
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The best time to visit the Florida Keys is during the shoulder seasons, April, May, and November, for a perfect balance of ideal weather, lower crowds, and affordable prices. These months offer warm temperatures with lower humidity, fewer chances of rain, and an overall pleasant atmosphere.
Here’s a breakdown by month:
April and May: The shoulder season offers excellent weather, with mild temperatures, low humidity, and less rain. Plus, you'll avoid the summer crowds.
November: Just after hurricane season, November brings calm weather, with pleasant temperatures and less humidity, making it a fantastic time to explore the Keys.
If you're looking to avoid crowds:
Winter (December–February): While the weather is perfect for escaping cold winters, December to February is the peak tourist season, leading to higher prices and more crowded attractions.
Summer (June–September): The summer months are the rainy season, with higher humidity, frequent thunderstorms, and occasional hurricanes. Though still warm, it’s best to have a flexible schedule if visiting during this time.
Pro Tip: To skip both crowds and the heat, plan your trip during the shoulder seasons in April, May, or November for the best value and weather.
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To fully experience the beauty and unique culture of the Florida Keys, a minimum of 5 to 7 days is recommended, especially if you're exploring beyond Key West. Here's how you can break it down:
Key Largo (1–2 days): The gateway to the Keys, ideal for outdoor adventures, diving, and exploring the beautiful John Pennekamp Coral Reef State Park.
Islamorada (1 day): Known for its relaxed atmosphere and beautiful beaches, Islamorada is perfect for water sports, fishing, and sunset dining.
Marathon (1–2 days): If you love pristine beaches and wildlife, Marathon is where you'll find some of the most scenic views in the Keys.
Key West (2–3 days): The most famous Key, known for its vibrant nightlife, art scene, and historical landmarks, like the Ernest Hemingway Home.
Whether you're exploring the Everglades or spending time in Key West, having at least a week lets you enjoy a slow-paced island life, and dive into the unique activities each Key offers.
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The best way to explore the Florida Keys is by driving along the iconic Overseas Highway (U.S. Route 1), which connects the islands and offers some of the most spectacular ocean views in the world. The scenic drive from Miami to Key West (159 miles) takes you through quaint islands, beautiful beaches, and stunning bridges, including the famous Seven Mile Bridge.
If you're not interested in driving:
Key West International Airport offers flights to the Keys with rental car options available for easy access to the islands.
Alternatively, local shuttles and taxis can also help you explore without a car.
Pro Tip: Rent a convertible car or motorcycle for a fun, open-air ride along the stunning Overseas Highway!
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The nicest Florida Key to visit depends on your preferences, but here are my top picks:
Key Largo: Best for outdoor adventures on land and sea. It’s home to the John Pennekamp Coral Reef State Park and great for snorkeling, scuba diving, and fishing.
Islamorada: Offers a little bit of everything—water sports, amazing sunsets, and wonderful restaurants. It’s perfect for a relaxed yet adventurous stay.
Marathon: Ideal for beach lovers. Marathon has some of the best beaches, and it’s also the gateway to the Sombrero Reef and Dolphin Research Center.
Big Pine Key: Best for nature lovers with wildlife and nature reserves, including the National Key Deer Refuge.
Key West: The cultural hub of the Keys, perfect for those who enjoy art, history, lively nightlife, and unique attractions.
Each Key has its own charm, but if you're looking for a blend of relaxation, adventure, and culture, Key West is hard to beat.
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The drive from Miami to Key West is 159 miles (256 km) and takes around 4 hours by car. The journey along U.S. Route 1, also known as the Overseas Highway, is filled with breathtaking ocean views and scenic landscapes.
If you’re driving for the first time, be sure to stop along the way at some of the small islands and beaches for a photo op. The drive itself is a unique experience, making it as memorable as the destination.
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Yes, the drive from Miami to Key West is absolutely worth it. The 160-mile route on U.S. Route 1 is famous for its scenic views, stunning bridges, and coastal landscapes. You'll pass through lush islands, with highlights like the Seven Mile Bridge, one of the most beautiful and iconic spots on the route.
However, some visitors find the drive long and monotonous, especially if they’re looking for a faster journey to Key West. But for those who enjoy a scenic road trip, this drive offers a unique experience that you won’t find anywhere else in the world.