Meet the Robb Report Travel Masters: 26 Luxury Specialists Who Can Make Your Dream Vacation a Reality

Welcome to the third annual list of Robb Report’s Travel Masters. 

Travel can be both profound and transformative. Exhilarating and unforgettable. But not always. The difference between a good trip and a great one—perhaps a life-changing one—is so often about tapping the right people to help plan it. It can be hard to know who to trust to create your dream adventure or even a jaunt back to your favorite destination. There are hundreds of travel specialists, after all, most of whom will argue convincingly that they have contacts and connections to open doors around the globe.

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Only a handful of operators worldwide, however, have the expertise, clout and ambition to make the unimaginable real. To celebrate them, and to help you, we have brought them together under this Masters of Luxury banner. There are barely more than two dozen, nearly all of them specialists in certain regions or types of journeys.

They come with our endorsement. 

We’ve worked closely with the first group on stories, including asking them to nominate the hotels they consider the greatest places to stay in the world, tapping them for insider scoops and asking their recommendations for the best travel products (cashmere’s the key, it seems).

We’ve also partnered with the Travel Masters for our new, luxury e-commerce site, The Vault, asking them to create unique, exclusive experiences solely for Robb Report readers—more of those, to come.

As always, if you’re traveling this year, don’t leave home without contacting one of them—and make sure to mention Robb Report sent you.

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1. Christopher Wilmot-Sitwell, Cazenove & Loyd

The 25-strong, UK-based agency, steered by the three-decade veteran Wilmot-Sitwell, is known for deftly combining adventure travel—think long-haul jaunts to hard-to-reach Asian and African sites—with no-beat-missed luxury. It was an early champion of sustainability: The firm is committed to offsetting the carbon impact of its own research trips via CommuniTree, a Nicaraguan reforestation project (clients can sign up, too).

2. Henry Cookson, Cookson Adventures

Henry Cookson worked as a horse-riding safari guide in Africa before establishing his London-based firm. He’s carved out a niche that focuses on a small number of elaborate adventures; a few dozen custom itineraries are developed on demand each year. If you want a private trip to Antarctica, there may be no team better to organize it: Henry holds the world record for kite-skiing to the Pole of Inaccessibility, and Cookson Adventures was the first private company to take a submersible to Antarctica. The firm’s also offering Octopus, the renowned 413-foot explorer yacht owned by the late Paul Allen, for charter in the polar reaches.

3. Cari Gray, Gray & Co.

If you’re outdoorsy, ready for anything and prepared to sweat, call Cari Gray. Few manage to design and book high-end active trips with more finesse than the Canadian, who lives in Santa Monica, Calif. Gray combines thrilling, adrenaline-powered programming with much-needed indulgence, whether that’s organizing biking in the mountains of Mallorca or chartering a fishing expedition in the waters off Chile.

4. John Clifford, International Travel Management

John Clifford has almost four decades of experience as a trip designer for high-net-worth folk. Over that time, he’s developed a particular reputation for catering to LGBTQ+ travelers. From his base in San Diego, Calif., Clifford works worldwide and he can as comfortably score you a last-minute Christmas vacay to Uxua in Trancoso as get you to Iceland’s Hotel Husafell in peak season. “My clients always get the best suite pre-blocked,” he says, “I often handpick it myself.”

5. Gary Portuesi & Jennifer Schwartz, Authentic Explorations

Hungry for Italy? Authentic Explorations is a go-to for any gourmet keen to indulge in truffles, bresaola and Barolo, among other Italian delicacies. Portuesi co-owns an Italian cooking school in NYC and thus certainly knows his stuff. A buyout of Massimo Bottura’s impossible-to-secure Osteria Francescana is easy enough for this team, but they’ll also happily supply a curated list of restaurants to your tastes. Of course, they’ll take care of booking them, too. AE has a headquarters stateside, as well as satellite offices in Florence and Sicily, giving it a head start on the ground in Italy. The company, formerly known as Authentic Italy, has recently broadened to other European vacation spots in recent years, including Croatia, Spain and Portugal.

