Cheeca Lodge & Spa: A Legendary Florida Keys Oasis for the Discerning Driver

The Driver's Arrival

The final stretch of the Florida Keys Overseas Highway is a mesmerizing blur of turquoise water and endless sky. After a spirited drive, the iconic Cheeca Lodge & Spa emerges like a welcome mirage in Islamorada. Pulling into the grand, palm-lined entrance, you immediately sense a shift in atmosphere. The valet is seamless, and as you step out of your car, the warm, salt-tinged air and the palpable sense of history tell you you've arrived somewhere special. This isn't just a place to stay; it's a destination that has been welcoming presidents and discerning travelers for decades.

A Storied Past

Cheeca Lodge's history is as rich and colorful as the Keys themselves. What began as the Olney Inn in 1946, hosting President Harry S. Truman on its opening day, has evolved into a sprawling 27-acre luxury resort. The property has seen its share of history, from withstanding hurricanes to being lovingly restored and expanded over the years. It was in the 1960s, under the ownership of A&P grocery heiress Cynthia "Che-Che" Twitchell, that the lodge truly began to take shape, with the addition of the main lobby, oceanfront villas, and tennis courts. This legacy of hospitality and understated luxury is evident in every corner of the resort.

The Accommodations

Whether you opt for a room with a view of the Jack Nicklaus-designed golf course or a lavish oceanfront suite, the accommodations at Cheeca Lodge are designed for relaxation and comfort. The rooms are spacious and elegantly appointed, with pillow-top mattresses, luxury linens, and private balconies to soak in the stunning views. For those seeking a more private experience, the stand-alone casitas offer a true home-away-from-home, complete with kitchens and other amenities. The oceanfront bungalows are particularly romantic, offering unobstructed views of the Atlantic.

The Experience

Cheeca Lodge is a playground for the active traveler. The list of amenities is extensive, from the 525-foot fishing pier (the longest in the Keys) to the full-service spa. You can spend your days on the water, with a complete line of watersports activities, or on land, with six lighted sport courts for tennis, pickleball, and more. The nine-hole, par-3 golf course is a unique feature, offering a challenging and scenic round. For those who prefer to relax, the two oceanfront pools and the adults-only spa pool provide a tranquil escape.

Dining at Cheeca

While the venue is primarily an accommodation, the dining options at Cheeca Lodge are a destination in themselves. From the fresh-off-the-boat seafood at Atlantic's Edge to the authentic Italian cuisine at Mia Cucina, there is something to satisfy every palate. The Tiki Bar is a classic Keys experience, perfect for a sunset cocktail, while the Lobby Bar offers a more refined setting for a pre-dinner drink.

Practical Information

• Parking: Valet parking is available and seamless.
• Reservations: Recommended, especially for dinner and spa treatments.
• Dress Code: Resort casual is appropriate throughout the property.
• Price Range: As a luxury resort, expect a premium price point, reflected in the $$$$ rating.

The Verdict

Cheeca Lodge & Spa is more than just a place to stay; it's an integral part of the Florida Keys experience. For the driver who has just conquered the Overseas Highway, it offers the perfect blend of luxury, relaxation, and activity. It's a place to recharge, to indulge, and to create lasting memories. Whether you're an avid angler, a golf enthusiast, or simply seeking a luxurious escape, Cheeca Lodge delivers on all fronts. It's a legendary resort that continues to set the standard for luxury in the Florida Keys.