When travel doesn't go the way you expect

From May 2025:

This past week I traveled with my boyfriend, James, to Florida to visit with my aunt who I haven't seen since 2016.

When you decide to travel, you might think that everything is going to be perfect. You pick out your flights, your seats, you expect to arrive on time.

We bought insurance, even though we were only booking flights because we were staying at my aunt's condo.

Our flights were booked directly with Delta. We booked the first flight of the day out of Burlington, VT. About 10 p.m. the night before, I received a text that said sorry for the inconvenience but we have canceled your flight. Don't worry, we booked you on another one. Instead of going through JFK, we were flying to Detroit, and it would add an hour on to our flight time. That was okay with me.

I looked at the flight, and they had upgraded us to First Class on the flight from Detroit to Ft. Lauderdale. I should mention that this was the first time that James was flying in his life. To be upgraded to First Class made this an amazing experience for him. The seats we bought were in the Main Cabin.

Surprisingly, there was a meal. He was seated behind me, and we both decided on the same meal. There was a gourmet mac and cheese with veggies and the most divine creme brûlée. I had not liked creme brûlée until I decided to give this one a try. I learned the lesson not to assume I don't like something just because I hadn't liked it in the past. The quality makes a BIG difference. James liked First Class so much that he was willing to upgrade on the way home, but there were no seats available.

We arrived, and my cousin was waiting by ground transportation. It had been even longer since I had seen him. He drove us back to the condo where my aunt met us at the door saying she was sick.

No one expects to go on vacation and hear that. In fact, I had planned this months in advance and was more concerned that I would show up sick. You never know. 99% of the time, I am not sick, but it usually isn't at a convenient time.

The next morning, we went to the beach with my cousin. The weather was cooler there. I found three tiny perfect seashells in the seaweed to add to my collection of memories from my various trips. I got one little strip of bad sunburn--must have missed a spot--that is still healing. But I also had the most amazing pistachio ice cream, got to walk in the sand at the water's edge and feel the peaceful waves washing over my feet, and walked near a natural park area.

The next day my aunt drove a little out of her way to drop us off at Flamingo Gardens. She knew that maybe I would like that and was willing to drive us out there. We saw tropical trees and plants, flamingoes, ibis, and lots of butterflies. I took multiple videos which I have shared on TikTok and am in the process of uploading to my Balanced Explorations You Tube Channel. I find it fun to take photos and make videos of my experiences and share them with you. I hope they are enlightening and fun for you as well.

And now, on to the next surprise of the trip. We went to Sawgrass Mills, a large mall. Coming from Vermont where there is not much shopping, we found it beneficial to do some clothes shopping. We quickly realized the clothing would not fit into the carry on duffle bags we had brought with us. We purchased a bag to check--which was filled with both what we brought with us and the new purchases.

We checked our bag on the day we left. The flight was delayed about 45 minutes to our first stop destination. We didn't pick up our baggage from baggage claim to go home until almost midnight and didn't arrive home until after midnight. At that point, we discovered that a corner of our bag had been torn.

I figured I would deal with it another day. We had some errands to run the day after we got back, and I wasn't able to check Delta's website until after 7 p.m. where I discovered they only give you 24 hours to make a claim and required you to go to an office at the airport to get a reference code. Of course, that office was likely closed at midnight and we were not going to make a special trip back to the airport over our bag. The insurance was secondary and required you to first go through the airline before filing a claim.

James was resigned to just letting it go. For him, the time involved was not worth the effort. But for me, Ms. Luxury Travel Advisor, I wasn't going to let it go. I decided I was going to find a way to get a reference code online. I had to log in under my Skymiles account and was able to send a message. Seems straightforward, right? However, the agent who came on immediately advised that they were helping multiple customers and to be patient. Then, they said they were going to open the file. THEN, I was told that I had stepped away and would need to wait for a new agent. And I was logged out or almost logged out multiple times. I'm not sure why the website didn't realize that I was still in the chat and keep me logged in.

Eventually, I was connected to someone who helped and sent me to a chatbot to answer questions and upload a couple of photos. At that point, the process was quick and easy. They offered, and James accepted, a replacement bag. It didn't seem fair to only get to use the bag once. He was sent an email directly to select the replacement bag he wanted, which should arrive in about a week. All's well that ends well.

From my standpoint, this trip was awesome and amazing. I go into any travel knowing that I don't know what's going to happen, and that's how I recommend you handle it as well. That's why it's always best to build extra time in. It gives you the opportunity to not miss out on too much. You can expect that things will go wrong, but it's all in your attitude and how you handle things that don't go your way. You can have a great travel experience even when things go wrong.

And it always helps to have someone in your corner, like me. I have access to experts around the world who will help me to customize your travel and lead to the best experiences--and sometimes the experiences are even better when you go with the flow. Now, James is always going to want to fly First Class.