25 Luxury Pros Who Can Make Your Dream Vacation a Reality

Welcome to the fourth 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 two dozen of them total, nearly all specialists in certain regions or types of journeys.

They come with our endorsement.

You’ll also regularly see their expertise in the magazine, 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). 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

Headquarters: London, U.K.
Areas of Expertise: Off-the-beaten-path luxury, South America, safari, adventure
Need to Know: He was an early advocate of a now-commonplace innovation: walking safaris, bringing guests safely closer to the African landscape than is ever possible in a 4×4.

The 25-strong agency is steered by the three-decade veteran Wilmot-Sitwell. He and that team are renowned for deftly combining adventure travel—think long-haul jaunts to hard-to-reach Asian and African sites—with no-beat-missed luxury. Canny touches include programming specialist private guides to follow clients from camp to camp and assist with birding, rather than relying on new guides at check-in every time. The firm itself was an early champion of sustainability, which is now an industry-wide obsession. It is committed to offsetting the carbon impact of its own research trips via CommuniTree, a Nicaraguan reforestation project (clients can sign up, too), and has long been a supporter of the Sol y Luna lodge in Peru’s Sacred Valley, where luxury accommodation underwrites pro-social programs in this economically disadvantaged rural area.

2. Henry Cookson, Cookson Adventures

Headquarters: London, U.K.
Areas of Expertise: Adventure, exploration, and record-breaking
Need to Know: Cookson is a world record–holder himself, for kite-skiing to the Pole of Inaccessibility.

Cookson’s niche is elaborate, discreet adventures, and his firm focuses on a handful each year—perhaps a few dozen at most. Think of him like a modern Indiana Jones, with an eclectic résumé that primes him to wrangle unusual, unforgettable trips; Cookson has worked as everything from a horseback safari guide to a sheep-station jackeroo to a Goldman Sachs banker. He founded his firm nearly 20 years ago after accidentally discovering travel as a business, entering a race to the Magnetic North Pole on a whim—and winning. Soon, he’d turned his firsthand knowledge of far-flung locales into a business, while also working on conservation and fundraising (he was the Duke of Sussex’s guide to the North Pole on a charity expedition 15 years ago). Fancy chartering a plane to a private round-the-world trip? Cookson’s team is the perfect partner.

3. Cari Gray, Gray & Co.

Headquarters: Santa Monica, Calif.
Areas of Expertise: Active trips, adventure, adrenaline
Need to Know: Gray first led a bike tour aged 22, taking 20 travelers on a 100-mile trip around France for a week, so she knows how to guide, firsthand.

If you’re outdoorsy, ready for anything, and prepared to sweat, call Gray. Few manage to design and book high-end active trips with more finesse than the Canadian, herself an avid sportswoman. Charmingly relentless, recovering lawyer 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. She trained with biking and walking specialist Butterfield & Robinson before striking out on her own 17 years ago; today, her tight-knit, lycra-clad team will pre-vet an itinerary, road-testing it themselves before risking the client’s time, better to anticipate any potential snafu. Even better, when planning trips like those biking ones which got her started, the staff-to-guest ratio is typically, at minimum, 2:1.

4. John Clifford, International Travel Management

Headquarters: San Diego, CA
Areas of Expertise: LGBTQ+ travel
Need to Know: Clifford first started working as an adviser aged just 18.

For the last four decades, hotel obsessive Clifford has been an ultrahigh-net-worth counselor, the ideal person to trust with a tricky getaway; he’s constantly roaming to recce the right rooms, so you can trust him not only when he suggests a property, but also the kind of room. “My clients always get the best suite pre-blocked,” he says. “I often handpick it myself.” New York–born, New Mexico–raised Clifford skipped college and dived straight into his passion, travel, scoping destinations firsthand from the outset. Clifford’s also carved out a niche for queer travelers, able to offer advice on LGBTQ+-friendly properties and destinations so that everyone can relax on vacation.

5. Gary Portuesi & Jennifer Schwartz, Authentic Explorations

Headquarters: New York, N.Y. and Florence, Italy
Areas of Expertise: Italy, Iceland, Croatia, Spain, Portugal
Need to Know: Schwartz is a licensed truffle hunter, so ask her to take you on a foraging trip in season.

