A born-and-bred Bermudian, Alison circulated the arty crowds of New York and Los Angeles as a screenwriter before returning to her homeland. That was four years ago, and she hasn’t looked back since.
An avid explorer of the world and woman of many talents whom we suspect may just be Superwoman in the flesh. This mother of three has two jobs she wouldn’t give up for the world and still finds the time to explore off-the-grid villages in remote parts of the world.
When she settled back in Bermuda, Alison started working for her family’s real estate business, and when she met William, Winnow’s second co-founder, she realized that she couldn’t pass up on the opportunity to team up with him to promote her beloved island, but also other destinations around the world that aren’t necessarily on the well-trodden bucket list travel trail, to travelers looking for more immersive ways to experience new places. “Our starting point was: why don’t more people come to our home island of Bermuda?”
“A lot of people were coming to Bermuda and not seeing the real Bermuda nor. There was a total disconnect,” she tells us. “People seeing its generic side, and sitting on crowded beaches, when it didn’t have to be that way - and that’s the same for many other destinations, not just Bermuda.”
When she realized William was on the same page she decided that despite an already busy lifestyle, getting people to see the local side to destinations was her calling. Fast-forward to the present and the pair have launched Winnow, a platform offering an edit of key experiences currently live in Bermuda and Aspen (with more to come in the US and Europe), led by local experts, many of whom she knows first-hand.
We aim to give travelers experiences you can’t just Google.
Aspen was a natural second choice for the duo as it’s niche enough to craft cherry-picked experiences, but it’s also on the radar for the Winnow demographic - meaning travelers looking to connect with nature, themselves and others.
For the Winnow co-founder, ever since her first visit to see a friend who was working out there (who happens to be the Winnow Rockies Destination Lead today), Aspen has always stood out, especially coming from Bermuda. “My flight was the last one to land before a big snow storm. It snowed for three days. Everything was covered in white. I had never experienced anything like that before. I just remember sitting in the hot tub as these big fluffy snowflakes fell down and thinking how beautiful it was.”
However, as well as providing the means to get under the surface of a dream destination, that extends beyond, for instance, spending days shuffling between a sun lounger and the ocean, it’s also important for Alison to convey a destination’s natural beauty from an ecological standpoint by encouraging people to explore the wildlife. And that’s where the importance of working with locals who are really in the know about a destination comes into play.
As a result, you’ll notice that Winnow offers a range of bespoke activities that almost always involves learning about the Bermuda’s biodiversity, from its famedto its as well as the option of for an even more immersive experience, allowing visitors to take away a lot more than a tan. And in Aspen, Winnow experiences allow travelers to explore the natural surroundings via to with a local expert. And all at the click of a button.
“There was no website where you could just go and book a quality experience that had been tried and tested by locals without going through an agent – and I know these experiences are of a high caliber because I’ve sourced them myself among my network.”
“As the project evolves, we’ve realized that Winnow is giving travelers who want to explore beyond the main sites ways of gaining genuine insight into a destination – essentially providing them with experiences you can’t just Google.”
Aspen for instance, is managed by a local insider within Alison’s close circle of friends, and that’s the way the Winnow founders want to keep it - ensuring that experiences are always sourced by someone they trust and who shares their vision of travel is essential in keeping up the quality and immersive local travel angle.
Travel should be experiential and authentic. That’s why I usually travel where I have local intel that allows me to get to know a place beyond the guidebook.
In fact, several years after having her third child, Alison undertook a big solo trip to South Africa and Mozambique to on a safari for a friend’s birthday. And it turned out to be one of her most memorable travel experiences.
“I was so busy leading up to it, I really did not have any expectations. Many friends of mine had been on safaris and go back every year because they love it so much. I was not sure if I would share their enthusiasm. Then you get to the bush and find yourself spending hours with these amazing animals just being still and watching them in their natural habitats. It really cleanses the mind from detritus of our fast-paced, complicated lives. Everything slows down so you can really soak in the awe of our beautiful planet and return to what is essential and nourishing in your life.”
However, it was in Botswana, while on a riding expedition through local villages that lay completely off the grid, that the expression ‘soul stirring experience’ truly came into its own for Alison. “It all felt so far removed from anything I had seen before,” Alison tells us. “And I was so grateful for being able to experience something so powerful, all thanks to my guide – a local who looked after horses in the area.”
While Alison knows that immersive experiences of the latter kind aren’t for everyone, there is a segment of people looking for something more than what’s offered on most travel sites, and the surge in volunteer travel confirms her initial feeling.
However, there are other options too. For instance, by traveling deeper, travelers are essentially investing in smaller local businesses as opposed to the larger corporations based offshore. And Winnow, a company which works only with locals, thus keeping the cycle short, is a great place to start.
Alison talks to us about what she wishes she could take credit for inventing and where she thinks travel is headed for the year ahead.
If you hadn't created Winnow, you would have...
One job! And I would have more time on my hands.
When you are traveling, you are stressed out if you don't have...
You wish you could take credit for...
Your most stand-out travel moment...
As mentioned above, horse-riding through the villages of Botswana.
On your nightstand in your hotel room when you're on the road, we would find…
Your pet peeve when you're traveling…
People who complain.
The app you use routinely…
The New York Times’ app.
Your best meal is…
It has to be a meal I had in Ibiza at a restaurant that overlooks two huge rocks that jut out of the ocean. The food was incredible. We had clams with a garlic broth – it was such a simple dish but the flavor was insane. It just goes to show how the best things can also be the simplest things.
Your comfort food is…
The latest series you binged on was…
I don’t really have time to watch series.
The top travel trend of 2019/2020 is…
I think that the next travel trend is options for people who don’t have children or who are looking for more adult-only vacations and hotels. And those who do have children are choosing to go away with friends instead; I mean, our parenting style today tends to be a lot more intense, so people are looking for a release.
Your absolutely favorite spot where you'd happily spend the rest of your life is…