Heather Whitehead: Adventure-Seeking Innkeeper

Living an active and healthful lifestyle is common in Key West. Whether transplants or native-born "conchs," residents are committed to the outdoors, cycling or walking to their respective jobs and contributing to the island's buzzing pedestrian vibe.

That makes a recent broken foot all the more frustrating for 36-year-old Heather Whitehead, the firecracker at the helm of the bustling Key West Hospitality Inns group, who thrives on all things athletic — and was downed by simply wearing high-heeled shoes.

"I even showed my X-ray photo on my Facebook page," said Whitehead, on whom the irony is not lost.

Within the last three years, Whitehead has hiked 13,000-plus-feet along Peru's Inca Trail to Machu Picchu, competed in a triathlon and cycled 165 miles from South Florida to Key West. She also joined several miles-long standup paddling jaunts including a circumnavigation of Key West, training for it with Stock Island's Lazy Dog paddleboard instructors each week.

"It's ridiculous, I know," she said of her foot cast and forced sedentary state. Though temporary, that state is additionally ironic because she recently won two bicycles in two separate fundraiser raffles.

Whitehead is officially part of the Lazy Dog Paddle Team, with several Florida races under her belt as well as some in North Carolina, Hawaii and offshore California. In June, she plans to race in New York and Lake Tahoe after she's fully healed.

It's the Long Island, N.Y., native's approachable attitude and abundant stick-to-it attitude that make her a successful member of her family's innkeeping venture alongside her father and two older sisters. It began with their Baron's Cove Inn in Sag Harbor.

"My father's been involved in hotels and restaurants for 40 years, and I was cleaning hotel rooms at age 9 with my sisters. We couldn't even see over the housekeeping cart," Whitehead recalled.

"I've worked in every position in a hotel — laundry room, housekeeping, lifeguard, maintenance, front desk, manager and marketing," she said.

Her solid background of work experience complemented her bachelor's degree in environmental science and wildlife management from the University of Maryland.

Whitehead's visits to the Keys began in the 1970s to see her grandmother, who was a longtime resident of Cudjoe Key. In 2006 she relocated to Key West after her father asked her to "just help out a bit" running his recently purchased Wicker Guesthouse.

"I'd never worked in a hotel before where the guests were always so happy to be staying with us (and of course to be in Key West)," she said. "It makes my job a lot more enjoyable to see everyone so happy to be here, and I really enjoy all the things we're working toward."

Today, the family business includes not just the Wicker Guesthouse but also the retro-style Ocean Breeze Inn, An Island Oasis conch house and cottages, and seven other Key West vacation rentals. All are green-friendly and some earned recognition from Florida's voluntary Green Lodging Program for their sustainable, environmentally friendly practices.

"All our lodgings are in Old Town," said Whitehead. "We prefer that so guests can park their car once and walk everywhere and see Key West."

Whitehead works primarily as the properties' director of marketing. She's also part owner, social media maven and overseer of what she calls an "absolutely wonderful team" of managers and employees who excel at showcasing the individual personalities of each property.

Giving back to the community is an important family trait woven into the business. A percentage of sales tax collected from the Wicker Guesthouse and Ocean Breeze Inn recently helped fund two Habitat for Humanity homes' mortgages. Whitehead's family and employees of the two hotels volunteered to help with building and remodeling the two homes.

Once her ankle is fully healed, the energetic innkeeper expects to push toward a new goal — tagging a world map with pushpins and marking her next "must-go" destinations. She's driven by her goal-oriented nature and a mantra she abides by: Get out of your own comfort zone.

"Those are the times when you truly learn about yourself," she said.

For now, Heather Whitehead is mastering standup paddling.

"I just love to get on the board and go, and I am lucky that I live here."

A Long Island, N.Y., native, Whitehead relocated to Key West in 2006.

A Long Island, N.Y., native, Whitehead relocated to Key West in 2006.

Whitehead's terrier, Lola, often paddles with her.

Whitehead's terrier, Lola, often paddles with her.

The Lazy Dog Paddle Team, with Lola.

The Lazy Dog Paddle Team, with Lola.

A hike to Peru's ancient Machu Picchu is pinned a "been there" destination on a world map hanging at home.

A hike to Peru's ancient Machu Picchu is pinned a "been there" destination on a world map hanging at home.

In London, a free-spirited Whitehead sports her signature smile.

In London, a free-spirited Whitehead sports her signature smile.

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