Travel Expert Shares Top Destinations & Her Secrets to Travelling For Free, Making Hundreds of Friends Worldwide

“I’ve always loved travelling,” she says. “But more than places, I find people inspiring. Their stories, their backgrounds, the way you can connect through food or shared experiences.”

That curiosity started young. Japan, her favourite destination, had captured her imagination long before she ever boarded a plane. “I was obsessed with manga and anime as a kid,” she laughs.

“I’ve visited 42 countries – and Japan & Costa Rica are the destinations I would happily go back to. Japan because it’s unique, the fast-paced and modern mixed with peace and respecting tradition, and incredible food - that mix gets me every time. Costa Rica is stunning, and the wildlife is breathtaking – I was also very moved by how much Costa Rican’s care about keeping their country pristine”.

Anna often found her travel dreams didn’t quite align with her friends’. “It’s not that I didn’t have people to travel with,” she explains. “It’s just that sometimes you want to go somewhere they don’t. Asia together? Amazing. But South or Central America? That was more my thing.”

While researching a trip to Costa Rica and yearning for freedom and connection, on a whim, she applied to be a Travel Co-ordinator, sending in a short video as part of her application. Months later, she found herself back in Costa Rica — this time leading a group of strangers on an adventure that would change how she saw travel entirely.

Anna says, “Being a coordinator is like a duck,” she says. “On the surface, you look calm. Underneath, you’re paddling like mad.”

Although her job, travelling with small groups of solo travellers in their 20s,30s and 40s, may look carefree and exciting, she says that preparation is constant — checking hotels, transport, contingency plans — and sometimes things go spectacularly wrong. On one Costa Rica trip, within three days, Anna had arranged three separate doctor’s appointments: a toothache, a stomach bug and a fractured thumb from volleyball. “Our group chat just turned into X-ray photos,” she laughs.

But it’s her background in theatre that really helps how she leads. “Producing shows teaches you empathy,” she explains. “People come in with different moods. My job is to make a safe space — and it’s the same on trips.”

That care pays off quickly. Anna usually sees groups click within days,. “Suddenly there are inside jokes. Banter. You can actually feel the energy shift.”

She says reading the room is instinctive: “I know when to joke, when to be gentle — I want to make people feel seen. Once they relax, the walls come down. Then they start joking with each other, it’s often easier for people open up in a new environment.”

“It becomes this little ecosystem,” Anna says. “For a week or two, that’s your whole world.”

Sometimes, those shared moments are wildly unexpected. Like the night in Kyoto when Anna’s group turned a bar into an impromptu karaoke dance floor — locals and strangers partied, singing and dancing together. “The owner just laughed and said we’d made his night.”

Or the Japanese onsen — a communal hot spring where nudity is non-negotiable. “At first some people in the group were nervous. We’d only known each other a few days,” she says. “Then suddenly it was like, ‘Oh — no one cares what I look like.’

Anna says moments like this matter - because they change people.

She has watched travellers surprise themselves — the woman terrified of heights who ended up zip-lining in Costa Rica, the shy participant who swore she’d never do karaoke and ended up loving it. “With the support of the group, people try things they never thought they would. And they feel proud of themselves for doing it.”

For Anna, there’s magic long after the trip ends. Group chats continue long after the flights home — sharing memes, jokes, memories and friendships. Many of her former travellers are now close friends. Some visit her in London. She visits them in Manchester, Portugal, Lisbon. “It’s like having a little family everywhere.”

Despite the pressures of logistics and responsibility— Anna never tires of it. She remembers sitting on a Caribbean beach after a trip, watching her group laugh together:

“I had this moment of thinking, ‘I’m here. I’ve always wanted to be here. And I’ve made sure everyone’s had the best time.’ It felt like achievement, I gave myself a pat on the back.”

For anyone scared of travelling solo, Anna’s message is simple: you don’t have to do it alone.

“Being part of a group keeps you safe, but it also opens you up,” she says. “You come home changed — not because of how far you travelled, but because of the people you shared it with.”

Anna works for WeRoad, a group travel company bringing together solo travellers, and that’s what keeps her saying yes to the next adventure — “watching strangers become friends is the most rewarding part of my job”.