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Kauai, nicknamed the Garden Island, now rivals Oahu and Maui for attracting well-to-do snowbirds. This is the cafe at the Princeville Hotel, where the romantic outdoor terrace was in ‘South Pacific.’Eric Noland

Warmer climes are pretty much guaranteed in most snowbird destinations south of the border. But retirees of means – those looking for upscale amenities, an active community and perhaps even adventure – want more than the usual.

"These people aren't going down looking for the early-bird specials and to play shuffleboard," says Stephen Fine, president of, which provides online resources and services for snowbirds.

The snowbird demographic "is younger both mentally and physically than in the past," he says, and they are increasingly benefiting from the largest transfer of wealth in Canadian history from aging parents. "It gives them the luxury to be able to enjoy this lifestyle in a high-end fashion."

High-net-worth vacationers are looking for places that are more cosmopolitan, with arts and culture to take in, classes and wellness programs to attend, interesting food and drink to try, as well as activities to do alone or in groups. Oh yes, and even the best weather conditions.

Here is a sampling of hot-spots that are new, hidden or a little off the beaten path.

Montecito, Calif.

An exclusive hamlet adjacent to Santa Barbara, Montecito's south-facing coastline and temperate climate have locals calling it the "American Riviera." Indeed, it's as much a summer destination for wealthy people escaping the heat in Texas and Florida as a winter destination for those who are fleeing from the cold in Canada and the United States' northern climes.

"I once heard the weather here described as 'freakishly pleasant,'" says Jasmine Tennis, a realtor at Riskin Partners, a luxury real-estate group in Montecito, who says the community boasts 350 days of sunshine a year.

It's a relatively small town, she says, with a greater population of about 15,000, although an additional 85,000 people live next door in Santa Barbara. It lies between Los Angeles and San Francisco, but visitors enjoy a vast arts and culture scene with entertainers and speakers making their way between the two cities.

Farmers' markets abound seven days a week, the food scene includes California gourmet and great Mexican choices (Julia Child was among its notable residents, and her favourite Mexican joint, La Super Rica Taqueria in Santa Barbara, is still going strong). Visitors will find wineries and great hiking in the nearby Santa Ynez mountains.

Properties range from a luxury condo one block from the beach on a golf course for less than $1-million (U.S.) to a home currently listed at $85-million, Ms. Tennis says. Snowbirds will find a healthy rental market as well as rental opportunities year-round if you own.

Residents value the laid-back atmosphere – "nobody here wants to be an extension of L.A.," she remarks – with historical touches such as white stucco walls and tiled roofs. Among new attractions in the area is the Funk Zone, with eateries, boutique tasting rooms and contemporary art galleries.

Princeville, Hawaii

Upscale snowbirds for many years have flocked to Oahu, with the state capital of Honolulu, and Maui, with its condos and beaches. But Kauai, nicknamed the Garden Island, now rivals these famous neighbours. The tony community of Princeville, on its far northern shore – indeed, the northernmost settlement in the state of Hawaii – offers boundless vistas, activities and opportunities to explore.

Princeville started as a coffee plantation in the mid-1800s and is now the largest planned development on the island. It is home to fine hotels and resorts, golf courses and trendy restaurants, not to mention some of the best scenery in the state, says Hank Drayton, who has been visiting Kauai since 1959 and owns a seasonal home in Princeville.

"The overall flavour of the place hasn't changed at all – it's the old Hawaii," he says, noting that Kauai includes Waimea Canyon, known as the Grand Canyon of the Pacific. In Princeville, verdant green mountains cascade down to sand beaches that barely a foot has touched.

"It's an absolutely beautiful place. It's a rainforest," Mr. Drayton says. "There's an ordinance that you may not build a building higher than a coconut tree."

Gourmet sandwich places, storied bookshops and trendy juice bars offer more cultured diversions. There's not much nightlife, he allows, although a bar and restaurant called Tahiti Nui offers live music and a funky aloha spirit.

Mr. Fine of notes that while Hawaii is a bit off the beaten track, visitors will find direct flights from Toronto as well as Canada's western cities.

Kiawah Island, S.C.