Hungry for Italy? The seven-year-old 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 N.Y.C. 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). Want a private, air-conditioned suite in a pole position to watch the thrilling finish of Siena’s Palio race? They’ve got one already primed. Then again, if you’ve always dreamed of being invited to the Ballo del Doge during Venice’s Carnival, just ask AE to get you a ticket. It’s deeply rooted in all 20 regions of Italy, as the company’s initial focus was solely on that country. It recently expanded to select other European destinations, such as Croatia, Spain, and Portugal.

6. Catherine Heald, Remote Lands

Headquarters: New York, N.Y. and Bangkok, Thailand
Areas of Expertise: Asia
Need to Know: Heald’s a multihyphenate: an early Columbia computer science grad, she’s also a fitness fanatic, including finishing the New York City Marathon in 101st place.

If you’re heading to multiple countries in Asia—from Japan to the Maldives to everything in between—there’s no better counsel than that of Heald. “I have devoted my life to Asia since moving to Hong Kong in 1987,” she says of her decision to jettison a promising career on Wall Street to board a plane to Asia with nothing but the phone numbers of two people, $1,000 in her pocket, and a passion for the continent. Heald and her team have expertise in major cities, but the farthest-flung spots are a specialty. Think Japan’s Yakushima Island 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. Heald has lunched with the Queen of Bhutan and has chartered a private plane to roam the most remote corners of Mongolia’s Gobi Desert. She’s also a close partner of Aman and works on programming the private-jet itineraries, which now run to connect its properties.

7. Tanya Dalton, Greaves India

Headquarters: London, U.K.
Areas of Expertise: India
Need to Know: Her expertise stretches beyond continental India. She particularly excited about the Andaman Islands, that isolated archipelago under India’s purview that’s becoming a barefoot luxe paradise where, she says, “you will find some of India’s—if not the world’s—best beaches.”

If you want to immerse yourself in the dazzling, gloriously overwhelming culture of India, there’s no one better to tap than Dalton, who is based between London and Goa but whose firm also has offices in Chicago and Delhi. Hers is a truly family business: Her Mumbai-born grandfather founded the company, who passed it on to Dalton’s mother and then to her, making it a four-decade veteran of wrangling the best experiences in India. That generational know-how and network confer a near-unparalleled level of insider access to anyone who travels under her auspices. Private palace? You got it. She can also wrangle suites in Rajasthani mansions or program tiger-centric safaris. The choice is yours.

8. Cédric Reversade, Unique Properties & Events

Headquarters: London, U.K. and Paris, France
Areas of Expertise: Villas and private homes in jet-set locales
Need to Know: His new Cabinet of Curiosities collection features exclusive-to-him villas that are crammed with blockbuster art, from Picasso to Louise Bourgeois, or ancient Egyptian artifacts.

Some call him the villa whisperer, and for good reason. Reversade has an unparalleled list of the world’s most exclusive private homes in every must-visit destination, from Saint-Tropez to Capri and beyond—the Jean Cocteau–designed Villa Santo Sospir, for example, or the Ungaro family’s organic, 160-acre farm in the Luberon. 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. If you’re ready to propose and keen to make sure she’ll say yes, just do as another client did when he wanted to pop the question in Saint-Tropez. “He ordered 3,000 Pierre de Ronsard roses. We had to get the best florist in the French Riviera to order them and hired five extra staff to cut them,” Reversade says. Thankfully, she did say yes—and Reversade was tasked with planning their Marrakech wedding.

9. Sandy Cunningham, Uncharted

Headquarters: Santa Barbara, Calif.
Areas of Expertise: Safari, outdoors, adventure, ski
Need to Know: She was born in South Africa and raised in what’s now Zimbabwe, exploring the Nyanga Mountains and dodging crocs and hippos on days spent idling ‘round Lake Kariba.

Cunningham’s firm is aptly named, as it specializes in adventures and safaris in remote destinations. Cunningham stayed on the continent to begin her career, working as a safari operator alongside her husband (and now business partner) Chip, running Richard Bonham’s Ol Donyo Wuas lodge. It means she knows the game, in every sense. Cunningham is adept at creating long-haul trips for large groups, too: She once booked a celebrity family into a private island in Seychelles. To avoid any shred of unwelcome publicity, she whisked the same family out a day earlier than planned, under cover of darkness, to avoid alerting any paparazzi. Sandy and Chip are also avid skiers, so don’t hesitate to tap them for a cat-ski trip to Crested Butte, one of her favorite spots.

