Florida Keys

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Room with a view at Cheeca Lodge in Islamorada.
Room with a view at Cheeca Lodge in Islamorada.

1. WHERE TO GO: Made up of six islands, Islamorada, nicknamed the “sportfishing capital of the world,” offers great diving, dining and shopping.

WHERE TO STAY: The 214-room Cheeca Lodge has it all—a Jack Nicklaus-designed golf course, a saltwater lagoon perfect for swimming and snorkeling, three onsite restaurants, and a luxurious spa. Anglers aren’t left out, either, since guests can fish right off of the resort’s 525-ft. pier (no need to bring your fishing rods—the resort can provide them). Guests can choose from West Indies-inspired rooms, suites or beachside bungalows, which boast private balconies with views of the ocean, gardens, lagoon and golf course. While the resort is perfect for families with its 1-bedroom suites, Camp Cheeca day camp, family fishing trips and other activities, couples also have privacy in adults-only Superior Beach Bungalows. Guests staying in bungalows can quickly reach the beach via a spiral staircase leading off the balcony. Rates start at $299 midweek during high season; bungalows start at $649.

ON THE WATER: Cheeca Lodge is right on the water and has an onsite full-service watersports facility, so your clients can hit the ocean any way they like. Anglers can go on a half- or full-day charter offshore, at the reef or backcountry in the bay. Those interested in getting deeper into backcountry fishing can take a kayak fishing trip in the Everglades National Park through the protected no-motor zones. The resort can also arrange specialty cruises, snorkeling trips and parasailing.

TOP ATTRACTION: Scuba divers will love exploring beneath the sea in Islamorada. The key features shallow coral reefs, tropical marine life, shipwrecks and the Aquarius, an underwater habitat for scientific research. Highlights include The Eagle, a ship that was sunk just for divers with sponge, coral and schools of fish, and Alligator Reef, the site of the USS Alligator (travelers will know the location by a lighthouse that doubles as a marker).

2. WHERE TO GO: Driving through the Lower Keys past the Seven Mile Bridge, travelers will come across a quieter area that’s home to beautiful beaches and state parks. One of these islands, Little Torch Key, is the jumping-off point for the exclusive private island resort, Little Palm Island.

WHERE TO STAY: While the Keys are a string of islands themselves connected by the Overseas Highway, Little Palm Island provides travelers an offshore escape to a private island of their own. The island vibe here is more in tune with the South Pacific than South Florida. VIP treatment starts when guests arrive at the Welcome Station on Little Torch Key for a motor yacht shuttle to the 5.5-acre island. Home to only 15 thatched-roof, air-conditioned bungalows with 30 oceanfront suites in total, Little Palm never has more than 60 guests at a time. Each bungalow has two 1-bedroom suites sporting private sundecks and outdoor showers with personal touches like a nameplate on the bungalow door. Don’t expect digital distractions, either. These sanctuaries are free of telephones, TVs and alarm clocks. While all of the suites are luxurious (there’s no bad room in the house), the top-tier rooms are the 1,000-sq.-ft. Island Grand Suites, outfitted with a beach area, two full baths (one of which has a claw-foot tub and glass doors opening up to ocean views), an outdoor hot tub, and iron and crystal chandeliers. The Island Romance Suite is just as dreamy, with a personal fire pit, private deck and jacuzzi tub. Rates range from $899 to $3,200 per night.

WHERE TO DINE: While guests can dine at The Dining Room, a candle-lit restaurant with a terrace overlooking the beach, or on the beach itself, those looking to get off the island can do so in style with an Ultimate Picnic. This dining perk takes on a new meaning on board The Lilyanna, for a private, 3-hour catamaran cruise with snorkel gear and a selection of breads, spreads, artisanal cheeses, Key Lime cookies and a bottle of Pinot Noir. Travelers can also jet off to another private island on board a seaplane for a 3-hour picnic complete with caviar on blinis, rose champagne, pate de foie gras, truffle butter and more.

TOP ATTRACTION: Nearby Looe Key Reef is one of the top dive spots in the Lower Keys, and guests can take a guided dive or snorkel trip to the barrier reef on board the Island Girl. The trip is catered to guests’ experience levels with an instructor to assist along the way.

3. WHERE TO GO: All roads lead to Key West—literally, the last stop on the Overseas Highway. The most famous of the Keys, travelers make their way to the Southernmost Point of the U.S. for a relaxing getaway that could include as much or as little activity as they want.

WHERE TO STAY: Located just one block from the end of world-famous Duval Street, The Reach, A Waldorf Astoria Resort is far from the crowds, but still close enough for guests to walk to some of the top sights in town. Located between the Southernmost Point marker and Higgs Beach, the 150-room hotel is set on a strip of private, natural beach—which is a big deal in Key West, since the beaches are known for being small, rocky and man-made. Private beach perks include beachside spa treatments from Spa al Mare, H2O Concierges offering mineral water spray and organizing watersport activities, and a pier perfect for catching the sunset. Rates start at $319 after April 20.

WHERE TO DINE: Half the fun of visiting Key West is enjoying the dining scene and its diverse cuisine. A few local favorites include the Cuban stand Sandy’s, tapas bar Santiago’s Bodega, brunch hotspot Blue Heaven and Sloppy Joe’s, Hemingway’s favorite bar.

TOP ATTRACTION: Sunset Celebration on Mallory Square is a nightly attraction that shouldn’t be missed, so tell your clients to head to the square and watch the show. The street party is filled with artists and stands selling local crafts and street food, as well as street performers vying for the crowd’s attention with everything from a pig to knives as props. Everything builds up to the sunset, a beautiful show out on the water with boats passing by on the horizon.

FESTIVAL SCENE: Key West is the host of many festivals throughout the year with themes as unique as the Annual Conch Shell Blowing Contest celebrating the city’s conch heritage and the Hemingway Days Festival, honoring the famous writer who resided in the city in the 1930s. Right before Halloween is Fantasy Fest, a costume party that really draws on the creativity of locals and visitors. This year, the festival takes place Oct. 17-26 with the theme of “Animéted Dreams and Adventures.” Events include everything from a royal coronation ball to a pet parade and masquerade, toga party, wet T-shirt contest and street fair.

contact information

Cheeca Lodge: (800) 327-2888; cheeca.com
The Florida Keys & Key West: fla-keys.com or fla-keys.com/traveltrade
Little Palm Island: (800) 343-8567; littlepalmisland.com or noblehousehotels.com/travel-professionals.aspx
The Reach, A Waldorf Astoria Resort: (888) 318-4316; reachresort.com or waldorfastoria3.hilton.com/en/about/travel-agents.html