This chapter probes the paradox of paradise: tourism is both Hawai‘i’s economic lifeblood and its Achilles’ heel. While visitor spending, which reached $17.8 billion in 2019 with more than 9 million arrivals by 2023, drives jobs, tax revenue, infrastructure, rural viability, and Native Hawaiian entrepreneurship, it also fuels steep housing costs, resource depletion, cultural commodification, and profit leakage to out‑of‑state corporations. It scrutinizes tourism’s fragile overdependence, dramatically exposed during COVID‑19, when arrivals plunged 99.5% in April 2020 and unemployment spiked to 22.3%. Amid closures, environmental reprieve such as a 42% increase in water clarity at Hanauma Bay and shifting public sentiment revealed the urgent need for regenerative, value-based tourism. Policy responses include Hawai‘i’s first “Green Fee,” destination management plans, reservation systems, volunteer stewardship programs, and financial support for community‑led agritourism and cultural initiatives. Featuring global best-practice comparisons, such as New Zealand’s visitor levy and Palau’s eco-pledge, this chapter explores regulatory tools including impact zones, ownership incentives, educational mandates, data sharing, and sector diversification into cultural, ecological, wellness, and educational tourism. It presents community-driven models such as Wai‘ānapanapa’s reservation policy and Kaua‘i’s volunteer programs that reclaim agency and identity. These interventions aim to redirect revenue to local enterprises and reduce strain on residents and ecosystems. Framing tourism not as a lifeline but as a bridge, this chapter advocates a shift from extractive to regenerative practices rooted in kuleana, aloha, and pono. It challenges Hawai‘i to embrace equitable, ecological, and cultural stewardship as foundational to tourism’s future.