Why I Started Happy Traveler

My Single Mom Story and Why I Started Happy Traveler

Travel fueled my soul. My first trip that made an impact on me was New York City in 1983.  My parents took me there for my 13th birthday. My mother and father were both decorators and appreciated fine decor so we stayed at the renowned  Plaza Hotel.  That was the beginning of me being a hotel snob. Thanks Mom. 

From there, I had the opportunity to study abroad during my senior year in college while at The University of Georgia.  Aix en Provence, France was the city I selected to study even though I studied Spanish throughout school.  Living in Florida, I studied Spanish, thinking it would serve me better.

My mother was born in Paris, France and had many French family living in Paris and Alsace.  I was to stay in France for one semester taking French 101….Bonjour, Je m’appelle, Hillary. After 3 months I could speak fairly well and I didn’t want to go home.  I then called home and ask my parents if I could stay longer. They said yes!  The year in Europe gave me the travel bug.  I traveled to 13 of the 50 countries in Europe most via a Euro-Rail train pass with a group of American friends I had made.

After graduating from college, my best friend Stacey, who I had known since I was 3 years old, also had the travel bug. She had a grandmother who traveled the world in luxury. QE2, Smithsonian journeys, you name it her grandmother did it.  She inspired my friend to travel the world and I was on board. Funny how grandparents have the ability to inspire you.

We made one big trip a year. Stacey was a teacher and I owned my owned my own digital ad agency. I had owned one of the first digital ad agencies in the USA, called .Com Marketing. So we took off during her school breaks. We used the reward miles from the millions of ad dollars spent on Google AdWords I placed for our clients on my credit card.  We were determined to see the world!  Our first trip was Jamaica to attend SumFest, the reggae music festival.  We are both huge reggae fans.  We went the next year to SunSplash, another reggae music festival.  We were hooked and got the travel bug.

Stacey’s grandmother passed away and told her on her death bed, “Darling go see the world”.  Her grandmother never made it to Ankor Wat, so we were determined to fulfill her grandmother’s wish and travel to Cambodia. Luckily I got invited to a Thai wedding of an ex boyfriend and I asked if I could bring a friend.  He said sure, and we were off to Thailand/Cambodia just like that! 

Our passports began to fill up…..China, Canada, Hawaii, Peru, Columbia, Mexico, India, Burkina Faso, Mali and Turkey.  Pretty impressive travel for two working girls in their 20’s and 30’s.  If you get to know me, I have some hysterical travel stories….some that are jaw dropping. Others I need a few glasses of wine to tell.   

Then in 2007, the travel ended and the diaper changing started.

Since I was a business owner of a very busy digital ad agency, life revolved around my business, speaking engagements and buying lots of digital media for our clients. Many of my clients were in the travel industry so that helped fulfill my travel needs living vicariously through the landing pages of vacations I was promoting, but not attending. 

I delayed getting married and having children due to my focus on my career. It was a path that I look back on and wonder what happened to my time?  That being said, my clock was ticking and I wanted a family so I proceeded to have a family on my own.  I am a single mother by choice, which means I had my children on my own via a donor. I had my first child at 37 and my second at 42.

I vowed that I would take my children traveling and show them the world at an early age.  Ha! What a joke.  I also vowed to never let them watch TV or eat chicken nuggets. Let’s just say my daughter is a chicken nugget connoisseur.

I didn’t travel with my children internationally, but I did take them on trips domestically in the USA.  While others thought I traveled extensively, I didn’t think so. My daughter’s teacher credited her A in social studies to the fact that we traveled as a family and my daughter was “worldly.”  I disagreed. While I loved showing my children the amazing U.S.A., I wanted to show them the world.

Traveling was difficult during this time, as I was going thru fertility treatments to have my second child. Traveling was pretty much out of the question during this time. You have to stay close to your doctor.

I would say from 2007 to 2014, I didn’t travel much with my children. I did travel internationally with my BFF, Stacey.  We traveled to Peru, Columbia, India and Turkey, sans kids.  I got re-fueled with travel. But my children still didn’t go outside of the states.

Family travel stressed me out. I have to admit it.

Why? Many reasons…  It was hard to travel through the airport.  I was nervous they would cry on the airplane.  I thought to myself, “What if I get sick on vacation, and I am the only adult?”   So much went through my mind.  Plus, any travel I did with my kids I didn’t get to do or see the sights that interested me. What about me! No crafted cocktails, no foodie walking tours, in bed by 9pm. Traveling with kids was exhausting.  And there are not any adults to talk to.   

Stressful traveling. My children wrestling at The Lincoln Memorial, Washington D.C.

So I started to ask friends to travel with me. I found that it is hard to convince friends to travel.  They say they want to travel, but when push comes to shove, they didn’t pull the trigger. If you have friends or family that travel with you and your children, consider yourself lucky.

My mom friends said, “Go on a cruise!” What? I vowed never to go on a cruise.  All of my friends said it is the best for families as you have the kids club and can have some down time to have a nice dinner, read a book or dance the night away. I was super skeptical. It was against everything I believed about authentic travel.  Our first family cruise was the Disney Cruise in 2015.  Whoa!  Amazing! Disney never said no to any request we asked.   If I could take my Disney waiters home with me I would. I fell in love with cruising.  Mind you, our first cruise, I took our nanny with us as I was so worried that I would hate it.  I even thought if I hated it, I could fly out of the next island stop. 

Then I had a turn of events that re-fueled my spirit.

