Tom Rupp

Tom was incredibly helpful! We were in the middle of wedding planning and suffering from major decision fatigue. We gave him a few parameters/guidance of what we were looking for and he made it happen! He was quick in his responses and would follow up and make sure that we had everything ready to go and make sure that we knew all of the information that we needed!

Tom is fantastic! Have so many wonderful things to say about Tom and his service. He created a wonderful trip for us to Croatia. He did a fabulous job with first asking us what our goals were, he then created a trip around that plus his recommendations. His recommendations were right on! We saw so much and experienced a trip of a lifetime around Tom’s itinerary and plans. He’s so incredibly organized. His organization created a very smooth trip. We had no issues or confusion of what to do next. Overall, we highly highly recommend Tom. We will definitely use Tom again for future trips. Thank you Tom for everything!

Tom is absolutely phenomenal! I was so overwhelmed with the entire wedding planning process and Tom was extremely understanding and helpful. He took the lead with booking this hotel block which took a HUGE weight off of my shoulders. Not only did he make it extremely easy for me, but he made it extremely easy for guests to book as well. He communicated so well with me and checked in constantly to ensure everything was going smoothly with guests booking their stay. We had a wonderful group block experience and it was all because of Tom!!

Our 10 day Family trip to Thailand, in January, 2026, was booked in May 2025. What a blessing it was to have Tom Rupp do the research and what can seem challenging work of booking flights, hotel accommodations, ferry rides, scuba certification excursions, and restaurant recommendations galore! He was a pleasure to work with, was readily available to answer any and all questions from the pre trip months to get our actual time in Thailand! Absolutely will HIGHLY recommend Tom Rupp to anyone wanting to book a trip and we will definitely ask him to book our next Family trip for 2027!! Thanks so very much Tom, you’re theee best!!

The trip truly began the moment I booked our flights, slightly prematurely, as I quickly realized I should have looped Tom in before confirming anything. Shortly after, we connected, and what followed was the most seamless and reassuring planning experience I could have asked for.

With less than six weeks before departure, the first major task was securing all of our hotels. I had done extensive research and had no shortage of options, but my natural indecisiveness and tendency toward analysis paralysis made the process overwhelming. Tom immediately stepped back to look at the bigger picture, considering logistics, travel time, proximity to train stations, and how we would actually experience each destination. This helped me make thoughtful, informed decisions that maximized both comfort and time.

I was incredibly anxious about investing so much into a Swiss ski trip and the possibility of making a mistake that could derail the entire experience. Tom completely alleviated that stress. He ensured every detail was booked, aligned, and organized, giving me total peace of mind. When our luggage was lost in London, I was able to focus solely on that issue, knowing everything else was already handled.

Even more impressively, when our flight to Switzerland was ultimately canceled, Tom was the calm, logical voice of reason I desperately needed while I was in full panic mode. He checked in with us daily throughout the trip, making sure everything was running smoothly and stepping in whenever needed. His support transformed what could have been an incredibly stressful journey into one that felt effortless, supported, and genuinely enjoyable.