“Do what you love and the money will follow.” When I heard Oprah Winfrey say that in an interview many years ago, it somehow stuck with me. And it was one of the first expressions that came to mind when I decided a year and a half ago to start an Italy travel-planning business. Of course, I wasn’t aiming to make billions like Oprah herself, but I took it more as encouragement that it’s possible to do what you love and make a living from it.

As I talked about in my previous Jewish Link article, my passion for all things Italy—and travel, in general—has spanned more than two decades. I read about Italy extensively, I spend an embarrassing amount of time researching it and I naturally often make it my travel destination when I am able to get away…without the kids.

So, when friends—and friends of friends—continuously called upon me to help them plan their Italy trip, it finally dawned on me that instead of treating this as a hobby, maybe I should consider taking it to another level and perhaps become an official travel planner. After being a stay-at-home mom for many years, I never thought it possible that in my mid 40s I could ever start my own business. However, the time was right. My kids were getting older and less dependent on me. But, at my age, could I really start a business? I was terrified of failure but, at the same time, I knew I had to do it. Five Star Italy—your Italian travel concierge and planner—was born.

I started slowly by taking the steps one must take to actually start a business. However, this quickly became real. What I, deep down in my heart, did not expect to happen, happened. I got clients! Many clients. Now, I know that should be a good thing. No, it should be a great thing. But, very soon I was faced with the reality that this was way more than a hobby. This was the real deal and there was way more involved in travel planning than I ever anticipated. So, instead of panicking (truth: I did do a little of that), I just dove in, did what I had to do and learned as I went along.

A humbling thought hit me early on; I was solely responsible for creating peoples’ once-in-a-lifetime trips and memories, making sure my clients’ experiences were nothing short of perfect. For some clients, it was their first trip to Italy. For others, it was something they had been dreaming about for many years. And, for all of them, they were spending their hard-earned money on a trip that they deserved to have exceed all their expectations. All those realizations were extremely sobering for me. This was officially not a hobby anymore. This was serious and it was something I not only wanted to succeed at, but I had to.

I didn’t think of myself as a “start up” but, looking back, I can definitely say there was a start-up phase. There were many days where there was no time to breathe, to sleep, to eat (silver lining: I lost five pounds). At the same time I was busy trip planning, I was also working hard to build partnerships in the industry.

At the beginning, going from zero to 60 felt, at times, quite overwhelming. But, when I came out the other side, I could clearly see how it was the best thing that ever happened to me. It forced me to face challenges and hurdles—oftentimes, simultaneously—head on. I learned a tremendous amount from each and every experience, which has now filled me with a confidence I’d never thought I’d have. To the point where I am now looking at ways to grow my business. Some clients have already reached out to me regarding the possibility of planning their next trip, whether to Spain, the Greek Islands or elsewhere. Although the name of my business specifies Italy, it is the the “Five Star” part of the name that will feed my business going forward. My passion to serve my clients with attention to every detail, to be accessible to them for anything they need and to deliver to them nothing short of a five-star experience, can and will extend to any vacation destination.

One of my concerns when starting Five Star Italy was: Will turning my love of Italy—and all travel—into a business diminish that love? Will it now become a chore, redundant? Will I have so much Italy overload that I will never want to return there myself? Not only were those fears completely unfounded, the opposite happened. With each new client, I became more and more energized, so eager to make them all fall in love with Italy the way I have. I heard the excitement in their voices to go to this place that they had dreamed about going to for so long and I wanted so badly to make it into everything they were expecting and more. I truly put my heart and soul into each trip as I felt immense responsibility to each of them.

The moment of truth arrived when my clients started leaving for their trips planned so long ago. Unexpectedly, I started to get the texts, the emails, the pictures! “This hotel is beyond amazing!” “This is the most beautiful place we’ve ever been to!” I especially loved getting all the pictures. Most clients I didn’t know by face, and then I would see them, in the pictures they sent me, smiling from ear to ear, standing along a cliff on the Amalfi Coast or by a canal in Venice. All the planning, and all the hard work more than paid off. My dream came true. My clients were all falling in love with Italy just the way I had on my first trip 20 years ago. I was overwhelmed with gratitude that my passion—turned into a business—was also something that would bring so much joy to people. It is my goal to have every trip be a trip where my clients will come back and say, “That was one of the best trips we have ever taken and we loved every minute.”

That is the essence of Five Star Italy. It is a company that will plan and personalize your Italian vacation from start to finish. One that Google could never plan for you; your itinerary is yours and yours only. You will be treated like VIPs at all the hotels you stay in. I happily relay all my little “secrets”—best places to walk and hike, to shop and to eat (and, of course, drink!). And so much more. In short, you are taken care of from the moment your plane takes off until the moment you land back home.

Although I have now planned trips for all sorts of clients—Jewish and not Jewish, younger and older—I see what it means to my Orthodox clientele to have a travel planner who understands their needs. It is a great relief for them to have someone who is not just familiar with their destination, but with Shabbat and kosher food as well. I can plan an itinerary for them that makes sense in terms of the ideal place to be for Shabbos and I can guide them about how to obtain the kosher food they may need while in Italy.

I was very fortunate to have been able to return to Italy this past summer. This was going to be a new experience for me. A vacation but a “work vacation.” Again, I worried. Would I enjoy it this time? I had many things on my to-do list but, most importantly, I had to look at everything with new eyes, discover new magical places for my future clients. And, once again, my concerns were completely unfounded. I visited several new destinations while re-visiting old favorites. I absolutely loved meeting my on-the-ground partners—tour guides, hotel managers—and sharing with them the passion to make sure our mutual guests always have 100% satisfaction. I made sure to visit new “off the beaten path” places so I can convey to my clients that Italy is way more than just Rome, Florence and Venice. Although those are a must, almost every place in between is a must, as well; Lake Como, Capri, Sicily, Tuscany, Puglia, to name a few. Each place will be sure to capture your heart.

I still have tons to learn and many ways I’d like to grow. I still have—and will probably always have—moments of self-doubt. But, I can honestly say that I also have moments when I feel like I am living my dream. To think that going to Italy is now a must for “business purposes,” I never would have believed that could be true! And, I am filled with gratitude to my family and friends who encouraged me to embark on a completely new and unknown journey, to Italy and beyond.

Rachelle Stepner, owner of Five Star Italy, can be reached at [email protected] or on Facebook @fivestaritaly. You can follow her on Instagram at Five.Star.Italy.

By Rachelle Stepner

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