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

Headquarters: New York, N.Y.
Areas of Expertise: Concierge-style travel
Need to Know: When founder Bill Fischer first pivoted to charging membership fees rather than commissions on bookings, he reinvented the travel-specialist model in a way that’s become the industry norm.

Max Rosenthal is the third generation of his family to join Fischer Travel. His grandfather Bill Fischer founded the New York–based firm, but the company currently run by his mom, Stacy. The nearly 40-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 members from the Kempinski in Aqaba to temporarily run the camp at a higher level.

11. Jules Maury, Scott Dunn Private

Headquarters: London, U.K.
Areas of Expertise: Multigen globetrotting, six-figure-plus family jaunts
Need to Know: Her first foray in trip-planning came as a 12-year-old when traveling with her sister and their parents were delayed—Maury found and booked a hotel for the pair.

The elegant, charming Maury grew up globetrotting. She was the daughter of a Dow Chemical exec whose career took him—and his daughters, including Jules—all over the world. Maury became a travel specialist by happenstance while living overseas (she’s called Hong Kong, South Africa, France, Australia, and Vietnam home at different points in her life). Friends persistently asked her advice due to her insiderish knowledge and fine taste, and eventually she repackaged that know-how into a high-flying career as a counselor to the highest-end travel niche. 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. One hot spot du jour: Scotland. “We’re overwhelmed with it,” she says, “People want to find the history of where their families come from, and make their children feel like they’re part of somewhere.”

12. Kevin Jackson, EXP Journeys

Headquarters: Solana Beach, Calif.
Areas of Expertise: Adventure, adrenaline, immersive trips
Need to Know: Jackson has scaled Mount Kilimanjaro in Tanzania 13 times and mountaineered up Mount Whitney, the highest peak in the continental U.S., 15 times.

When money is truly no object, B-Corp-certified EXP Journeys comes in. Jackson and his team create bespoke, one-time-only events in extraordinary locations, often with six-figure budgets or higher. He’s known for adventure—custom bike tours around Ted Turner Reserve, for example—as well as immersive experiences, which involve creating impromptu worlds in any given location. He helped a group of guys punch up their annual getaway via a buyout of Amangiri where they were trained by Navy SEALS to finesse their paintball skills before battling 100 pro ballers in a staged fight to rescue hostages, and created a $400,000 James Bond–style adventure for three couples, which included a cocktail party filled with extras dressed as guests and staffers, and a grand finale to defuse “explosives” on a yacht. He has helped guests discover a new dinosaur species with a well-known paleontologist at a dig in the southwest, and even hosted a dinner arranged in partnership with the Navajo Nation that saw travelers break bread with one of the last-living Navajo Code Talkers from World War II.

13. Jonathan Alder, Jonathan’s Travels

Headquarters: Orlando, Fla.
Areas of Expertise: Off-grid, Asia, safari, luxe Disney
Need to Know: Ask Alder for recommendations on concerts and clubs—he’s an avid D.J., piano, and timpani player.

30,000 trips. 70+ countries. Alder is a veteran travel planner with a deep firsthand knowledge of many destinations (he’s also a dab hand at turning a trip to Disney World into a true five-star experience, thanks to his base’s close proximity to the Mouse House in Florida). He’s personally logged more than 100 days on safari, and 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 Mara 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. Skip Thailand’s overtrafficked upper reaches, he says, for Luang Prabang in Laos: “It’s probably your vision of northern Thailand, and Laos is my favorite country in that region.”

14. Stuart Rigg, Southern Crossings

Headquarters: Sydney, Australia
Areas of Expertise: Australia, New Zealand
Need to Know: Don’t forget Fiji—the Pacific island nation is another area of expertise for Riggs and his team, a cultural contrast to Down Under.

For more than 30 years, Rigg has helped travelers explore his region in luxury. Logistics and connections of all kinds are tricky Down Under, 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. Rigg has got a deep bench of knowledge from across the region, whether you want to explore the Great Barrier Reef—he’ll suggest accommodation and activities depending on whether you’re avid divers or just keen to dip a toe in the waters, then relax on a deserted beach—or try to score access to the best wineries in Perth-adjacent Margaret River region.

