The Best Active Travel With A Woman’s Touch

Otto I. Eovaldi

As travel quickly rebounds from the COVID-19 pandemic, one of the strongest sectors has been active and adventure travel. Americans took up new outdoor activities such as cycling and hiking, which saw massive growth during the pandemic, and now they want to take that on the road. At the same time, many realized that life is unpredictable and having great travel experiences now, not “someday,” is important. The more “Bucket List” type trips, from safaris to epic hiking routes like the Tour du Mont Blanc, have also seen jumps in bookings.

Many of the leading tour companies specializing in these kinds of trips are reporting record reservations, and travelers are booking big active and travel trips into late 2023, a year and a half out. Active and adventure travel is my favorite kind of travel, but these trips can be expensive and require advance commitment, so it is important to choose wisely. The knowledge and personalities of the individual guides is key to your enjoyment, and with complex logistics, often in far-flung or exotic locales, you need to use an organization with expertise in this kind of planning and execution. Strong networks of local contacts get you the best, most unique or most charming accommodations, the best meals along the way and memorable local, immersive experiences.

Since summer is prime vacation travel time and many Americans are starting to plan their return to travel right now, I’m devoting June to profiling and speaking with the women who run some of the best tour operators in the business. After all, the majority of travel decisions and bookings are made by women, so whether you are traveling solo, with other women, or with your husband, boyfriend or partner, you might appreciate the perspective these women have about what will make your trip the best. The first entry was Butterfield & Robinson (read here). Today I’m featuring Gray & Co.

Cari Gray is the founder and owner of Gray & Co., widely known as the industry’s most luxurious active travel tour company, specializing in cycling, hiking and multi-sport trips. That’s because, unlike the competition, they do not offer any catalog itineraries or scheduled group trips at all. Every single trip they do is totally bespoke, custom-made for their clients based on when they want to travel, where they want to travel, what kind of physical and non-physical activities they want to do, and how much of each. Every preference from food likes to cultural interests to the composition of the group is taken into account, and each trip is meticulously led by a high staff-to-traveler ratio of guides and support vehicles. This is especially well-suited for diverse groups such as those with greatly varying activity levels or multi-generational family outings. It also makes Gray & Co. one of the few top choices for serious mountain bikers, something most top cycling tour operators skip over. It is probably the smallest company ever to win Travel + Leisure Magazine’s World’s Best Tour Operator (for all categories, not just active travel), also makes Conde Nast Traveler’s Readers’ Choice and Expert Lists, and has received accolades from many publications including Robb Report and AFAR. While its customer base skews very wealthy, Cari Gray has proven again and again that you get what you pay for.

“From my earliest memory growing up on the prairies of Canada, I’ve loved exploring the world with my peripatetic parents who took me to all six inhabited continents. After law school, I traded in legal practice for a job at Butterfield & Robinson where I spent the next decade-plus biking, hiking and exploring the best of the world. Gray & Co. was started in 2009 when the niche of specializing in ultra-luxe travel for travellers who preferred private jets grew quickly. At Gray & Co., we take custom experiences and activities to new heights. We’ve got amazing repeat travellers who ask us where to go when they fire up their planes or yachts filled with toys.”

Q: Have you seen an increased interest in active travel among women travelers in the past few years?

A: Wellness has gained momentum for both men and women over the past few years, from yoga to hiking and more. The pandemic got people out of the gym or studio and empowered/directed them into the great outdoors, from hiking trails, to bike paths to kayaks and so much more. Women are amazing travellers and appreciate how we set them up to win – they are resilient, curious, passionate and FUN!

Q: Have you done anything as a company to encourage or facilitate travel by women?

A: Most of our guides and planners are women, and since all our trips are custom, we can really cater activity specifically to our travellers. It’s funny – men are more likely to overestimate their athletic ability, and women to underestimate. So, we always keep that in mind and make sure women have all the choice and flexibility to do both that they want, and what they’re capable of – with plenty of support of course!

Q: Almost all of your guides and staff are women. That is unusual, so why?

