Incentive trips often come with packed schedules, required sessions, and group dinners that feel more formal than fun. But the incentive trip we recently organized for a client in Key Largo, Florida, took a different approach.
Hosted at Baker’s Cay Resort, the goal was to create an experience that actually felt like a reward for top performers.
The event was a success, not just because of the ocean views or the Key lime pie (though those didn’t hurt), but because we gave attendees room to choose how they spent their time. The flexible structure made it feel less like an obligation and more like something they wanted to be part of.
Setting the stage.
The incentive trip ran from Wednesday through Sunday, with 60 total attendees, including guests, company leadership, and sponsors. The vibe was laid-back and celebratory from the moment they arrived.
Guests were welcomed with mimosas and local snacks in our hospitality lounge, which doubled as a social hub with shaded outdoor views and tropical floral arrangements. This space became a daily hangout for many attendees.
From there, we kept things intentionally light: two main events were “strongly encouraged” (a welcome reception on the beach and a final-night celebration), but everything else was up to the attendee.
Result? Almost everyone joined in because the experiences were fun and built around how people like to unwind.
Why this trip really matters.
Most of the attendees were franchisees, running their own businesses while being part of a larger brand family. This trip was also a rare chance for them to connect face-to-face.
Whether it was trading stories over morning coffee or swapping ideas at sunset happy hour, the value of peer-to-peer networking was huge. Many left feeling recharged, inspired, and better connected to their community.
Designing “optional” that doesn’t feel optional.
We knew from the start that this group of top-performing sales reps wasn’t the type to sit through long presentations. These attendees thrive on energy and connection.
So we gave them a choose-your-own-adventure style agenda with real perks.
Highlights included:
- 🐠 Glass-bottom boat cruise through John Pennekamp Coral Reef State Park
- 🏖️ Private beach hangout at Coconut Beach with a tiki bar, shaded seating, big water floats, snacks, and drinks
- 🌴 Complimentary paddleboards, bikes, and clear kayaks from the resort
- 🧖♀️ Spa day options and free time to explore Key Largo
- 🚗 Rental car access for those who wanted to drive to Key West or extend their trip into Miami
Nothing was mandatory, but the laid-back schedule allowed most attendees to naturally gravitate toward group activities.
They mingled, networked, and laughed on the beach with their colleagues. It didn’t feel forced. It felt like a reward.
The venue: Baker’s Cay Resort.
Baker’s Cay is a hidden gem in Key Largo. It’s small enough to feel private, but full of charm and amenities. The beaches are quiet, the sunsets are gorgeous, and the atmosphere is relaxing.
The welcome reception was held on Hammock Beach with toes in the sand, cocktails in hand, and a sunset that needed no filters. We didn’t need any elaborate decor, thanks to the natural beauty of mangrove trees and beach views.
And the final night celebration was a heartfelt sendoff. Guests felt pampered, celebrated, and seen for the hard work that got them there.
Why this incentive trip worked.
This incentive trip was meant to set the tone for the upcoming year, providing great options and letting people opt in because they wanted to.
Here’s what made this trip work:
✅ Structure without pressure. Two anchor events gave the trip a framework, but everything else was open.
✅ Thoughtful activities. We created itineraries worth participating in.
✅ Logistical ease. With two nearby airports (Miami and Fort Lauderdale), arranged transportation, and clear communication, getting to paradise was simple.
✅ The right kind of vibe. The Florida Keys are naturally slower-paced. No wild nightlife or overstimulation. Just great food, island time, and space to relax.
The takeaway.
Incentive trips don’t have to be rigid to be successful. The more freedom you build into the experience, the more likely people are to participate (if you’ve planned things right).
We created an agenda for attendees that was flexible but enticing, structured but never stiff. And the result? A group of high performers who showed up, connected, and left feeling rewarded.
Ready to plan your next incentive trip?
Our project management team can help you plan your next incentive trip with intention, choose experiences that fit the vibe, and let your attendees take the wheel.
When the setting is this good, and the options are this fun, they'll dive in (no pressure needed). Book a meeting with our team to chat about your next incentive trip.
