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Islamorada, FL

About IslamoradaIslamorada (I-lah-mor-AH-dah) is a fishing haven spread over the islands of Lower Matecumbe Key, Plantation Key, Upper Matecumbe Key and Windley Key. Its purplish appearance from a distance caused the Spanish to call it the “purple isle” (isla morada). The wreck of the galleon Herrera, 2.5 miles off Whale Harbour Bridge, offers opportunities for underwater exploration and photography.

Indian Key Historic State Park, a half-mile southeast of Lower Matecumbe Key, is an 11-acre uninhabited island. This lavish paradise of notorious wrecker Capt. Jacob Housman was destroyed in 1840 when the captain's misuse of power prompted a Native American uprising. The ruins of houses and cisterns are now choked by vegetation planted by physician and botanist Dr. Henry Perrine, who conducted plant experiments at the settlement in 1838. The site is accessible only by canoe or kayak due to damage sustained during past storms. For park information phone (305) 664-2540; for boat rentals phone (305) 664-9814.

Lignumvitae Key Botanical State Park can be reached only by private or chartered boat from the marinas at the western end of Islamorada. Because of its high elevation and the sensitive management of former owner William Matheson, the island retains a singular plant community and is a fine example of a West Indian hardwood hammock. Indigenous and introduced trees blossom at various times but are best viewed in spring or early summer.

Matheson House, built of coral in 1919 and furnished in 1930s styles, remains unchanged. A stone wall, possibly built by Spanish explorers as a navigation aid, extends the length of the island. Walking shoes and mosquito repellent are essential. For park information phone (305) 664-2540; for boat information phone (305) 664-9814.

Visitor Centers Islamorada Chamber of Commerce 87100 Overseas Hwy. Islamorada, FL 33036. Phone:(305)664-4503 or (800)322-5397

ShoppingOutfit yourself with fishing and snorkeling gear as well as well-priced outdoor wear at World Wide Sportsman (gulfside at 81576 Overseas Hwy.). Hop on the full-size replica of Ernest Hemingway’s boat, Pilar, and ride the old-fashioned glass elevator to the second floor of this department store for the outdoor sports lover.

Looking for a one-of-a-kind piece of art? You're sure to find something at the galleries making up the Morada Way Arts and Cultural District (oceanside off US 1, mile marker 82 between Palm Avenue and Beach Road). If you haven’t had any luck with your rod and reel, you can still reel in the big one at Redbone Gallery (oceanside off US 1, mile marker 82 at 200 Morada Way), home to a sizable collection of contemporary and traditional fishing and sporting art ranging from oil paintings in brilliant colors to Audubonesque etchings. Peruse a prized painting by the famed marine artist at Pasta Pantaleo's Signature Gallery (81599 Old US 1) or at Roberto/Russell Galleries (81888 Overseas Hwy.).

Meander in and out of tiny cottages in a serene garden setting at Rain Barrel Artisan Village (86700 Overseas Hwy.) and you’ll happen upon objets d’art such as pottery, glass, sculpture and paintings made by resident artists. Look out for the 30-foot-tall lobster standing guard in front of the village.

Beautify your home inside and out with a purchase from the Banyan Tree Garden & Boutique (on US 1 at mile marker 81.2). Outside the shop, wander through a magical mix of beautiful botanicals under the shade of a towering banyan tree. Inside, unearth a sophisticated collection of jewelry, women's clothing, plants and home décor. Casa Mar Village (US 1 at mile marker 90.7) offers clothing and accessories shops and rentals for water sports. You'll find ocean-inspired fuzed glass at Seaside Glassworks (81902 Overseas Hwy.), tropical-themed art at Michelle Nicole Lowe Gallery (81904 Overseas Hwy.), local handcrafted gifts at The Mystical Mermaid (82245 Overseas Hwy.), and pottery and bronze and copper sculptures at Old Road Gallery (88888 Overseas Hwy.).

Those in search of fashionable threads in Islamorada will come upon several key shops between mile markers 81 and 83. Lion’s Lair Swimwear (82185 Overseas Hwy.) specializes in maillots, bikinis with mix and match tops and bottoms, and lingerie in a wide range of sizes. The helpful staff is well-versed in finding the perfect fit for any body type.

Latitude 25 Clothing Co. (82748 Overseas Hwy.) carries guys’ and gals’ casual attire, swimwear and sunglasses by brands such as Tommy Bahama and Body Glove; shoes by Crocs and Havaianas; Key West Aloe toiletries; and a large assortment of kitschy Keys décor including coasters and bowls shaped like alligators and parrots, palm-tree etched wine glasses and tiki bar dishes. There’s also an extensive section devoted to pets featuring collars, toys and natural foods. The Islamorada Mercantile (81904 Overseas Hwy.) features clothing, housewares and clocks made of driftwood.

The Islamorada Marketplace on 90 farmers market (90311 Old Hwy. at mile marker 90) is open Fri. 10-3 seasonally.

NightlifeIslamorada may be lacking in its quantity of watering holes, but this fisherman’s paradise has a few places to go and have a cold one after a day of reeling them in from the deep blue sea. Savor your choice of bourbon or whiskey cocktails while listing to live music at oo-tray, 80939 Overseas Hwy. Phone (305) 922-2027.

Look for the sign with a pink pig to find Hog Heaven Sports Bar & Grill (on US 1 at mile marker 85.3). This local hangout is just off one of the many bridges that connect the islands, so there’s a fantastic view of the Atlantic Ocean. Inside, 21 flat-screen TVs, good pub grub, pool tables and video games create a roadhouse/sports bar vibe. Phone (305) 664-9669.

A giant two-dimensional mermaid points you in the direction of Lorelei Restaurant & Cabana Bar (gulfside on US 1 at mile marker 82). This family-friendly, open-air alehouse sits on the dock; you can sit under a thatched umbrella, tuck into lunch or dinner, have a drink or two and listen as local musicians serenade the sunset. Phone (305) 664-2692.

Vacationers and locals alike flock to the two bars at Postcard Inn Beach Resort at Holiday Isle (84001 Overseas Hwy.). Down an electric lemonade and do the electric slide at the rockin’ Holiday Isle Tiki Bar or have a mai tai at Rum Runner’s Island Bar, a tropical tree house comprising staggered tiers of tiki huts. Phone (305) 664-2321.

Take refuge from the usual fast-paced Keys nightlife at the Zane Grey Long Key Lounge (81576 Overseas Hwy.) on the second floor of World Wide Sportsman. The walls, bar and fireplace are sheathed in carved mahogany at this sophisticated, masculine pub decorated in the style of an English hunting lodge; handwritten notes and fishing reels are some of novelist Grey’s memorabilia on display. Relax on the balcony with cocktails and bask in the sun’s fading glow as it slowly sets behind the boats in the adjacent marina. Phone (305) 664-9271.

Things to Do Theater of the Sea

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Islamorada, FL

Top AAA Diamond Hotels

AAA’s in-person hotel evaluations are unscheduled to ensure the inspector has an experience similar to that of members. To pass inspection, all hotels must meet the same rigorous standards for cleanliness, comfort and hospitality. These hotels receive a AAA Diamond designation that tells members what type of experience to expect.

Islander Resort

82100 Overseas Hwy. Islamorada, FL 33036

Amara Cay Resort

80001 Overseas Hwy. Islamorada, FL 33036

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Cheeca Lodge & Spa

81801 Overseas Hwy. Islamorada, FL 33036

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