“By this time of year, winter is 1/2 way through. Key West gets us out of the cold and puts everyone in a refreshing state of mind…. It’s impossible not to be in a good mood,” says Paul Simoneau, vp of Casualty Brokerage at RLI Corp. Each year Simoneau brings a group of 35 executives scattered around the country to Key West for the company’s annual performance and sales meeting.
“It’s like real estate,” he says. “It’s all about location. Key West is easy to get to from the rest of the country, it has the best weather in January, and it’s compact enough that there’s no need to rent a car, but there’s still plenty to see and do.”
One of his group’s favorite activities last year was a literature and libations-themed scavenger hunt. Each team was required to take a portrait-style photo of an Ernest Hemingway look-alike. For many in the group, approaching a Hemingway look-alike on the street required a little preparatory character research.
“If you stop for a few beers while undertaking this task, that’s very acceptable,” says Simoneau.
Scavenger hunts are just one of the many tropical island-themed activities that Nadene Grossman, owner of DMC We’ve Got the Keys, plans for Simoneau and her other clients. The only constant is celebrating the island lifestyle.
“Key West is two miles by four miles and yet there’s more to do on this island than in some major cities. Paul has been coming down for the last 12 years and we still find new things for his group year after year.”
What about the time-honored Key West sunset cruise?
Simoneau says, “We question that each trip—is it getting old? Are people getting sick of this activity? Two thirds of the group is the same every year, but we always leave it in. It’s that good, the sunset cruise is Key West.”
Just some of the other aquatic activities that Grossman customizes include: deep sea fishing tournaments and cooking up the day’s catch for dinner; snorkeling trips on North America’s only living coral reef; island shipwreck tours in the Fleming Key Channel; biplane flights over the backcountry to see stingrays, sharks and dolphins; and ecotours on a Skipjack sailboat exploring the mangroves and marine life.
Also, the “Ultimate Adventure” is a great all-day trip that involves snorkeling, jetskiing, a water-based rock climbing wall, paddle boards, parasailing and kayaking. Grossman had one group of 250 from the Midwest, “and many had never even seen the ocean…. The crew made it easy for beginners to try so many different water activities in one day.”
WINE & DINEAROUNDS Home to America’s greatest author during the 1930s, the Hemingway House is a popular private dining venue for planners like Jamie Kiger, a senior meeting planner with Nationwide Insurance. She organized a Cuban theme dinner, cigar rolling, Cuban music and a tour through the museum during cocktail hour for her incentive group.”
“We rented the house for the evening and it was beautifully set up with a tent, dinner and look-alike Hemingways,” says Kiger. “They tied [the event] into the history, making it interesting without being boring. It’s perfect for 80-90 people.”
Anyone who’s been to Key West knows the restaurants are as eclectic and laid-back as the locals. Conch Republic Seafood is a great option for larger groups up to 500. It’s the largest bar in Key West with the most extensive selections of rum. Grossman notes, “They make the best mojitos, have wonderful fresh fish and it’s right on the water.”
Simoneau likes Grand Café, located in an old Victorian-style home, and the bustling waterfront Half Shell Raw Bar. “This is the place to get your hands dirty,” he says. “You wear a bib and eat at a picnic table; it has a loud, easygoing vibe and it’s a nice mix of tourists and locals.”
A little more upscale, Truman’s Little White House is a palatial Bahamian-style mansion on large leafy grounds for up to 400 for cocktails and 250 for sit-down dinners. You can really impress 12-14 bigwigs with a VIP Presidential Dinner where they’ll dine white-glove at Truman’s own dinner table.
Here’s another authentic Keys experience. The Audubon House & Tropical Gardens is an exquisite verdant setting in one of Key West’s great historic homes for 125-person receptions, surrounded by orchids and exotic trees lit up at night. “It’s simply magical,” says Grossman.
Also look into brunch or receptions on the outdoor patio or sweeping oceanfront lawn at the revered Casa Marina Resort, Waldorf Astoria—the grande dame hotel of the Florida Keys, built by oil/railway magnate Henry Flagler. The 311 newly renovated rooms/suites include Italian floors, painted wooden window shutters and elliptical dining tables with teak captains’ chairs. In the 1920s-era lobby, the original antique wood floors and ceilings have been preserved, leading into airy meeting space with ocean views. Total function space is 22,600 sf, and there’s no better place for brunch in the Keys. Except maybe Pepe’s on the other side of the island, considered the oldest restaurant in the islands.
