More than 15 years ago Mark Pankhurst purchased his first island home on Montserrat. Slightly more than a year later, he and his wife purchased a home more than 1,200 miles west, in the Cayman Islands. Both locations reinforced Pankhurst’s initial desires to own an island home. "It was just the ability to have excellent, consistent, sunny weather and a place where you felt safe living," he says.

But both islands also presented Pankhurst with reasons to leave.

In the case of Montserrat, the island’s central mountain—Soufrière Hills—happened to be a volcano that, although previously dormant, erupted in 1995 and forced two-thirds of the island’s inhabitants to evacuate. In the Cayman Islands, the influx of tourists from regular cruise ship visits, which Pankhurst says doubled the island’s population for seven or eight hours a day and produced "7,000 strangers wandering around," disrupted the laid-back lifestyle that he and his wife were seeking. "It’s a wonderful place to visit," he says. "We just didn’t find it a good place to live."

But Turks and Caicos, where Pank-hurst and his wife currently reside, provides the ideal island setting where they can enjoy life at a slower pace and escape the harsh winters that plague Toronto and Philadelphia, two cities where the couple previously had lived for many years. "The saying down here is you don’t have to shovel the sand," Pankhurst says with a laugh.

While the homes on the following pages provide excellent examples of island living at its finest, they are but a few of the many out there waiting to be discovered.

Venture out and explore. Your island paradise is waiting.

Lahaina, Hawaii
Located in the seaside town of Lahaina in West Maui—once the capital of the Hawaiian Islands and the center of the world’s whaling industry—this almost 9,000-square-foot home takes full advantage of its oceanfront location, as every room boasts views of the Pacific and glimpses of the neighboring island of Lanai. It was completed in 2009 and incorporates a Pacific Rim style of architecture, where walls of glass and rock intermix. The estate offers seven bedrooms and eight and a half bathrooms, as well as a 529-square-foot, oceanfront ohana living area—the Hawaiian equivalent of a guesthouse.

Other notable features of the home include a mezzanine section overlooking the great room that includes a sports bar with pool and game tables; an open kitchen with a separate, enclosed butler’s kitchen; and an oceanfront pool complete with spa and waterfalls.
$14.9 million; Island Sotheby’s International Realty

Providenciales, Turks and Caicos
This hilltop home overlooking the southern shore of the island of Providenciales in Turks and Caicos is aptly named Bajacu, which in the language of the Caribbean natives means “rising sun.” Given the home’s 270-degree view of the sea, an unobstructed sight of the sunrise is all but guaranteed.

Designed by Mexican architect Marco Aldaco in 2004 and updated in 2006, this 9,500-square-foot home also includes 3,500 square feet of open deck space. Decorated with Chinese, Indonesian, and African antiques, this island estate offers five bedrooms, seven bathrooms, and a formal dining room that can seat 16. The home is surrounded by nearly 13 acres of tropical gardens and fruit trees. Two infinity pools cascade into one another and wrap around the property, beginning at the master bedroom and culminating at the pergola. But for those longing for a dip in the warm Caribbean waters, a natural stone path meanders down the hillside and to the sea.
$16.5 million; Grace Bay Realty

Abaco, Bahamas
At this 9,970-square-foot home—named Aurora—a swimming pool and Jacuzzi form the centerpiece of the property, which is surrounded by the main house and two guest cottages. The main residence includes five bedrooms, two of which are master suites—and all have access to the upstairs veranda that overlooks the pool and guest cottages. Each bedroom also has its own private ocean-facing veranda that offers views of the Abaco Club golf course and the Atlantic Ocean beyond.

Built in 2006, the home, which is part of a gated community, includes a great room punctuated by open fireplaces and high ceilings; a fully equipped bar, game room, and entertainment area; and a separate garage capable of storing three golf carts. An advanced electronic system allows all of the home’s systems—temperature, audio, security, and so forth—to be controlled remotely via the Internet. The property also includes all hurricane-strength windows and a copper roof, rendering it well suited for even extreme tropical storms.
$9.75 million; H.G. Christie Ltd.

Kiawah Island, South Carolina
Built in 2009, this 7,363-square-foot home has eight bedrooms, nine bathrooms, and more than 3,000 square feet of outdoor living space comprising a piazza, a summer kitchen, covered porches, a pool, and a deck. The property boasts almost two acres of land and a private boardwalk that offers direct access to the beach. A floor-to-ceiling stone fireplace serves as the architectural centerpiece of the great room, but the room’s main draw is the ocean view afforded through three sets of French doors that open up to the home’s outdoor living space. For those who prefer to skip the foyer’s grand circular staircase, an elevator offers easy access from floor to floor. An expansive garage has parking space for eight cars.

Separated from the main house is a guesthouse with three bedrooms, three bathrooms, a full kitchen, and easy access to the beach. With ownership comes the opportunity to join the Kiawah Island Club, which offers tennis, squash, and other health club activities, not to mention golf on the Pete Dye–designed Ocean Course.
$11.98 million; Kiawah Island Real Estate

Grand Cayman, Cayman Islands
Most notable about this 48,000-square-foot home, aside from the calm waters of Grand Cayman’s South Sound only steps from its rear courtyard, is the 5,000-square-foot great room, a central room split over three levels, accented by six chandeliers and two grand staircases, and capable of accommodating more than 100 guests for a banquet-style function. A 400-bottle wine room adds to this home’s entertaining possibilities, as do the eight bedroom suites—including two master suites—all of which offer bathrooms with showers or soaking tubs.

Other features of this estate include a sprawling lounge, highlighted by a Moroccan bar, billiard table, and 52-inch LCD television; his and her studies; a home theater equipped with a 10-foot-wide screen; and a grotto-concealed Jacuzzi. When it comes to fitness, the estate also is well equipped, with a tennis court, cricket net, golf simulator, and a fitness room full of Precor exercise equipment. Spread out over 1.4 acres, the home is within walking distance of rugby, tennis, and squash clubs, but with 250 feet of white sandy beach and a shaded cabana, it is aptly suited for those who prefer to make relaxation their main pursuit. A four-car garage offers ample parking, but those looking to make a more elaborate entrance can take advantage of the property’s helipad.
$59.5 million; Cayman Islands Sotheby’s International Realty

Smiths, Bermuda
Designed and built in the style of European Renaissance architect Andrea Palladio, this 14,850-square-foot villa stretches over three acres of manicured gardens, which share space with tennis and bocce courts as well as life-size bronze sculptures of African wildlife, such as zebras and giraffes. Living examples of wildlife abound inside, thanks to an aquarium and a multilevel aviary that is home to more than 100 species of exotic birds.
The home’s great room—highlighted by 21.5-foot ceilings—can accommodate more than 100 guests when combined with the adjoining library and offers views of the Caribbean Sea and the aviary. Four bedroom suites and six bathrooms round out the estate, with an additional four bedrooms available in the guest and staff cottages. A dock and three moorings point to plenty of ways to take advantage of the waters of Harrington Sound.
$19.5 million; Rego Sotheby’s International Realty