Full-time work opportunities in Key West, Florida
Hello!
RED Hospitality & Leisure is excited to be recruiting team members to work with us in Key West. Florida at Sebago Watersports.
Sebago Watersports is a certified Great Place To Work!
Sebago Key West is Key West’s favorite watersports and activities company. We pride ourselves on offering the best tours, with the best staff, at a great value. Our crew is fantastic. Our food is always freshly prepared. And we never compromise on our ships or safety. Sebago Watersports started in 1988 with the purchase of our first catamaran, the famous racing Sebago. For over 30 years, Sebago has provided visitors and locals with true Key West sailing experiences. We are proud to be the longest established day-charter catamaran operation in the continental United States. Our fleet of catamarans and crew run multiple trips a day to offer Sunset, Snorkel, Power Adventures, Parasailing and Island Explorations.
Check us out on your favorite social channel and apply for one of our open positions today!

CURRENT OPENINGS
All positions below are available in Key West, Key Largo and the US Virgin Islands
Supervisor: Operations Manager
Starting Pay: $50 - $170/trip + tips (trip pay increases with each additional boat you get checked off on see scale below)
RED Hospitality is recruiting team members to work with us in Key West at Sebago Watersports and in Key Largo at The Bungalows.
Sebago Key West takes great pride in being Key West’s favorite watersports and tour company because we offer the best tours at a great value.
We also run marine and service operations at an island oasis for downtime and disconnecting, called the Bungalows Key Largo, which rewrites the rule book on inclusive getaways. Our intimate adults-only (ages 21+ only) resort sits within a botanical garden edged by 1000 feet of ocean shoreline, just a few miles from the warm waters of the Gulf Stream. We offer Sunset, Snorkel, Eco-Tours, Island Exploring and Swimming trips daily on Duffy, Worldcat, Axopar, Gemini and Tiki Boats for hotel guests. These vessels are new, beautiful and state-of-the-art.
General Job Description
Our 65’ sailing catamarans and 37’ Axopar provide trips in and around the Florida Keys and we are seeking enthusiastic, dedicated and team-oriented crew members and captains. We are seeking mates, 6pax Captains (50 ton, 100ton) with sailing endorsements. No fishing.
We are also hiring a concierge to work at our indoor, gulf-front experiences desk to help guests book local tours and activities with RED Hospitality.
We are seeking team members who excel at customer service, enjoy communicating with guests aboard the vessel and have a passion for boating in the islands. Great customer service, punctuality and reliability are an absolute must. RED offers opportunities for the right individuals to grow in a variety of different positions and are offering both seasonal and full time opportunities. Housing/relocation assistance is being offered on a case-by-case basis.
Captain Job Responsibilities may include but are not limited to:
- Safe operation of a USCG Inspected Vessel – Powerboats and Sailboats
- Responsible for all crew and passengers’ safety while under way and on the dock
- Pre-trip provisioning, preparation, and vessel inspection, post-trip cleaning and resupply
- Providing an enjoyable, informational and elevated guest experience throughout the excursion (includes serving food and beverage)
- Assist Captain of vessel with lines, raising sails, mooring and all other aspects of daily operation of the vessel.
- Issue snorkel gear in a professional clean and hospitable manner
- Conduct Snorkel Briefing on the way to reef
- Assist guest with getting into the water
- Lifeguard, monitor and provide rescue to snorkelers when necessary
- Assist guest when they exit the water, ensuring safe exit
- Routine maintenance and communication of critical maintenance needs
- Managing assigned crew member(s)
- Other tasks as requested by Management
Job Requirements
- Current USCG credentials for TCI destinations
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- Current First Aid/CPR, TWIC Card
- Active STCW95 certification
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- Working outside in the water and under the sun, previous day charter experience a plus
- Basic knowledge of maintenance of vessels a plus
- Team player, positive and enthusiastic attitude
- Flexibility in scheduling
Supervisor: Captain and Operations Manager
Starting Pay: $20 – 120/trip + tips (trip pay increases with each additional boat you get checked off on see scale below)
“Exceptional Experiences by Exceptional People.” RED (Resort, Experience and Destination Services) Hospitality and Leisure is a leading provider of vertically integrated resort services and experiences, including watersports, beach, pool, concierge, transportation, and destination management services. Our organization specializes in providing critical guest-facing departments with subject matter experts, passionate associates, and dedicated management.
