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Tailored Travels

Tailored Travels

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I’ve been too busy traveling to focus on social media!! And that’s exactly how I want you to feel on your next trip with Tailored Travels.

When we plan your custom itinerary, our goal is for you to be so engulfed into the experience whil

Unlike travel agencies, Tailored Travels accommodates any and all niche requests!

Are you looking for the best gluten free restaurants in Italy and must eat dishes? A local jeweler who hand makes your dream piece? Or a photographer to capture the mo

Whether it’s 24 hours or 24 days, working with Tailored Travels means a better experience for you!

Just two days ago, we got reached out to by a client asking if we could plan a single day for their family while in Chicago this upcoming weeke

And its clients like this, I decided to launch Tailored Travels.

I’ve always loved to host, travel and tell stories. Behind the camera, building a charcuterie board and landing in a new destination is when I’m happiest. Designing your o

I fell in love with Europe when I lived there in 2016.

The travel bug bit me much earlier than that, but immersing myself in Italian culture and traveling almost every weekend, opened my mind up to all that I had to explore in this world. Now havin

Meet Your Travel Designer - Jessie

Hi, I’m Jessie! If you’re like me, you’ve experienced life’s most special memories while traveling. Whether it’s a short drive away for a quick weekend, or three weeks on the other end

Don’t get me wrong - I love an afternoon strolling Tuscan vineyards, indulging on some of the worlds best foods, or an afternoon on the most perfect white sand beach sipping on a cocktail, but I also swoon over America’s wonders.

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Welcome to Tailored Travels - a custom travel design planning service! We create curated travel experiences, specific to individual wants and dreams. No trip is too big or small. Our expertise will enhance every travel opportunity to make your great