Miami to Key West: Luxury Stays & Scenic Stops en Route

 

Miami to Key West: Luxury Stays & Scenic Stops en Route

A journey from Miami to Key West isn’t just a road trip—it’s an unforgettable experience that combines tropical beauty, luxury accommodations, and unforgettable coastal views. Whether you're in a convertible soaking up the sun or in a luxury SUV enjoying a smooth ride, the 165-mile stretch down the Overseas Highway (U.S. Route 1) offers a perfect blend of natural beauty and refined relaxation. For those looking to indulge in the best, this article covers the top luxury stays and must-see scenic stops that will make your Miami to Key West trip truly exceptional.

Setting Off from Miami: Where the Journey Begins

Start your adventure in Miami, a vibrant city known for its art deco charm, world-class restaurants, and beaches that stretch for miles. Before hitting the road, consider a stay at the Faena Hotel Miami Beach or the St. Regis Bal Harbour Resort—both offer indulgent accommodations, private beach access, and five-star service.

For a quick pre-drive treat, grab a gourmet coffee at Panther Coffee in Wynwood or a tropical fruit bowl at Joe & The Juice. Then, head south with your GPS set to paradise.

Luxury Stays Along the Way

Though the drive from Miami to Key West can be done in about 3.5 to 4 hours, spreading it over a couple of days lets you savor the beauty of the Florida Keys. Here are some top-tier places to stay along the way:

1. Playa Largo Resort & Spa – Key Largo

Located at Mile Marker 97 in Key Largo, this Autograph Collection property is an oasis of luxury. Nestled along the bay, Playa Largo offers private bungalows, a serene beach, a full-service spa, and romantic fire pits under the stars. It’s an ideal first stop to unwind after leaving Miami.

2. Cheeca Lodge & Spa – Islamorada

Roughly 45 minutes further, Cheeca Lodge blends Old Florida charm with modern luxury. Private beachfront, on-site golf course, and a wellness-focused spa make it a favorite for upscale travelers. Dining at Atlantic’s Edge, their seafood-centric restaurant, is a must.

3. Hawks Cay Resort – Duck Key

Hawks Cay, located on Duck Key, is a family-friendly but undeniably upscale destination. With lagoon-style pools, a saltwater lagoon, and on-site dolphin encounters, this resort is a hidden gem. Their calm water villas offer seclusion, while still enjoying resort amenities.

Scenic Stops You Shouldn’t Miss

The Overseas Highway is famed for its 42 bridges, each offering a view more spectacular than the last. But the drive isn’t just about the road—it’s also about the detours and stops that define the journey.

1. John Pennekamp Coral Reef State Park – Key Largo

This underwater state park is a marine wonderland. You can take a glass-bottom boat tour, go snorkeling over coral reefs, or kayak through mangroves. Even if you're not diving in, the visitor center and aquarium are worth a quick stop.

2. The Rain Barrel Artisan Village – Islamorada

Located at Mile Marker 86.7, this quirky, colorful village of shops and art galleries is hard to miss—especially with the giant lobster statue ("Big Betsy") out front. Great place for souvenirs or local artwork.

3. Robbie’s of Islamorada

Feed the famous tarpon at Robbie’s Marina, rent a paddleboard, or enjoy waterfront dining. It’s fun, casual, and one of the most photographed stops on the route.

4. Seven Mile Bridge – Marathon

Driving this iconic bridge is a highlight in itself. The original bridge (now a pedestrian path) runs alongside the modern structure and offers a surreal walking experience surrounded by open ocean on both sides.

5. Bahia Honda State Park

Often considered one of the most beautiful beaches in the Keys, Bahia Honda offers powder-white sands, crystal-clear waters, and an abandoned railway bridge that's a favorite for photographers. Take a short detour and stretch your legs here—you won’t regret it.

Arriving in Key West: Where Luxury Meets Laid-Back Living

Once you reach Key West, the southernmost city in the continental U.S., you'll find a blend of Caribbean flair, historic charm, and island indulgence. Despite its laid-back attitude, Key West doesn’t skimp on luxury.

Top Luxury Stays in Key West:

• Ocean Key Resort & Spa: Located at the end of Duval Street, this oceanfront resort offers panoramic sunset views, an award-winning spa, and rooms with private balconies.

• The Perry Hotel & Marina Key West: Located at Stock Island just before entering Old Town, this modern luxury hotel offers chic industrial design, a top-rated seafood restaurant, and yacht marina access.

• Casa Marina Key West (by Waldorf Astoria): A historic landmark with private beach access, this hotel combines old-world elegance with contemporary comfort.

Things to Indulge in While in Key West:

• Sunset Sail on a Catamaran: Book a champagne sunset cruise or a private luxury yacht charter to truly absorb the beauty of the Keys.

• Fine Dining at Latitudes: Located on Sunset Key, this upscale beachfront restaurant is only accessible by ferry and offers exquisite cuisine under swaying palms.

• Explore Ernest Hemingway’s House: A cultural detour worth making, this beautifully preserved home gives insight into one of America’s greatest writers.

Best Time to Travel

For fewer crowds and milder weather, plan your Miami to Key West trip between November and April. This period avoids hurricane season and offers cooler evenings—perfect for sipping cocktails on oceanfront decks.

Tips for a Luxury Road Trip Experience

• Hire a Convertible or Exotic Car: Driving a luxury car adds to the adventure, especially with the wind in your hair as you cruise over endless blue waters.

• Book Accommodations in Advance: Especially during peak season, high-end hotels in the Keys fill up quickly.

• Pack Light, Pack Smart: Lightweight resort wear, sunscreen, sunglasses, and water shoes are essentials for enjoying both comfort and activities.

• Don’t Rush the Drive: The Florida Keys aren’t meant to be sped through. The joy lies in meandering stops, delicious seafood shacks, and postcard-worthy views.

Final Thoughts

The journey from Miami to Key West is more than just a scenic drive—it's a tropical escape lined with luxury accommodations, postcard-worthy views, and immersive experiences that delight the senses. From opulent resorts in Key Largo and Islamorada to chic boutique hotels in Key West, this route is tailor-made for those seeking indulgence and inspiration. Whether it’s your first visit or a return trip, this luxurious coastal adventure never fails to impress.

Pack your bags, roll down the windows, and let the sea breeze guide your way—paradise awaits.