In the Florida Keys, Meetings are Uniquely Unconventional

Meetings in the Florida Keys & Key West, easily accessible at the southern tip of Florida’s peninsula, are unconventional and memorable. The 125-mile-long island chain is stunningly framed by both the azure-hued Atlantic Ocean and the aquamarine-tinged Gulf of Mexico.

Keys activities are easily personalised, curated or customised for ‘bleisure’ travel, the blending of business with leisure activities that makes learning, bonding and unwinding a breeze.

With today’s meetings all about engagement, immersion and entertainment, hard-driving boomer, millennial and Generation X executives can be assured their time at work in the Keys will include time at play.

Meetings can be booked aboard a yacht or tall ship, at a Civil War–era fort, or even at historic homes and gardens once occupied by Ernest Hemingway and President Harry S. Truman. For a truly unique experience, groups can book a seaplane for a one-of-a-kind day trip to richly historic and remote Dry Tortugas National Park.

Here's a selection of what’s new:

Keys Accommodations

The new adults-only Bungalows Key Largo, is the first all-inclusive property to open in the island chain. Set over 12-acres, the 135-unit ‘luxury inclusive’ resort offers amenities including 4,000 square feet of indoor and outdoor event space, two in-ground pools, 1,000 feet of shoreline, 800-square-foot bungalows, a Sunset Tiki Bar, Zen Garden Spa, a 38-foot sailing catamaran and 40-foot Intrepid powerboat. Dining venues include Bogie & Bacall’s, Sea Señor, Fish Tales and Largo Larry’s food truck. Rates include golf cart pick-up and drop-off service, lodging, food and premium beverages, amenities, water toys and on-site activities.

In Key Largo, the 200-room, 13-acre Baker’s Cay Resort is open as the Florida Keys’ only Curio Collection by Hilton. The resort features 25,000 square feet with a variety of venues for meetings of up to 400 people, a 4,000-square-foot ballroom and a 7,000-square-foot lawn. Outside meeting spaces include Hammock Beach, Coconut Beach and a lower deck with an 800-square-foot pool. Dining venues include the casual Calusa for breakfast and dinner with panoramic Florida Bay views, Dry Rocks for upscale beachside dining with live music and fire pits, a mobile food truck and a pool and Tiki beach bar. Amenities include the Cay-1 program with on- and off-property activities and an Aveda Green House salon.

The recently revamped 25-acre oceanfront 114-room Islander Resort in Islamorada hosts groups and weekday corporate meetings. Offering 138 guest rooms, suites and bayside townhome units, it is a greenhotels.com member. It features contemporary cottage-style units with screened-in lanais, a new 6,000-square-foot Great Lawn and 110,000-square-foot beachfront event space, a 2,760-square-foot Blue Marlin Ballroom and Tarpon Terrace, and 25 nearby two-story, two-bedroom bayside townhomes. Activities and amenities available include snorkelling trips, sunset sails, two oceanfront pools, an expansive private beach plus massage and wellness services. Dining concepts include the casual poolside Tides Beachside Bar & Grill and Elements Lounge & Restaurant.

In Islamorada, the 214-room, 27-acre oceanfront Cheeca Lodge & Spa has undergone a $25 million transformation. The property offers 4,600 total square feet of versatile space and a Tahitian-style Spa Island with six outdoor venues and an adults-only pool. The Bougainvillea Ballroom, its largest meeting space, has 12-foot ceilings and 2,100 square feet for up to 150 attendees. Located on the lodge’s second floor, the 1,900-square-foot Sunrise Ballroom and Oceanfront Terrace host meetings of up to 110. Groups can plan a sunrise breakfast on a 39-foot motor catamaran or an event on nearby Indian Key. A third oceanfront pool and second Tiki bar are scheduled for completion by late spring.

The Angler House Marina in Islamorada can accommodate up to 60 for corporate retreats, welcome parties or fishing tournaments in an atmosphere of old Florida charm, surrounded by natural hardwood hammock and mangroves. The venue has added three houseboat villas. It includes a two-story Tiki hut with the Canoe Club bar, dock, soft Bermuda-grass lawns, flat-screen TVs, an outdoor kitchen and pool.

