Fly into Miami and take the hour-and-a-half drive south through Homestead and Florida City along US-1 (observe the new bridges and middle lane blockers painted a pretty blue, for heightened safety). It’s hard to believe there’s nothing but water to your right and left. Another option is to fly into the Marathon Airport (MTH) and drive 40 minutes north.
Stay at the Cheeca Lodge and Spa at mile marker 82 (everything in the Keys is judged by mile markers; not exits or street names). Located on Upper Matecumbe Key in Islamorada, this 27-acre property is truly unique to the Keys. cheeca.com
Eat on-property at Cheeca at the Atlantic’s Edge. Menus change depending on the season’s catch, including pan roasted grouper with smashed boniato, asparagus and mango beurre blanc. For dessert, try key lime meringue served with raspberry and mango coulis or the chocolate lava cake, depending on your mood. A dessert wine washes it all down. Visit Matt at the outside tiki bar that is beautifully lit at night and ask for his favorite drink to make, Cheeca’s Tropical Illusion (Malibu rum, light rum, Crème de Banana, orange and pineapple juice and a splash of grenadine).
Snorkel in the continental U.S.’s only living coral reef on an excursion reserved at the Water Sports Tiki Hut, located at the start of Cheeca’s 525-foot pier. When Captain Joanie gives you the option of Cheeca Rocks or Alligator Point, be sure to opt for the longer boat ride about four-and-a-half miles out to Alligator Point. The water color farther off the Keys shore turns to Caribbean blue, and you’ll be surrounded by hundreds of yellow fins and sergeant majors almost close enough to touch. Don’t be frightened by the couple barracudas seemingly following you around — they may have sharp teeth but usually don’t bite.
Relax at poolside cabanas, equipped with personalized butler service, ceiling fans, flat screen plasma TV, and a refrigerator filled with soft drinks, a fruit smoothie and fruit platter. Half-day rentals are $69. Full-day rentals are $129. You can usually reserve the cabanas the day of, but in high season, it is best to reserve the day before.
Notice all the history around you. A church, two-room school- house and cemetary were built on what is now Cheeca Lodge beach in 1909. But the Great Labor Day Hurricane of 1935 killed almost 1,000 people and destroyed the church and school. Today, a one-winged angel thrown 1,000 feet away from the property during the storm still watches over the cemetary at Cheeca.
Find long sandy beaches that are a rarity in the Keys. While a public beach at Matecumbe (Mile Marker 73.5) will do in a pinch, to satisfy a serious beach craving, cruise south to Bahia Honda State Park (Mile Marker 37) at Big Pine Key. Considered one of Florida’s finest strands, Bahia Honda encompasses more than 500 acres — including two beaches — with bathtub-like water deep enough for swimming and snorkeling close to shore. The park’s bonus is a nature trail at the end of Sandspur Beach.
Dive on an 18th century Spanish galleon, the San Pedro, which inspired the creation of the San Pedro Underwater Archaeological Park. Located about a mile off Indian Key in just 18 feet of water, the wreck doesn’t much resemble a ship anymore, but keep the faith … artifacts and even coins still show up in these waters from time to time.
Climb to the highest elevation in the Keys on Lignumvitae Key, a state park and botanical site off Islamorada that is accessible only by boat (or kayak or canoe). More than 130 species of trees grow on the isle, including the lignum vitae, once a favorite of boatbuilders because it is perhaps the world’s hardest wood. Oh, yes, that highest point? It’s a less-than-breathtaking 18 feet.
Learn more at fla-keys.com/islamorada.