Ellen H.
They Booked a Trip, They Didn’t Plan Our Trip
We trusted Pack Up + Go with our 15th anniversary, and the planning completely missed the mark. I wanted to love this concept, and I get that the element of surprise means giving up some control. But that’s exactly why the planning and personalization matter so much.This was our 15-year wedding anniversary. Vacations are a luxury, especially right now. Childcare over a holiday weekend is a big lift. We trusted this company with about $3,500 and a milestone we only get once, but the planning never reflected that. I gave them a huge amount of information: where we’ve lived, what we enjoy, what we don’t, specific examples of memorable things we’ve done. And I specifically wrote, “We don’t need a bunch of activities, just one great unique one.” We were sent to Chicago, a city we have been to at least ten times. I didn’t explicitly say, don’t send us to Chicago, and I can own that. But I gave them the major cities we had lived in, surrounding that area, and tons of context. For a service built on personalization, there were obvious dots to connect here. After the trip went wrong, Pack Up + Go told me they thought we probably would have liked their outdoor adventure trip better than the one I purchased. If that was apparent from my questionnaire, why wasn’t I contacted before they spent our money? That could have been a simple call or email. The one great experience they chose was a helicopter ride over Navy Pier during fireworks. I had specifically told them, we had already done a Grand Canyon helicopter tour. I don’t understand how that became the centerpiece. And due to a credit card authorization problem on their end, we didn’t even get to take the flight. We arrived early, followed instructions, and the helicopter company was trying to help us work around it. I called Pack Up + Go, was told not to pay myself, and to wait for a call back that didn’t come. Because the flight was tied to the fireworks, we missed both. I wound up crying in the helipad parking lot, not because of a helicopter ride, but because it was our 15th anniversary and the whole trip felt unconsidered. The smaller details didn’t line up either. We were told to bring an outfit for an evening out. I purchased one and packed it. Pack Up + Go had already made our restaurant reservations. One was a casual farmhouse bar and one was a pizza place. It wasn’t bad food, just nothing like what their own packing instructions implied. Our hotel was a standard room with nothing marking the occasion. I was told they had informed the hotel, but nothing reflected it. Customer service was kind and quick to refund their fee and the helicopter we didn’t get. I appreciate their kindness but- Good customer service after a poorly planned trip doesn’t replace good planning before it. We still paid for the flights and hotel because yes, we technically used them. But here’s the problem. I never would have spent my money on that trip in the first place. That’s what makes this kind of service different. You’re surrendering approval power, trusting that the planning and judgment are worth it. I gave them everything they needed to ask a question or flag a mismatch before booking. vacations are too expensive and milestone moments too rare for that kind of miss. We don’t get another 15th anniversary. That’s why this is one star.
Response from Pack Up + GoSep 13, 2026
Thank you for sharing this, and congratulations on 15 years. We are truly sorry this trip didn't reflect your special milestone the way it should have. We know you spoke to our Director of Operations at length after your initial outreach. Though she was able to issue a service fee refund and pass your feedback on to the team to begin making changes, we understand that this doesn't undo the experience itself. We are grateful you took the time to talk it through with us, and your feedback is already shaping how we handle detailed questionnaires like yours going forward. We'll follow up privately to address anything that still feels unresolved, and we hope for the chance to plan a trip for you that gets it right whenever you're ready. All the best, the Pack Up + Go team




