Steve Case's Top Travel Bets: Costa Rica, Luxury Rentals, and Real Communities

AOL co-founder Steve Case says his new Waldorf Astoria resort reflects more than just a real estate play. His hope is that the future of high-end tourism lies in community connections rather than resorts that are literally walled gardens.

Steve Case's latest hospitality project debuted in April on a Costa Rican peninsula that his investment firm has owned for nearly two decades. The Waldorf Astoria Costa Rica at Punta Cacique represents more than just another luxury resort.

The AOL co-founder purchased the 600-acre Punta Cacique in 2006 through Revolution Places, his hospitality investment arm. After weathering the 2008 financial crisis and years of planning, Case has opened a resort that he hopes encourages guests to venture beyond its borders into local Costa Rican communities.

It's part of Case's broader vision for travel as the executive chairman of Exclusive Resorts and the owner of several hotels worldwide. "When I first visited Costa Rica, which is over 20 years ago, it kind of felt like Hawaii when I was growing up 50 or 60 years ago," Case said. "It was just pivoting from farming to tourism."

Born in Honolulu just before the state's admission to the Union in 1959, Case witnessed the islands evolve from an agricultural economy to a tourism powerhouse. The key, he argues, was creating vibrant destinations.

"What I think people love about going to Hawaii is they venture out of the hotel to travel, drive around the island, and stop at some local restaurant," Case explains. "They use a resort as sort of a launch pad to explore real Hawaii."