About The Tailored Traveler

At the Tailored Traveler, our goal is to make your trip absolutely perfect. Our philosophy is to treat all of our clients like family. To do this, our expert Hosts carefully design and manage every single detail. Whether it is your first time in Florida or your fiftieth, we want to get to know you before we plan any part of your vacation. From there, we will begin carefully designing your experience, taking into account the smallest details of events, weather, trends, new spots, and more.

During the entirety of your trip, your dedicated TT Host will be at your service. We will make sure that you are comfortable and relaxed from beginning to end. Above all, we want you to enjoy your time in our beautiful home state and to truly feel like family by the end of your travels. Our promise to you is that our company and our Hosts will do whatever it takes to make your trip perfect and 100% tailored for you.

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If you're ready to book your dream vacation

Why Choose The Tailored Traveler?

We’re with you from beginning to end. Not just over the phone or email, but in person. We know that traveling to new places can be difficult and even intimidating without someone there to help guide you. That is why our hosts are dedicated to you, and only you, during the entirety of your stay.

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Our story

Meet the Owners

With inspiration from our own travels and prior experience in the tourism industry, we started The Tailored Traveler in July 2018. Through our own experiences across the globe, we realized the true merit and importance of experiencing the world with the ones you love, but that sometimes traveling can be difficult and complicated. So, we decided to take our passion for travel, our planning and organizational skills, and our love for our home state to provide travelers with the best, most personalized, and most luxurious experience possible. After all, there are many different paths to take in your travels around the world, but we would love to make this path yours entirely.

Jenna & Matt

The Tailored Traveler

Your experienced local hosts

Meet our team

Our Vehicle

Sprinter Van

2018 Mercedes Sprinter

Above all, our first priority is safety. Our second is comfort. That is why we don't settle for anything less than the top of the line 2018 Mercedes Sprinter Van. With room for 11, we can accommodate groups, small and large. In addition, this vehicle is built for maximum comfort for our longer trips.

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