A: Since we specialize in crafting private trips around the globe, we recruit multi-lingual, athletic, highly capable and collaborative team members. We also offer a very flexible work environment. As a result, we have had a solid core at Gray & Co. since we started in 2009 and most of them just happen to be women!

Q: What trends have you been seen recently or expect for the future in terms of types of travel or who is traveling?

A: We see couples, friends, mulit-gen, girlfriend getaways – all of the above. They come to us since they know that we can cater to all ages, abilities, interests and more. It’s about the best balance of time together, time apart – crafting the days but also making sure there’s plenty of choice and flexibility.

Also we’ve seen a trend towards wanting to reconnect with friends and/or family around the world.

Q: What destinations are hot right now and going forward?

A: Right now, there are a variety of destinations we see appealing to women:

After being home or restricted for the pandemic, they want to go to those iconic places that they have seen or read about: Machu Picchu trails, Galapagos animals, Patagonia windswept landscapes, Tuscany’s towers, Paris bakeries and more. Some adventurous folks have decided to go beyond where they go regularly, so Croatia, Greece, Iceland, and Norway are all on the upswing

Domestic travel is still very hot. Travel within the U.S. got better-appreciated over the pandemic, and road trips are still fun! Women love the many stylish new and renovated resorts and spas. There are more new wellness and outdoor options, especially on the East Coast, such as Blackberry Mountain, High Hampton, and the new Southall Farm.

Wine areas continue to flourish for tourism. Just look at the explosion of new options in Napa (The Madrona, Stanly Ranch, etc.), as well as Santa Ynez, Oregon’s Willamette Valley, etc. Globally you see the expansion of Six Senses (Israel, Ibiza) and Auberge Resorts (Los Olivos, Bishops Lodge, Alta Gracia). Guest ranches are also popular with women and families, and are sold out everywhere this year, from the ultimate Ranch at Brush Creek, Wyoming to Three Bars Ranch in British Columbia.

Q: What does your company do to make travel as great as it can be – what makes your company special?

A: We take custom/private/bespoke to the highest levels possible in the planning and production of the trips. Our guide producers and local experts review all aspects of the trip before the travellers arrive – meeting with hoteliers, chefs, yoga instructors, massage therapists, local experts and re-inspecting the bike or hike routes in advance. We’re always on the lookout for what is new or original and unique/exclusive experiences, events, meals, encounters etc. Once the trip is underway, our team keeps all these things running seamlessly, pivoting effortlessly for weather or changing preferences. They are there to make sure that choice and flexibility remain paramount!

Q: Do you have any advice for planning a trip or picking a trip or destination?

A: Until we have a better control of the pandemic, it’s important to travel with COVID tests and EMED proctored tests in your carry-on in case of delays or travel changes. Make sure you have plenty of your prescriptions in case you do get delayed returning home.

If you are travelling with kids, keep yourself rested, travel early in the day, and choose hotels with pools, places to roam, and good kids menus or room service.

Keep in mind transfers between points on your itinerary. We always try to keep them to a minimum so that travellers are on bikes, trails, paths, exploring and learning as much as possible. When you do have to move, make sure that vehicles, planes, or helicopters are spacious and comfortable. Good planning makes a big difference!

Q: Any other thoughts that you think would be of interest to active travelers or women travelers?

A: The world is getting easier and safer to explore for women. There are more bike lanes within cities and across countries. When we first started cycling in Australia a decade ago, no one was biking the Barossa or on Kangaroo Island or Margaret River – now there are bike paths and routes everywhere! Advances like e-bikes are opening up new territories and distances and evening out disparities between couples and friends. Cycling is getting a higher profile, and that is for all kinds of cycling. More and more trails and caminos are being identified and marked for hikers: now it’s easier hike in Kumano Koda, Japan or Iwate, Tasmania. There are new trails in the Cinque Terre, Alpe Adria etc. We just had some women hike the Via Francigena trail in Tuscany from Florence to Siena – stunning!

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