An island escape, no passport necessary, you say? Done. A honeymoon in the Florida Keys absolutely nails perfect beach days and sunset cocktails in the Lower 48, but this 120-mile island chain also has a lot to offer when you’re ready to climb (or tumble) out of the hammock. Think driving the most breathtaking stretch of U.S. 1 in your ride of choice (top down, of course), strapping on a tank for some serious diving, and chartering a yacht or a seaplane to see the Keys at their best—from the air or the ocean. And, if your bride likes a bit of fishing, well, she’s a keeper, but you’ve also just hit the honeymoon jackpot. Whether you’re down for the barefoot angler’s vibe of Key Largo, Islamorada, and Marathon, the outdoorsy wonder of the Lower Keys, or the quirky culture of Key West, you can rely on the Florida Keys to wow.
—Rebecca Wallwork
The Pros & Cons of The Florida Keys
As the southernmost part of the continental U.S., the Keys has Caribbean-like weather year-round. We’re talking sunny skies and warm temps in the low-seventies to mid-eighties. However, you’ve no doubt heard of a little something called hurricane season, and while it is not always eventful, it is real. (See: Hurricane Irma, which did extensive damage along the Florida Keys in September 2017.)
The summer and fall months are the most prone to storms but if you’re lucky enough to dodge those, it’s still likely to be hot and humid. (Though, the ocean breezes do help.) Winter and spring are the best times to honeymoon in the Keys; but you will pay accordingly and be more likely to share your beach with snowbirds escaping the cold in the Midwest, Northeast and Canada. If you like to live on the edge (because you never want to take up too much room, No Fear!) and plan your getaway between June and November, you may want to consider travel insurance in addition to your finest linens and Panama hat. And if any of that info is scaring you off, then take a look right here.
Where to Stay in the Florida Keys
Accommodations in the Keys run the gamut from kitschy to ritzy. To avoid digs decorated in angler’s chic—fake marlin on the wall, a ‘Gone Fishin’ sign—your best honeymoon bets are large resorts, luxury hotels, private islands, and quaint B&Bs. Even humble options in the Keys are pricey, so budget at least $500/night and expect to pay closer to $1,000/night for suites and villas at the higher-end resorts.
Bungalows Key Largo is a brand new all-inclusive resort opening soon, bringing a touch of luxury to the most accessible part of the Keys, about an hour and twenty-minute drive south of Miami. Bungalows set on the beachfront and in the middle of tropical gardens have secluded verandas with soaking tubs (and in some cases, outdoor showers). Meals and premium beverages are included in the all-inclusive rates, along with daily yoga and non-motorized water sports like kayaking and paddle-boarding.
A little further down U.S. 1 in Islamorada, The Moorings Village has a well-earned reputation as an exclusive retreat, with just 19 private villas nestled among 18 coconut palm-filled acres. If the colonial-style porches and beachfront palms look familiar, it’s probably because the resort served as the Rayburn family’s property in the Netflix series Bloodline (yes, that’s the one with the coach from Friday Night Lights).
If you’re planning far in advance and your honeymoon is on the calendar for mid-2019 or beyond, check out one of the Florida Keys’ most exclusive escapes, Little Palm Island, located in the windswept Lower Keys. High-end and peaceful, its 30 beach-chic suites have a total Blue Lagoon vibe—thatched roofs and butterfly netting; some suites come with their own Jacuzzi tubs, fire pits and private outdoor bamboo showers. The resort is in the midst of an extensive renovation but expects to welcome guests back for the summer 2019 season. This is one worth putting on your wish list if your dates align.
In Key West, historic inns add a bit of character to your sun-soaked getaway and The Marquesa Hotel is an elegant pick. It features four buildings set around a garden, two pools, and a location close to the town’s best bars and restaurants.
For more secluded surroundings—that still provide access to the restaurants and nightlife of Duval Street—check out Sunset Key Cottages, a 27-acre island just 500 yards off Key West, accessible by the resort’s private ferry. Breakfast baskets are delivered to the doorsteps of each of the 40 three and four-bedroom cottages each morning, and a ‘Conch Cruise’ delivers ice cream every afternoon (but does it have an annoying jingle like the Good Humor truck?). The resort’s restaurant, Latitudes, will earn major points in the romance department, with tables set right on the beach.
Other honeymoon-worthy resorts in the Keys include Cheeca Lodge in Islamorada, and Casa Marina, a Waldorf Astoria Resort in a prime location on the Atlantic oceanfront in Key West.
