How to upgrade your next vacation to Key West and the Florida Keys

On the beach at Little Palm Island.

An easy drive from Miami, the Florida Keys have a reputation for their laid-back and somewhat rustic nature. But you just have to know where to look to find the finer things. Here’s your expert guide to the latest, greatest and most luxurious location, from Key Largo to Key West.

Staying in the Keys

Florida Keys
Amara Cay Resort

Check into the boutique Marquesa Hotel (marquesa.com), which oozes Old Florida charm throughout its four restored Victorian-style cottages. Twenty-seven uniquely decorated guest rooms are outfitted in high-gloss Brazilian cherrywood floors and furniture from the West Indies, Philippines and England. 

The Marker (themarkerkeywest.com), which opened in 2015 at the Historic Seaport, channels Key West’s vernacular architecture with its tin roof and courtyard pool. Thoroughly modern guest rooms are awash in bright blues and crisp whites.

For a taste of Key West history, Casa Marina (casamarinaresort.com) was conceived by oil tycoon Henry Flagler. Today, the resort retains its Mediterranean opulence with a grand Cypress wood lobby and stucco arcades opening up to the sprawling oceanfroont poolscape—one of the prettiest scenes on the island.

The Reach (reachresort.com), Casa Marina’s sister property, underwent a $32 million redesign and renovation in 2008 that added to the allure of this subtropical playground along Key West’s only natural beach.

Luxurious, Local Keys Restaurants

Miami tacos
Fish tacos at Latitudes in Key West.

Longtime locals and husband-wife duo Thomas Quartararo and Kristen Onderdonk have opened a pair of new restaurants — Thirsty Mermaid (thirstymermaidkeywest.com) and Little Pearl (littlepearlkeywest.com) — in the span of about a year; they’ve become the hottest tables in town. The former was inspired by oyster bars and sidewalk cafes in New York City’s West Village, while the latter offers a slightly more rarefied dining experience with inventive takes on classic dishes and locally caught seafood.

The following formula never fails when it comes to a romantic dinner in Key West: Reserve a table on the patio at Latitudes (sunsetkeycottages.com) for an hour before sunset, catch the ferry to Sunset Key, order a bottle of Champagne, and dine by torchlight on lobster-encrusted grouper. Unobstructed views of the sunset as sailboats are icing on the cake — or Key lime pie.

Specialty Cocktails and Drinks

When The Other Side (carolinesotherside.com) opened in 2014, it upped the ante for craft cocktails in Key West. Here’s the place to sip a Banana Bread Old Fashioned (Jameson, banana liqueur, black walnut bitters) in a speakeasy-style lounge inside a Victorian mansion off Duval Street.

Another place with a speakeasy vibe, Point 5 (915duval.com) boasts an impressive wine list, classic cocktails and small plates that come from the kitchen of celebrated restaurant Nine One Five, located downstairs.

Things to Do in Key West

Florida keys
Schooner Hindu at Fort Zachary Taylor State Park.

Set sail with a wine tasting, cheese and charcuterie aboard the Schooner Hindu (sailschoonerhindu.com), an elegant wooden vessel that dates to 1925.

Skip the two-hour ferry ride to Dry Tortugas National Park and opt instead for a private seaplane (keywestseaplanecharters.com) with unreal bird’s-eye views of the glistening aquamarine water.

Florida Keys
Skip traffic – take a sea plane.

Take a stroll along Eaton Street to discover what’s becoming known as Key West’s cultural corridor, thanks to a collection of arts institutions within the span of two blocks, including The Studios of Key West (tskw.org), a local branch of Miami’s Books & Books (booksandbookskw.com) owned by legendary author and Key West resident Judy Blume, The Key West Theater (thekeywesttheater.com) and Tropic Cinema (tropiccinema.com).

For the perfect tasteful souvenir, duck into Besame Mucho (besamemucho.net), a charming cottage in the heart of Bahama Village where you’ll find a menagerie of handmade jewelry, accessories, home goods, books and apothecary.

Florida Keys Resort Escapes

Key West
On the beach at Little Palm Island.

Mile Marker 97: The first newly built resort in Key Largo in 20 years, Playa Largo Resort & Spa brings an unprecedented air of luxury to the uppermost key. playalargoresort.com.

Mile Marker 80: Awash in natural wood and stone, with floor-to-ceiling windows overlooking the water, Amara Cay Resort’s guest rooms are a posh retreat in Islamorada. amaracayresort.com.

Mile Marker 28: Play out your Robinson Crusoe fantasies at Little Palm Island, accessible by wooden ferry and where 15 thatched-roof bungalows and a dreamy spa await. littlepalmisland.com.

Mile Marker 5: Stock Island, the sleepy longtime home to commercial fishermen and artist studios, is ready to welcome visitors to its first hotels: Oceans Edge and The Perry, both set on marinas for easy access to offshore pleasures. oceansedgekeywest.com, perrykeywest.com. 

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