15. Alex Wix, Wix Squared

Headquarters: Marrakech, Morocco
Areas of Expertise: Morocco, Australia, Asia, U.K.
Need to Know: If you’re ready to surrender to her expertise entirely, opt for one of her Mystery Travel trips, where a surprise itinerary is crafted to a client’s likes and interests.

Longtime luxury-travel specialist Alex Wix only launched her own firm less than a decade 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 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 or roster an astronomer to help with stargazing in the inky blackness of the sand dunes at night, a regular request from visitors today. Wix loves a personal touch, too: She once organized silver and gold temari (Japanese ornaments) for one couple traveling to Japan. The next big project for this expat Brit: tackling trips to the British Isles, where she was born and bred, and bringing her signature expertise to that region.

16. Ashley Isaacs Ganz, Artisans of Leisure

Headquarters: New York, N.Y.
Areas of Expertise: Private tours and insider access in Europe, the Middle East, Asia
Need to Know: Try a few words of Japanese with Ganz, who spent two years living and teaching in the country as part of the JET program.

Ganz and her firm have 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. The company has also coordinated a wealthy family’s private-jet adventure to Greece, France, and the U.K., as well as polo-playing in Rajasthan and private martial arts sessions with masters in Japan, not to mention mentoring of would-be Margot Fonteyns via one-on-one sessions with household-name prima ballerinas. Ganz is also a hotel obsessive and has the GMs of the world’s best properties on speed dial. Some of her favorites include “my home away from home” Claridge’s in London, plus the “meticulously maintained” Brenners Park in Germany, and La Mamounia, the grande dame of Marrakech, which she says is “iconic, legendary, and still current.”

17. Sunil Metcalfe, Black Tomato

Headquarters: New York, N.Y. and London, U.K.
Areas of Expertise: Unstuffy, upscale trips
Need to Know: Metcalfe’s a superstitious traveler: He always eats or cooks a cuisine inspired by a client’s trip before they leave, as a good-luck charm for a smooth trip (and it usually works).

London-born, Metcalfe shuttles between the U.K. and the U.S., servicing ultrahigh-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, with the goal of broaden its appeal to a younger moneyed clientele. It remains one of the buzziest operators thanks to the cachet and connections of Metcalfe. He has 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. This year Metcalfe is also ready for the extraordinary eclipse in August: He has arranged a private yacht positioned in open water off Ibiza, a 90-foot Leopard with a crew of two and a private chef, which will tour Formentera before hitting open water for the best views of that near-sunset eclipse.

18. Jaclyn Sienna India, Sienna Charles

Headquarters: Beverly Hills, Calif.
Areas of Expertise: Concierge-style luxury trips
Need to Know: The much-missed Philly-based Le Bec-Fin restaurant was where Jaclyn got her start, as a server, so she has an innate instinct for five-star customer handling.

India’s clients pay an annual retainer, starting at $75,000, to keep her on speed dial, as she doubles as a lifestyle concierge and travel agent (among her non-NDA’d client base: George W. Bush and Mariah Carey). If a villa on the Côte d’Azur in summer or a yacht in Sardinia’s seas is your focus, consider adding the firm to your contacts—if you can, as she limits her client base to around 100 families. Want a private breakfast on top of the Arc de Triomphe? She’s done that. Backstage passes to a J.Lo concert? That, too. When booking travel, India focuses on villas more than hotels: “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 firsthand. That way, she can vouch for their quality without concern.

19. Ileana Von Hirsch, Five Star Greece

Headquarters: London, U.K.
Areas of Expertise: Greece and its islands
Need to Know: Von Hirsch spent time in New York working as a set designer, so she excels in creating the perfect backdrop to events.

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 in a summertime emergency? Just ask von Hirsch, whose expertise and connections in Greece are unparalleled. She says she and her sisters “come from an old and impoverished Greek shipping family” and only stumbled into the travel business when they inherited what she calls “an extravagantly beautiful but impractical beach house” on the island of Ithaca. They 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. Her secret to success is simple, she says: “Brutal honesty and high standards.”

