How to Become a Travel Planner

The two questions I get most about my life are: How do you live in Italy? And how did you become a travel planner?

A few months back I shared a blog on how I make it possible to live half the year in Italy. Now it’s time to discuss how I started my career and company Travel Italian Style. I am the CEO, Founder, and head Travel Planner (not travel agent) of TIS. I created this company after about 8 years of sharing travel advice for Italy with friends and family.

As a former tour leader in Italy and someone who had lived in Bella Italia for many years, I loved sharing my knowledge and would gladly offer this at no cost. I was working full time in the wine and events industry and it was enjoyable. Until one day I realized I was damn good at creating these travel plans and it was taking up more time then my full time job! In 2014 I officially started my own company.

If you are reading this article there is a good chance you have a similar background or you have the idea to start your own travel business too. Before you get started I thought it may be useful to share some practical tips I learned to consider before you dive into the business..

 Me chocolate making with our team in Sicily - 2015

Me chocolate making with our team in Sicily - 2015

  1. What is your “Why?”

This is a very good place to start.Why are you choosing this as a career? Do you like to plan and organize? Do you like socializing with people? Or maybe you just love Italy and traveling there.

The love of Italy was always in the back of my mind when creating this business. However, being a travel planner came about because of my knowledge of living and working abroad. I was able to help people and I loved that feeling!

Since I made this commitment my life has changed quite a bit. When I am here in this country you can find me researching, on the phone, focused on social media, or at meetings with vendors. Italy is more about working and less like my past vacations here. Some days I can not leave my hotel room or apartment. Even during a warm evening autumn Saturday evening (like tonight in Rome)!

While I enjoy about 99 percent of my time, at the end of the day this is work and I am committed to it. I am rarely casually strolling the cobble stone streets ignoring the ringing of my phone while enjoying a gelato. Or if this is happening there is a good chance a call will come through or I will have business to attend right smack in the middle.

Now to be fair, I am just 4 years into the business and I know my time will free up. I also chose to live in Italy half the year so I do get my time now and then to enjoy. However, if you are looking to launch a similar company it’s good to see a bit of the life behind the scenes. Not just what some social media shows us.

Yes, I have figured out a way to travel and enjoy my life while I am here. So can you. But I want to be clear. If you are doing to to look for free travel opportunities this is not the job. If you are doing this because you went to Italy (or any destination) just once and want to figure out a way to get back there or get a visa. I am also not sure if this is for you just yet. I really encourage you to visit a few more times before launching. Get to know the a city or country as a work location not vacation spot. Then see how you feel.

Being a travel planner is a little bit like my days of being a wedding and events planner. People wait for this big day for years and they trust you to execute. Many only get this one chance to travel so you they are counting on you. I encourage you to really love what you do and remember it’s about others not you.

First take a look at this list. If you feel ok with the following I say to keep reading!

  • I am ok with working long hours (15+) even when traveling.

  • I am ok with always have my phone in hand (especially during high season).

  • I am ok with sacrificing my own vacation for another persons.

  • I am ok with spending my own money to explore and research Italy (or fill in the destination of your choice).

  • Yes, I have patience.

I apologize if this sounds harsh. Listen, I really do not want to discourage you. However, I wrote this blog to give you the truth behind starting a travel business so you can be fully prepared when launching yourself. So it’s good to get the wheels turning and really dig deep. There are many travel planners out there. And there is plenty of work for everyone. However, be prepared to work it lady (or man)!

Figure out you “Why” and start to save your money. Then you are off to a good start.

 Our clients enjoying a homemade dinner in Basilicata - 2017

Our clients enjoying a homemade dinner in Basilicata - 2017

 

2. Find a Niche.

I know everyone says this, right? Well that is because it’s really important. This was the toughest part for me. When I started my company I wanted to create personalized and authentic experiences. However, I realized I was missing a bit of me.

 How I found my niche. Speaking about life and spirituality and selling Italian Travel. I was honored to be recommended to speak for TEDx! Germany - 2016

How I found my niche. Speaking about life and spirituality and selling Italian Travel. I was honored to be recommended to speak for TEDx! Germany - 2016

I enjoyed spirituality, public speaking, living in Italy, and writing. So I combined my love of all these things and became the TEDx speaking Travel Planner that lives 6 months in Italy and 6 months in NYC, haha! So now my clients reflect that. It’s a bit difficult to explain here but it works.

The point of finding that THING that makes you different is to keep the passion alive for you and to stand out. Do you special in women empowerment or biking? Are you a poetry fanatic or history buff?

These days it is common to hear travel planners say they are luxury travel, specialist, selling authentic experiences,adventure travel, outdoors gurus, overall travel experts, etc. It’s ok to use this terminology as well as it clarifies for the client.

However, I would not make that your niche. These are all very common. So try to put a twist in it and find one focus (if you can). If not choosing a particular kind of travel is a great way to start. Then start to test out a few markets. Take a chance to show your expertise. It may be the slower path but it’s worth it!

 Speaking for the National Organization of Italian American Women at Ciprani on Wall Street in 2016 with Fellow Italian American Entrepreneur Friends. We were featured in press in Italy and USA.

Speaking for the National Organization of Italian American Women at Ciprani on Wall Street in 2016 with Fellow Italian American Entrepreneur Friends. We were featured in press in Italy and USA.

 

3. Do you want to be a Travel Planner or a Travel Agent?

I can not give you an exact definition in order to clearly state the difference between these two careers. However, I personally decided I did not want to work only off commission, which most travel agents do. I also found most travel agents work with a host agency. A host agency is a company that assists home based agents with running their business. They interact and negotiate with most vendors so all you have to do is sell!

