
Jamie Rosenbaum
She/HerBased in Chicago
English
Jamie Rosenbaum
Ask me about
My Story
For me, travel is a way of adding beauty and meaning to my life — a chance to find wonder in both the grand adventures and the everyday small discoveries.
Travel Style
I specialize in designing seamless, elevated itineraries that transform life’s biggest milestones into unforgettable journeys. With a curated approach and insider access, I take the stress out of travel planning so you can focus on celebrating every moment.
Reviews (21)
Mary Alice S.
13 days ago
Jamie is an exceptional travel advisor. We were a party of 5 with a lot of questions, and Jamie was always available to us to answer any questions. If she didn't have the answer immediately, she was able to find it quickly from the venues. Booking with international hotels and cruise lines is a challenge! Using an experienced TA like Jamie made our trip much less stressful for everyone. I will definitely use her again!
Stephanie K.
16 days ago
Jamie went above and beyond making sure all of our details were handled well before hand, even reminding us to take certain things and showing us things we never even though of. And we are experienced travelers - so this was truly an amazing experience!
Candace C.
about 2 months ago
Jamie has been great to work with and made the process so easy! Her communication was great and I felt relieved of the stress that comes along with booking a trip. It was a great experience! I would recommend her to any and all of my friends and family, and we will work with Jamie on our future adventures!
Cory G.
about 2 months ago
Jamie guided us to Playa Mujeres for our joint 50th and it was exactly the right call! Overall it was a great trip and I'm so glad she steered us there!
The hotel choice fit the group's vibe, and she planned special group dinners and surprise celebrations during our private boat day! Everything felt dialed in.
It was close to a year of planning for a long weekend full of fun, thanks to her amazing guidance and support. We got to focus on celebrating instead of logistics, and everything just worked.
Jaime M.
about 2 months ago
Planning a milestone birthday with a big group could have easily turned into us organizing our own party but Jamie completely took that lift off our shoulders. She managed all guest communication, tracked bookings and details, and kept everyone informed so we didn’t have to answer a hundred texts or emails.
She handled the boat charter, dinner reservations, transfers, and all the behind-the-scenes logistics that make a group trip actually work. It was such a relief to have her guidance throughout the process and to know she was keeping everything moving.
What I appreciated most was that even though she was managing so much, it always felt collaborative and aligned with what we wanted. The trip felt personal to us, we just didn’t have to carry the weight of planning it.
Mary Alice S.
13 days ago
Jamie is an exceptional travel advisor. We were a party of 5 with a lot of questions, and Jamie was always available to us to answer any questions. If she didn't have the answer immediately, she was able to find it quickly from the venues. Booking with international hotels and cruise lines is a challenge! Using an experienced TA like Jamie made our trip much less stressful for everyone. I will definitely use her again!
Stephanie K.
16 days ago
Jamie went above and beyond making sure all of our details were handled well before hand, even reminding us to take certain things and showing us things we never even though of. And we are experienced travelers - so this was truly an amazing experience!
Candace C.
about 2 months ago
Jamie has been great to work with and made the process so easy! Her communication was great and I felt relieved of the stress that comes along with booking a trip. It was a great experience! I would recommend her to any and all of my friends and family, and we will work with Jamie on our future adventures!
Cory G.
about 2 months ago
Jamie guided us to Playa Mujeres for our joint 50th and it was exactly the right call! Overall it was a great trip and I'm so glad she steered us there!
The hotel choice fit the group's vibe, and she planned special group dinners and surprise celebrations during our private boat day! Everything felt dialed in.
It was close to a year of planning for a long weekend full of fun, thanks to her amazing guidance and support. We got to focus on celebrating instead of logistics, and everything just worked.
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