20. James Jayasundera, Ampersand

Headquarters: London, UK
Areas of Expertise: Southeast Asia, Indian subcontinent
Need to Know: His passion for hospitality is such that he co-owns a boutique hotel on a fynbos reserve, 7 Koppies, in South Africa’s Franschhoek.

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 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 family of 12 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.

21. Andrea Grisdale, IC Bellagio

Headquarters: Lake Como, Italy
Areas of Expertise: La dolce vita
Need to Know: Grisdale’s a lake whisperer, from Como to Garda—and no wonder, as she was born and brought up in the U.K.’s own Lake District.

Grisdale worked as a holiday rep around the world before being assigned to handle trips in Italy. She quickly discovered her passion for the country and pivoted to high-end travel-wrangling focused solely on every aspect of la dolce vita. Grisdale’s eclectic background makes 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 a fan of La Fiermontina).

22. Gwen Kozlowski, Exeter International

Headquarters: Tampa, Fla.
Areas of Expertise: Central Europe, including Austria, Hungary, Poland
Need to Know: Kozlowski’s a Christmas market connoisseur: go for the smaller one at Vienna’s Karlsplatz and Krakow in Poland for the minimum crowds and max charm.

Kozlowski’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. Kozlowski’s the ultimate expert on all things Mittel Europe, with know-how that spans the Balkans (Aman Sveti Stefan should reopen there, finally, this year, she says) to the Black Sea. Her approach is a hybrid between travel specialist and ground operator, so her 10-strong team has direct, hands-on control of everything they recommend. Family history is a frequent request, as with a six-strong group accompanied around Poland by a genealogist.

23. Jason Squatriglia, Your Favorite Travel Agent

Headquarters: New York City, N.Y. and Palm Beach, Fla.
Areas of Expertise: Insider event access, concierge-style trip management
Need to Know: Squatriglia once took the world’s longest flight, from N.Y.C. to Singapore, simply to pick up a jewelry box and deliver it to the client, who lived in Beverly Hills.

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. Squatriglia’s known for wrangling rooms when none seem available—he’s primed with a bio of his clients to persuade seemingly overbooked hoteliers, as they begin vetting would-be guests. 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.

24. Virginia Irurita, Made for Spain & Portugal

Headquarters: Madrid, Spain
Areas of Expertise: Spain and Portugal
Need to Know: Ask her for advice, in particular, about Cádiz, the Ribera del Duero wine region, and Madrid; she has homes in all three places.

Irurita’s childhood was shaped by travel and deeded her a love for her home country. “My father made sure that I slept in every parador and pousada, discovering the magic of every monument, church, art collection, and regional gastronomy of the Iberian Peninsula,” she says now. After working for Citibank for two decades, she finally surrendered to that childhood passion and set up her company in 1999. Its fiefdom is Spain and Portugal—as she proudly proclaims—and there’s no one better connected on the peninsula. She’s also now eyeing that overlooked Pyrenean country of Andorra for some trips, recommending a few days in its breezy, Switzerland-like summer climate as a break between sightseeing in Madrid and Barcelona. “It’s an oasis, and a paradise in summer because nobody is there,” she says.

25. Mark Lakin, The Legacy Untold

Headquarters: New York, N.Y,
Areas of expertise: Japan, safari, Antarctica, New Zealand
Need to Know: Lakin segued into travel designing after his work as a photographer so impressed one collector that they asked him to come along to document the trip.

Before he worked as a gallerist and photographer, Lakin was a successful, if unfulfilled, corporate lawyer, so travel is his third act—and one he’s embraced with gusto. His credo focuses on transformative travel: access-driven but purpose-led, so the connections he wrangles on clients’ behalf should also be meaningful and impactful for the destination. Think helping place a satellite collar on a wild cheetah in Kenya for conservation purposes or giving a mud bath to an adopted orphan baby rhino. He has paired travelers with 17th-generation Japanese knifemakers for sharpening classes and even created a family-immersion trip to Japan that included soba noodle–making, Samurai sword lessons, and feeding the wild deer in Nara. One other standout: creating a custom AfrikaBurn for a 30-plus group of avid Burning Man attendees, buying out Singita Sasakwa in Tanzania’s Serengeti, and rostering it with a team of international D.J.s.