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Florida Keys/Key West

At the southern tip of the Florida peninsula, visitors leave the mainland—and the mainstream—behind in the Florida Keys, a 125-mile island chain connected by 42 bridges and connecting visitors to tropical relaxation so scenic, it seems to have sprung from an artist's paintbrush.

Within this landscape and seascape of emerald harbors, waving palms, windswept beaches and a coastline woven by vivid mangrove trees, visitors indulge in such traditional island pleasures as swimming, boating, fishing and snorkeling—the entire chain is a designated National Marine Sanctuary—while also getting their feet wet as amateur dolphin trainers and diving into a burgeoning cultural scene.

In fact, many groups might be tempted to forget the pie chart and go straight for the Key Lime Pie here, but these islands are as ready for meetings as they are for adventure, with facilities for small luxury incentives and large conventions alike, including one of the region's most secluded resorts, Little Palm Island on Little Torch Key, and one of its largest convention properties, Hawks Cay Resort on Duck Key.

If you've been to the Keys before, you know about the one-of-a-kind hotels and resorts set just off the Overseas Highway—the southernmost leg of U.S. Highway 1—and fronting either Florida Bay, the Atlantic Ocean or the Gulf of Mexico. But you'll also find a fair share of national chains here, notes Jack Meier, destination sales manager for the Florida Keys & Key West.

"One of the things we like to point out is the number of national flags represented in the Keys," he says. "We've got Marriott, Sheraton, Waldorf Astoria, Doubletree, Hyatt and more. We're pretty well represented."

Meanwhile, the dip in visitor numbers that the Keys experienced in recent recession years is starting to trend back upward.

"We just had a great winter," Meier reports. "Groups are booking earnestly for 2012 and 2013, and the momentum is starting to come back. We're also seeing longer booking windows."

Turning the economic corner, though, is just one bright spot among many in "America's Caribbean," a getaway that groups won't soon forget.

Upper Keys
The first key waiting on the other side of mainland Florida is also the largest in the island chain: Key Largo, famed setting for the Humphrey Bogart movie of the same name and considered one of the world's premier dive destinations.

Much of that diving is done at John Pennekamp Coral Reef State Park, the country's first underwater preserve, which celebrated its 50th anniversary in 2010 but offers the timeless attractions of colorful fish and coral set just beneath the surface of brilliant waters. One of the most popular dive and snorkel sites here is the nine-foot "Christ of the Abyss" statue, a replica of a similar figure in the Mediterranean. Groups that prefer to stay dry can also take the park's Spirit of Pennekamp glass-bottom boat tour, offering spectacular views of this amazing underwater realm.

Key Largo is also just across Florida Bay from the Everglades, and local operators can outfit groups for kayaking the shallow flats in between, as guides point out local flora and fauna. Animal encounters are also waiting at the key's Dolphin Cove Research & Education Center, where groups of up to 36 can swim with dolphins and tour the marine education facility.

Leaving Key Largo, next up along the Overseas Highway are the islands of Islamorada—including Plantation, Windley and Upper and Lower Matecumbe Keys—known as the "Sport-Fishing Capital of the World" and boasting more professional charter boats than anywhere else in the state, if not the nation. If you're dealing with a group of landlubbers, you can still enjoy something "fishy" at Robbie's Marina, where 50 to 100 tarpon visit daily and linger for hours as visitors hand feed them.

But aquatic adventures aren't the only activity on the agenda here. A group of Islamorada galleries, restaurants and shops have formed the Morada Bay Arts & Cultural District, set just off the Overseas Highway and featuring Art Walks on the third Thursday of each month that include live music in a street festival setting.

"It seems like every month, we get more and more people. It's really becoming very popular here," says Carol DelCorio, a sales associate at Gallery Morada, one of the participating venues.

Meanwhile, Upper Keys properties offer some of the largest meeting space in the island chain. The Hilton Key Largo Resort, for one, has over 17,000 square feet of flexible meeting space, including two ballrooms; the Ocean Reef Club on Key Largo boasts 30,000 square feet of meeting space; and Islamorada's Cheeca Lodge & Spa offers a 4,600-square-foot conference center along with a new rooftop lounge for corporate events and private functions.

