Standing in a bar one night in Santorini, Ken Kessler struck up a conversation with a chatty blonde. An experienced traveler, the retired salesman from Evanston, Illinois, was astonished to find out that she lived in Nairobi, Kenya. "I'm in the safari business," she told him.
Months later, that late-night encounter led to an unforgettable trip to Africa for Kessler, his wife and daughter -- their entire experience coordinated by that same blonde, Lisa Rolls, a professional guide and co-owner of Virgin Bush Safaris.
"It was a chance encounter, so I took a chance," explains Kessler, who still marvels at Rolls' impact on his trip. At one point she floated the idea of seeing the house where "Out of Africa" was filmed. Her friend, an artist, owns the home and they went to see it.
"You can plan all you want, but you can't get the same experience as with a well-connected guide," says Kessler. "They know everybody."
With the proliferation of guides out there, it is more important than ever to sift out the best -- those who are able to plan ahead, anticipate travelers' interests and react resourcefully to spontaneous ideas. Before booking a tour, Kessler suggests, ask for two or three past traveler references, and ask passengers extensively about their experiences.
The onus of a great experience doesn't lie with an escort alone, though. To make the most of the time, a savvy traveler should research enough to give clear direction. Sharper parameters at the outset allow for a more satisfying outcome, which is one of the reasons many of the best upscale guides have clearly established niches. Here is our elite list of the world's greatest guides, with expertise that spans from Rome to the veldt of Africa.
Antwerp: Tanguy Ottomer
Antwerp is arguably the edgiest fashion hub in Europe -- its local Royal Academy of Fine Arts still churns out experimental designers keen on aping the success of past luminaries such as the Antwerp Six and Martin Margiela.
Tanguy Ottomer can wrangle access to some of the city's more rarefied ateliers, as well as steer shoppers through its passel of funky concept stores. "You've already seen London, Paris or Milan," he says with a shrug. "Antwerp has this fresh feeling." Rates start at $135 an hour.
Africa: Virgin Bush Safaris, Cindi Crain and Lisa Rolls
These onetime Manhattan media execs founded Virgin Bush Safaris as a way to fulfill their dream of living in the veldt of East Africa. More than a decade later, Crain (pictured here) and Rolls are as dedicated as ever, having established working relationships with the United Nations and the Convention on International Trade in Endangered Species of Wild Fauna and Flora (CITES) to buff their prestigious safari credentials.
They pre-interview clients before developing custom programs, focusing on one of three countries: Kenya, Tanzania and Rwanda (where visitors can now go gorilla-trekking). Virgin Bush's reputation for barefoot luxury is well earned, evidenced by the private home on a cliff top at Kenya's Watamu Coast, which sometimes accommodates guests, complete with a private beach. Rates start at $850 a day.
Beijing: Jia Yan (Rainbow)
Though her given name is Jia Yan, everyone calls her Rainbow. Barely 30 but already a decade-long veteran, the young guide is one of Beijing's finest, thanks to her sunny demeanor (hence that nickname) and her resourcefulness. She is as adroit at translating the top sights of the 798 Art District as she is the menu at a restaurant tucked inside a hutong lean-to. She once took an American couple to the local temple, where Beijingers pray for babies, and heard from them three months later that the wife was pregnant. Rates start at $1,999 (two-day itinerary).
Istanbul: Nirvana Asaduryan
There is no more exciting or intimidating a shopping mecca than Istanbul's Grand Bazaar. To navigate its 60 or so streets and thousands of stands -- not to mention haggle hard on prices -- it is vital to have a seasoned guide like Nirvana Asaduryan. "My soul clears there," she says of the five-century-old complex. "My father owned two jewelry stores, so since I was 7 or 8 I've breathed the air of the bazaar."
She is a stylish, charming, sharp-eyed companion, able to spot a bargain or a ripoff in equal measure. Though she now runs a team of impressive guides, Asaduryan will gladly step in herself for VIP tours. Rates start at $200 per half-day tour (includes guide and chauffeur-driven SUV).
London: Sarah Douglas
With partner Sam Livingstone, Sarah Douglas juggles her time teaching at the Royal College of Art with running a boutique firm that has re-imagined the role of a guide. With an approach more akin to a consultancy than a tour operator, the pair uses its art- and design-world connections to create custom itineraries around London, whether visiting one of the last custom cobblers in the British capital or taking tours of the top temporary art shows personally hosted by the curator. Rates start at $2,350 a day.
Rome: Iris Carulli
Iris Carulli is the go-to guide for museum groups and the arterati when they make a pit stop in Rome, and such popularity among her peers is a sign of her clout. Trained at the Courtauld Institute of Art in London, Carulli deftly draws the ancient city's disparate cultural pasts together, showing the common thread from Rome through to the present day.
A typical stroll might take in Janiculum Hill, Bramante's Tempietto, the Borghese Fountain (where Galileo demonstrated his telescope for the first time) and even Anita Garibaldi's tomb. Rates start at $107 (two hours).
Tokyo: Shinji Nohara
Former journalist Shinji Nohara is a genial, chatty companion with an encyclopedic knowledge of the hidden foodie dens that dot the city, many of them tucked upstairs away from the casual passerby. He is just as equipped to showcase the best seiro-soba (cold-noodle) joint in the city, just steps from the bustle of Harajuku's main crossing, as an old-style Japanese coffee joint where a 70-something barista hand-pours each artisanal cup (take that, Starbucks). Rates start at $440 a day; 81-90/3043-8138; email@example.com.