It’s the dog days of summer, which means travel season is in high gear. Perhaps you’ve decamped to the Hamptons or maybe ventured a teensy bit further to Newport or Martha’s Vineyard. Or maybe you’re in the mood for a change, for a little adventure. Just in time to squeeze in one more vacation before fashion week, a handful of travel start-ups have cropped up for those craving not just an itinerary but a lifestyle experience. “Curated” is the word that comes up most often when speaking to their founders. Meet the new travel agents of the Instagram age:


Sailing Collective,

Dayyan Armstrong founded the Sailing Collective to make his lifelong hobby more easily accessible. But make no mistake — his yacht-chartering, Brooklyn-based company is more hipster than WASP. Trips to the British Virgin Islands, Thailand, Italy, Croatia and more can include a fleet of up to eight boats, with each itinerary carefully designed to take vacationers to hidden spots. A local’s beachside shack in Jost Van Dyke, for example, becomes a private outdoor dinner party serving up johnnycakes, conch and mahimahi to guests. “We are traveling to these coves or towns that are either completely inaccessible by other means or just very difficult [to get to],” Armstrong says. The site has several features that set it aside from the Expedias and Kayaks of the world: users get to have an embedded experience, helping with the day-to-day chores of boating, assisting with cooking, cleaning and yes, sailing. “You’re being a real explorer,” says Armstrong. “It places you in a position to really articulate your own adventure.” And to make the experience more seamless, vacationers fill out questionnaires ahead of the trip so that they’ll be matched to a boat with like-minded people — think of it as Tinder for sailing. Dayyan is very clear though: it’s not all work and no play. “We’re always in motion sailing from one island to another, in this active form, but the ethos of what we do is to enforce an absolute chilling, so to speak,” he says. Right on.


The Cultivist,

To say Marlies Verhoeven and Daisy Peat have connections is an understatement. Before they branched out on their own, they ran Sotheby’s Preferred (a loyalty program for the auction house’s VIP clients) for six years. In a sense, their new art club endeavor, The Cultivist, offers up that network to a select group of applicants — after a careful vetting process — to gain access to museums, art fairs and events around the world.

Officially launched in June, The Cultivist provides free (and front-of-the-line) entry to partner museums — including the Metropolitan Museum of Art, the Louvre, Museo del Prado and Uffizi Gallery — as well as personalized itineraries for those traveling to more removed locales. Partnerships with major museums are more official (there’s even a grid of Ph.D. students who have signed on to be Cultivist tour guides), but it’s the relationships with local gallery owners and artists that offer real added value — members are tapping into the pair’s art expertise. “One of our members is traveling to Baku [capital of Azerbaijan] in the autumn,” explains Peat. “So we’re building her a bespoke itinerary and connecting her with local artists.”

In its first year, the club is capped at 1,000 members and each pays $2,500 in annual dues. “We put a lot of effort into every single one of our members and we need to make sure that they are going to get something out of it,” Peat says. “It’s not something flippant for them, so we need to be able to understand what their needs are — where do they live, where do they travel, what artists might they be interested in — so that we can make sure that we’re making that service as bespoke as possible for them.” Eventually, there will be a Cultivist app that members can use as a guide in each city, should they desire the DIY approach.


Oasis Collections,

Founded by Parker Stanberry in 2009, Oasis Collections is like a cross between Airbnb and Soho House. During a trip to Buenos Aires seven years ago, Stanberry was disenchanted with the average selection of hotel options, but didn’t feel totally comfortable renting on his own. So he started Oasis Collections to mediate the transaction between home owners and guests. “I was trying to solve for the knowledge gap or support gap that you have when you hit the ground in a place,” says Stanberry. Centralized offices in each city (currently there are 15) are essentially hipper hotel concierges, who will check you in, troubleshoot problems like iffy wireless connections and serve as local tour guides. “If you want to call them every day and have them actually walk you around the neighborhood and show you some top spots, then they can, but if you’re also not really interested and you just want to be checked in by a nice person and sort of left alone, then that can happen too,” says Stanberry.

In Buenos Aires and Rio de Janeiro, guests also have access to members’ only clubs — à la Soho House — with bars, pools and social events. In other cities (this year, the company expanded outside of South America, adding New York, London, Paris, Barcelona and Los Angeles to its locations), Stanberry has teamed up with reciprocal clubs, like The Hospital Club in London and The Norwood Club in New York. Since locals can join year-round, he hopes that the clubs will make guests feel immersed in the culture. “[We want you to] feel like a local, feel like an expert without having to spend a ton of time prior to your trip doing research,” he says. Another way he wants you to feel totally at home — one that New Yorkers in particular will appreciate — is by partnering with ClassPass and GlamSquad. “So that you’re able to execute those elements of a normal life that you want to be able to do when you’re traveling,” he says. Most importantly, he wants to make this kind of travel affordable. “When you say bespoke and curation you automatically assume super high-end; what we’re trying to do is make it more premium-mass,” says Stanberry. “I think that’s pretty cool.”

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