Puerto Rico's tourism authority has teamed up with TLC on a sweepstakes tied to 90 Day: Hunt for Love Season 2, which films on the island. Two winners will take home a package worth nearly $5,000 — and you don't need to have watched a single episode to enter.
The giveaway opened on September 28, 2026, and stays live until January 25, 2027. Entry is deliberately simple: head to the Hunt for Love sweepstakes page and submit your name, contact details, city and state. Winners get notified by email shortly after the closing date.
So what's actually in the prize? Each grand-prize winner gets round-trip economy flights for two from a major US hub, plus four nights at La Concha Resort in San Juan with breakfast daily and a dinner at Levant, the resort's restaurant. Beyond the hotel, the package includes two tickets to Toro Verde Adventure Park — home to one of the world's longest ziplines, high in the island's mountain interior — and a pair of $100 dining credits to spend at participating restaurants in DISTRITO T-Mobile, San Juan's lively entertainment and food district. A curated itinerary rounds it out, leaning into nightlife, romance and downtime.
The timing is no accident. The sweepstakes marks the launch of 90 Day: Hunt for Love Season 2, set in Puerto Rico and featuring singles from the wider 90 Day Fiancé universe. Even if reality TV isn't your thing, the show doubles as a showcase of the island's food and entertainment scene, which is essentially what the prize package is built around.
Why it matters: this is a genuinely usable prize rather than a gimmick. Flights from the US mainland to San Juan are often under four hours from East Coast hubs, the resort sits right on Condado beach, and the included experiences mix adventure, dining and beach time in one short break. If you're planning a couples' trip or a friends' getaway to the Caribbean anyway, spending two minutes on an entry form costs nothing. Just remember the entry window closes January 25, 2027, and the fine print limits it to travellers entering from US cities and states.
