For the average tourist a trip to Hawaii might involve a crowded Honolulu beach, some fruity drinks, perhaps a flower lei. But for those with bigger bank accounts and perhaps the right connections, a completely different Hawaii paradise awaits.

Carved into the lava of the Big Island’s Kona coast, Kukio is Hawaii’s most exclusive neighborhood. The enclave grew out of the adjacent development to the north called Hualalai, when property owners decided they wanted to form an even more restricted community. While Hualalai has a Four Seasons Hotel and welcomes day-trippers, Kukio is open only to homeowners and their guests–you can’t even enter its gates without the express permission of a homeowner. Many of the owners travel from the Bay Area, where a private flying club dubbed the “Kona Shuttle” whisks them to the island and on Thursdays and back again on Sundays.
Billionaire Michael Dell is a major player in both communities: his $64.7 million (assessed value), 18,500-square-foot Raptor Residence (No. 5 on the above aerial shot) is the crown jewel of the Kukio development. Dell's property comprises three lots and sits atop the broadest stretch of waterfront of all the homes in the community; the home boasts seven bedrooms, seven full baths and five half-baths. Dell is also a part owner in Hualalai, which he acquired via his private investment firm in 2006.
Dell’s next-door neighbor is Paul Hazen (No. 4 on the aerial), chairman of KKR Financial Holding Corporation and the former chairman and CEO of Wells Fargo WFC +0.19%. His $26.7 million (assessed value)10,000-square-foot home  has been featured in Architectural Digest. One door further down sits the getaway home of tech investor David L. Anderson, of Palo Alto’s Sutter Hill Ventures. His 7,938-square-foot home (No. 3) boasts five bedrooms, five and a half baths, and direct access to the beach. And next door to Anderson is David Roux (No. 1), cofounder of Silver Lake, the firm that helped Dell take his eponymous company private last year. Roux purchased his home for $20 million in 2007.
Just behind Roux’s home lies the Kona coast getaway of another Silicon Valley capitalist, Bandel Carano of Oak Investment Partners. His 14,680-square-foot home (No. 2) is assessed at $19.7 million and includes seven bedrooms and 11 baths. Carano may not be a household name, but he’s influential: he sits on the board of Kratos, a contractor whose clients include the U.S. government’s national security agencies.
The exclusive community of Hualalai is where 45-year-old Ken Griffin, the billionaire founder of hedge fund Citadel, has chosen to own two homes (Nos. 6 on the aerial). One, a $17 million (2011 purchase price), 5,600-square-foot Balinese-style oceanfront home, boasts an infinity pool. The other, a $13 million (2010 purchase price) property, lies just 318 feet away. Griffin’s nearby neighbor is fellow billionaire George Roberts, one of the founders of private equity giant KKR. Roberts’ home (No. 7), assessed at $22.1 million, lies on the point of Hualalai, giving Roberts panoramic ocean views unmarred by any neighbors.