Kiawah Island, a luxury resort community just south of Charleston, has 16 km of pristine beaches, more than 48 km of hiking and biking trails as well as award-winning tennis facilities and golf courses.

Chris Randolph, a partner at Kiawah Partners, the master developer of the gated island, says that since its founding 40 years ago, Kiawah has provided an "unparalleled, private natural setting for families to better connect and focus on what really matters: time with their friends and loved ones."

Kiawah has stayed true its master plan, to construct an island community with a keen respect for nature and a strong emphasis on preservation. The developers are known for their commitment to protecting wildlife and natural habitats while integrating miles of leisure trails and parks.

"When they want to plug back in, they can take advantage of Kiawah's other great amenity, Charleston, to enjoy one of America's top cultural and culinary destinations," Mr. Randolph says.

Kiawah's 4,200 property owners come from more than 40 states and about a dozen countries. Roughly 80 per cent enjoy Kiawah as a second home, vacation home or pre-retirement home. Residential offerings range from cottages to single-family homes, with prices ranging from $200,000 to more than $20-million.

Kiawah Partners also owns and operates the Kiawah Island Club, which includes two private golf courses and clubhouses, a sports pavilion with squash and tennis courts, a spa, beach club and restaurants.

Snell Isle, Fla.

This exclusive community lies next to St. Petersburg, a city once considered a sleepy retirement area but which is now undergoing a renaissance with upscale condo residences, new museums and a whole lot of vibe.

The area was also largely untouched by the recent hurricanes that wreaked havoc along much of Florida's shoreline, says Nadine Appelt, a realtor at Keller Williams Realty in St. Petersburg. "We got lucky."

Snell Isle has many charms for the well-to-do. The area is named for local developer C. Perry Snell, a Kentucky druggist who moved to St. Petersburg in 1900 and began buying properties and turning them into residential neighborhoods. The area also includes the Vinoy Renaissance St. Petersburg Resort & Golf Club, which is listed on the National Register of Historic Places.

More than 80 per cent of the homes on Snell Isle have waterfront views, Ms. Appelt says. She notes that its shoreline is more about boating than beaches, with many lots right on the water and prices at $2-million and up. "The area is becoming more high-end by the second," she notes, with prices rising as much as 20 per cent year over year.

Residents enjoy cycling and nature trails, paddle-boarding and outdoor yoga, Ms. Appelt says. Nearby Eckerd College has a large adult-learning annex.

Ambitious local chefs have embraced the farm-to-table trend, microbreweries abound and young entrepreneurs are encouraged to start businesses. Among the new hip and diverse developments in St. Pete's is the Grand Central District, home to restaurants, bars, antique shops and art galleries.

Paradise Valley, Ariz.

Any place that calls itself paradise had better live up to the name, and this enclave perched between Scottsdale and Phoenix certainly seems to. Home to about a dozen posh resorts and a population of 14,000 with a median income of $150,000 (U.S.), the elegant town offers some of the most exclusive and luxurious real estate in Arizona.

"Paradise Valley is very much an elite community," says Rick Morielli, a Canadian transplant who is broker-owner of Can-ix Realty, which serves Canadians who are snowbirds as well as those relocating to the greater Phoenix area, which is the fifth-largest city in the United States.

"People are drawn to our perfect, super-consistent weather, at 18 to 25 degrees for most of the winter, and we have almost no humidity," Mr. Morielli says. "There's no earthquakes, no hurricanes, no nasty weather."

The mid-range price for homes in Paradise Valley is about $1.8-million, he says. The town includes the Mummy Mountain Preserve Trust, which has stunning views and desert flora and fauna, while Paradise Valley also boasts one of the world's top-rated spas.

Golf is huge. Among the high-end courses in and around Paradise Valley is the Tournament Players Club of Scottsdale, home of the Phoenix Open. The area also boasts the popular Barrett-Jackson auto show and two NASCAR races each year. Phoenix, meanwhile, is home to professional sports teams as well as museums, the ballet, symphony and theatre.

After over a hundred days on the market, a large mansion in a desirable Toronto neighbourhood ended up selling for $4,300,000.