Simoneau notes that most of the restaurants, resorts and activities are within walking distance, so groups don’t have to pay for shuttles or car rentals. “It also eliminates distraction and keeps people together,” he says.
Attendees will save some money in dry cleaning, too. Jack Meier, destination manager at Florida Keys & Key West Tourism Council, says, “The only time you see someone wearing a tie in the Keys is if they’re going to court. There are day shorts and sandals and dress shorts and sandals. It’s a very laid-back place with a quirkiness that’s hard to replicate.”
Grossman notes that planners love the laid-back vibe even when they have an upscale wine pairing dinner or a jazz cocktail party. “In Key West you’ll end up with your shoes off at the end of the event, that’s a fact.”
FLIPPER WAS HERE Swimming with dolphins is not something new but it takes on a special kinship with the playful mammals at the education-oriented Dolphin Research Center. It’s located on Grassy Key near the island of Marathon in the Middle Keys, and if there’s one under-promoted group experience in the islands, this is it. Half of the fun is listening to the staff describe the unique personalities of the individual inhabitants.
Many of the dolphins that have come through here have been rescued from accidents at sea. Others became ill in aquariums and some were born here. The dolphins are free to leap over the submerged fences, and many do, but they always return because the food is better. While underwater, you can hear the dolphins communicating through clicking and soft squealing sounds, and the pace is more relaxed, without a lot of staged interactions.
While staff members point out the history of the dolphins, it’s soon evident who everyone’s favorites are. They go in-depth into the plight of the animals and the marine eco-system in the Keys. They also talk about their work with special needs children who react surprisingly well when in contact with these magnificent creatures.
MEETINGS IN MARGARITAVILLE Less than one hour south of Miami International, the civilized and members-only Ocean Reef Club is a self-contained island community north of Key Largo at the northern tip of the Keys. There are only five golf courses in the islands and three of them are here (two are available for visitors). A private airstrip and world-class marina add to the adventurous drama and sense of seclusion.
“The privacy and exclusivity are very important, it gets people’s attention and creates excitement,” says Richard Weinstein, vp of sales/marketing. “And then once they’re here, there’s that laid-back feeling that tends to inspire good interaction among the group. And that’s what it’s all about.”
Accommodations include The Inn, with 144 rooms, 95 of which are waterfront, and about 150 cottages and homes spread out around the golf courses and marina.
A host of charter boats are on hand for fishing tournaments and snorkel/scuba excursions, while group kayaking is popular through the backcountry. The general vibe can range from barefoot bonfires on the beach to elegant champagne and caviar-catered croquet lessons at the regulation croquet club. Indoor meeting capacity is 30,000 sf, with two ballrooms hosting 500/700, and everyone zips around in their own private golf cart.
About 90 minutes south of Miami on the island of Islamorada, the legendary 212-room Cheeca Lodge & Spa reopens next month following a complete renovation. Unlike Ocean Reef, Cheeca is wholly integrated with the funky and footloose community of the Upper Florida Keys.
“Tell planners they can walk across the street and have a great Florida Keys meal at Mad Dog’s,” says Jeffrey Baldasarre, director of sales/marketing.
The ambience within Cheeca’s borders, however, is decidedly luxurious. President Bush Sr. made many a trip to the 27-acre resort to fish for big grouper and mahi-mahi five minutes offshore. Groups can fish right off the pier if they want, or bring in the big deep sea sportfishers for tournaments near the reef or out in the Gulf Stream. And then take the catch over to Mad Dog’s!
“The choices are endless with fishing,” says Baldasarre. He especially recommends flats fishing for trying something new. Anglers stand on the bow of shallow boats while the captain poles through water only 18 inches deep. He also suggests sailing lessons and snorkel scavenger hunts along the reef using underwater cameras, for groups up to 50. That, and just soaking in the island. “Today, I saw a mango tree, a banana tree, some hermit crabs and a couple manta rays,” he says. “For a city boy, that’s pretty cool.”