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 (4)
Daniel G.
travel to Santorini
4 days ago
I cannot say enough great things about my travel advisor. The entire trip was planned and detailed to perfection, from the accommodations and transportation to the activities and recommendations. Everything was seamless, thoughtfully organized, and exactly what I needed to be able to relax and enjoy my vacation without worrying about the logistics. My travel advisor was amazing throughout the entire process, always helpful, responsive, and attentive. You could truly tell how much time and care went into planning every detail. I would highly recommend both the hotel and my travel advisor to anyone looking for an amazing, stress-free travel experience!
Brianna M.
travel to Alberta
8 days ago
Jillian was extremely helpful and thorough during the entire process. She always kept us updated on the accommodations and excursions, and she was always happy to answer any questions we had. The trip ran so smoothly and super organized, I can’t wait to book my next trip with her!
Brianna I.
travel to Philadelphia
16 days ago
Jillian was an absolute pleasure to work with. She made an otherwise daunting experience enjoyable and easy! Her expertise and research made our trip one of the best ones we’ve ever taken. I would work with Jillian in the future without a doubt! She was friendly and approachable and always seemed happy to answer my questions. 10/10 would recommend!
Andriana P.
travel to Miami
11 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
Daniel G.
travel to Santorini
4 days ago
I cannot say enough great things about my travel advisor. The entire trip was planned and detailed to perfection, from the accommodations and transportation to the activities and recommendations. Everything was seamless, thoughtfully organized, and exactly what I needed to be able to relax and enjoy my vacation without worrying about the logistics. My travel advisor was amazing throughout the entire process, always helpful, responsive, and attentive. You could truly tell how much time and care went into planning every detail. I would highly recommend both the hotel and my travel advisor to anyone looking for an amazing, stress-free travel experience!
Brianna M.
travel to Alberta
8 days ago
Jillian was extremely helpful and thorough during the entire process. She always kept us updated on the accommodations and excursions, and she was always happy to answer any questions we had. The trip ran so smoothly and super organized, I can’t wait to book my next trip with her!
Brianna I.
travel to Philadelphia
16 days ago
Jillian was an absolute pleasure to work with. She made an otherwise daunting experience enjoyable and easy! Her expertise and research made our trip one of the best ones we’ve ever taken. I would work with Jillian in the future without a doubt! She was friendly and approachable and always seemed happy to answer my questions. 10/10 would recommend!
Andriana P.
travel to Miami
11 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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