The 60-acre Hawks Cay Resort on Duck Key recently completed a $50 million renovation. It has 20,000 square feet of waterfront meeting space with two ballrooms; the 5,733-square-foot Dolphin Ballroom can accommodate up to 480. Team-building activities can include a welcome reception, sunrise yoga, swimming with five resident bottlenose dolphins, pool parties, sunset cruises, fishing excursions, boat charters and a farewell brunch. The Preferred Hotel Group Lifestyle Collection and AAA Four Diamond Award–rated resort offers 250 two- and three-bedroom villas and 177 guest rooms. Dining venues include Angler and Ale restaurant and the new Sixty-one Prime and Hawks Cay Marketplace. A new adults-only pool area offers a grill and bar serving specialty drinks.

Marathon’s 24-acre, all-new 199-unit Isla Bella Beach Resort, located at the Seven Mile Bridge Oceanside, is scheduled to open in early April. The luxury beach resort’s 24,000 square feet of event space includes a 4,000-square-foot Hibiscus Center for meetings of 25 to 300, covered patio areas, three banquet rooms, five pools, four food and beverage concepts, a 1,000-square-foot fitness centre, full-service marina and a sunset pier. Two custom MOKE beach cruisers can be creatively incorporated into events. A 4,000-square-foot Il Mare Spa has five treatment rooms, spa lounge and couples massage room. Dining venues include Il Postino, an oceanfront Neapolitan-style Italian restaurant; The Beach Bar; The Burger Palace and Manatee Bay Marketplace, a waterfront cafe with shopping. Bocce, croquet, oversized chess, fire pits, complimentary bicycles, water sports and guided fishing expeditions are on-site.

The 178-room Margaritaville Key West Resort & Marina, steps from Key West’s Mallory Square, offers newly refurbished suites and creatively styled meeting amenities. Margaritaville features 16,000 square feet of flexible indoor and outdoor function space including the 300-capacity Truman Ballroom and nine breakout rooms. Offerings include Vitamin D Breaks with coffee served outdoors; H₂Ospitality Suites, staged in a fully equipped yacht anchored at the resort’s marina; and Sun & Sea Venues, allowing groups to maximize outdoor time with an on-board meeting or team-building excursion on a catamaran. The resort is home to a full-service 37-slip marina with water sports, indoor and outdoor dining options, waterside shops and live entertainment.

The 216-room Marriott Key West Beachside offers Key West’s largest ballroom at 5,673 square feet and nearly 10,000 square feet of meeting space. A 16-slip dock and pier accommodate boats with a maximum 40-foot length and 13-foot beam. The property, with seven breakout rooms and outdoor function space, offers upgraded air walls and carpeting. It has complimentary Wi-Fi throughout the hotel and accommodates in-house audio-visual requirements.

On Stock Island, the 20-acre Oceans Edge Key West Hotel & Marina features a 575-square-foot conference space for 12 people. Oceans Edge also has a partnership with Key West Harbour for use of its marina restaurant space to accommodate up to 60. The resort’s 175 suites and rooms, each offering waterfront balconies, range from 382 to 575 square feet. Suites feature a private living room, wet bar, flat-screen TV, local art and custom furnishings. The property’s on-site marina has 111 wet and 52 dry slips. The Yellowfin Bar and Grill, with dock-to-dish dining, also has group space.

Keys Activities

Key Largo Bike and Adventure Tours features an escorted ‘Taste of the Keys’ tour, its most popular bike tour for casual riders, for up to 12 people in the Upper Keys with a 10-mile trek from Tavernier to Islamorada. The tour stops at local beaches, coffee shops, art galleries and craft breweries. Cyclists get a van ride back.

Other themed bicycle tours are offered as well.

Up the Keys Eco Tours has launched ‘volun-tours’ that allow groups to experience the Keys’ marine environment for a day. The operator has teamed up with the non-profit volunteer ‘Conch Republic Marine Army’ and Big Pine Kayak Adventures for a guided tour and kayak excursion. Visitors can learn about the Lower Keys’ history, culture, ecology and Key deer, plant mangrove seedlings and pick up debris. Guided tours leave Key West with door-to-door service in air-conditioned 15-passenger vans.

Groups of up to 50 can participate in an hour-long Marine Science Eco Experience, showcasing Keys sea turtles and nesting, the importance of coral reefs, marine mammals, sharks, rays and mangroves, and invasive species such as lionfish and green iguanas. “The program unites visitors with our marine environment throughout the Florida Keys,” said founder Sherri Paris, a marine scientist in Key West. Programmes can be arranged at resorts including Baker’s Cay Resort and Ocean Pointe Suites in Key Largo; Amara Cay, Cheeca Lodge & Spa, La Siesta Resort and Marina and Postcard Inn in Islamorada; Hyatt Place and Marriott Courtyard in Marathon; and Casa Marina, Havana Cabana, Hyatt Beach House, Hyatt Centric, Hyatt Sunset Harbor, Hyatt Windward Pointe, Sheraton Suites and Southernmost Beach Resort in Key West.

