10 Best Places for Christmas Shopping in Islamorada and Key West

It's easy to play Santa Claus in Islamorada and Key West, where you're sure to find the perfect gift for everyone on your Christmas list. You'll find galleries and boutiques expertly curated by their owners filled with vintage European treasure, creative up-cycled goods, 3-D crafts and whimsical local art. Shops packed with butterfly-themed gifts and outdoors gear showcase the goods for nature-lovers and fishermen. For the gourmands, wrap up the tastes of Key West from hot peppers to cool Key lime. Who knew vacation could be so productive? Check out my top ten shopping guide...

Holiday Hot Spot--Christmas in Key West

Photo by Chad Newman

While it may seem counter-intuitive to head to a tropical locale for a dose of holiday spirit, Key West in December is a wonderland of festive surprises. Take resident Eddie Chapman, decked out in a fuzzy reindeer suit and red Converse sneakers, riding the bucking mechanical bull at Cowboy Bill’s Honky Tonk Saloon. After he was tossed off to a round of cheers from the 80-plus Santas and elves joining him on a merry bar crawl down Duval Street, he flashed his prankster grin and said, “There’s a lot of joy here.”

This holiday whimsy spills across Key West — the island at the southernmost tip of the Florida Keys. Walking through the Old Town district, my eye was drawn to the twinkling lights and icicles that laced the gingerbread millwork on the Victorian homes. Giant snowflakes hung from wraparound balconies, and red ribbons and green garland really gave the columns stripes. Candy canes, penguins and even snowmen bloomed alongside bougainvillea and hibiscus.

To kick off the season, I joined merrymakers on the Holiday Lights Conch Tour Train. On the hour- long ride, I coasted through the balmy night air, taking in the festive sights and singing “Jingle Bells” at the top of my lungs.\More seasonal cheer awaited on the Holiday Historic Inn Tour. Map in hand, I followed the path of this two-hour self-guided walking tour through shaded neighborhoods, where innkeepers open the doors to their bed-and-breakfasts — six different properties each night, welcoming the public and sating us with wine and festive bites. On a past tour, the Mermaid and the Alligator B&B charmed me so much that I planned a return stay.

Poinsettias and nutcrackers adorn its porch and line the brick walkway of the 1904 Victorian house tucked away on Truman Avenue, one of Old Town’s main thoroughfares. A life-size stuffed Santa wearing a Hawaiian shirt relaxed in a hammock between two palms. “Of course, the elves are still working up north,” co-owner Dean Carlson deadpanned. “Santa disappears on Christmas Eve and is back the next day holding a cocktail.”

Inside, every inch of the inn was impeccably decorated with a mix of traditional and tropical. A 10- foot Fraser fir, with mermaid and alligator ornaments, was set against walls of Dade County pine, a native wood rarely available to today’s builders.

My guest room was Audubon-inspired, with soft yellows and browns, high ceilings, louvered shutters and a private garden door. I woke to the famous Key West roosters crowing, church bells tolling, and scents of jasmine and fresh-baked banana bread mingling in the air. Michelle, a stylish 20-something from Italy, and resident mascots Havana and Caya, two flat-coated retrievers, joined me for a breakfast of frittatas and coffee poolside near the namesake statue of a mermaid kissing an alligator.

Early evening is prime time to visit the renovated Historic Seaport district’s Harbor Walk of Lights, a boardwalk decked out with Christmas trees and towering palms wrapped in lights. The seaport hosts various events as part of the Bight Before Christmas Holiday Celebration; the Lighted Boat Parade is one you don’t want to miss.

Prime viewing for the spectacle is at the Schooner Wharf Bar, where the boats cruise close to the docks and judging station. As families and friends celebrated both on land and on water, I felt the pull of this small, close-knit community at the very end of U.S. Highway 1. You truly can go south and find a holiday spirit worthy of the North Pole.

Portions of this blog originally appeared in Florida Travel + Life Magazine.