Jillian DiRoma
She/Her
Based in New York
English
Jillian DiRoma
Ask me about
My Story
Assistant Principal by day, passport stamper by night! When the school bell rings, I trade hall passes for boarding passes—ready to help you plan your next unforgettable adventure. Whether it's a weekend escape or a bucket list journey, let's make your travel dreams a reality!
Travel Style
My travel style? Call it “choose your own adventure.”
One week I’m backpacking through hostels, living off snacks from local markets. The next, I’m sipping cocktails at a beach resort pretending I belong on a travel magazine cover. I’ve hiked mountains for sunrise views, danced on yachts with friends, and happily done nothing at all at a good all-inclusive. Family trip? I’m the one with the snacks, the sunscreen, and the playlist.
High-end or low-key, solo or squad—if it involves a suitcase and a good vibe, I’m there.
Stay connected
Reviews (1)
Andriana P.
7 months ago
From start to finish, Jillian was exceptional!! She made sure everything was perfect for my mini birthday getaway with my girlfriends!! Everything went smoothly, and I couldn’t be happier to recommend her for anyone looking for a reliable, thoughtful travel advisor. The birthday cake when I got to my room was the sweetest gesture ever!! Thank you for making my 40th so memorable!! <3
Andriana P.
7 months ago
From start to finish, Jillian was exceptional!! She made sure everything was perfect for my mini birthday getaway with my girlfriends!! Everything went smoothly, and I couldn’t be happier to recommend her for anyone looking for a reliable, thoughtful travel advisor. The birthday cake when I got to my room was the sweetest gesture ever!! Thank you for making my 40th so memorable!! <3
Travel photos
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