Want to See Vermont? Or the World? Jump at the Chance to Travel with The Island Hopper

Sponsored by The Island Hopper

When Yankee‘s travel editor, Kim Knox Beckius, caught up with Tricia Heaton and her daughter, Courteney, they were on the other side of the world, “in a darling hotel in Amsterdam, along one of the canals.” They were adjusting to the time change and scouting the city before continuing on to Italy to greet their next group of “Hoppers.”

In just three years, the retired special education teacher and recent college grad have grown their Vermont-based tour company, The Island Hopper, by… leaps! Their 2024 excursions, as close to home as Vermont’s country roads and as far away as the plains of Kenya, sold out instantly. The Island Hopper (yes, we’ll find out what’s behind that curious name) promises something extraordinary for travelers, predominantly women. These trips are about experiencing places in community with others and sparking creativity that enhances joy and a sense of wellbeing. These are restorative retreats, not exhausting tours, led by women who understand travel’s power to nourish the soul.

Of course, Kim wanted to know how Tricia and Courteney started the business, as well as what the future holds. “Listen in” on their conversation.

Kim: What made you decide to launch a travel company?

Tricia: In 2022, I was staying at a villa I had visited before in Lucca, and I just blurted out: “I have to bring women back here.” I have Italian friends who have a hospitality business, and I asked them, “Will you help me?” They immediately jumped in and were very enthusiastic and found a villa for us. Then, I asked Courteney if she would help me. Courtney has traveled a great deal in her life, and she jumped at the opportunity.

Kim: How did you market the trip?

Tricia: I’m a needlepointer, and I posted on my Instagram account: “If I ran a trip to a villa in Italy, would anyone want to come and needlepoint with me?” And 300 women said yes.

So I went ahead and rented the villa. We took 60 women to Tuscany our first year, 20 at a time, and it was fantastic. We created a whole business about international adventures where women joyfully gather and create art and community.

Kim: You’re offering trips in New England now, too, right?

Tricia: Yes, some of our travelers said, “You write about Vermont all the time. Can we come to Vermont? So we partnered with the Barrows House in Dorset, and we had about 20 women participate in our first Creative Summer Camp for Women, and another 27 this year. We’ll offer the program for the third time in 2025.

Kim: Tell me about your upcoming fall 2024 trip to Kenya.

Tricia: We have partnered with the Kenya Drylands Education Fund, a U.S. nonprofit and a Kenya NGO. It was founded by Sarah Hadden and Ahmed “Kura” Omar. I have traveled to Kenya with them before. They started very small, collecting pencils, and now they build schools. They’ve built a library and a sports center. They have done tremendous work getting water into the drought-stricken drylands. 

When we started this business, I asked Sarah and Kura if they would welcome our Island Hoppers. They gratefully said yes, so we are going in October… 21 of us. The majority of the people traveling with us went to Italy with us last year. A few of them are bringing husbands, so this will be our first co-ed trip. The first of many, we hope.

Kim: Oh, so are you moving away from women-only tours?

Tricia: No, we are not going to give up those all-women trips because we find there are so many women who want to travel but don’t have anyone to travel with. Most of our clients are active women between the ages of 48 and 80. We have widows; we have women who have never married. We have women who are divorced. We have women whose husbands won’t travel.

About 50% of them come solo. Some have said, “I didn’t tell anyone I knew because I didn’t want them to come with me.” And what happens is when you remove women from their communities and people they know, they can speak really freely. They’re able to connect with other women, really tell their story, and be their genuine selves. 

Courteney and I sit at the end of the dinner table, and we watch what happens over the week. The first night, they’re kind of quiet. Next night it gets a little bit more lively. The third night, it’s loud, and the fourth night they’re screaming from one end of the table to the next. There’s just a magic we know how to create.

I did not anticipate what was going to happen with these friendships among our Island Hoppers. One woman sent me a note and said, you introduced me to my best friends. Some of these groups are so tight they are having their own reunions. Our Kenya trip will have women who were on all of our different Italy trips who don’t know each other yet. So our community is mixing now, which is really fabulous.

Kim: What are some of the special touches you bring to your tours?

Tricia: We have little journals for our Hoppers. We always have little projects, special gifts. We do a book club on every trip, so everybody gets a book in the mail before the trip. We work with Northshire Bookstore here in Vermont.

Kim: Tell me about the origins of your business name, The Island Hopper.

Tricia: Courteney has an autoimmune disease we had never heard of before, and she was in college in Colorado while going through the process of being diagnosed. I had a small needlepoint mail order business at the time. I just decided I couldn’t worry about shipping needlepoint anymore. I needed the freedom to go to appointments with her when needed. So I lived between Vermont and one island after another island in Florida, and I started a travel blog called The Island Hopper.

I thought our first Italy trip was going to be a one and done kind of thing. But after we sold three trips to Italy in eight hours, I knew we had to do more. We have a wonderful following of people who want to travel with us. I have had two branding people suggest we change the name. And so we went to our clients and said, “We’re thinking of changing our name. Maybe The Island Hopper doesn’t work.” And all of them said, “No, no, no, we love it. We love being Island Hoppers. We hop continents, and we love the vibe of it.” So we listened to our people.

Kim: It’s such a fun name. You’ve made me want to be a Hopper. What are your plans for growing the business moving into 2025?

Tricia: We’re taking two women with us to Italy who we are going to train to run trips for us. The more trips we run the better. We are also increasing our trips to Vermont. In addition to our summer retreat, we’re adding a fall trip in 2025. What’s better than fall in Vermont? We’re also looking to expand to other countries. Courteney is also going to work on launching some trips for younger people.

Courteney: My mom constantly reminds me to dream bigger. The dreams we started with are not the dreams we have now, and we’ve done things we never thought we would do.

Tricia: Our clients don’t just want to travel. These women want to get out and adventure and see the world, and we love them. We’ll take them anywhere, as many times as they want to go.

Kim: What’s the best way to find out about trips before they sell out?

Tricia: Our email list subscribers find out about new trips first. You can also follow us on Instagram @theislandhoppertrips.