It’s hard-maybe impossible-to beat that level of service.

Forbes Magazine
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Putting guest satisfaction first...

Private Clubs
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Choice and flexibility are very expensive luxuries, but that’s what makes a bespoke itinerary truly unique.

Departures, Black Ink
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Gray guides clients to every corner of the globe...

Forbes Magazine
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Cari Gray has travelled the world – initially as her parents’ excess baggage on overseas work assignments, and later as an insatiable explorer in her own right. After becoming a lawyer, she quickly ascertained that her passion for travel trumped legalese.

For the next 15 years, Cari worked for the luxury biking and walking company, Butterfield & Robinson. Her many roles at B&R included Guide, Researcher, Global Marketing & Public Relations Director. She continues to work very closely with high-end industry organizations and trendsetters.

As the woman who always knows where to go next, Cari’s words and views have been captured in such publications as Travel + LeisureExecutive TravelerEverett Potter’s Travel Report and Black Ink. She is a Contributing Editor to the American Express Platinum Departures Magazine, and sits on the board of the AFAR Travel Advisory Council.

Cari founded Gray & Co. in 2008. Ever since, she has been crafting a select number of active journeys for discerning travellers. Gray & Co. supports sustainable and responsible travel practices and is an active member of the Adventure Travel Trade Association. Gray & Co. proudly sponsors a “Ride for Heart” team for the Heart & Stroke Foundation.


With her extensive background in both hospitality and design, Julia lends her creative and stylish hand to all aspects of Gray & Co. From her base in Toronto, she helps keep the wheels in motion and on track as Gray & Co.’s Director of Operations. Some of Julia’s favourite Gray & Co. destinations include the Atacama Desert, Mallorca, the Amalfi Coast, Uruguay and Ireland.


Canadian-born Carolyn’s passion for travel was ignited by a year of travel and volunteer work in Southeast Asia and Africa. After completing her masters in Business and Italian at University of Edinburgh, she worked in London for a cutting-edge software company before joining Gray & Co. Carolyn enjoys scuba diving, triathlon, golf, and hiking. Carolyn has not only examined the pavement and absorbed the marvels of nearly 20 countries, she also guided trips in California, France, Utah, Australia, New Zealand, Argentina, Colombia, Chile, and Mallorca.


Annie spent her early years growing up with five siblings and travelling the world competing in ski events. She later attended the University of Dalhousie before launching a career in film and television production. Her innate passion for active travel, coupled with her multi-lingual prowess, has led her to explore more than 40 countries. When she isn’t travelling, you will find Annie cycling year-round in her hometown of Toronto. A true wanderer at heart—and unofficial “kid whisperer”—Annie is right at home planning, producing, and guiding trips for all ages at Gray & Co.


Born in Buenos Aires, Paola began her career in Ushuaia, Patagonia. For over a decade, she expertly guided and planned trips for Butterfield & Robinson. Paola has executed Gray & Co. trips in South Africa, Australia, Chile, Uruguay, Italy, Spain, Argentina, the United States, and beyond. She has amazing passion for people, biking, yoga and design.


Silvia’s passions include travel and sports. As a mind coach and trainer, she helps elite athletes reach their performance goals. As an active travel guide, she leads trips all over the world, including her beloved home country, Italy.  When not coaching or guiding, Silvia can be found kite surfing or training for a triathlon. She’s recently guided Gray & Co. trips in Sicily, Puglia, Provence, The Veneto, Mallorca, Texas, Northern Argentina, and the Atacama Desert, Chile.


Stephanie has guided and biked around such Gray & Co.’s hot spots as France, Morocco, South Africa, California, Mallorca, Northern Argentina, and the Atacama Desert, Chile. She is now based out of Montreal where her company Ma Bicyclette offers the best day trips around Montreal and along the St. Lawrence River.


A native of Cape Town, Jacqui achieved a doctorate in molecular biology and dipped her toes into big pharma before following her passion for tourism. Her sharp intellect and omnipresent curiosity mean that she’s as up to date on global politics as she is on local African creatures and environments. She’s also a superb athlete – on two-feet as well a two-wheels. Jacqui has been on the Gray & Co. team since the company’s debut trip – in South Africa of course!


