Don’t expect a little thing like an ocean to stop the fun in Florida. At land’s end in South Florida, where the Everglades makes its marshy way toward the sea, a group of islands picks up the journey across the Atlantic and Florida Bay, leapfrogging toward the southwest for over a hundred miles before ending on a high note—one of the most unabashedly eccentric cities in the U.S.
But before you get to Key West, there are dozens of other islands to explore, and depending how you structure your group’s visit, your itinerary may take in all, or just a few, of them.
In many ways, that decision can depend on which way you hold your map—that is, whether your adventure in the Florida Keys begins or ends in Key West.
All-Access Pass
"We’ve got plenty of lift coming down here, getting into Key West," says Jack Meier, destination sales manager for the Florida Keys & Key West, referring to Key West International Airport, which welcomes US Airways, Delta and American Eagle, among other carriers, as well as direct seasonal service from Cape Air and private charters.
But if you start your Keys trek in the other direction, flying into MIA and perhaps tacking on a night in South Beach, you’ll be taking "the drive," a one-of-a-kind voyage across turquoise waters that stretch toward the horizon in every direction, courtesy of the Overseas Highway, which for many visitors is an integral part of the true Keys experience.
Connecting the Keys to the mainland and to each other, the Overseas Highway, constructed on the foundation of an old railroad, spans 113 miles of roadway and 42 bridges, including the Seven Mile Bridge, which stretches 6.79 miles across open water and was referred to upon its completion as "the eighth wonder of the world."
But the accolades for this remarkable highway, which has undergone extensive maintenance over the years, keep coming. In October 2009, it was named an "All-American Road," the highest recognition possible under the National Scenic Byways program established by the U.S. Congress in 1991. Only 30 other roadways in the nation, including the Blue Ridge Parkway, Alaska’s Seward Highway and Historic Route 66, have earned the prestigious title, and the Overseas Highway is the first in Florida.
Playtime
The entire journey from Miami to Key West takes less than four hours, but with so much to do and see along the way, you can count on stopping a few (or a few dozen) times. Heading into Key Largo, the first and longest of the islands, Key Largo Hammock Botanical State Park is a great place for groups to relax and stretch their legs as they take in rare tree snails, mangrove cuckoos, Schaus swallowtail butterflies and butterfly orchids.
Adventure above and below the waves is waiting at nearby John Pennekamp Coral Reef State Park, the country’s first underwater preserve, where 600 species of fish and 55 varieties of coral live just beneath the surface of crystal-clear waters. On land, environmental trails wind through tropical hammocks of gumbo limbo, strangler fig, tamarind, wild coffee and mahogany trees.
What’s offshore is the big draw for most visitors to Islamorada, the next group of islands along the Overseas Highway, which sit within 10 to 20 miles of Gulf Stream waters that bring in seasonal visitors such as sailfish, marlin, kingfish, wahoo and tuna, close enough to be targeted by small-boat anglers.
Small wonder Islamorada is known as the "Sport Fishing Capital of the World," though it’s also tops in sheer concentration of professional offshore charter boats with tournament-grade captains, which can lead your group to a big catch or big underwater adventures featuring tropical fish, sponges, soft and hard corals, and crustaceans that congregate along natural and artificial reefs.
Heading into the Middle Keys, also known as the Islands of Marathon, you’ll want to block out some time at the Dolphin Research Center on Grassy Key, where interaction programs include Trainer for a Day, pairing visitors with trainers as they learn to feed and play with dolphins, and Researcher for a Day, which puts you on a research team with marine scientists, collecting data and learning all about dolphins and sea lions.
"They can structure an entire buyout of the facility for a day or cater programming as far as dolphin encounters, either wet or dry," Meier says. "They also will tailor a program to budget and to a group’s specific needs or objectives."
Leaving the Middle Keys, the soaring Seven Mile Bridge leads to the rustic Lower Keys, home to two national wildlife refuges, a national marine sanctuary and a state park. Your group might glimpse the endangered Key deer, a subspecies of the Virginia white-tailed deer, at the National Key Deer Refuge. Attendees can also board kayaks, canoes and boats to explore the open water and islands of the Great White Heron National Wildlife Refuge, home and breeding ground of North America’s largest wading birds.
If you don’t get sidetracked by Bahia Honda State Park, site of one of the top beaches in the U.S., the next stop along the Overseas Highway is a full stop in colorful, irreverent Key West, a haven for both pirates and presidents, where history and free-spirited fun converge on narrow, tree-shaded lanes fronted by art galleries, boutiques, pubs and breezy Victorian and Bahamian-style homes, many converted into cafes and bed-and-breakfast inns.
A few of the most historic old Key West homes also function as museums and group event space, including the Ernest Hemingway Home and Museum, where the Nobel Prize-winning author lived and worked for more than 10 years and where groups today can enjoy private tours and dinner on the lush grounds.
Venue Variety
In addition to its many B&Bs, though, Key West is also home to some of the larger convention properties in the island chain, including the recently upgraded, 311-room Casa Marina Resort & Beach Club, with 11,000 square feet of conference space; and the Westin Key West Resort & Marina, whose prime location next to Mallory Square, site of Key West’s nightly sunset celebration, is matched by its 16,000 square feet of indoor and outdoor function space, a 37-slip marina offering a complete range of water sports, and its nearby sister property, Sunset Key Guest Cottages.
Ample meeting space is also found an hour away at Hawk’s Cay Resort on Duck Key, a self-contained, 60-acre retreat where groups can enjoy fishing, dolphin interaction programs, swimming in five pools and water sports like kiteboarding, in addition to 25,000 square feet of function space, much of it with ocean views. In Islamorada, newly renovated Cheeca Lodge offers more than 4,500 square feet of conference space, while the laid-back Holiday Isle Resort & Marina gets down to business with beachfront meeting space and complete meeting packages.
Continuing to Key Largo, properties include the Ocean Reef Club, with 30,000 square feet of indoor function space, and Marriott’s Key Largo Bay Resort, home to 15,000 square feet of meeting space, including a 5,000-square-foot waterfront conference center.
On a smaller scale is Holiday Inn Key Largo Resort & Marina, with over 3,000 square feet of meeting space and an additional 2,000 square feet in its outdoor Tiki Hut pavilion.