General Job Description:
We are seeking enthusiastic, dedicated and team-oriented crew members and captains. Our 65’ sailing catamaran (Lady Lynsey III) will provide trips in and around the Ritz-Carlton Grace Bay. We are seeking team members who excel at customer service, enjoy communicating with guests aboard the vessel and have a passion for boating in the islands. RED offers opportunities for the right individuals to grow in a variety of different positions.
Job Responsibilities may include but are not limited to:
- Safe operation of a USCG Inspected Vessel – Powerboats and Sailboats
- Pre-trip provisioning, preparation, and vessel inspection
- Provide an enjoyable, information and elevated guest experience throughout the excursion (includes serving food and beverage)
- Post-trip cleaning and resupply
- Routine maintenance and communication of critical maintenance needs
- In-water and topside snorkel instruction and supervision
- Other tasks as requested by Captain and Management
Job Requirements
- Current USCG credentials for TCI destinations
- Current First Aid/CPR, TWIC Card
- Working outside in the water and under the sun, previous day charter experience a plus
- Basic knowledge of maintenance of vessels a plus
- Flexibility in scheduling
- Team player, positive and enthusiastic attitude
Starting Pay: $12/hour plus sizeable commission. Benefits offered.
“Exceptional Experiences by Exceptional People.” RED (Resort, Experience and Destination Services) Hospitality and Leisure is a leading provider of vertically integrated resort services and experiences, including watersports, concierge, transportation, and destination management services. Our organization specializes in providing critical guest-facing departments with subject matter experts, passionate associates, and dedicated management.
Job Responsibilities include, but are not limited to:
- Collaborating with the Guest Relations team to personalize the pre-arrival process for guests, including VIPs, and to begin the sales and planning process for their upcoming stay
- Reading guest cues and taking the initiative to not only fulfill guests’ requests, but to anticipate their needs and exceed their expectations
- Provide guests with knowledgeable information of land and water activities on-site, coordination of transportation and sightseeing options, as well as other operational duties
- Proactively research, communicate, and follow through in a timely manner with all guest requests
- Act as a single point of contact who exemplifies best-in-class skills for problem resolution
Job Requirements
- Welcoming and acknowledging all guests according to company standards, anticipating and addressing guests’ service needs, and thanking guests with genuine appreciation
- Ability to create positive and lasting relationships with all individuals who approach the desk and contact concierge via email or telephone
- Have a proficient understanding of Fareharbor and Microsoft Suite (Windows, Excel, Outlook)
- Ability to prioritize, organize and follow-up to a high volume of guest and management requests
- Embody a positive attitude
- Ability to be an enthusiastic self-starter with strong organizational skills
- Must be able to write English in a professional manner, as well as communicate verbally at the same level
- Previous concierge and luxury resort experience desired
“Exceptional Experiences by Exceptional People.” RED (Resort, Experience and Destination Services) Hospitality and Leisure is a leading provider of vertically integrated resort services and experiences, including watersports, concierge, transportation, and destination management services. Our organization specializes in providing critical guest-facing departments with subject matter experts, passionate associates, and dedicated management.
Position: Reservationist
Sebago Watersports is hiring for a full-time check-in reservation agent in a beautiful waterfront office. Duties include checking in guests for boat tours, phone reservations for Sebago tours and preferred vendors and retail sales. $15/hour plus competitive commission. Benefits offered.
Position: Commission Sales Agent
Sebago Watersports is hiring for a full-time commission sales agent. Job includes selling guests our watersports tours, jet ski rentals, scooter rentals, etc. for our busy downtown booth locations. Must be motivated and outgoing. Computer/iPad and cell phone required. Commission only position.
PURCHASE A SEBAGO WATERSPORTS GIFT CARD
Gift Cards are great for any special occasion including:
- Anniversaries
- Birthdays
- Holidays
- Weddings
- Bachelor/Bachelorette Parties