Andrew’s work with Gray & Co. began when he was the senior travel editor at Departures magazine and covered Cari’s launch of the company. His travels with Gray & Co. include Southern Italy’s Puglia, Mallorca’s Palma and South Africa’s Cape Winelands. A true believer and consummate fan, today, he ensures that all company communications are fun to read, correct, informative, enticing and consistent with the brand. When not wielding his pen (or, more often, laptop keyboard) for Gray & Co., he’s got his finger on the luxe pulse, writing stories for such publications as AFARArchitectural Digest, Conde Nast Traveler, Robb Report and Travel + Leisure. Longtime New Yorkers and inveterate travelers, he and his husband — dads to an active, adventurous toddler — now split their days between Boston and Provincetown, on Cape Cod.


Hannah has been a part of Gray & Co. trips to Greece, Portugal, and Ireland. Her exposure to travel at an early age, love of the outdoors, and insatiable appetite for history has ignited her love of globetrotting. She has a duel degree in education and classics from Queen’s University and her passion to see the world has taken her to over twenty countries.


Patricio Daly is Argentine, passionate about mountain climbing since he was 9 years old, achieved Aconcagua peak (6969 mts) at the age of 20 and dedicated himself to guiding clients in the South American Andes. He is a Mountain Bike Guide from Lanin National Park, WFR certified and an Archery National Instructor. He has guided clients in trekking and climbing expeditions in Patagonia and Mendoza. Biking and kayaking with clients in the Argentine and Chilean Andes. Climbed the Domuyo Volcano (4250mts), guided clients to the peak of the Lanin volcano ( 3776 mts) in Argentina and led groups in San Martin de los Andes Patagonia, where he lives.


After years of travelling the world as an executive for Microsoft and Yahoo, John now balances his time between global technical consulting and media production, specializing in travel and cause-related projects. His most recent Gray & Co. forays have included biking in Texas, Aspen, Catalonia, Uruguay, Chile, Whistler, and Argentina.


James has been a part of Gray & Co. trips to New Zealand, Chile, Argentina, Spain, Italy, Whistler, and Texas. As an engineer specializing in Water Resources, he’s the master of any map, GPS and elevation profile. He loves to hike, bike and surf around the world.


Dylan is a native South African who, at an early age, started competing in elite mountain biking events. He went on to win national and world titles in Trials, Cross-Country, Four-Cross, Marathon and Downhill races. These days, Dylan is a father of two, owner of a high-end bike shop in Cape Town and host of cycling events.


Born in Africa, Laura spent her formative years exploring family farms in Zimbabwe where, with the exposure at a young age to places like Lake Kariba and Mana Pools, she developed a passion for nature and wildlife. This lead to a career as a safari guide, where she has managed lodges and guided at some of the top establishments in South Africa, Zambia, and Tanzania. More comfortable on her feet or a bicycle, she’s naturally moved towards leading active trips, equally happy tracking elephants on foot or riding through the Cape Winelands.


A native Texan, Tim moved to southern Brazil at the age of nine and began his life of international travel and outdoor adventure. After a successful career in construction project management, he moved into the outdoor industry managing Cycology Bicycles and Little River Trading Co. in Maryville, TN. He’s been a chief bicycle mechanic for the Tour De Smokies, CEO Challenge, Tour De Cure, Cherohala Challenge among many others. Living in the foothills of the Great Smoky Mountains offers him the opportunity to share the beauty of Appalachia with like-minded adventurers.


Claire Reyes’ casual elegance and deeply caring nature make her an extraordinary Gray & Co. guide who easily anticipates travellers’ needs. She has guided cycling trips in New Zealand, Czech Republic, Provence, Puglia, North Carolina, and more. When not on a bike, Claire keeps busy designing brands and websites and most recently completed a masters degree at Rutgers University.


When not doing social work in her native Québec, Cora brings her serious cycling prowess, charm and extensive global guiding experience to Gray & Co. trips. Places she loves to guide include France, Québec and Morocco. Most recently, Cora led Gray & Co. bike trips in South Africa and the vineyards of California.