Travel Planning 101: How To Kick-Start The Travel Planning Business Of Your Dreams

Travel Planning 101 How To Kick Start The Travel Planning Business Of Your Dreams Travel Planning 101: How To Kick-Start The Travel Planning Business Of Your Dreams


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I’m so excited about today’s guest because I’m talking to Madeline Jhawar, who is one of the leading experts in travel planning. Madeline founded Italy Beyond the Obvious over a decade ago, after years of being the go-to person for friends and family members’ questions regarding travel to Italy. She had lived in Italy for several years, spoke the language, was super passionate about the culture, and eventually decided to turn her knowledge and expertise on Italy into a business. Madeline is one of the pioneers of this travel planning movement because she created her business before travel planning was a big thing.

In today’s episode, Madeline tells us all about her journey on how she became that travel planning expert and how she founded and grew Italy Beyond the Obvious. She also breaks down the differences between travel planners and travel agents, which is really important because there are some distinct differences in terms of the way each makes money, the legal implications for both, and of course there are pros and cons on either side.

After founding Italy Beyond the Obvious, a few years ago Madeline founded Travel Beyond the Obvious, which is an incredible program that teaches people how to become successful travel planners and run their own businesses. Again, she breaks down how you get started, how you can find your first customers and discusses the importance of niching down and having expertise in a particular region or area.

We’ve had a few travel planners on the show before, but this is the first episode that really breaks down what a travel planner is and how you can succeed in building your own travel planning business. I felt so inspired by the end of my conversation with Madeline, it’s a fascinating interview and I hope you enjoy it.

Founding Italy Beyond the Obvious

Madeline spent about five years in Italy for many different reasons. The first time she went to Italy, she was an exchange student after high school, and then she just kept coming back. First as a nanny, then as a tour guide for Butterfield and Robinson, and finally in her role as Southern European Operations Manager. At that point, she had lived in Italy for years, and people in her life would often ask her for advice when they wanted to travel to Italy. 

“I was the go-to person for everything Italy, and I loved it. People would call me, and they would say, where should I go? What should I do? And I was like, oh, I have so many ideas.”

When she had her kids, Madeline quit her job, because she had to travel too much for work. Instead, she wanted to get into the travel industry. She looked into becoming a travel agent and signed up for some newsletters, but she realized they were just trying to market stuff she didn’t need. “I know how to put together trips. I know, I lived there. I know the small towns. I know the logistics. I know the train schedules. I know the local holidays. I know how to search for amazing accommodations.”

She decided to just put up a website and charge fees for her time and expertise instead, like a consultant, and see if anybody would go for that. That was thirteen years ago, and Madeline even has people working for her now. So, travel planning is something people want, and the fee-based expertise has worked.

What is the difference between a travel planner and a travel agent?

Madeline calls herself a travel expert because she has a deep expertise. She is the expert who plans fantastic custom trips for people, but only for travel in Italy. She works directly with the client and doesn’t choose any hotels or activities based on commissions. “I charge my fees, which are separate and then everything else is totally transparent to the client. So, I don’t sell packages. There’s no middlemen, there’s no markups.”

While a travel planner is an expert who works directly with the customer, a travel agent is more of a generalist who has the relationships to be able to sell a great variety of packages and gets paid through commissions.

Madeline gives the example that a travel agent might sell a package that’s $20,000. “And in there, there are markups, there are middlemen and there are the travel agent commissions. And so people sometimes think like, oh, I don’t pay my travel agent anything. Well, yes, you do. It’s wrapped up. It’s in that package.”

What’s involved in travel planning?

Madeline explains the five-step process of her service. She starts with the creative overall itinerary, which involves asking questions such as “why are you going to Italy? Have you been there before? Who are the travelers? How much energy do they have? What are your interests?”

Then follows accommodations, tourism activities, logistics, and food and restaurants. At every one of those steps, Madeline suggests what she thinks the client will love, and then they say yes or no to that. Her recommendations are curated, because nowadays the main issue people face when planning their own travel is information overload. 

Madeline has even created an app that further supports people during their trip, so they have updated information at their fingertips while they are in Italy.

Teaching people how to become a travel planner

In order to start a travel planning business, you really need deep expertise on a specific destination. For years, Madeline had clients asking her if she could offer travel planning for other destinations, but even though she had some knowledge, it wasn’t enough to offer this service. On the other hand, experts on other destinations also came to her, asking her to teach them how to become a travel planner.

One day, a woman sent her a six-page Google doc full of questions, and Madeline realized she could turn this into a course. She created a step-by-step practical video course, and she thought she would just tell people about that when they emailed her with questions. But then she met her business partner who had a bigger vision and together they grew the course and community into something much bigger.

How to find customers as a travel planner

There isn’t one right way to approach marketing as a travel planner. You don’t have to be on every social media platform, but you need to be on some of them. Madeline also encourages people to set up their Google business page, because it helps you to be found on Google.

Another big thing you want to consider is trust. People have to trust you before they will give you their money. “People are searching online and they’re going to type in your company name, your name. They’re going to say, who is this person? Who’s behind the website? Is this a real person? Do I know them? Do I like them? Do I trust them? Do I want to give them my money? Am I even going to click to schedule a call? Am I even going to email them?”

Madeline says “Italy beyond the Obvious today is at 50% organic search customers and 50% referrals. So that’s how we get our customers today.” So, content marketing and SEO are a large part of her marketing strategy.

More from this episode

  • Do you need to go through any licensing to become an official travel planner? Or are there any legal requirements like there are for travel agents?
  • How many clients can you take on as a travel planner if you’re working alone and want to make sure you can manage your workload? Does it depend on the complexity of the trips you plan?
  • What are the most important criteria, the secret sauce, to running a successful travel planning agency nowadays?
  • Besides Covid, what are the biggest challenges Madeline has faced in the last 13 years of running her business?


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Kara Myers


I’m a former tourism professional turned web designer and podcaster. Tune in each week as I interview inspirational women crushing it in the travel industry. 

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