By Madeline Bilis
Homebuyers are increasingly flocking to destinations that reflect not just how they live—but what they love. From fishing and boating to surfing and wine appreciation, personal pursuits are shaping where people choose to set down new roots.
A Home with roots
Healdsburg, Calif.
Amy and Mark Garrett have always felt at home among vineyards. Long-time residents of the San Francisco Bay Area, the couple have been coming to the Napa and Sonoma valleys for more than 30 years; their daughter was even married in the wine country. So when their golden years opened the opportunity for them to relocate there, the couple had little hesitation when it came to location.
While touring properties throughout the twin wine counties of Northern California, they realized Healdsburg had everything they were looking for. “We fell in love with its small-town charm,” Mark says. “Healdsburg brings all the attributes of the California wine region together: wineries, food, scenery, and great weather.”
They soon settled on an Estate Homesite to build their own custom wine country home at Montage Residences Healdsburg. Set among 258 private acres adjacent to the Montage Healdsburg resort, the community appealed to the couple for its immersion in the wine scene, both literally (residences overlook Montage’s own vineyards) and figuratively (nearly everyone the couple met had an interest, or even a business, in the wine industry, Mark says).
Indeed, wine is central to everything at Montage Healdsburg. The resort’s Hazel Hill restaurant is guided by a terroir-to-table philosophy and a robust wine list overseen by a team of sommeliers. Residents also have the option to arrange multicourse, chef-prepared meals in their homes. Another draw for oenophiles? Owners can set out with renowned vintner Jesse Katz on behind-the-scenes winery tours and intimate dinners at his acclaimed Aperture Cellars. Montage’s vineyards are another source of enjoyment for residents; during the annual harvest, they can join in picking grapes across the resort’s 12 acres of malbec, sauvignon blanc, and cabernet franc vines.
For the Garretts, who are now involved in the local Healdsburg Jazz among other organizations, it all comes together in a beautiful blend of passion and culture they couldn’t find anywhere else. “What’s better than living in an area that allows you to enjoy your hobbies?” Mark asks. “Montage Healdsburg allows us to live in that ideal community.”
Boater’s Paradise
Bahamas
Long before Shannon and Bob Werner purchased a residence at Montage Cay—a 53-acre private-island resort and residential community set to open in the Abaco Islands—the New Hampshire–based couple already had a fondness for the Bahamas. For them, the Caribbean nation comprised of nearly 700 islands and more than 2,400 cays and islets (most of which remain uninhabited) was a place for discovery, where together, they would zip along crystalline waters on their 90-foot yacht, scuba diving, snorkeling, and exploring untouched reefs.
So when they learned last year that they could enjoy those activities steps from their front door, they jumped at the opportunity. “We wanted a turnkey experience right in the middle of all the action for boating,” Shannon says. Montage Cay’s 51 fully furnished homes presented just that: All residences are nestled into their own enclaves with private pools, gardens, and terraces. Many even have their own private beachfront, connecting owners directly to the water. The resort also offers homeowners access to a Spa Montage, guided nautical excursions, signature dining options, and other opportunities for outdoor recreation—all of which were attractive to the Werners. But it was the island’s 46-slip, deep-water luxury marina, which can accommodate vessels up to 100 feet, that sealed the deal. “It’s probably the most protected marina in the Bahamas so it really protects your assets,” Shannon says, adding that the couple plan to moor a new 35-foot powerboat there.
For Bob, the decision ultimately came down not to finances or investment, but to lifestyle: “Having these amenities for boating on Montage Cay ensures that we’ll be surrounded by like-minded people”—something, he adds, previous generations didn’t necessarily factor into their second-home purchases. “Our grandparents weren’t buying a lake house because they were into water skiing. It was just a lake house,” he says. “Our generation has grown up with hobbies, and you don’t give that up when you retire; you work toward that time when you can do even more of it. And that’s what we’re doing at Montage Cay.
The Ultimate Catch
Barbados
On Barbados’s Platinum Coast, life has always revolved around the sea. Fishing isn’t just recreation—it’s ritual, a way of connecting with neighbors, friends, and the island itself. “Fishing really is part of our culture,” says Betty Cathrow, a Barbados native and an agent with the real estate brokerage Terra Luxury. “It’s how people connect with one
another here.”
That spirit has recently lured a new wave of homeowners to Pendry Residences Barbados, a collection of 46 contemporary homes set to open in 2027 along one of the island’s most coveted stretches of shoreline. Designed for a seamless relationship with the ocean, the two- to five-bedroom residences embrace their surroundings with expansive terraces and interiors that balance modern refinement with Caribbean ease; many also come with infinity-edge pools.
Located on the island’s West Coast in St. Peter, Pendry Barbados will be anchored by the Pendry Marina and Yacht Club, a lively waterfront hub with 110 berths where owners can moor their own boats or charter a crewed vessel through the resort’s Compass Sports program. “A lot of homeowners will go out fishing for barracuda, mahi-mahi, sailfish, and tuna,” Cathrow says. “There’s a huge amount of fish to be caught.”
But it’s more than the thrill of the chase that connects fishing fans to the island; it’s the Barbadian culture. “One of the number one things people tell me has brought them to Barbados is the people,” Cathrow says. “Our lifestyle is the key reason people buy homes here—it’s laid-back, it’s social, and it’s all about connection.
Riding a new wave
Punta Mita, Mexico
Peter Burke caught his first wave in Mexico nearly two decades ago. It was a pivotal moment—enough to bring the Orange County–based entrepreneur back to Riviera Nayarit year after year—and during those ensuing trips, he and his wife, Karen, discovered more outdoor pursuits. “We absolutely love surfing, but there’s also horseback riding, fishing, cycling, and golfing. We’re golf fanatics,” he says. “And the margaritas aren’t bad either.”
That combined appreciation for the great outdoors and good living ultimately led Burke to Punta Mita, a 1,500-acre private community where the water is warm, the waves are good, and the golf is world-class (both courses there are Jack Nicklaus Signature designs). Since its opening in 1999, Punta Mita has set the standard for luxury vacation-home communities, and soon Montage Punta Mita and Pendry Punta Mita will offer new residential opportunities that raise the bar even further. Montage’s 62 three- and four-bedroom private homes will embrace their surroundings with expansive terraces that look out over the Pacific Ocean and Litibu Bay; 32 Pendry Residences will feature turnkey contemporary design and sit on a lush, 30-acre stretch near La Lancha, one of the best surf breaks in Riviera Nayarit.
For Burke, who has owned a vacation home in the broader Punta Mita community for more than a decade, the new arrivals promise an easy convergence of all the things he loves most about the area. “Montage offers that perfect blend: lifestyle, hospitality, friendship. Everyone here loves their sports and their hobbies,” he says, adding that resort amenities like tennis and pickleball courts, beach clubs, and wellness facilities—like the forthcoming Spa Montage—have expanded the couple’s ever-growing list of hobbies, as well as their social circle. “Community is really important to us. We’ve made some great friends in Punta Mita over the years.”