6. Catherine Heald, Remote Lands

If you’re heading to multiple countries in Asia—from Japan to the Maldives and everything in between—there’s no better counsel than that of Catherine Heald. “I have devoted my life to Asia since moving to Hong Kong in 1987,” she says. Heald and her team have expertise in major cities, but the farthest flung spots are a specialty. Think: Japan’s Yakushima or India’s Sikkim. Heald’s trips often support good causes: Clients who travel to Siem Reap, for example, may dig a water well for a local family as part of their journey. Of course, travelers can expect a good dose of luxury, too.

7. Tanya Dalton, Greaves India

Dalton’s firm, with offices in London, Chicago and Delhi, has a firm handle on all things India. The family business, founded by her Mumbai-born grandfather and later run by her mother, has been around for more than four decades. As a result, Dalton has the ability to grant access to closely guarded sites in Southeast Asia’s largest country. Private palace? You got it. She can also wrangle suites in Rajasthani or program tiger-centric safaris. The choice is yours.

8. Cedric Reversade, Unique Properties & Events

Some call him the villa whisperer, and for good reason. Cedric Reversade, who splits his time between London and Paris, has an unparalleled list of the world’s most exclusive private homes in every must-visit destination, from Saint-Tropez to Capri. Many of the lavish pads are only available (discreetly) via his firm. He and business partner Paul Maxime Koskas don’t simply rent out properties, either. The duo’s point of difference has long been the concierge service that comes bundled with the rental; it’s like having an ultra-connected EA in any place you vacation.

9. Sandy Cunningham, Uncharted

Sandy Cunningham’s firm Uncharted is aptly named, as it specializes in adventures and safaris in remote destinations. She began her career as a safari operator in East Africa, so she knows the game. Cunningham is adept at creating long-haul trips for large groups, too: She once booked a celebrity family into a private island in Seychelles without publicity, for instance. She has also proved she can safeguard a traveler’s privacy: She whisked the same family out a day earlier than planned, under cover of darkness, to avoid alerting any paparazzi.

10. Max Rosenthal & Stacy Fischer-Rosenthal, Fischer Travel

Max Rosenthal (center) is the third generation of his family to join Fischer Travel. The New York-based firm was founded by his grandfather Bill Fischer, but is currently run by his mom Stacy. The 30-strong operation is more like a members-only club than a conventional travel agency, with a $150,000 initiation fee and annual dues of $25,000. For that, the team opens up its little black book to create one-off experiences worldwide. Indeed, it was Fischer Travel clients who were the first to experience Camp Sarika at Amangiri a month before it opened to anyone else. Another client wanted to see Wadi Rum in Jordan, but the local hotel didn’t pass Fischer’s quality control, so the team shipped in 10 staff from the Kempinski in Aqaba to temporarily run the camp at a higher level.

11. Jean Sanz Bernay, JSB Journeys

US native Jean Sanz Bernay of the six-person boutique operation JSB Journeys has an affinity for all things Latin America. “I’ve traveled through, and lived in, every nook and cranny of South and Central America.” She has connections across the continent and continues to cater to all manner of requests. One client, for example, needed a last-minute, after-midnight jewelry store appointment in Lima to pick out his wife’s present, and another requested a strict kosher trip to Argentina with dinner at a local rabbi’s home.

12. Jules Maury, Scott Dunn Private

The elegant, charming Jules Maury grew up globetrotting. She was the daughter of a Dow Chemical exec whose career took him (and his family) all over the world. Maury became a travel specialist by happenstance while living overseas; friends persistently asked her advice due to her insiderish knowledge and fine taste. Now she’s made it her career. Based in London, she runs the ultra-elite offshoot of Scott Dunn. Maury’s team focuses on custom itineraries worldwide, with an emphasis on forging access to the impossible.

13. Deborah Calmeyer, Roar Africa

Zimbabwe-born Deborah Calmeyer is the go-to Africa expert for any ultra-high-net-worth traveler. She has on the ground offices in both Nairobi and Cape Town, plus headquarters in NYC. Roar Africa offers traditional safaris, but Calmeyer has also established a standalone division that ups the ante on the already-luxe trips. Roar Privé‘s focus is villa exclusive rentals in the bush. It also offers private-jet-based safaris, which have proven so popular that they regularly sell out months in advance.

