Join Team Weekendr
At D’Weekendr, we believe travel should feel safe, exciting, and meaningful. We partner with passionate, reliable, and community-minded individuals who help us create unforgettable experiences for our guests. Whether it’s driving, guiding, interpreting, or providing companionship, our contractors play a key role in making travelers feel welcomed, supported, and inspired while exploring Tobago.
If you’re professional, dependable, and love sharing the beauty of our island, we’d love to work with you!
Trinidad Openings
Drivers, Companions/Chaperones, Language Interpreters
Tobago Openings
Companions/Chaperones, Drivers, Language Interpreters
*On call & commission based
Become A Companion/Chaperone
Offer safe, friendly, and reliable company for female, solo, small group, and underaged travelers during activities, excursions, or social outings. Chaperones provide reassurance, local insight, and a welcoming presence, helping travelers feel at ease while exploring Tobago.
Become A Private Driver
Provide safe, reliable, and comfortable transport for guests across Tobago. Drivers must be professional, punctual, and knowledgeable about local routes and attractions, ensuring each journey is smooth, enjoyable, and stress-free.
Become A Language Interpreter
Support international and diverse travelers by bridging language barriers. Interpreters help guests feel comfortable and included while ensuring accurate communication during tours, activities, and experiences.
D'Weekendr Leisure Hub 