How This Dad Makes Bucket List Vacations a Reality

Andrew Heiskell has taken his family all around the world. “Travel is in our blood,” the investment portfolio manager says of his group of four. With his wife Erin, and kids Aidan, 15, and Sydney, 12, Heiskell has skied the slopes of Colorado’s Beaver Creek and learned local recipes from a private chef in Costa Rica. But it wasn’t until he won a trip to the Cayman Islands with Exclusive Resorts, a private travel club designed for families, that dream vacations became simpler than ever.

“They just made everything seamless and carefree for us,” he says of his first stay with the club, noting an Exclusive Resorts’ ambassador took care of every travel and planning detail from dinner reservations to custom excursions. They booked the Boston-based family and their friends one of the company’s privately owned villas: The Ritz-Carlton, Grand Cayman four-bedroom villa on storied Seven Mile Beach. Set far enough away from the hotel for privacy, but close enough to allow for the two families to partake in the resort’s buzz and amenities when desired, the experience on Grand Cayman introduced the Heiskell crew to the delights possible with an Exclusive Resorts membership. Heiskell still talks about the luxe and roomy four-bedroom villa, the private boat ride that picked them up right outside their door, and the ace concierge. (Every family is matched with a dedicated on-site team to manage every detail. Need groceries? They’ll get them. A night out? They’ll book it. Just ask.)

After their Cayman trip, the Heiskells petitioned to join the private travel club, which welcomes just 200 families a year. As with any club, Exclusive Resorts members pay a one-time initiation fee (starting at $195,000 for a 10-year plan) and annual dues (just $1,595 per plan day, including during peak season).* Since 2002, the Club’s offerings have boomed; its vacation portfolio now contains more than 300-plus residences and 50-plus curated experiences spanning all seven continents.

Knowing they had a long list of future trips in mind — including safaris, spa weekends, and ski holidays — the Heiskells were finally able to commit to making family time a priority. “We just returned from the Galápagos,” shares Heiskell, who notes that a family trip to the remote Ecuadorian national park would have been nearly impossible to arrange on his own. He raves not just about the animals they spotted—from blue-footed boobies to iguanas to penguins — but also about the stellar service and accommodations on board the members-only National Geographic Lindblad expedition ship, Exclusive’s partner.

With 15 trips under their belt, the Heiskells will be the first to say that the members club is worth every penny. “We’ve loved being all together in one space, but not on top of one another. We’ve loved the chance to make memories together,” says Heiskell. Perhaps the best thing about Exclusive Resorts? There’s always another bucket list trip waiting in the wings. “We live for that!” he says. Surely his family agrees.

*The Annual Dues amount reflected herein is inclusive of certain services, benefits, and access rights. See ExclusiveResorts.com for more information.