(1) Background: Intensive care unit (ICU) survivors from severe COVID-19 acute respiratory distress syndrome (CARDS) with chronic critical illness (CCI) may be considered vast resource consumers with a poor prognosis. We hypothesized that a holistic approach combining an early intensive rehabilitation with a protocol of difficult weaning would improve patient outcomes (2) Methods: A single-center retrospective study in a five-bed post-ICU weaning and intensive rehabilitation center with a dedicated fitness room specifically equipped to safely deliver physical activity sessions in frail patients with CCI. (3) Results: Among 502 CARDS patients admitted to the ICU from March 2020 to March 2022, 50 consecutive tracheostomized patients were included in the program. After a median of 39 ICU days, 25 days of rehabilitation were needed to restore patients’ autonomy (ADL, from 0 to 6; p < 0.001), to significantly improve their aerobic capacity (6-min walking test distance, from 0 to 253 m; p < 0.001) and to reduce patients’ vulnerability (frailty score, from 7 to 3; p < 0.001) and hospital anxiety and depression scale (HADS, from 18 to 10; p < 0.001). Forty-eight decannulated patients (96%) were discharged home. (4) Conclusions: A protocolized weaning strategy combined with early intensive rehabilitation in a dedicated specialized center boosted the physical and mental recovery.