Middle and Lower Keys
From ocean depths to sky-blue heights, the Middle Keys, also known as the islands of Marathon, have a lock on fun and excitement.

"In a nutshell, the islands of Marathon offer so much to do, whether a group wants to work on team building or a planner needs activities for spouse and kids programs," says Daniel Samess, CEO of the Greater Marathon Chamber of Commerce and Visitor Center.

Team building and education combine at the Dolphin Research Center on Grassy Key, where a variety of interaction programs include Researcher for a Day, which allows attendees to become part of a research team, exploring the intelligence of dolphins and sea lions and getting real, hands-on responsibilities as well as personalized instruction.

Heading upward from there, Marathon's Island Hoppers helicopter tours has expanded its menu of aerial adventures with a new Scenic Shoreline Flight, which soars over the Middle Keys and Islamorada before skimming the backcountry of the Everglades and Ten Thousand Islands. Departing from Marathon Airport, the 4.5-hour tour includes lunch at the Cabbage Key Inn on the mainland near Fort Myers. The maximum number of passengers is three.

"It's a great tour," says Dave Odom, Island Hoppers' owner and pilot. "We also offer 15-minute scenic flights if you want to get more people in on the fun."

"Fun" is also the key word at places like Crane Point, a 63.5-acre archaeological site featuring a wild bird rehabilitation center, a butterfly garden and nature trails that wind through a natural Florida Keys hardwood hammock.

At meeting time, the islands of Marathon are home to a number of properties catering to groups, including Hawks Cay, with over 20,000 square feet of meeting space and a private event catamaran; and Tranquility Bay Beach House Resort, with indoor meeting space for up to 30 and a 3,000-square-foot private beach.

New on the scene in the Middle Keys is the Holiday Inn Express & Suites, with 134 rooms and a 24-hour business center; and a new conference and event facility at the Coral Lagoon Resort that accommodates up to 75.

In the "what a way to go" category is leaving the Middle Keys over the Seven Mile Bridge, which is the longest segmental bridge in the world and rises over the Gulf of Mexico on one side and the Atlantic on the other. At the bridge's end are the Lower Keys and a host of natural adventures, from kayaking the open water and islands of the Great White Heron National Wildlife Refuge, home and breeding ground of one of North America's largest wading birds, to following a nature trail through the National Key Deer Refuge, home to the tiny, elusive Key Deer, a relative of the Virginia white-tailed deer and about the height of a medium-sized dog.

Key West
The final stop on the Overseas Highway is Key West, one of the nation's oldest towns and geographically closer to Cuba than to Miami. It's said that this idiosyncratic, two-mile-by-four-mile island has nurtured the talents of more writers per capita than any other city in the country—Ernest Hemingway and Tennessee Williams among them—and today, scores of published authors reside in Key West, either full time or part time. Accordingly, the island has a busy cultural scene, with venues that include the Red Barn Theatre, presenting live comedy, musical theater and cabaret shows; the Tennessee Williams Theatre, offering stage, dance and musical productions; and the Waterfront Playhouse, located at famed Mallory Square and into its 71st season in 2011.

That sense of artistic awareness in Key West is part of the island's free, easygoing spirit. It's simply impossible not to relax here, whether you're strolling the narrow, tree-shaded lanes en route to historic sites like the Hemingway Home or the Truman Little White House, or gathering for a reception at the Audubon House & Tropical Gardens, filled with works by the renowned 19th-century ornithologist, John James Audubon.

With its Victorian architecture, heritage sites and many museums, you might expect to traverse Key West via horse and carriage, but the city is up to date when it comes to transportation. In fact, AirTran Airways introduced nonstop jet service between Tampa and the newly expanded Key West International Airport in March.

Meanwhile, the city recently welcomed a new property—the Silver Palms Inn—which opened in historic Old Town and joins such established properties as the historic Casa Marina, A Waldorf Astoria Resort, featuring more than 22,000 square feet of event space, and the Ocean Key Resort & Spa, set near Mallory Square and offering 8,670 square feet of meeting space.

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About the author
Lisa Simundson