Being a travel planner means you may find yourself working independently.

I believe both jobs are essential to travel and are a great choice. It just depends what fits your lifestyle best.

If you are looking to be a travel agent I recommend researching companies such as Virtuoso.


4. Find the Right Vendors for YOU.

The most important part of this job is building a rapport with ethical and trustworthy people. If you decide to work independently I recommend meeting as many vendors as possible face to face. If you can’t make that happen then the host agency may be the better choice for you to start. Why? Because you are working as the middle (wo)man here and it’s important your clients are being taken care of by people you are rely on.

There are lots of things that go on in the back end of a business. You need to understand this.

How do you find them? Research. But my advice is not always to look for the “best” but the person who fits your needs.


5. Do I need insurance and how do I do my taxes?

Yes you need Insurance and you need to become an incorporated company to cover yourself. Don’t risk it!

Contact your lawyer, accountant, and your insurance provider to find out what plan is best for you.

 
 Grape Stomping and Harvest Celebration in Tuscany organized by Travel Italian Style and our Local Tuscan Friends. Chianti - 2016

Grape Stomping and Harvest Celebration in Tuscany organized by Travel Italian Style and our Local Tuscan Friends. Chianti - 2016

 

6. Remember that not everyone travels just like you.

I know it’s exciting to sell someone all the amazing places you love. But guess what? Not everyone likes those places or excursions. Just because you want people to visit small off the beaten path location does not mean your clients all want to do that.

You have to be open to all, especially in the beginning. It’s their vacation not yours. Just try to use your expertise in the best way possible to guide them.

But it’s also ok to say no to clients that are not fitting. My point is not to push but instead listen to your clients.

 
 Living my best life possible. Each year I spend 6 months in Italy and 6 months in NYC. When in Italy I travel from region to region but most recently have been basing myself on the Amalfi Coast for 2 months during the summer months. Amalfi Coast - 2018

Living my best life possible. Each year I spend 6 months in Italy and 6 months in NYC. When in Italy I travel from region to region but most recently have been basing myself on the Amalfi Coast for 2 months during the summer months. Amalfi Coast - 2018

 

7. Can this be your main income?

Just as I mentioned in my How to Live in Italy for 6 Months article. Be sure you have enough income saved when starting your business. Of course you can make a career out of being a travel planner. However, why not start this career while still working part time or full time at another job if possible.

The first few years are for figuring out where to make investments and take chances! I am a big believer in being spontaneous and adventurous. But use your money wisely and save. Debt is not cool.


8. Get out there and network!

Meet as many people as possible. Get out there and learn. However, one suggestion would be to learn and grow with your fellow travel industry people but in the most ethical way possible. This means supporting each other and recognizing the people that have helped you along the way.

  • BIG NO NO’s with Networking
    I do not recommend hiring me or another travel planner (AKA: pretending to travel in order to learn the business). This also includes sending suspect emails to see if you can figure out how they work or to find out our vendors. HA!

    • I can’t believe I even have to write this. However, it happens and has happened to me. This is not the right route and a waste of time. You will get caught and make your company not look so great. So do your research and ask for help when you need it. Avoid trying to skip ahead without doing the work.

  • I do not recommend copying another website that you like

    • Remember to keep yourself unique. Why would you want to have the same company as someone els?!

  • I do not recommend you take too much inspirations from another person’s story, bio, Instagram or niche that is well known. This also means not to poach another agents clients on social media.

    • I know it looks like other people are making millions and you would like to do the same. However, before doing any of the above remember these points. That company may not be doing as well as you think, this makes you not so original, and it’s not worth dealing with their lawyers. Yes, we all have lawyers for this boring legal stuff. Again, you can be inspired but go back to my earlier point about find that THING about you.

      In summary do the right thing. I read a fabulous book years ago recommend to me by a friend called Karmic Management. I recommend it.

Speaking of networking events. If you attend the NY Times Travel Show in 2019 you can find me and fellow Italian travel guru’s on the Italy Panel! Stay Tuned for Details I would love to meet you there!


I hope this practical advice to get started as a Travel Planner was helpful! There are of course many more steps. However, once you get through these beginning stages you can then find your way to the right people and places. Or as I always believe, those doors will open up for you. Prepare yourself but not afraid to follow you own path!

If you are interested in learning more about the steps to take to starting a business I offer hourly consulting calls. I can assist you getting started and finding the right networks for you.

You can book a call here! After your booking I will follow up with details on payment and rates.
Or feel free to email info@travelitalianstyle.com for more details!

Thank you all again for being a part of my journey! I am enjoying every moment of this ride and I wish you all the best on your new venture.


“Most things have been done but, they have not been done by you.”

-Elizabeth Gilbert - Big Magic


3M0A2236 copy.jpg

MEET CASSANDRA
CEO, FOUNDER, AND TRAVEL PLANNER FOR TRAVEL ITALIAN STYLE


Cassandra Santoro is the CEO and Founder of Travel Italian Style. As a personal trip planner, Cassandra is known for her expertise in Italian travel with a focus on authentic and inspiring experiences.

She also leads motivational talks in hopes to inspire others on her journey. Cassandra's highlight appearance was being a speaker in Germany for TEDx DHBW Mannheim.

Cassandra currently lives between Brooklyn, NY & Italy. Follow her adventures of life between two countries on Instagram.