At the Key West Butterfly & Nature Conservatory, fans of resident pink flamingos Rhett and Scarlett, a male and female breeding pair, can ‘Flamingle’ with the creatures during daily hour-long encounters. The conservatory is the only butterfly facility in the United States housing flamingos. Groups of four to six can get up close and personal during the exclusive ‘Flamingle’ experience. Human participants sit in a white gazebo overlooking the pond and lushly planted conservatory, while Rhett and Scarlett walk free and interact as they choose. Participants are not allowed to touch the flamingos but are encouraged to communicate and socialize with them.

In Key Largo, the new Kingdom Escape Games offers escape rooms and games for groups of up to eight. They include ‘Rendyth’s Revenge’ room, a live-action escape adventure in which players need to work together to complete a mission. A second and third room are planned. Under 18s must be accompanied by an adult. Another team-building activity is available daily at Key West Room Escape at Casa Antigua in Key West. Escape activities include Jail Break Havana, Pirate Treasure Hunt, Escape Papa’s Study and Disco Inferno. Author Ernest Hemingway and his wife Pauline once stayed at the property which was one of the city’s first hotels. Private rooms are offered for up to 10 participants and 50 or more participants qualify for a 15 percent discount.

Keys Food Activities

Key Largo Chocolates & Ice Cream, the Keys’ only chocolatier, offers educational and fun chocolate-making classes on request for groups of 10 to 22 people. Classes are about 2.5 hours long and include hors d’oeuvres, wine and a kitchen tour. Participants can take their chocolate creations with them. The emporium features handmade truffles, specialty chocolate bark with Key lime and pistachios, and ‘chocodiles’ — 9-inch-long crocodiles of white or dark chocolate. Homemade ice cream includes Key lime pie and dulce de leche flavours.

At Key West Key Lime Pie Co. groups can create mini–Key lime pies of graham cracker crust, Key lime filling and whipped topping. Prices are $20 per person (around £15). The tangy treat, linked to Key West’s history, is believed to have been originated in the 1800s by ‘Aunt Sally,’ a cook for Key West’s first millionaire and ship salvager, William Curry. Spongers and fishermen made it on board their vessels with simple ingredients that didn’t require refrigeration.

Key West Food Tours features a three-hour Southernmost Food Tasting & Cultural Walking Tour that spotlights Cuban and Caribbean influences in food and culture. The 1.4-mile tour stops at five venues where participants sample treats such as Cuban roast pork, fresh fish, a signature rum cocktail and Key lime pie. Tasting venues include El Siboney, Bad Boy Burrito, The Speakeasy Inn & Rum Bar, Blue Heaven and Mangoes. Tours for adults are $75 (around £57).

The Hemingway Rum Co. Distillery in Key West hosts private groups of up to 275 people and plans to open a 2,400-square-foot event centre this year. The 8,200-square-foot brick attraction, once a tobacco warehouse, houses the Papa’s Pilar Rum production facility, experience centre, tasting room and trading post. A 350-gallon still produces up to 80 gallons of rum daily from molasses, yeast and water. Thirty-minute tours are offered from 11 a.m. to 4 p.m. daily.

Keys Transportation   

Small groups needing a ride on Islamorada’s Upper Matecumbe Key after shopping, dining or gallery hopping can take Freebee Islamorada, a free electric vehicle ride service available Thursdays to Sundays. Freebee’s service is offered Thursdays and Fridays from 4pm to midnight, Saturdays from noon to midnight, and Sundays from 11am to 8pm.

Key West’s free hop-on, hop-off Duval Loop bus service makes it easy for groups to travel around the island’s Historic Seaport and downtown Duval Street districts without using cars. The Duval Loop bus operates daily from 6am to midnight year-round, with 18 stops for car-free access to Mallory Square, Truman Waterfront Park and downtown attractions, hotels, museums, boutiques and eateries. The route begins at the city’s Park N Ride station on Caroline Street, proceeds to Simonton Street and Front Street near the waterfront, up Whitehead Street and to the park, to the area near the Southernmost Point marker, down Simonton to Fleming, then to White Street and back to the Park N Ride. The service operates four pink-and-blue buses. The loop takes about 30 minutes.