Pineapple Escapes Travel — Local services in Oglesby

Using this company was a truly horrible experience. My boyfriend and I were planning a trip to Italy and felt like it would be great to have someone help us with the planning process and get nice places for good deals. We paid $350 to Jamie, and it was a really bad experience from then on out. We didn’t get the $350 back even though she did absolutely nothing but stress us out.

Every email we got from her started off very negative, saying how we didn’t have time to plan the trip and that everything was already booked. We know we started a little late in the game, but one time saying it is enough. On top of that, she took a week off in the beginning of planning the trip…. If you’re telling us how we’re so pressed for time wouldn’t you give us a warning you’ll be out of office for a week? Or maybe give the project to someone who had the time to plan it? We felt that was extremely unprofessional.

We had a pretty solid idea of what we wanted to do, things we wanted to see, and areas we wanted to stay in. We gave her our budgets, but told her we were mostly flexible. She took that flexibility snd RAN with it, sending us itineraries for an almost 20k trip, which was an insane deviation from our budgets. She also completely ignored a lot of our requests, like for example she even said we should road trip, and then sent an itinerary with private cars for every transport.

When it was time to book the hotels, Jamie sent us either options that totaled 10k, or extremely terrible options with horrible reviews. The hotels she chose, when you looked them up, were about $100 a night (with some deviations), but the total package was coming out to over 10k - an insane price and more than double the budget we gave. The hotels were not nice, and extremely far from the locations we wanted to see. She said there was nothing available, but we found incredible places, and there were tons of options available.

I felt like we were really being scammed, so I sat down to look for hotels and found gorgeous places for way under our budget, and I much more centralized locations. I couldn’t believe that this expert travel agent couldn’t do better to plan this trip. It really seemed like she was sending us hotels that gave her a kickback, or really terrible options with bad reviews to try and force us to choose the more luxury option that worked for her interests. I’m not sure if that’s true, but that’s how it felt.

We ended up booking everything on our own, have a wonderful trip planned, and are saving THOUSANDS (I cannot express this enough…. THOUUUSANDS) of dollars. This travel agency, or at least the travel agent Jamie, is a complete scam.

RESPONSE TO BUSINESS: Not wanting to spend over $10,000 on just hotels alone (and hotels that were over an hour outside of the cities we wanted to see and were not very nice) is not having an unreasonable budget. It's just irresponsible and poor...

I cannot recommend this company’s services. Throughout our most recent booking interaction we encountered alarming unprofessionalism. Kayla became combative when we tried to adjust our trip because of a newly issued travel advisory. Without confirming with us, she canceled our trip just seven days before departure, then refused a refund and insisted our travel insurance only entitled us to a credit. (That same insurance has provided us a full refund on a separate trip, so we know that claim is inaccurate.) When we requested to speak directly with the owner, Jamie, she refused to take our call and insisted on keeping all communication via email, which felt evasive and unprofessional. This trip had been years in the making; we’d already postponed it multiple times due to a cancer diagnosis and passing of a family member. The dismissive way Kayla and Jamie handled this situation lacked any sense of empathy or accountability and has completely soured our trust in using a travel agent again.

Edit: Legal action was not considered until Jamie refused to communicate with us by phone. As previously mentioned, we had purchased the exact same travel insurance for another trip that we later canceled and received a full refund for. Additionally, the attorney was unable to provide proof of the detailed explanation of the travel insurance coverage that had...

5 Stars – A Seamless and Unforgettable Greece Trip Thanks to Lisa at Pineapple Escapes!

Our trip to Greece was absolutely incredible, all thanks to Lisa at Pineapple Escapes! She handled every detail—from flights, ferries, and hotels to transfers, guides, and tours—and everything was perfectly organized.

We started in Athens, then flew to Santorini, where our hotel had the most amazing caldera views and breakfast served to our balcony each morning at our preferred time. Lisa arranged a private boat tour around Santorini, a guided walk through historic Kastelli Square, a wine tasting at Domaine Sigalas, and a cooking class that ended in the cutest little Greek village—all unforgettable experiences.

Next, we took a ferry to Paros, where our hotel was lovely and relaxing, with a beach just a short walk away. On our last night, we flew back to Athens, and the hotel Lisa booked had a perfect location and a rooftop restaurant overlooking the Acropolis lit up at night—the ideal ending to our trip.

Every transfer was prompt, the service was warm and professional, and we never had to worry about a thing. I can’t recommend Lisa at Pineapple Escapes highly enough. If you’re planning a trip to Greece, she will make it easy, personal, and...