From Key Largo, the northernmost of the Florida Keys, to Key West, the southernmost point of the U.S., the 125-mile island chain that makes up The Keys is a spectacular chain of tropical islands that promises heavenly warm breezes and pristine turquoise waters.
Naturally, it’s a haven for every kind of water sport imaginable. Deep-sea fishing is just one of those sports, and Key West’s own long-ago resident, iconic author Ernest Hemingway, not only participated in but also wrote about fishing adventures in several of his novels, perhaps most notably, The Old Man and the Sea.
And for those who have a passion for literature and history, Key West is especially full of interesting places to explore.
“Forever linked with literary legend Ernest Hemingway, who lived and wrote in Key West throughout the 1930s, the Florida Keys are the perfect destination for attendees to reawaken their creativity, re-prioritize meaningful goals and rejuvenate their spirits in a calm and serene atmosphere,” said Jack Meier, group sales manager for the Florida Keys & Key West tourism council.
To be sure, there are plenty of places to pay homage to Hemingway, and one place to get up-close-and-personal to the Nobel and Pulitzer Prize winner is The Ernest Hemingway Home & Museum, where Ernest lived with his second wife, Pauline. Groups can hold events in this Spanish Colonial villa where Hemingway lived and wrote some of his most famous works. The grounds are available for up to 100 people, and private house tours including a peek into his writing studio can be arranged as part of the event.
“We’ve had catered events where we’ve hired a Hemingway lookalike and given out pearls and fedoras for guests to get into the spirit,” said Darlene Plisko, general manager of the DMC, Hello! Florida. Guests can’t miss the dozens of six-toed cats roaming the property, believed to be descendants of Hemingway’s first cat, Snowball.
At the Custom House, now a museum run by the Key West Art & Historical Society, an art exhibit focusing on Hemingway’s life and impact on Key West is on permanent loan. Depicting Hemingway: Guy Harvey Sketches ‘The Old Man and the Sea’ features 59 original pen-and-ink drawings by the renowned marine wildlife artist and conservationist.
“We can host up to 200 for a cocktail party on our spectacular wraparound porch, the first floor of the house and the grounds. The building is called the ‘Crown Jewel of Key West’ because its style of architecture, usually found in the north, is so unique to the area. It’s such a historically significant building to hold an event, and especially beautiful at sunset,” said the Society’s executive director, Michael Gieda.
Nearby, Key West’s Harry S. Truman Little White House, Florida’s only presidential museum, is also used for functions. The late U.S. president spent more than six months at this tropical retreat during his 1945-1953 administration. The grounds can accommodate groups as large as 400 people, while smaller groups can utilize the president’s own dining room, living room and south porch for dinners. Private museum tours can be included.
Artist John James Audubon made his mark drawing tropical birds of The Keys and the Dry Tortugas. At the Audubon House & Tropical Gardens, across from Mallory Square in the heart of Old Town Key West, Audubon’s first edition works and lithographs are on display. The Audubon House was once home to a sea captain who made his fortune finding the spoils of shipwrecks.
The antiques-filled home is surrounded by lush gardens with rare tropical palms, orchids and other colorful flora. The back deck of this historic home provides a breathtaking setting for up to 100 guests, and the gardens can host up to 250 for a cocktail party or 150 for a seated dinner.
Unique Hotel Experiences
Hotels in The Keys offer some unique activities for groups, as well.
“In the Florida Keys and Key West, there’s no cookie-cutter approach,” said Meier of the Florida Keys & Key West tourism council. “Each of our properties has its own unique assets and attributes. It’s a matter of fitting the right group with the best property. We tell planners, ‘Let’s find the right fit.’”
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Historic Casa Marina, A Waldorf Astoria Resort conceived by railroad tycoon Henry Flagler, opened in 1920. Listed in the National Register for Historic Places, the hotel was once owned by the U.S. Navy and used as officers’ quarters for the duration of World War II.
Today, Casa Marina has spectacular events for groups on Key West’s largest private beach.
Groups are “quickly immersed in the Key West lifestyle with teambuilding and breakout activities, from sand-sculpting workshops to sunset cruises and snorkel tours,” said Andrew Rosuck, director of sales and marketing.
In addition, the Margaritaville Key West Resort & Marina, located on the waterfront, is a great spot to set sail from one of its 37 boat slips. Once on the water, an on-board buffet may feature local fish and produce, and the resort’s popular Whole Fish Grouper Taco Carving Station. Margaritaville features an on-site marina and a conference/culinary team that focuses on local experiential food and beverage.
Two hotels that sit side by side—The Gates Hotel Key West and 24° North Hotel Key West—share the striking photography of Jorge de la Torriente, owner of De La Gallery in Key West, ensuring awe-inspiring exhibitions for guests.
“Because of our relationship with the gallery owner, we can have a cocktail party in the gallery while Jorge de la Torriente talks to the group about his work,” said Lee Sheehan, director of sales and marketing for both hotels. “We can also put together tours and tastings of the Key West First Legal Rum Distillery with its owner, Paul Menta.”
The hotels can also organize cigar-rolling classes with Danny DiFabio, owner of Rodriguez Cigar Factory. Rodriguez cigars are hand-rolled, cured and aged in the traditional Cuban style. Finally, both hotels can put together scavenger hunts where teams find landmarks of historical importance around Key West.
“These types of experiences are beneficial to teams, allowing them to have fun and also work together,” Sheehan said. “Tapping into the creative side of people allows them to express themselves differently than they may in the workplace.”
The Faro Blanco Resort and Yacht Club in Marathon is an exclusive Hyatt Place Resort known for its signature landmark lighthouse built in the 1950s. Yacht excursions are the norm here.
“You can choose a private charter boat to host a board meeting on the beautiful waters of the Florida Keys,” said Corinne Dean, director of sales and marketing.
Also available are croquet, corn hole and Jenga on the sprawling lawn of the resort.
Within the conference center of the Islander Resort, a Guy Harvey Outpost in Islamorada, the Florida Keys History & Discovery Center is where groups can learn about the building of Flagler’s railroad, Spanish shipwrecks and pirates. The conference center has a large two-story ocean-facing porch that serves as prefunction space for events. Groups can also use the lush garden area just steps from the beach.
In Key Largo, guests of the Ocean Reef Club can put together a beach bonfire and roast marshmallows to create the perfect s’more. Other options include stand-up paddleboard races or the ultimate challenge: the cardboard boat regatta. Teams are given identical sets of materials—cardboard, paddles, plastic wrap and duct tape—and one hour to build a boat. Teams then race against each other in the Buccaneer Island Lagoon on-property.
