Looking for an island retreat with the ease of a mainland destination? Stretching 120 miles off the southern tip of Florida, the Keys are the answer. A five-hour flight from New York and seven hours from the West Coast brings you to incredible beauty and unforgettable adventure.
Each island has its own vibe, but they share a laid-back attitude. Here we focus on two of our favorites.

Key West

Like your favorite Jimmy Buffet song come to life, the southernmost city in the continental U.S. welcomes you with a big smile. Carol Shaughnessy, Deputy Bureau Chief of the Florida Keys News Bureau, says it best: “Key West is full of friends you haven’t met yet.” Make your wedding as traditional or as eccentric as you can imagine, with a ceremony at a historic landmark like the Audubon House and Tropical Gardens or Ernest Hemingway Home and Museum, or a funky vow-exchange on (or even under) the water. Key West is also one of the most popular U.S. destinations for same-sex weddings.

STAY

Pier House Resort & Spa – Conveniently located on the edge of Old Town, this full-service hotel includes a private beach and is steps away from Duval Street’s many attractions.

PLAY

Ibis Bay Paddle Sports – For an adventure you won’t find anywhere else in Key West, book a Nightrider Experience paddleboard excursion in a lucite-bottomed kayak. Two thousand lumen-waterproof light bars give you an unforgettable glimpse of the brilliant aquatic landscape.

EAT

Blue Heaven – Home of legendary eggs benedict. We also loved the key lime pie with meringue that’s about a foot high.

Azur Restaurant – Perfect for a rehearsal dinner, where two families getting to know each other can bond over family-style, Mediterranean-influenced shared plates.

Islamorada

“The Purple Isle” is the destination of choice for couples seeking an upscale destination a bit off-the-beaten-track. Located on the southern side of the Keys, Islamorada is known as the “sportfishing capital of the world.” Anglers will find more than 500 species of fish and much more. Luxury resorts coexist with quaint lodgings within easy reach of world-class restaurants and a vibrant arts community.

STAY

Cheeca Lodge & Spa – Named one of Travel + Leisure’s “Best of the Florida Keys” destination resorts, Cheeca sets the standard for luxury in Islamorada. The property’s white-sand beach and cerulean waters are the perfect backdrop for weddings. The resort welcomes all couples with picture-perfect celebrations from the intimate to the grand.

EAT

Morada Bay Beach Café – This outdoor Caribbean-inspired bistro café serves up the freshest seafood and most spectacular sunsets you’ll find in Islamorada.

They say once you get sand in your shoes, you’ll return to the Keys again and again. With so much to explore and experience, count on it…you’ll be back.

Photos courtesy of (in order of appearance): Florida Keys Convention and Visitors Bureau (1st) and Cheeca Lodge and Spa (2nd -4th).