Heather
Pros and Cons of Portland, ME
Pros: Easiest trip I've ever "planned" for. The company is wonderful at communicating before and during the trip, and were very thoughtful in using our preferences for planning activities. I also appreciated that dinner reservations were made but we were not locked into them, as long as we let the restaurants know in advanced. It was also very thoughtful that we were given our flight location and time a bit earlier than usual, since our "home" airport is 3 hours away, and the flight out was very early in the morning. Cons: Mostly inconveniences and a couple minor issues of miscommunication, but no major cons. Firstly, our return flight was crazy early (6 AM), due to a misinterpretation of when I wanted to return "home." There was also an instance where we were told the wrong meet-up location for a tour, and we kept playing phone tag with Pack Up and Go and the tour company (but worked it out). Our hotel was lovely--aesthetically pleasing, convenient location, and I appreciated that it wasn't a cookie-cutter design, but for such a long stay, a hot tub or some other amenities would have been nice. We also ended up canceling most of the dinner reservations, either because the menus didn't appeal or because they were not conveniently located to us or to anything else of interest. Very few of them seemed to highlight what the region was known for. Lastly, the location (Portland, Maine) was a lovely surprise, but said location during early May was not really conducive to an 8-day trip. There's not a whole lot to do or see outside of the Old Port and Arts District, especially not before Memorial Day (nor is anything outside those areas easy to get to by foot or reliable public transport, though we did have an Uber credit). People kept mentioning how "walkable" downtown Portland is, but it's actually quite hilly, and many of the roads are uneven and paved with bricks or cobble stones. I would recommend using this company, and may use it again, myself, but would probably "cheat" and open the envelope a few days early so I could be a bit more prepared.
Response from Pack Up + GoJun 13, 2026
We're glad to hear you enjoyed Portland even with the little bumps along the way! We definitely pride ourselves on our 24/7 communication with our travelers, before, during, and after their trip so I'm happy to hear you felt heard + supported while on your trip with us. Our trip planners try to make dinner reservations for our travelers based on their interests, but you always have the freedom to change them! We want to make sure our travelers feel guided but not locked into an itinerary if they want to make changes! I'm sorry to hear that you were disappointed with your flight time. We typically stray away from early flights for our travelers and only book if we've been in discussion with the traveler based on their departure day schedule. It seems like there was some miscommunication here. If you travel with us again in the future, always feel free to let us know what you're thinking via email, phone, or text! While we definitely want to maintain the element of surprise, we're more than flexible to hear your thoughts + expectations!




