Old friends and new moms Kim Cross and Kim Haik restored their pre-baby mojo with kiteboarding lessions.

Key West Kiteboading
Credit: Chris M. Rogers

Loving new motherhood but craving adventures beyond grocery shopping with toddlers, these high school pals—water-skier Kim Cross and windsurfer Kim Haik, who grew up playing on the same Florida waters—shared a quest to reawaken the women they were before kids. Both married to mancation veterans, the Kims made a pact to take their first-ever girls' trip to the Conch Republic, known for its Key lime margaritas, off-the-mainland mentality, and one of the country's best kiteboarding schools.

Trip Rx: The nexus of windsurfing and waterskiing, kiteboarding promised an exciting challenge. "I figured Kim Haik [the windsurfer] could teach me how to read the wind," says Kim Cross (the skier). "And I could share tips on board skills." The Kite House training grounds—a knee-deep sandbar in the open water, a boat ride away from power lines, trees, and other hazards—are the perfect setting to learn kiteboarding safely, no matter which way the wind blows.

Before the Trip: Bikini Deadline = serious motivation. "I finally got to the gym three days a week for the first time since Ella was born," says Kim Haik. Through epic phone tag and text-a-thons, the working moms supported each other's fitness goals and kept in touch better than ever.

The Rendezvous: After landing at Miami International Airport (where wearing big Jackie O glasses makes people think you're famous), the gals rented a red Mustang convertible (really famous). The three-hour cruise down U.S. 1 provided ample time to catch up and commiserate about juggling careers, toddlers, and inconvenient watersports.

Moment of Truth: Learning to dive the kite, harness the wind, rise out of the water, and skim along the sea after months of hearing "That's too hard/dangerous/insane!" We won't lie: This sport is only for those who love adrenaline and are relatively athletic. But after a few days of lessons with top-notch instruction, it's totally doable. "We've taught more than 6,000 students," says Kite House founder Paul Menta, a kiteboarding pro who's been teaching since the sport's inception in the 1990s. "Only four have been unable to learn." (Tip: It's all about flying the kite.)

Ultimate Stress-Buster: Pedaling a candy-colored beach cruiser through this 2- by 4-mile key, you see why Conch Republicans prefer a world where wild chickens are protected, happy hour starts at 9 a.m., and Friday means turtle races at a local bar. A former mayor once made a political point by water-skiing to Cuba. Really.

Favorite Discovery: Navigating a stand-up paddle-board through the secret mangrove tunnels that bisect the island and offer a peek into locals' backyards. This amazingly easy new sport (a kiteboarder's Plan B on windless days) delivers the stoke of surfing without all those pesky waves.

Happy Hour: Relaxing, frosty 'rita in hand, under the palms at Parrot Key, a small resort with a full-service pool bar and two- and three-bedroom condos.

After Dark: Mango Coladas, Wild Mushroom Martinis (an app, not a drink), and local yellowtail snapper with passion fruit buerre blanc and mango relish—all highlights at Mangoes, a James Beard-noted "Floribbean" restaurant with prime real estate on buzzing Duval Street.

The Trip Effect: Kim Haik inspired her dad to try kiteboarding. Kim Cross got her 70-year-old mother and 2-year-old son into stand-up paddleboarding. ("MiMi" bought a board and is teaching others, including Mrs. Haik.) The Kims vow to make the girls' trip an annual event.