I had an “Ah ha” moment during a family camp.  My daughter, who was 5 at the time, and I went to a family camp in North Georgia, called Camp Ramah. This is where I learned that family travel can be fun for both the parent and the child.

At this family camp we spent meals together.   However, during the day we were split into different tracks for the adults and the children. The counselors took the children for the day.  After the evening campfire, all the parents put their children to sleep.  And then it was parent time!

The camp had arranged nightly adult activities that started at 10:30pm. We then left our rooms with our kids sleeping,  and prayed they would not awake.  The counselors were all sitting in the hall watching to re-direct the kids if they should wake and get them back to sleep. Most parents, say they could never do this, but we all did it and were thrilled with the opportunity to learn how to make sushi at 11:30 at night.  “Wow”, I thought, this concept is really cool.  The parents had a unique summer camp experience with other adults and so did the children. 

Family camp…..family travel.  Could this be a concept that could work for family travel groups?

My second “Ah ha” moment, was a trip to Israel, in 2016 with JWRP, on a Mom’s trip. I was selected to go with the Orlando group after a series of interviews and an application.   We were 500 women from around the world traveling throughout Israel with no kids. I had a defining moment on this Mom’s Israel trip. This moment  inspired me to get over my fear of traveling with my children.  I also decided to lose weight.  I felt that it was hindering my energy levels. You need lots of energy to travel with kids, I found out.

So I started to look into traveling with my kids internationally. I was disappointed as most of the family travel tour operators were the typical mom and dad plus 2 children. Being a single mom, I didn’t want to feel like a third wheel.

I scoured the web for single parent family travel and was disappointed that many of the single parent travel sites were closed or non- existent.

I then started two closed Facebook groups for both Single Parent Travel and Single Mothers By Choice Travel.  Single parents signed up in droves. These single parents were traveling and traveling internationally with their babies on their backs.  I was very impressed.

Some were like me and had family travel trepidation. They had the money, but not the confidence.  The notion that the majority of single parents are in poverty is false. Many single parents today do very well for themselves.

Finding resorts or destinations that cater to the single parent took hours and hours of research. Finding a resort that had a kids club that would take various ages of children was hair pulling.  Why didn’t I hire a travel agent? I didn’t know any of them existed for single parents until l started digging deeper.

I wanted a site that had multiple single parent family tours with liked minded single parents, not a single parent dating vacation.  Couldn’t find it.  So I decided to build what I want to see in the travel industry.  Single parent family travel opportunities.

In April of 2018, I met Sally Black of vacationkids.com. She was wonderful, full of travel information and believed in what I wanted to do. We hit it off.  She sent me her book, Fearless Vacations. 

Sally said that a family has 15 times during the life of a child to go on vacation before they don’t want to vacation with Mom anymore. That stat freaked me out and I decided to make sure that I was going to take advantage of the precious vacation time left with my children.

As for me, I wanted to travel with other single moms. Single parents love to travel, but many, like me, want to travel with other single parents.  I wanted to put the kids to bed, open up a bottle of wine, laugh with others and enjoy my vacation at the end of a busy kid filled sight- seeing day.   But where are these single parent family tours to be found? 

I founded HappyTraveler out of frustration with the lack of attention given to the single parent travel market.  Which in my opinion, is a untapped niche. With 40% of parents being single, there was little focus on this group of people who have a desire to travel. 

Single Parent Family TravelOur logo makes me happy.

I hope this site inspires you to show your children the world and know that we have your back.  You can travel with other single parents and open that bottle of wine at the end of the day with a new friend and be a happy traveler with your children.

We want to hear your ideas on how you have achieved being a Happy Traveler.

Hillary Bressler


Happy Traveler


Professional bio

Hillary Bressler is a travel and hospitality digital marketing expert with 20 years solely focused on digital marketing.    

Ms. Bressler is the quintessential “Digital Marketing Swiss Army knife” – she has the tools, skills, and experience to improve any organization’s market position. She has been marketing and selling online since 1994 and has more than twenty years of digital marketing experience, including seventeen years as CEO of .Com Marketing, a top interactive ad agency in the U.S.

Ms. Bressler has a track record in spotting industry trends and capitalizing on them before the competition. She continues to be an innovator and has a keen eye for marketing practices that are sure fire winners. An example: she led major brands to become the first advertiser on LinkedIn and Facebook and launched aggressive ads on Google Ad Words in 2001. Her greatest strengths are in online sales conversion, lead generation systems, integrating technology and operations, and a generator of new ideas.

Ms. Bressler is a graduate of the Grady School of Journalism at the University of Georgia receiving her Bachelors in advertising. Her experience at UGA provided an opportunity to study in France.

Ms. Bressler currently serves on the board of Full Sail University as digital advisor.  She is instrumental in integrating digital curriculum into entertainment, arts and technology bachelor and master degrees.  Most recently she acts as the Digital Advisor to FounderMark, which has built a focused portfolio of early-stage mobile properties and apps.

Ms. Bressler’s agency, .Com Marketing was successfully acquired in 2014 by Edgecore which was later acquired by Mindstream Media.  She currently acts as a fractional CMO for PinchHit Partners where she pinch hits for travel companies that are seeking CMO executive leadership and marketing.  Ms. Bressler also runs www.happytraveler.com as a source for single parent family travel.

Hillary grew up in Orlando, Fl., and lives in Orlando with her young children, Emma and Levi.

Contact me

Hillary Bressler