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Rachelle Stepner

Why I Became an Italy Travel Planner

Updated: Feb 23, 2020

People aren’t surprised when I tell them I am a Travel Planner. However, when I tell them I’m an Italy Travel Planner, that is when I get a reaction.  “Really?  Why Italy?”.  Inside, I’m thinking, “Isn’t it obvious??!!”  But, I have to remind myself, not everyone has been obsessing over Italy for the last 20 years like I have, and many people know it’s a nice place to visit but are not really familiar with it.  And, that’s exactly why I started doing what I’m doing.  Because people do know it’s a nice place to visit, choose it as their next trip and then are like deer in headlights because they don’t know where to even begin in the planning process.  More importantly, I became an Italy Travel Planner because I truly want everyone who goes there to fall in love with it as deeply as I have. I am more than eager to share all I have learned and experienced over the years. Italy is unique in that it has countless regions, cities and towns that are begging to be explored. If you have never been to Italy, it is almost impossible to decide where to go first. Rome, Venice and Florence are obvious.  But, what about the Amalfi Coast and Capri?  What about Tuscany?  What about Sicily, Puglia, Lake Como, Portofino, Umbria???  How in the world to decide?  You want them all!!  As you should.

Pitigliano, Tuscany - Photo taken by Five Star Italy

This is my favorite part of the trip planning process; clients telling me their dates of travel and what they think they’re interested in. The wheels start turning in my head right away as I begin figuring out how to get them to see as much as possible without it feeling rushed.  I love incorporating an unexpected day trip that enables the clients to experience an entire region without moving hotels.  I love teaching clients about towns and places that they never even heard of. Italy is a challenge and I love a challenge.  Yes, it is easy (for the most part) to get around. There is high speed train travel, Mercedes sedans for your day trips and luxury boats to sail you along the coast. The challenge lies in deciding where to go, how long to go for, how will you get from point A to point B and how to maximize your time along the way.  This is why hiring a Travel Planner (ahem) is so essential.  And, no more so, than for a country like Italy.  When there are so many places to explore- and so much to experience within each of those places- an Italy expert is indispensable. Why does Italy have such an allure? Short answer: Because it has everything you want in a vacation. Long answer: Because it has everything you want in a vacation and is a country like no other.  It has some of the most breathtaking scenery in the world, arguably the best food and shopping in the world and some of the most magnificent hotels in the world. As if that’s not enough, the art alone is worth coming for (have you ever seen The David or the Sistine Chapel in person??). A history lover wouldn’t know where to begin!  How about beginning with a Michelin starred dinner sitting beneath ancient ruins and a starry sky?  Whether you are a shopaholic, foodie, art lover, historian or, just someone who wants to lie by a cliffside pool 1000 feet over the sea, Italy is calling you. In no other place, can you travel from city to city, or town to town, and feel like you have arrived in a completely new country.  Yes, the scenery will still be beautiful, the food and wine will still be stellar, but the feel, the architecture, the magic, will be different.  Each destination casts a different spell upon its visitors.  Even within Tuscany, no two villages are alike. You can visit ten medieval towns and you will have ten different experiences. For all these reasons, and more, that is why I love Italy and that is why I chose to be an Italy Travel Planner. #LIVINGTHEDREAM








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