Just 70 miles south of Miami as you enter Key Largo, Florida, the mainland gives way to turquoise waters, swaying palms and a ribbon of highway that stretches 113 miles to Key West. Connected by the iconic Overseas Highway, the Florida Keys unfold island by island, offering a bucket-list backdrop that feels both aspirational and attainable for meetings and events.
While the archipelago features airports in Key West and Marathon, a high ratio of attendees may opt to rent a car at Miami International Airport to drive to their final destination because the panoramic views along the stunning Overseas Highway are just that spectacular.
[Related: Read the 2026 Meetings Florida Supplement]
“The Florida Keys feel like five different destinations in one,” said Ed Simon, executive vice president and chief sales officer for Visit Florida Keys & Key West. “Each island has its own personality, but they all work well for incentive and executive retreats. We have that Caribbean vibe people love, without the hassle of needing a passport.”
From lively and energetic to quiet and nature-driven, planners can align the setting with their program goals.
“If you start in Key West, which is that bucket-list stop most people recognize, you’ll find a lively, walkable place where there’s always something going on,” said Simon, adding that as you head up into the Lower Keys and Big Pine Key, it becomes much more nature focused with a slower pace. “Marathon and Duck Key offer a fantastic mix of resort amenities and water activities, and then you have Islamorada, known as the Sportfishing Capital of the World. And finally, Key Largo … home to John Pennekamp Coral Reef State Park, known as the gateway to some of the nation’s top diving and snorkeling experiences.”
4 Fantastic Offsites
Key West Cooking Show
Ready to elevate your offsite with a private “dinnertainment” experience that blends culinary demonstration, island history and hands-on flavor? The Key West Cooking Show is set in an intimate, historic kitchen setting and encourages connection through shared tables and storytelling, including curated wine pairings and cocktail crafting.
Ocean Clean-Up
For groups prioritizing sustainability, the nonprofit Conch Republic Marine Army offers hands-on marine conservation outings. Weekly cleanup excursions depart from Marathon, Key West and other Keys locations to remove marine debris, protect mangrove habitats and safeguard waterways.
Sandbar & Float
Spray Watersports at Three Waters Resort & Marina invites guests to experience Tropic Like It’s Hot, a 28-foot cruising vessel that departs from The Cove, the resort’s exclusive adults-only enclave. The adventure leads to Islamorada Sandbar, where up to 18 guests can unwind on premium BOTE loungers and soak in a day of sun.
Education + Conservation
For an offsite activity that combines education, conservation and group engagement, Marathon’s nonprofit Turtle Hospital rehabilitation center is dedicated to the rescue, care and release of endangered sea turtles, with a guided, behind-the-scenes look at how injured marine wildlife is treated and returned to the ocean.
Getting There
The Florida Keys are served by four airports, with Miami International Airport and Ft. Lauderdale-Hollywood International Airport being about 70 miles from Key Largo and 185 miles from Key West, which is home to newly renovated Key West International Airport. Marathon, located about 50 miles from Key West and 50 miles from Key Largo, offers Florida Keys International Airport.
