The actress, 41, brought more than 15 people with her in two private jets for fun, sun, food and drink at a lavish private estate in Cabo San Lucas.
Her guests included her manager, Aleen Keshishian, her filmmaker brother Alek Keshishian, as well as good friends Chelsea Handler and yoga instructor Mandy Ingber.
The well-apportioned estate included a gym, a pool and lush grounds where Aniston's friends could wander and explore, as well as a private chef on call to cater to every food and drink whim – including plenty of vodka for Chelsea, of course.
The group also shared a Mexican-themed Thanksgiving meal that included chips, salsa and margaritas.
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Aniston spent the trip "enjoying herself with her friends – relaxing, drinking and eating," a source tells PEOPLE. But she also worked out every day, including yoga sessions with Ingber.
The actress "looked amazingly fit," the source adds, and "seemed to have a great time just relaxing and hanging out with her friends."