Published: October 2009
Q: Cashing Out?
A: Drain your 401(k) (or what's left of it) in...
Text by Greg Melville + Sarah Tuff
Haleiwa, Hawaii
Pop. 2,225

One thing is becoming clear: Boomers will not go quietly into retirement. Consider Haleiwa, 30 miles north of Honolulu on Oahu’s North Shore. While more than 40 percent of the town’s 2,300 residents are over age 45, there’s hardly a nine-iron-wielding retiree among them. “I shudder to think what it would be like hanging around the country club waiting for a tee time,” says Michael Fox, a 51-year-old Idaho native who sold his business in 2007 and bought a home here. “I may be retired, but I still want to go out and surf and mountain bike. And there’s a bunch of people here my age who feel the same way.” /

In summer, Haleiwa is little more than a sleepy collection of restaurants and storefronts with nine-foot surfboards as entryways. But in winter, waves the size of your old office building pound the shore, and the contests begin. (The Vans Triple Crown kicks things off in November.) But hold on there, Jack LaLanne. Before paddling out to the Toilet Bowl, the trickiest surf spot off Haleiwa, try a mellow session of bodysurfing at Makapuu (surfnsea.com). Matsumoto’s Shave Ice, a bit touristy but with the best flavors in town, is your reward. (Get the li hing mui, a salty-sweet red Chinese spice mix.) Inland, the Ko‘olau Range, a half-hour drive east, has singletrack with ocean views (three-hour guided ride, $125; bikehawaii.com).

Haleiwa has come a long way since its modest start as a sugar mill community, so before you go, examine your portfolio. The median home price here is about $600,000. But there are (relative) bargains: One-bedroom condos (right along the beach, no less) go for about $350,000. Despite Haleiwa’s hefty average cost of living, “it still manages to be low-key,” Fox points out. “If you’re going to move here, you probably have some tie to surfing—and that makes it well worth it.”

$385,000 buys: A two-bedroom oceanfront condo.
Job market: Need a playcheck? Try tourism or the town’s growing surfboard shaping industry.
The local lifestyle: Bring the grandkids for Christmas, when an old-fashioned parade marches through town and Santa hears wish lists beneath a monkeypod tree.

BY THE NUMBERS:
40%: Residents over the age of 45
.5: Miles from Haleiwa to North Shore surfing
1: Miles to Haleiwa Senior Citizen medical center
$55: One-hour stand-up paddleboarding lesson at Haleiwa’s Surf n’ Sea


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Austin, Texas
Pop. 757,688

It was only a matter of time before the Woodstock generation found the country’s new live-music capital. In the past three years, the riverside college town has seen its 55-plus population jump a staggering 83 percent. More than 200 jazz, blues, country, and rock venues, endless road cycling in the surrounding Hill Country, 300 annual days of sunshine, and average January temperatures of 60 degrees could explain why.

Apalachicola, Florida
Pop. 2,210

Relax. This isn’t the Florida your aunt’s bunco group retired to. Pre–Civil War and Victorian homes, art galleries, and Southern manners balance the hardworking fishing heritage of Apalachicola. Instead of playing shuffleboard, spend your days kayaking the Forgotten Coast barrier islands, fishing for redfish and tarpon, or hiking through 571,088-acre Apalachicola National Forest. And in lieu of early bird specials, keep your nights free for sampling the specialty at Boss Oyster and checking out film festivals at the Dixie Theater.