Why we wish you were here
Because you’re looking for an elegant, quiet place on the sunrise side of the Keys, without the drive on to the middle or lower end of the island chain – or all the way to Key West.
The Islands of Islamorada has the views, the amenities and the vibe of a five-star resort – without much of the five-star expense – about an hour and a half from Miami. There are drawbacks – most notably, you have to go off property for a sit-down restaurant.
But all of Islamorada is just outside the gate here, with fine restaurants and beer gardens an easy drive or bike ride away on U.S. 1.
What’s cooking
There’s no restaurant on property, but you can get breakfast and lunch items from a menu prepared 9 a.m.-5 p.m. on site and delivered wherever you are on the property. (Yes, even there).
The Mahi Mahi sandwich that comes hot out of a food truck/trailer in the parking lot by the pickleball court – served blackened, grilled or fried on a brioche bun with lettuce, tomato, onion and tartar sauce – is one of the best I’ve had in the Keys. (There, I’ve said it.)
For more formal dining – if such a thing’s possible in oh-so-laid-back Islamorada – there’s Morada Bay (81600 Overseas Highway), for Seafood Mac N Cheese, Mahi Mahi Street Tacos, among other main courses; and a fine slice of Key lime pie. Just down the road, Papa Joe’s Waterfront (79786 Overseas Highway), has Creekstone Farm Wagyu Short Rib, General Joe’s Surf n Turf Stir Fry and the catch of the day – which on this particular day happened to be grouper – the kitchen knows how to grill just right. Come for the sunsets and cocktails at both of these restaurants, stay for the food.
What’s drinking
Sandbar Sunday, Sun Session IPA, Iguana Bait and Go Fish are on tap cold at the Tiki Bar by the pool and fire pit. Larry the barman can also mix you a wine-based cocktail – and keep you entertained through several rounds with stories of his Spring Break glory days as a bartender at The Candy Store and Summer’s On the Beach in Fort Lauderdale and Penrod’s in Miami. At sunset, look carefully both ways and cross U.S. 1 to Morada Bay (81600 Overseas Highway) for an Island Vibes Martini – Gin, St. Germaine Liqueur, Lime Juice, Triple Sec and Lemonade. Look carefully both ways across U.S. 1 on the way back.
Overheard
“There is a magic about this place. The way it’s been designed. The vibe. Romantic for two people. Relaxing for retired people who want to spend time with friends. For families with kids, it’s a very safe environment and we have a beautiful playground. Girls’ night, bachelors … it can be anything you like. And we have the most beautiful sunrises.” – Wasan Manati, Director of Operations
Don’t miss part I
The neighborhood
There’s as much – or as little – as you want to do at The Islands of Islamorada. But there also are interesting sites to explore an easy walk or bike ride away. 
Don’t miss part II
A sunset cruise
Sure, sunrises are beautiful on the Atlantic side of Islamorada – but seeing one requires getting up on the sun’s exacting schedule. Sunsets are easier – no waking up early required – and Capt. Rob Reiner of Cheeca Rocks Charters (cheecarockscharters.com) can pick up as many as six sunset-seekers from the marina at The Islands in his 24-foot Sea Hunt 239. Capt. Reiner has seen some sunsets in his 19 years as a charter-boat captain – and he’s a maestro at getting his guests out and into position on the Florida Bay side of Islamorada for maximum effect. After the main event, glide toward shore in the dusk and ask Capt. Reiner to drop you off at Papa Joe’s Waterfront on U.S. 1. He’ll be off work until the next sunset, but you can use Islamorada’s Freebee app to summon a free ride the rest of the way back to The Islands.
Don’t miss part III
Feeding the fish
Check out a golf club and a bio-degradable “golf ball” of fish food, tee up on a patch of artificial turf at the end of the Marina and whack it “Happy-Gilmore” style into the ocean. Score yourself a hole in one.
Could miss
A beach
You’re in the Keys, so you already know the narrow strip between land and sea here can be rocky and hard. The 600-foot private beach at The Islands is no exception, though management softens the transition with regular renourishments. There’s at least always a soft sandy stretch high along the water here, where the loungers are lined up; but you may want to bring some water shoes or flip flops to wade into the water to where the Atlantic gets deep enough for a swim. Or take out one of the kayaks, available to guests. Or just enjoy the beach under an umbrella from a lounger. Sometimes it’s enough just to know the ocean’s there.
IF YOU GO
The Islands of Islamorada
82779 Old Highway, Islamorada, FL 33036, 305-440-3255, theislandsofislamorada.com.
Featuring 22 three-story, four-bedroom/four-bath, 4,067-sq.-ft. ocean-view villas — “ranging from direct waterfront settings to elevated coastal vantage points” — each with full kitchens, living and dining spaces, three outdoor lounge areas, two balconies, two-car garage with storage, private laundry room, some with elevator; and eight one-bedroom 656-sq.-ft. oceanview suites. Private beach, two pools, hot tub, fire pit, marina with boat slips, pickleball courts, game areas, beer and wine waterfront bar, available breakfast and lunch delivery on property, playground, electric vehicle charging station, high-speed internet, available in-villa spa and private chef services, among other amenities. Starting rates: Suites: $800, Villas: $2,000, “pending seasonality.”
