The Ultimate Guide to Planning a Corporate Retreat in the Florida Keys
- Grassy Flats
- Aug 12
- 2 min read
Whether you're looking to spark innovation, strengthen company culture, or simply give your team a well-deserved escape, a corporate retreat in the Florida Keys is more than just a getaway—it’s an investment in your people. And when you choose a destination like Grassy Flats Resort, you’re setting the stage for a retreat your team will talk about for years.
Here’s everything you need to plan a seamless, productive, and unforgettable retreat in one of the most beautiful places in the country.
Step 1: Choose the Right Location
Why the Florida Keys?
Tucked away at the southernmost edge of Florida, the Keys offer a true escape from the everyday. No towering office buildings, no packed city streets—just miles of turquoise water, warm breezes, and a slower pace. It’s far enough from your team’s usual routine to feel like a real getaway, but still easily accessible via major airports like Miami or Key West.
Why Grassy Flats Resort?
Unlike massive resorts or conference centers, Grassy Flats offers a boutique, eco-conscious experience that’s ideal for smaller, high-impact groups. With oceanfront accommodations, open-air gathering spaces, and curated experiences, it’s designed to make work feel a little more like play.
Step 2: Book Accommodations Early
Corporate retreats often happen in peak seasons (fall, winter, or spring), so it’s important to secure rooms early. Grassy Flats offers a variety of suites and rooms that can be blocked for groups, plus amenities like:
Kayaks and paddle boards
On-Site Dining and Catering
Customized group activities
Step 3: Design a Balanced Itinerary
The best retreats strike a balance between structure and spontaneity. We recommend a mix of:
Team-building, workshops, or strategy sessions (nothing says team building like a friendly competition on The Rhum Runner!)
Free time or planned activities
Group dinners or rum tastings at The Rhum House
Grassy Flats staff can help coordinate activities with trusted local partners—from fishing charters to island-style wellness sessions.
Step 4: Feed the Team (Well)
Food fuels collaboration. Whether you're hosting a group dinner or grabbing drinks at the tiki bar, Grassy Flats focuses on locally sourced, fresh ingredients with menus that work for all dietary needs.
Step 5: Add Purposeful Downtime
Retreats aren’t about overfilling the schedule—they’re about creating space. Let your team enjoy pool time, seaside lounging, or a morning paddle board session. These unscheduled moments often lead to the biggest breakthroughs.
Step 6: Set Clear Goals (But Keep It Light)
Before you arrive, define what success looks like. Whether it's team alignment, project planning, or simply recharging, having a few clear objectives helps guide your schedule—and makes it easier to measure ROI after.
That said, this is also a time to unwind. Casual conversations over coconut drinks can spark just as many ideas as a formal meeting room.
Make This Year’s Retreat One to Remember
Your team deserves more than another stuffy hotel conference room. A retreat at Grassy Flats Resort in the Florida Keys offers connection, clarity, and just the right amount of sun-drenched serenity.
Ready to start planning?
Fill out our form here for a personalized quote!