Women in Travel: Embracing the Adventure of Business Ownership

As a tour director, a huge contributor to my job satisfaction has been the relationships I’ve developed with incredible colleagues around the country. Women in travel are well represented, not only over the road with groups where my role lies, but also behind the scenes, in support operations and right on up to chief administrators and owners.

I noticed early on that many women in travel have embraced the challenges of heading their own businesses devoted to designing and operating tours for their clients. I reached out to several of these women about their varied paths to success and was delighted by the articulate, thoughtful responses from two women well estabished and respected in this field. I was also struck by how well their answers affirmed each other’s: although their companies’ missions are distinct, they have discovered similar paths and rewards in the travel business, with steady, targeted growth and supportive relationships being common themes.

Their insights are useful not only to those considering a foray into the booming market for group travel but to anyone seeking models for success in the business world. For the rest of us, they offer wonderful experiences and places to entrust with our quests for new adventures!

women in travel

Helen Medler has owned and operated Hawthorne Tours of Salem, Massachusetts for 28 years. She specializes in custom-designed tours, from the culturally enlightening to the just plain fun, throughout New England and well beyond, primarily for pre-formed groups such as corporations, clubs, schools, churches and families and friends. Her team can provide meet-and-greet and local guide services in the greater Boston area. In addition, she has designed dozens of tour possibilities to explore on her web site but can tweak each itinerary to a group’s liking or start from scratch for the tour of your dreams.

women in travelJudi Wineland bought AdventureWomen Travel along with her two adult daughters just over a year ago, but she’s been in the business a long time. Her company specializes in experiential travel to unusual destinations for women of all ages, helping them to get outside their comfort zones both physically and socially with the aid of trusted travel directors. Mt. Kilimanjaro? Morocco? Peru? Bhutan? and many more: these are truly special opportunities for women to grow and bond.

Here are the things I wondered about women in travel, and Helen and Judi’s responses:

What prompted you to establish or assume leadership of your travel business?


Hawthorne Tours was owned by a friend who was looking to go into semi-retirement. The business, at the time, was a local, small receptive, and I felt that I could take what was already established and add my experience planning tours for groups throughout the Eastern U.S.


I am the owner of quite a few businesses. When one is an entrepreneur, one sees opportunity practically everywhere. It is hard not to want to be part of so many endeavors, but when the past owner of AdventureWomen approached me to buy her company, my daughters and I saw an extraordinary opportunity. Opportunity is often about building on the history, skills, and assets of a core company. AdventureWomen had the foundation, and we saw the opportunity to take a strong foundation and build a company that would expand its offerings to more women – from Boomers to Millenials.

What skills, understandings, and connections were you able to carry into your new position from a prior role or career, and what did you have to learn?


My degree from Salem State University was in social work. Directly after graduation in 1973, I had the opportunity for a summer job as a tour manager for a local motorcoach company. These were the early days of motorcoach travel, so the norm was “on the job” training. But, I was hooked. I had the opportunity to travel throughout the United States and never looked back. After the summer was over, I was asked to work in the group sales department, and I decided that this was the field that best fit my personality. My social work degree utilized many of those “people” skills that are easily transferred into the tourism field.

After acquiring Hawthorne Tours, the learning curve was going from employee to business owner. The “business” side of the business was an area that was really all new. I was fortunate to have great advisors who were patient with me!


I have been in the adventure travel industry for 40 years next year. With those 40 years come contacts that few could understand. At 28 years old, I met partners around the world who became life friends, who supported me, and who ran phenomenal ground operations. You see, being in the adventure travel business is about relationships. We were a small band, a small tribe of people who were seeking off-the-beaten-track adventures…going to remote places that few had been. The connections we had—and now (daughters) Nicole and Erica have—are lifelong commitments to one other. It means that we are there to support each other through thick and thin.

Regarding practical matters, what did you need? Think financial investments, legal requirements, personnel, materials, space…


I purchased Hawthorne Tours in October of 1993. As I mentioned, this was a small business, but it was well established. My predecessor had a team of local guides in place and hosted a lunch to introduce me to this great group of people. I secured a lawyer to handle the incorporation and took guidance from a Small Business Advisor. My husband had his CPA, so he took care of setting up the accounting, etc. Then, I joined organizations and had so many people who mentored me through those early years. I was able to have steady growth and add on employees as I grew, and move to larger office spaces at a pace that was comfortable.


AdventureWomen is not a start-up company, but we are treating it as a startup. We needed to purchase the assets of AdventureWomen, we needed to legally start our entity, AdventureWomen LLC; we needed office space, computer access, plus investment in key growth areas: PR with WEILL, SEO, new website, branding which included tag lines, logos, and a new look. Although the past ownership was a team of two, we envisioned a team of four. Growth was our mission.

Looking back, are there things you wish you’d known or would have done differently in making this move?


Actually, no. I am happy that I was able to start slow and learn at a pace that was not too overwhelming. Had I known back then what I am responsible for now, I don’t know if I would have taken the leap! Confidence in what you can do is based on experience. So, those early building blocks were important to the success I have now.


Nothing…we were fortunate to have drilled down with the past owner, spent time with her, and kept her key personnel on staff.

Are there special considerations, advantages, or challenges you believe you have faced in the industry that you can share with other women in travel?


The travel industry is exceptional in the opportunities that are presented to women. I have never felt impeded in any way. What this industry values is trust. Trust between clients, and trust with vendors and suppliers. If you treat everyone fairly and follow through on promises you have made, you will be respected in your field.


As a woman in any industry, there are incredible challenges. Being taken seriously by fellow compatriots who, in this industry, were predominately men has been a challenge. But, to be honest, being a woman in this industry was an anomaly and often in developing nations I was so different than the norm that I received special attention. But if I was with a man, I lost my role as a leader, as my male friend won the attention.

Where do you see the travel industry going over the next five to ten years, and what role will your company play in that?


Looking back on the last 10 years, and seeing how technology has changed this industry, it is hard to imagine what 10 years in the future will bring. I do think that on the adult side of travel, the baby boomer market will once again revolutionize travel. They are active, involved, interested, and want tours that reflect this “living with gusto” lifestyle. Since all of our tours are customized to meet the needs of each client, we will plan each tour to reflect their interests.


The travel industry will go where the buyers go…perhaps Boomers buying transformational travel, or Millenials buying experiential travel…

What do you love about your job?


Well, I really do love my job. The opportunities that have been presented to me have been tremendous. First, I have an incredible staff. These are unbelievable women who care about this company and do their very best each day to offer a great experience to our young travelers, as well as adults. My success is built on the great people who are part of this company. The office staff, the tour managers and guides are the face of this company and I feel so lucky to work with all of them.

I have met other wonderful women in travel through my memberships in tourism organizations. We are a happy and gregarious group and quickly become friends over the years. Every convention is filled with laughter and hugs. It’s wonderful.

And lastly, this business has allowed me to help support my family and share the joy of travel with my husband, children, grandchildren and my friends. I am truly blessed to have spent the last 25 years with all the people that make up Hawthorne Tours. How could you not love this job??


Everything…it is my life.