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Meet Beth Rubin of Olive Tree Escapes in River North

Today we’d like to introduce you to Beth Rubin.

Beth, can you briefly walk us through your story – how you started and how you got to where you are today.
I started in the travel industry in 2000 – I had just come back to Chicago after student teaching on a study abroad program in Italy. I was teaching photography for an art school, so I had a very strong background in art history – having spent time up close and personal with all of the Renaissance works you find in Florence, Rome, Venice, etc.

Before going to Italy, I had been in the publishing industry in my previous life and knew I wanted to try something new. There was an ad in the local paper for a start-up travel company, so I decided I’d take that until I figured out what I wanted to do… Almost 18 years later and my resume is still on a floppy disc. I took on the challenge of itinerary planning, and rose to the top of the company pretty quickly and stayed there until I no longer felt like it was a good fit.

I had really enjoyed working with the clients – getting to know them as people, what they liked to see and do, how they liked to travel. I wanted something more – I wanted to work with the clients I wanted to work with, and offer the services I felt were worthwhile experiences. I didn’t want to just sell something to someone because it made money. I always want to put that extra personal touch into each trip I plan. This is why people come back to me time and again, and this is why I was on the Travel + Leisure A List of top travel specialists to Italy, twice.

So in March of 2017, I struck out on my own and opened Olive Tree Escapes – designers of luxury bespoke journeys to Italy and Croatia.

Overall, has it been relatively smooth? If not, what were some of the struggles along the way?
Definitely not. It was hard to extricate myself from the old and move to the new. Not only for the old company but for clients that expected the same business model from my new company. I had to leave my comfort zone, but I needed a new challenge, and I needed to follow my own dreams – not the dreams of someone else. It was also a struggle to move from being a colleague to being an employer – there is that fine line you have to watch when it comes to friendships and business.

Alright – so let’s talk business. Tell us about Olive Tree Escapes – what should we know?
Olive Tree Escapes is a travel company that provides luxury bespoke journeys to Italy, Croatia, Slovenia, and Montenegro. We specialize in designing upscale and customized experiences for the discerning traveler. What sets us apart is that we focus 100% on the Mediterranean area in order to achieve a level of expertise a notch higher than large-spanning operators, and our travel designers are US-based to help you plan the trip, while you still get the full support from our on-site offices in Italy and Croatia.

I am very proud of the fact that I know all of the suppliers I do business with on a personal level – I travel to Italy 3-4 times per year and visit with these people. I try out the tours, I stay in the hotels, I drink the wine… But the one thing I am most proud of is that I now operate a woman-owned business. Hard to believe that in this day and age this is still a bragging right, but it is true. In fact, one of the craziest things about the travel industry itself is that it is primarily operated by women, but the majority of actual owners are men. So the women are doing all the work, and the men are collecting the profits.

Any shoutouts? Who else deserves credit in this story – who has played a meaningful role?
My mentor was the man who originally hired me back in 2000. He has since passed away, but he really took me under his wing that first year, and then consequently let me spread my wings once he realized what I was capable of accomplishing.

Now, with the birth of Olive Tree Escapes, I owe a debt of gratitude to my family – specifically my husband, who told me night after night, month after month that it was time to break off on my own and start doing what was best for me. The clients that I had previously worked with went out of their way to find out where I had landed – I am still getting calls and emails from people who googled my name and wanted to work with me again. All of this and the exceptional team I have assembled have made this such a great new adventure.

How do you, personally, define success? What’s your criteria, the markers you’re looking out for, etc?
I define success based on the happiness of my clients – when they return with happy memories, and they are so grateful, it really makes my day/month/year. Especially when I have planned a trip for a travel agent’s client, and the agent says something like “you made me look so good”.

Contact Info:

  • Address: 320 W. Ohio St.-3W Chicago, IL 60654
  • Website: www.otescapes.com
  • Phone: 312-257-2432
  • Email: beth@otescapes.com
Image Credit: Ingrid Bonne


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