14. Kevin Jackson, EXP Journeys

When money is truly no object, EXP Journeys comes in. Jackson and his team create bespoke, one-time-only events in extraordinary locations, often with six-figure budgets or higher. Take the dinosaur dig in the southwest, for instance, in which guests helped discover a new species with a well-known paleontologist. Another standout was a dinner arranged in partnership with Navajo Nation that saw travelers break bread with the last living Navajo Code Talker from World War II.

15. Jonathan Alder, Jonathan’s Travels

Florida-based Jonathan Alder is another Africa insider: He once dropped everything to fly to East Africa to scout private aircraft for clients to use on a month-long trip across the continent. He recommends camps like Angama in the Masai Mara: Come for the walking safari, stay for the glass of champagne overlooking the valley. “It’s the exact spot where the movie poster for Out of Africa was taken,” he says. As a bonus, Alder is also an expert in Japan.

16. Stuart Rigg, Southern Crossings

For more than 30 years, Sydney-based Stuart Rigg has helped travelers explore Australia and New Zealand. Logistics and connections of all kinds are tricky Downunder, so his assistance is particularly welcome. There’s virtually no request he can’t find a way to fulfill. In fact, one celebrity tasked Rigg with organizing his 50th birthday at a mansion in Sydney. The manse’s gym had to be fully refitted and the A/C recalibrated to ensure the traveler’s ideal temp. The birthday bash itself was on a private island right in the heart of Sydney Harbour.

17. Julian Harrison, Premier Tours

Julian Harrison was born and raised in South Africa, before working as a guide there. This primed him to run a travel firm focused squarely on the continent. Beyond luxe safaris, Premier Tours offers trips to often-overlooked islands, like the Bazaruto Archipelago. Harrison is also known for working wonders when problems strike; whether that’s commandeering an aircraft to whisk clients from an unexpected flood in Kenya or handling immigration issues when a pet-chewed passport prevented a traveler from entering Johannesburg. (Harrison arranged a special appointment at the US embassy to replace the passport in situ.)

18. Alex Wix, Wix Squared

Longtime luxury travel specialist Alex Wix only launched her firm seven years ago, but she has become a go-to for trips to Morocco (where she’s based), Australia and Asia. Her expertise is in the hard-to-reach spots in those three territories, though it’s in Morocco where her connections are truly unmatched. For example, she can arrange a candlelit canyon dinner near a luxury camp in the picturesque Agafay desert. Wix loves a personal touch, too: She once organized silver and gold Temari (Japanese ornaments) for one couple traveling to Japan.

19. Ashley Isaacs Ganz, Artisans of Leisure

Artisans of Leisure is known for its ultra-luxe private tours of Europe, the Middle East and Asia. The NYC-based firm has previously arranged a visit to a nuclear research lab in France (CERN) and a rendezvous with a well-known Bernese Mountain Dog for some Silicon Valley-based millennials. It has also coordinated a wealthy family’s private-jet adventure to Greece, France and the UK. If you’ve always wanted to score the best room at the Ritz Paris or Claridge’s in London, Ashley Ganz can guarantee it.

20. Sunil Metcalfe, Black Tomato

London-born, Metcalfe shuttles between the UK and the US, servicing ultra high net worth clients on both sides of the Atlantic for Black Tomato. The firm, founded in 2005, was intended to disrupt the stuffily old-fashioned approach that dominated luxe travel, intending to broaden its appeal to a younger moneyed clientele. It remains one of the buzziest operators thanks to the cachet and connections of Metcalfe; he’s arranged everything from a pop-up spa in the heart of the Yucatan at Chichen Itza for a group of friends keen for RR&R (ruins, rest and relaxation) to an impromptu flyby from the Norwegian Air Force Fleet while fishing-mad clients cooked their catch in Norway ‘s Lofoten Islands.

