Islamorada's kinda got it going on.
Somehow, without much fanfare, it has reached a tipping point where, because of a batch of new eateries and resorts, it feels like the "cool" Key.
That wasn't always the case - in the past, the Florida town's venues had tried to out "Key" each other with tired nautical themes, conch shells galore, fried food and steak (not that there's anything wrong with steak). Now you'll find two local beer producers, a global eatery with a whiskey bar, an olive oil shop, a taco spot, serious sea-to-table cuisine, and a new crop of stylish places to crash.
The property that arguably stated the uptick in Islamorada's hipness is Casa Morada (136 Madeira Rd., Islamorada; 305-664-0044; casamorada.com), a 16-room micro-resort renovated in 2003 where midcentury modern simplicity meets oversized palm fronds (think less Margaritaville and more Palm Springs). Outdoor showers lead out to a Raymond Jungles-designed garden, which in turn leads to a bayside bar where sunsets will crush your cynicism. It's pet-friendly, yoga-friendly, cellphone-discouraging, and there are no kids under 16, all of which leads to a sense of camaraderie among guests. Don't leave without borrowing the free snorkeling gear to hang with the lobsters and snappers along the sea wall.
The renovation race picked up this year as both Amara Cay (80001 Overseas Hwy., Islamorada; 305-664-0073; amaracayresort.com) and Pelican Cove (84457 Overseas Hwy., Islamorada; 305-664-4435; pelicancovehotel.com) opened after profound gut rebuilds.
Amara was once a Hampton Inn with a big Outback Steakhouse. Now it's an open, airy boho-beachy 110-room hotel with interiors by Edge of Architecture out of Coral Gables. There's a tongue-in-cheek image of a square grouper on the back bar, earth tones all over the place, wood-finished flooring and a facade of beautiful cypress trunks in the lobby along with really fun basket chairs dangling from the ceiling. The place strikes a nice balance between elevating its environs, and keeping things accessible - families loaf at the pool while hip travelers snag beach chairs and veg out with views of the grass flats - more serene than anything on South Beach. And the property is large enough to support a sophisticated restaurant, Oltremare Ristorante, which plates contemporary Italian fare. Chef Dario Olivera sources clams from Cedar Key and runs up to Key Largo Farmers Market for fresh fish.
Pelican Cove, once an uninspired white-tile kind of place adjacent to the formerly notorious Holiday Isle (slated for a big renovation this fall), was gut-renovated last year and offers 66 rooms in a modernist rustic mood via sandy wood, pops of color, and surprisingly slick walk-in showers done in subway tile. Though not a huge property, it would be pretty easy just to chillax here - they've got a marina, a cool little pool area, paddleboards, and Wild & Lime, an eatery geared toward drinking while gazing at the ocean.
It's hard to keep culinary talent in a small town, and Islamorada is certainly a small town, but chef Michael Ledwith chose to buck the trend. He opened Chef Michael's (81671 Overseas Hwy., Islamorada; 305-664-0640; foodtotalkabout.com) three years ago, borrowing farm-to-table methods and applying them to the sea. His relationships with local captains bring left-of-center species such as tilefish, tripletail, snowy grouper, mystic grouper, hogfish and even lionfish to the table. And don't leave without trying the chocolate mousse cake.
Though not new, Pierre's (81600 Overseas Hwy., Islamorada; 305-664-3225; moradabay.com/pierres/), across the street, was rumored to be for sale a few months back. Instead, the plantation-style restaurant procured a new chef, Ishmael Toro (formerly of Miami's Novecento), who's bringing stuff such as mofongo lobster to the menu.
Just down US-1, Oo-Tray (80900 Overseas Hwy., Islamorada; 305-922-2027; oo-tray.com) aspires to "global cuisine with a local farm-to-table flavor" fueled by chef David Matlock, an alum of Thomas Keller's Bouchon in Yountville, Calif. He whips up outside-the-box items such as duck wings with bourbon and caramel; bahn mi sandwiches; and a bone-in pork entree with bacon jam and pineapple chimichurri. The bar is all about whiskey, with esoteric stuff like Willett and Belle Meade bourbon, and Balcones True Blue whiskey from Texas.
Hailing from Key West, Bad Boy Burrito (81868 Overseas Hwy., Islamorada; 305-440-3951) is hidden in the Village Square, a shady alcove behind the Trading Post. It opened last month and offers delicious Cal-Mex-style grub with a Floribbean influence. Try the Key West pink shrimp taco with charred pineapple habanero sauce, or the Baja fish tacos: beer-battered local mahi mahi, shaved cabbage and chipotle aioli. Drinks rock as well, with offering such as local mango smoothies, star fruit juice, and Mexican ice coffee made with dulce de leche. Also in the Village Square alcove sits Urbn Grdn (305-537-6770; urbngrdn.org), a juice bar that moved from US-1 in early July, and crafts juices from South Florida produce. The Katy Pear (kale, pear cucumber, lime) and the Blue Maca (blueberry, banana, vanilla, fresh almond milk, maca) shine.
Just up the street find Olive Morada (82229 Overseas Hwy., Islamorada; 305-735-4375; olivemorada.com), an olive oil and gourmet emporium that opened in December. They've got 42 oils and balsamic vinegars, but be sure ask for a sample of the Jimmy Buffett special - Persian lime olive oil mixed with coconut white balsamic vinegar, and keep and eye out for other goods, like Key Lime Curd and wild hibiscus flowers in syrup.
Next door, the Islamorada Beer Company (82229 Overseas Hwy., Islamorada; 305-440-2162; islamoradabeerco.com), which brews upstate and opened its doors here in October, offering flights of brews like their Sandbar Sunday American Wheat Ale, or Channel Marker IPA, a light noted pale ale.
For a microbrewery that brews on-site, hit Florida Keys Brewing Company (200 Morada Way, Islamorada; 305-916-5206; floridakeysbrewingco.com), situated off the strip in a row of funky warehouses. Though it opened just five months ago, the tasting room already feels homey, and the brews are gaining local love. Try the Honey Bottomed Blonde, made with local Keys honey, or the Hogfish Amber, an American amber with floral and citrus notes. They've even occasionally age their Run Aground Brown ale in rum barrels for two months - if you're lucky they'll have some in stock.
Of course if you just have to get your fix of "old" Islamorada, then belly up to the bar during sunset at Lorelei Restaurant & Cabana Bar (96 Madeira Rd, Islamorada; 305-664-2692; loreleicabanabar.com), watch the fishing charters pull in, and witness why this hamlet is known as a "quaint little drinking town with a fishing problem."