Travel Squad Nightmare: You Shouldn’t Travel With Everyone

It’s easy to look at someone and say “he/she likes to travel, we should go on a trip.” Sometimes before resorting to a solo trip, you may look within your circle to see who would be a good candidate for a trip. You see a flight deal and post, “who wants to go?” Since I like to travel, I was approached by a ” friend” to go on a trip. Usually, it’s hard to find someone to travel with so I was ecstatic and agreed to it. Here’s why I will be hesitant to add new people to my travel squad in the future.

Before the Travel Squad Trip 

After being approached for the trip, I worked on finding a flight. This was before my hacking days and before flights were cheap. I was able to find a flight out of DC to the destination for $1,500 I’m still salty about the amount. The rest of the travel squad were all flight attendants and I knew only the person that invited me. They were able to get discounted flights to the destination. I was able to get a buddy pass to DC. I wasn’t worried about the hotel because I’d won a $500 voucher from Expedia and the destination has very cheap hotels. So everything was booked but then I received a phone call from the “host” to ask if I could cancel my room and we all go in on a suite at the same hotel. This is where I should have said no but since it was both of our birthdays the way it was pitched made it seem like it was the same price as a room. I was able to cancel my room and get my voucher back.

The host was then to collect the balance via PayPal. We were sailing along and everyone noted in the group chat that they paid until weeks before this INTERNATIONAL trip, the host asked about different hotels in the area that were cheaper. Then called and asked could I book the hotel because her card didn’t have the max to cover the hotel and promised to send me the money via PayPal. Flag number 2. I then booked the suite using the $500 voucher as my payment towards the room and would get cash back since I more than paid for my portion. Days before the trip the host called and said PayPal messed up her balance and is working with the bank to get the money back. It was a very elaborate story and I believed her because we’ve known each other since our pre-teens. At that point, there was nothing to do but continue on. Learning how PayPal works after the fact, I think she purchased stuff via PayPal and it ate away at the balance she collected as opposed to using a card. the night before I was told one more person dropped out and would not make it and she didn’t get the money from that person before they canceled.

Read 8 things to consider before picking a travel buddy or adding new people to your travel squad.

During the trip

We all flew to the destination separately. I was the last to arrive and my silly self allowed them to check in before me by putting the host’s name on the reservation. I arrived and received my own room but the host and friend were in the master suite and I had not received one dollar toward the suite. I privately messaged her and was told I would have the money any day now. The trip went on and I maintained a positive attitude. I’d done the most research and booked tours so I could write for the blog.

Travel Squad Nightmare

After the trip

We went our separate ways home and that’s when more lies began. We worked out a payment plan. Months dragged on to pay the balance, I would see photos of the person at events out of the country and I’m thinking where the hell is my money? Finally, at the end when still a good portion owed she told me she lost her job and would borrow the money from a family member and would pay me back. I kept asking and asking and months went by it is now years later and I never got the money. This created a spiral of debt on the credit card because that was not a debt I was prepared to pay off. That important milestone birthday trip was ruined for me. I sometimes can’t even look at the photos because I get pissed off.

Looking back

In hindsight, I should have not agreed to go on this trip. I should have vetted this travel squad more carefully. Now, I use questions from a travel squad application that I’ve created. You can download a free copy here. I wasn’t working at the time and deals were not good at the time. There are so many things I would have done differently like just not go and try to get my money back on the flight or a credit for another trip or just gone solo. You may think my choices were foolish but there were things such as excitement for a milestone birthday trip and thinking I could trust someone I’ve known for almost 20 years.



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I’m not sure I’ll ever go on a travel squad trip. I have my few select friends and a significant other. They are the ones I can trust. I still put some travel for us on a card because I believe in booking travel on a credit card for the perks and points. However, the ones I trust PayPal me the day I book or we split the bookings equally. In the future, if I decide to add new people to my travel squad, I will be sure to not take on any additional costs to my portion of the trip. I will ask if the person has a major credit card. It is important because they need to be able to book travel but also if something happens to your debit card abroad, you need to have an emergency credit card. Also, I would use a travel agent or purchase from a package so that no one has to be responsible for the entire hotel room etc. Check out more tips for picking people to add to your travel squad here. You can’t travel with everyone who likes to travel.

Have you been burned by new members in your travel squad? How did you bounce back? Comment below!


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A cautionary tale of choosing the right people to travel with.

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Travel Squad Nightmare: You Shouldn\'t Travel With Everyone

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