New Options for Meetings in the Florida Keys & Key West

The 125-mile-long Florida Keys and Key West island chain offers myriad outdoor experiences for team-bonding activities, paired with enhanced meeting facilities at subtropical resorts. To that effect, the Keys are a good island destination for meetings, typically of 15 to 100 attendees, providing opportunities to extend their mid-week business gatherings with pre- or post- leisure stays.

The island chain is easily accessible from major U.S. cities with more than 20 nonstop flights to Key West International Airport (EYW). Later this year, United Airlines is to begin operating daily nonstop flights to EYW from Newark’s Liberty, Chicago O’Hare, Houston’s George Bush Intercontinental, and Washington D.C.’s Dulles International Airports.

Keys Airlift

Airline seat capacity is increasing on flights between several major cities and Key West International Airport (EYW), which is undergoing a Concourse A expansion to be completed by summer 2025. JetBlue is to resume nonstop service October 29 to EYW from Boston Logan International Airport on 140-seat Airbus A220-300 aircraft, with nonstop daily service scheduled in January. On November 5, American Airlines is to add a second daily nonstop flight to EYW from Washington D.C.’s Ronald Reagan Washington National Airport on a 76-seat Embraer 175. Also November 5, Delta Air Lines is to resume its nonstop winter seasonal flight to EYW from New York City’s LaGuardia Airport on a 70-seat Embraer 170. Starting November 28, United Airlines is to operate two daily nonstop flights to EYW from Newark Liberty International Airport: one on a Boeing 737-700 and one on a 70-seat Embraer 170. Additionally, December 21 United is to begin operating daily nonstop flights to EYW on 126-seat Boeing 737-700 aircraft from Chicago O’Hare, Houston’s George Bush Intercontinental, and Washington D.C.’s Dulles international airports, replacing its 70-seat Embraer 170 aircraft on those three routes.

Keys Accommodations

Islamorada’s 27-acre oceanfront Cheeca Lodge & Spa—with 243 rooms and suites, 11 stand-alone casitas, a total 70,000 square feet of event space—offers a new stand-alone 10,000-square-foot Islamorada Ballroom. It accommodates up to 1,500 for receptions and 788 for banquet-style dinners. Forty-three new oceanfront suites each offer over 550 square feet, a private balcony and open-air spa tub. The Casitas at Cheeca Lodge offer personalized butler service and one- and two-bedroom units from 750 to 2,100 square feet. Casita group buyouts are offered.

The Islamorada Resort Collection is to offer 376 island-inspired guestrooms, 12 dining outlets, 80,000 square feet of meeting space and a fishing fleet. The Collection includes the 110-room Amara Cay Resort, the 52-unit La Siesta Resort & Villas, and a new resort and marina at mile marker 84 to be unveiled in 2024. When completed, the new resort is to include 214 guestrooms, seven culinary options, two retail shops and a full-service marina. The Tiki Bar will also undergo renovations. Group activities include offshore and backcountry fishing and ocean adventures by Spray Watersports, with a 26-mile jet ski tour of backcountry mangroves, wildlife preserves and other attractions.

The Middle Keys’ newest luxury property, the 24-acre, 199-unit Isla Bella Beach Resort in Marathon, has more than 20,000 square feet of function space including 16,000 of outdoor space and a 2,800-square-foot Hibiscus Event Center. For new groups of 20 or more rooms per night and with a minimum F&B purchase, group perks include an “It’s 5 O’Clock Somewhere” welcome reception, breakfast vouchers at Marketplace, private pool for a day, fee-waived indoor meeting space, reduced outdoor site fees, room upgrades, one complimentary room night for 40 booked, and reduced resort and parking fees. Restrictions may apply. The Virtuoso Preferred resort’s offerings include a new Sushi Cabana, to open this winter; on-site charters for fishing, diving and watersports; a 4,000-square-foot spa, five pools and three F&B venues.

The 311-room Casa Marina Key West, Curio Collection by Hilton, has unveiled extensive renovations including a new 5,000-square-foot oceanfront event lawn, adding to its existing 11,000 square feet of indoor event space—which includes the newly enhanced 3,100-square-foot historic Flagler’s Ballroom, 2,600-square-foot Grand Ballroom and 5,000-square-foot Keys Ballroom. New elements include four new F&B outlets and upgraded piers utilized for watersports. Group activities include scavenger hunts, jet ski tours, private snorkeling trips on a luxury catamaran and golf tournaments. Nine event spaces accommodate from 10 to 500.

