posted August 14, 2025
Guest Adventures - Recreation Supervisor
Compensation: NA
Job Description

Guest Adventures Supervisor at Cheeca Lodge & Spa
Join Our Team: Northwood Hospitality LLC, operating Cheeca Lodge & Spa in Islamorada, FL, is seeking an experienced and enthusiastic Guest Adventures Supervisor. Step into a leadership role where you will support the Guest Adventures Manager in enhancing our guests' experience by overseeing the recreation team and ensuring the smooth operation of our recreational amenities.
Key Responsibilities:
- Team Leadership: Assist the Guest Adventures Manager in leading and supervising a diverse team, including pool and beach attendants and adventure activity coordinators. Provide guidance, training, and support to ensure high standards of service.
- Guest Engagement: Inform guests about available activities and assist them with recreational equipment like bikes, kayaks, paddle boards, and golfing gear. Ensure guests have a memorable experience by offering personalized recommendations and directions to resort amenities and local attractions.
- Operational Oversight: Oversee the maintenance of cleanliness and orderliness around pools, beaches, and piers, ensuring all areas are free of debris. Ensure that towels are distributed and collected efficiently and that lounge areas are tidy and welcoming.
- Safety and Compliance: Monitor the safety of recreational activities and ensure all equipment is in good working condition. Enforce safety guidelines and procedures to provide a secure environment for guests.
- Administrative Duties: Assist in scheduling staff, managing inventory, and maintaining records related to recreational activities and equipment. Provide feedback to the manager on staff performance and guest satisfaction.
Required:
- Supervisory experience in a hospitality/resort
- At least 18 years of age
- Valid driver’s license
- Able to swim and work confidently near water
- Ability to stand/walk up to 8 hours and lift up to 25 pounds
- Able to work outdoors in Florida weather conditions
- Ability to speak, read, and write in English

Preferred:
- One year of experience in hospitality or recreation
- Bilingual (Spanish preferred)
- CPR/First Aid certification
Why Join Cheeca Lodge & Spa: As a Guest Adventures Supervisor, you will play a crucial role in ensuring our guests have memorable and exciting experiences. At Cheeca Lodge & Spa, we offer a dynamic work environment with opportunities to interact with guests from around the world in a stunning Florida Keys setting. Join us to make each guest's stay unforgettable and lead a team dedicated to excellence.
Cheeca Lodge and Spa
Hotel with 214 Rooms
WELCOME TO CHEECA
A Legendary Tropical Hideaway
Since 1946 the historic Cheeca Lodge & Spa has enchanted guests with world-class fishing, exceptional accommodations, and gracious hospitality. Come experience this lush oceanfront retreat, considered the premier luxury resort in the Florida Keys.
The Legend of Our Grand Florida Keys Hotel Resort
You've found it...the crown jewel of Islamorada Florida Keys hotels.
Hardy Keys pioneers called Conchs chose this very beach to carve out a tenacious living in the isolated beauty of the undiscovered Florida Keys. Here, they formed a Methodist congregation and built a two-room school house and a cemetery. Cheeca has preserved this Pioneer Cemetery, where members of the founding families of Islamorada are buried. You can explore it today; it is a designated historical site. The Angel with the Broken Wing watches over the grave of Etta Pinder, who died in 1914. Here lies the first footprint of Islamorada – "Purple Isle" in Spanish.
The early 1940's brought electricity and fresh water. Mrs. Clara Mae Downey from Olney, Maryland, opened the Olney Inn in 1946. She described this early bellwether of Cheeca as "different – rather comparable to the tropical estate of a gifted host." Clara's first guest was President Harry Truman, who cherished his time loafing around the pool and wondering amidst the resort's 22 quaint bungalows.
Fast horses, high society and a healthy dose of Keys vivacity marked the reign of the Twitchell Family in the 1960's. Cynthia, better known as "Chee," was an heiress to the A&P grocery chain and owner of a top thoroughbred racing farm. "We took my nickname, combined it with my husband Carl's, and came up with "Cheeca," she recalled. The Twitchells completely refurbished the property, adding the main lodge, the oceanfront villas, tennis courts, golf course and Cheeca's trademark wooden fishing pier. Chee raised miniature tarpon and her beloved seahorses in the aquariums throughout the resort. "Suzy the Seahorse" became Cheeca's mascot and logo, gracing the resort's menus, brochures, towels and linens.
Avid outdoorsman and Coca Cola magnate Carl Navarre purchased Cheeca Lodge in 1976, hosting his Fortune 500 friends in for sunny days of sportfishing and golf. Celebrities flocked to the hotel and famous guests were reeling in giant bonefish right off the resort's pier. The "Sportfishing Capital of the World" was born, seducing wealthy adventurers from around the world.
In 2005, Cheeca Lodge underwent over $30 million dollars in renovations, restoring the property and its surrounding grounds to their original grandeur, ensuring that we will be a cherished destination for generations to come. Following a fire on New Year's Eve 2008, the Main Lodge was completely rebuilt once again, with a fabulous open-air lobby, a spectacular oceanfront banquet room with panoramic views, and an exclusive indoor / outdoor lounge area for club members.
81801 Overseas Highway
Islamorada, FL 33036
Website www.CheecaJobs.com
Managed by Northwood Hospitality
Current Job Openings
- Barista Bartender - Lobby Bars
- Bartender - Morada Bay Beach Club
- Bartenders - Tiki and Pool Bars
- Bellperson and Valet
- Cook
- Guest Adventures - Recreation Supervisor
- Human Resources Coordinator
- Line Cook - Morada Bay Beach Club
- Front Desk Agent
- Cook
- Pool Tech with CPO
- Resort Restaurant Server
- Resort Security Officer
- Resort Spa Director
- Room Attendant / Housekeeping
- Spa Attendant
- Sushi Cooks - Nikai Restaurant
- Baker - Pastry Cook
- Guest Adventures Recreation Activities
- Maintenance Engineer
- Manager - Engineering and Maintenance
- Prep Cook - Resort
- Restaurant Busser
- Restaurant Host / Hostess
- Server - Morada Bay Beach Cafe
- Stewarding / Dishwasher
- Accounting Clerk