21. Jaclyn Sienna India, Sienna Charles

Jaclyn Sienna India’s clients pay an annual retainer to keep her on speed dial, as she doubles as a lifestyle concierge and travel agent. If a villa on the Côte d’Azur in summer or a yacht in Sardinia’s seas is your focus, consider adding the Beverly Hills-based firm to your contacts. Sienna focuses on villas more than hotels, explaining: “It’s hard to get someone who has three homes worth $30 million or more each excited about a new hotel—hotels don’t offer the level of service they once did.” Another key differentiator when it comes to Sienna’s programming is the fact that all the guides she recommends have been sourced first-hand. That way, she can vouch for their quality without concern.

22. Ileana Von Hirsch, Five Star Greece

Need a villa worthy of Onassis in his pomp? Want to access the Acropolis in ways that even VIPs can’t wrangle? Last minute charter to Corfu a summertime emergency? Just ask von Hirsch, whose expertise and connections in Greece are unparalleled. She stumbled into the business when she and her sisters inherited what she calls “an extravagantly beautiful but impractical beach house” on a beach there, and had to find a way to commercialize it if they were to keep it (It didn’t hurt that Madonna was one of their first renters) von Hirsch quickly became the go-to broker for friends’ high-end villas, before expanding into all things Greece on both land and sea.

23. James Jayasundera, Ampersand

London-based and Rome-raised, Jayasundera and his five-strong team are go-to experts for tailor made tours to the Indian subcontinent, east and Southeast Asia. They can handle everything from a party at Rambagh Palace in Jaipur for a famous singer-songwriter and 100 friends who’d flown in by private jet from around the world to a multigenerational family needing 16 suites every time their private plane touched down on a nine-day whistlestop trip from the tigers at Ranthambore to Agra’s Taj Mahal. Jayasundera started early, noting the preferences of each of his twelve-strong family as they traveled constantly, in his childhood—attention to detail is his obsession. Inclusivity is a longtime passion, with a strong presence in the LGBTQ community among both staff and clients.

24. Andrea Grisdale, IC Bellagio

Grisdale may be British born but has lived and worked in Bellagio, Lake Como for more than 25 years, making her the perfect bridge between Italy and international visitors (she doesn’t outsource, but handles operations entirely in-house with her 31-strong team). Her expertise spans all 20 of the country’s regions, from the Dolomites in the north to Sicily. She can plan energetic, outdoorsy itineraries, like a recent 12-day romp through Umbria and Tuscany, cycling around Assisi and walking the Pilgrim’s Way in Val D’Orcia, or steer clients away from Capri and Co to visit charming, thoroughly Italian spots like Lecce and Matera instead (she’s also a fan of La Fiermontina)

25. Gwen Kozlowski, Exeter International

Gwen’s first job in travel was working in the reservations department of Eastern Airlines—at least until the carrier shuttered barely 18 months after she started there. Still, she was determined to carve out a career in that field, and her determination next earned her a job at a travel agency; her career has continued apace since then, always defined by that same will-only-take-yes-for-an-answer demeanor. Tampa-based Kozlowski’s the ultimate expert in Eastern Europe and the Balkans, from Austria to Poland, Montenegro to Hungary or Germany. Her approach is a hybrid between travel specialist and ground operator, so her 18-strong team has direct, hands-on control of everything they recommend. Family history is a frequent request, as with a six-strong group which was accompanied around Poland by a genealogist.

26. Jason Squatriglia, Your Favorite Travel Agent

Among his peers, Squatriglia’s a relative newcomer, pivoting full-time to travel in the pandemic’s wake, but his lifelong obsession with the industry—and ability to network—primed him for immediate success (he started his first business aged 14, and sold it to help fund college). “I’m a 24/7 concierge—anything the client needs, I book and then manage,” he explains of his approach. Need premium seats for the gymnastics at the Paris Olympics with your adult daughters? Backstage Broadway meet and greet experiences? Last-minute private shopping appointments during Fashion Week at Hermès (and be offered an exotic mini Kelly during the visit for sale)? They’re all Squatriglia’s past successes. He splits his time between NYC, Palm Beach and the Hudson Valley.