Cheeca Lodge is one of those storied Florida Keys resorts that most frequenters of the islands have heard of, if not visited themselves. Around two hours away from Miami by car, it’s a longtime favorite of locals and a popular destination for weddings, too. If you’re here, though, you’re probably curious what all the hype’s about.
The independent, historical property nestled along Islamorada’s coast has hosted numerous U.S. presidents, pro athletes, prominent executives and Hollywood stars since opening in 1946. Even with its high profile, though, the vibe at Cheeca is leisurely and laid back. This is a sprawling, sporty tropical getaway with updated accommodations, golf and tennis facilities, a spa and all the amenities you’d expect from a luxury Keys resort.
I checked in at Cheeca Lodge this summer—my favorite time to go, for the thinner crowds and lower rates—and came away, as usual, supremely relaxed and wishing I’d booked a couple extra nights longer. If your idea of a perfect vacation includes a fun mix of things to do and places to eat and drink both on and off property (plus endless conch fritters and frozen drinks), Cheeca fits the bill.
My previous stays have all been with other couples and without children. Though it’s a family-friendly resort, those visits were marked by epic snorkel excursions, long days at the pool and nights at the tiki bar—and they never felt cramped by kiddos. This summer was the first time we brought along offspring of our own, my eight-month-old baby, and the trip was more memorable than ever.
Accommodations
With 243 rooms and suites, Cheeca offers numerous lodging options with views of the ocean, lush gardens, a lagoon or the manicured golf course. Even the most basic guest rooms come with a balcony to enjoy the salty air with your morning coffee. Larger accommodations, like the two-bedroom casitas, boast wrap-around porches, private beach terraces, butler service and more. Especially in the slow summer months, the variety of accommodations makes Cheeca accessible for a range of budgets.
During this trip, we booked one of the resort’s new Premier Oceanfront King Suites for a more luxurious stay. Though the majority of Cheeca looks to have received its last major facelift in the 2000s (I’d call it a well-maintained Keys take on Tuscan), the 43 new Premier suites are decidedly contemporary, with a palette of light natural tones, floor-to-ceiling windows and a massive freestanding tub on the open-air lanai.
Even with the baby and his pack-and-play, our room was spacious, with plenty of room to move about at night without waking him (and the lanai was a great place to hang with friends after he went to bed). Other room types, like the one- and two-bedroom suites, might work better for larger families, and some even come with kitchenettes and dedicated parking spots right downstairs.
Things to Do
Beyond the accommodations, Cheeca packs plenty to do and eat on its 27 acres. There are two oceanfront family pools that never feel overrun with screaming kids—but if you want to go adults-only, there’s a third pool for that, adjacent to the spa. Beyond the pools, there’s a 525-foot fishing pier (the longest in the Florida Keys) and a beach dotted with Adirondacks and lounge chairs.
This isn’t really a spot for splashing in the ocean, since the water here is super shallow and rocky. But there are water activities aplenty, from kayaks and paddle boarding to eco-tours and sunset cruises—not to mention Islamorada’s world-famous fishing—so you’re by no means trapped on land. When you would rather stay dry, tennis and golf are great ways to pass the time, along with yoga on the beach, bicycles, the fitness center and spa with six treatment rooms.
Food & Drink
When it comes to dining, there are three restaurants on the resort. My favorite is Atlantic’s Edge, an idyllic spot for oceanfront brunch on the patio. For snacks and happy hour vibes, order from the tiki bars: The conch fritters and smoked fish dip are my go-to's, paired with a piña colada (a dark rum floater is optional, but highly recommended). As the sun sets, head to any number of nearby local restaurants for a quintessential Keys dinner on the water. Several spots, like Lazy Days, will cook up your day’s catch if you bring it.
The most memorable meal of this trip was dinner at Pierre’s, a French fusion restaurant and lounge across the street from Cheeca’s main property. If you go, time your meal to catch a stunning sunset over Florida Bay and step out onto the second-floor balcony for a photo. The dishes here are prepared with regional ingredients, so be sure to ask your server for their freshest recommendations. The seared jumbo scallops with fresh saffron linguine was a highlight during my visit.
End your big night with a nightcap downstairs at Pierre’s Green Flash Lounge. The bartenders will mix you something potent to carry out to the Adirondacks on the sand, where you’ll promptly want to kick off your shoes and hang a while. After, it’s probably time to head back to the hotel and rest up, since you won’t find many spots open past 11pm in this relatively sleepy section of the Keys.
Neighborhood
Islamorada is a village of around 7,000 residents that spans six of the Florida Keys. Known for its coral reefs and excellent sportfishing, Islamorada was also the location for much of the action in the Netflix series Bloodline.
Nearby
1. Robbie's of Islamorada: This roadside marina has become pretty touristy in recent years, but it's still a fun pitstop to experience the uniquely Keys pastime of hand-feeding massive tarpon off the dock.
2. Islamorada Brewery & Distillery: This family and pet-friendly brewery and distillery is stocked with lots of fun, refrigerated to-go offerings for your next boating excursion. The colorful Florida Keys Brewing Co. often hosts live music in its garden.
3. Alligator Reef Light House: If snorkeling is on your agenda, ask your boat crew to visit this cool iron skeleton lighthouse built in 1873. Decommissioned in 2014, it's now a picturesque spot of protected reef with plenty of wildlife to explore.