Do you love a scenic road trip? If so, a Florida Keys road trip down to Key West was one of our favourites! For our complete, curated trip to Miami and the Florida Keys, including an itinerary with links to hotels, restaurants and activities, see the full website page here.
Islamorada
A little over two hours south of Miami airport, Islamorada is the first stop on our Florida Keys road trip. This quaint village is nestled about a third of the way down the Keys. Known for its laid-back charm and stunning sunsets it is the ideal first stop on your journey.
Casa Morada is a boutique, oceanfront hotel that feels like a hidden oasis. Its whitewashed, wooden buildings are complemented by lush tropical gardens, making it feel intimate and tranquil. The airy, minimalist rooms open up to private terraces, where you can sip coffee while gazing at the water. Complimentary yoga sessions by the ocean were on offer during our last stay: an ideal way to start the day.
While you’re staying in Islamorada, Lorelei Cabana Bar & Restaurant is an easy-going waterfront spot for sundowners. With live music playing and the chatter of locals filling the air, it is the perfect first chilled out Florida Keys road trip experience.
Driving down the Keys
Driving down the Keys is an experience in itself, with music playing and windows down. The narrow Overseas Highway stretches over a series of bridges and causeways, with the vast Atlantic on one side and the Gulf of Mexico on the other.
Finally, you reach Key West, a lively town at the southernmost tip of your Florida Keys road trip. Known for its eclectic atmosphere, Ernest Hemingway’s legendary home and a buzzing nightlife scene, it’s a blend of bohemian energy and coastal charm.
Sunset Key Cottages
A short boat ride from Key West takes you to Sunset Key Cottages, a private island resort offering the ultimate in luxury and seclusion. You stay in one of the charming white-washed cottages, surrounded by swaying palm trees and lush gardens. Lazy afternoons can be spent soaking in the ocean views from the porch or swinging in a hammock. There is also a decent sized pool to have a change of relaxation spot from the beach.
Key West
A visit to Key West wouldn’t be complete without exploring its lively and colourful streets. You can spend a day wandering through Duval Street, where boutiques, quirky galleries and bustling cafés line the sidewalks. For a taste of Key West’s party spirit, there are plenty of lively bars including Sloppy Joe’s and The Green Parrot.
A Florida Keys road trip is a great vacation, with a super scenic drive, chilled out beach vibes and a lively town in Key West. It is up there with the most memorable and enjoyable road trips we’ve done. It’s also an idea combination with a short break to Miami. We did this dual-site trip in just seven days.
Check out our website here for a complete, curated trip to Miami and the Florida Keys, including an itinerary with links to hotels, restaurants and activities.