Best Florida Keys Attractions and Activities
You see all that water and immediately think “beach time,” but before you start wondering how to fit your surfboard in your suitcase, know that “beach” here does not mean Hawaii or California-like swells. Calmer waters on both the Atlantic Ocean and Gulf of Mexico sides of the archipelago make for more chilled-out swimming, snorkeling, kayaking, and paddle-boarding—‘SUP-style or in a paddleboard yoga class. Just make sure to pack properly. There are a few larger areas like Fort Zachary Taylor Historic State Park in Key West and Bahia Honda State Park in Big Pine Key, but generally the beaches of the Keys don’t have dunes for days. The fact that there are so many intimate coves and inlets to explore, however, makes up for it.
One thing the Keys does do bigger and better? Sunsets. Lots of resorts, bars, restaurants and boat cruises celebrate this happiest hour of the day with live music and drinks specials, but the spectacular swathes of color in the sky are just as memorable—and considerably more romantic—when enjoyed as a party of two. Stay on or visit the Gulf side of the Keys for front row seats to the nightly performance.
For shows of a more musical nature, head to Key West, the hub of all things culture and entertainment in the Keys, and home to a string of historic good-time bars like Sloppy Joe’s, Capt. Tony’s Saloon (the original Sloppy Joe’s), and The Green Parrot. While in the “Conch Republic,” take a spin through the galleries (and more bars) in Old Town, tour the Hemingway House and pop into the local bookstore, Books & Books at The Studios of Key West, where you can ask co-owner, YA author legend Judy Blume (“Superfudge!”), to recommend some vacation reading.
From Key West all the way up to Key Largo, the most Keys thing you can do is get on a boat—and you won’t have to go far to find one to charter or hop aboard for a leisurely sail. For major props with your S.O., book a cruise on the African Queen, the original steamboat that starred in the 1951 movie of the same name (ask Grandma about it, it’s an AFI Top 100 film), now docked in Key Largo.
Want to go deeper? The area is full of dive sites where experienced and aspiring divers can explore show-off coral, creepy shipwrecks and a statue of Christ that has served as an altar for underwater marriages. The biggest dive sites include the Florida Keys National Maritime Sanctuary and Key Largo’s John Pennekamp Coral Reef State Park. Fancy some bad-ass fort action with your scuba or snorkel plans? Hit up the Dry Tortugas National Park. It’s made up of seven small islands located almost 70 miles west of Key West, and home to the imposing Fort Jefferson above ground, and wrecks and coral reefs beneath the surface. You’ll have to set aside a whole day for this one; it’s only accessible by boat or seaplane and the easiest option is the ferry from Key West. You can also camp on the grounds overnight if you make arrangements in advance.
Best Florida Keys Restaurants & Bars
First thing’s first: how do you feel about fish? Naturally, the Keys is a pescatarian’s paradise, and the best thing to eat almost anywhere is the catch of the day. If fishing is on your itinerary, you can even catch your own dinner and take it to a restaurant where the chef will do all the hard work. In Marathon, head for Lazy Days South, in Key Largo, Buzzard’s Roost Restaurant, and if you’re in Key West, pop on over to Hogfish Bar & Grill in nearby Stock Island, a rustic fishing village with a growing hipster vibe.
The Keys is known for its shoes-optional, fried-everything kind of spots—and, along with the cold beer and rum drinks, they’re part of what makes the area so much fun. But this being your honeymoon, you’ll no doubt want something a little more refined for a few special meals. In Islamorada, Pierre’s Restaurant is fancy and French—its setting in a beautiful plantation house with breezy verandas is one of the most romantic in the Keys. You’ll find most of the region’s similarly upscale spots in Key West: Louie’s Backyard is a local institution, serving Caribbean-American food and delicious sunsets, and Antonia’s is a high-end Italian trattoria right on Duval Street. Back on the casual side, Blue Heaven is a great pick for a quintessential Key West meal: lobster Benedict or pancakes rule at breakfast, and the burger is one of the best in town. You’ll dine in the backyard, usually with live music and the local roosters strolling by. The Key Lime Pie at Blue Heaven is justifiably famous but if your dessert needs demand something richer, pop by Better Than Sex, which bills itself as Key West’s only dessert and cocktail restaurant. The names of the dishes and drinks will make you roll your eyes—“The Klimax” is a glass of red wine in a white-chocolate-rimmed glass—but the sweet treats are totally worth it once you get past the cringe factor.