Keys Attractions

In Key Largo, the Reef Environmental Education Foundation (REEF) offers The Interpretive Center for small groups, providing educational experiences about fish identification, lionfish or mangrove ecology. REEF’s headquarters is a classic conch-style house, known as the oldest building in the Upper Keys still in its original location. A new $5 million, 4,000-square-foot, two-story Marine Conservation Center with a second-floor balcony—home an ocean exploration gallery and three centers for discovery science, ocean outreach and program planning—is targeted for completion in 2025, providing space for groups of up to 80.

In Islamorada, the Florida Keys History & Discovery Center focuses on the Keys’ maritime history, the Florida Keys Over-Sea Railroad and exhibits about the island chain’s reef ecosystem. A second-floor 35-seat theater screens documentaries. The first floor showcases Upper Keys history including First Nation people, early Spanish treasure hunters and pirates. A “Coral Reef Exploration Exhibit” has three aquariums, interactive kiosks and views on monitors of coral reef ecosystems.

In the Middle Keys at Dolphin Research Center, groups can meet dolphins and participate in interactive experiences. It offers two separate meeting rooms: the 702-square-foot Key Largo Room and the 672-square-foot Key West Room, each with a full-screen monitor and Wi-Fi, and hosting up to 70 attendees theater-style or 44 for dinner. The 378-square-foot porch hosts smaller breakouts or an al fresco meal.

In Marathon at Crane Point Hammock Museum & Nature Trails, the mid-century 2,500-square-foot Crane House—built in 1954 and designed and furnished in the style of Wahl Snyder, a student of architect Frank Lloyd Wright—is unique to the Keys and can host up to 70. It’s listed on the National Register of Historic Places. In addition, an antique 84-foot-long red railroad car provides space for 25 to 30 attendees. Crane Point, preserved by the Florida Keys Land and Sea Trust as one of the Keys’ most sensitive environmental and archeological sites, also includes a museum, historic Bahamian-style Adderley House, “fish pedicures,” a well-stocked gift shop and nature trails. Crane Point also is the all-new home for the Marathon Wild Bird Center, with new educational bird enclosures, hospital and rehabilitation facility.

At Mote Marine Laboratory’s Elizabeth Moore International Center for Coral Reef Research & Restoration on Summerland Key in the Lower Keys, groups can book a private tour of the land-based coral nursery, with outdoor research and indoor labs, to learn how Keys scientists are restoring Florida’s coral reef. The facility has classroom space for 25, and continental breakfasts and bag lunches can be arranged. Mote also offers private group tours and interactive coral experiences at its satellite coral nurseries at Reefhouse Resort & Marina in Key Largo, and at Bud N’ Mary’s marina in Islamorada.

On Key West’s Truman Waterfront, the 6,000-square-foot Florida Keys Eco-Discovery Center offers new exhibits highlighting Florida Keys mangrove, coral and seagrass habitats. A freestanding main exhibit focuses on the Florida Keys National Marine Sanctuary, with others showcasing the science behind coral restoration. There’s also an exhibit on shipwrecks and maritime history left by the wrecks. A conference room seats 30 and there’s access to a small kitchenette.

Keys Tours

In Marathon, the Pigeon Key Visitor Center and a custom-designed Pigeon Key Express train offer daily tours departing from the Pigeon Key Gift Shop at 10 a.m., 11:30 a.m., 1 p.m. and 2:30 p.m. The colorful train, with two 30-passenger coaches, travels along a 2.2-mile restored span of the Old Seven Mile Bridge. Lying beneath “Old Seven,” the tiny island of Pigeon Key was a camp for workers building the bridge in the early 1900s and offers restored buildings and a museum. Visitors can swim, snorkel, fish and shop at an on-island gift shop. Train tours can be booked online 14 days in advance.

Keys Podcast

Meeting and incentive planners and event attendees can explore the Keys’ heritage through a new 30-episode documentary-style “Florida Keys Traveler” podcast that showcases 200 years of the island chain’s history. The podcast spotlights local personalities, attractions and venues in each of the Keys’ five districts: Key Largo, Islamorada, Marathon, Big Pine Key and Florida’s Lower Keys, and Key West.

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