For as long as I can remember, I have always loved airplanes and traveling. I have been fortunate enough to have taken many a trip, both for work and pleasure. Many of these vacations have been paid for using miles and credit card points, and I enjoy playing the game! 

As fun as travel can be, very often it’s stressful as things go wrong with our plans. There are flight delays and cancellations, weather issues, mechanical issues abd sometimes things for no reason go awry. I’ve had my own fair share of delays and issues and have learned a few tips and tricks along the way to make things easier – or at least to reduce the pain when something goes wrong!

Try to make smart plans

One of our most recent trips was to Italy and we had quite the epic itinerary. We really wanted to do Emirates business class but that only flew out of New York. We had to get a flight out of Norfolk, VA as that’s where BabyMoneyFinance and SegundoMoneyFinance were being dropped off for the time being. However, our flights were not on the same itinerary as it was easier to book separately since we were on separate airlines. We had a United trip booked that got us to NYC with about 8 hours of a layover, and we did have to change airports. I’ve learned as best you can know when things will be tight and when you have wiggle room. For such a trip like this, I knew we would need more wiggle room! 

The day of our flight – it was supposed to be at 10am, at 3am we got a text message saying our United flight was delayed and that we had been rebooked for a 6pm flight. I didn’t see this text until 6am when I woke up to get ready for what I thought would be our 10am flight. Yikes. This was right after United had their epic meltdown in early July of 2023 and I had very little faith that United would even get us there by 8pm…which would have been tough for our 10:30pm Emirates flight. Thankfully NYC is a big airport with lots of flights and from Norfolk we could fly American or Delta with direct flights. I did something I’d never done before and we booked a same day flight on Delta. I booked us a 3pm flight thinking we still needed to play it safe with timing! It was a good thing we did – our Delta flight was delayed by 3 hours so our 5pm arrival turned into 8pm! Thankfully we had enough time!

Start to learn if and when you should build in a little extra wiggle room in your itinerary, and be somewhat aware of how to pivot when needed! 

The sweet perks of Emirates Business Class

Know what your carrier is offering

We had planned our epic Asian vacation and had paid for it all with miles. We had a few days in Singapore, then onto Thailand then onto Vietnam. We had lots of little planes and trains along the way. We leveraged my Chase Sapphire Reserve to get into the lounge prior for our flight to New York where we’d then take a flight to Asia. Despite no weather (I always check!) all of a sudden our flight was delayed. No worries I thought, we had time with our layover. But then it got pushed back again to the point we’d miss our layover. 

I quickly got on the phone with Delta and had Mrs Money head to a gate agent to get some help. I had us split up to see who got to the front of the line first! While waiting to be helped, I went ahead and pulled up other flights into nearby airports. The NYC area has 3 airports so perhaps we could get on another flight? It turns out yes, it was possible! There was a flight to Newark, NJ that got in with enough time for us to make a connection. It was tight – we hopped right into a cab and quickly got over to JFK but we made it!

The lesson learned here that saved us – we know what our carrier was offering. Our connecting flight was part of our itinerary through Skyteam, so Delta was willing to work with us because if we missed that flight it would have been quite the issue making the Asia flight up! Because the new flight was the same day – we didn’t have any fees and were able to easily change our flights to the Newark flight. By knowing a bit of how travel itineraries worked – we were able to pivot! 

Know what your reward credit card can help with

I did a good post a while back on some of the lesser known benefits of reward credit cards – like flight cancellations and flight delays. Some cards will offer compensation for things like food or clothing/toiletries when your flight is delayed. Some cards will help you rebook and pay for out of pocket costs, if and when your airline won’t (although often they will!). Take a few minutes and read through some of the features of your credit card. Or sites like the Points Guy (a YMF favorite!) do the fine print reading and summarize it for you – here’s an example for one of my cards.

Travel disruptions will occur and the more tools you have in your tool belt that you know how to use – the better prepared you’ll be!

Know how to last minute search 

As in my recent Italian trip example, we ended up in quite a bind with United letting us down and me having 0 confidence that they could have gotten us to our destination on time. So, we had to book a last minute flight on Delta! However we did have options and I used sites like kayak.com or expedia to get a lay of the land. Familiarize yourself with the airport you’re flying into – are there other airports nearby? NYC for example has 3 and they are just a cab ride away. Chicago has 2 airports and then many cities will have airports maybe 1-2 hour drive from each other. Also get comfortable taking different airlines – as mentioned to NYC I knew who was flying out of Norfolk. Plan for the worst but hope for the best! 

One other example was when we were grabbing gelato in San Gimignano and I logged onto wifi to check my email, only to see a frantic SOS email from our hotel that we were about to check into later that afternoon telling me their a/c had broke! July in Italy especially this July was HOT and we were not super keen on staying somewhere with just a fan. So, we didn’t panic (too much) and assessed our options. Thankfully the hotel we had not pre-paid for and they said they would not charge a last minute cancellation fee or anything like that. So we were starting fresh. From there we did a few google searches and landed on booking.com which had plenty of solid options. We read a few reviews, compared prices vs location and landed on a new spot that ended up working out super well! 

Sometimes you have to pivot so first learn to assess the situation and then learn how to make a new decision!

Know it’s a cost of traveling!

Finally, travel never goes off without a hiccup here and there. No matter how well you plan your trip out there will be something that goes wrong! That’s ok too – travel exists in the real world, a real world where things happen! Try not to get too stressed, learn how to leave wiggle room, assess, decide and move on! Remember you’re on vacation and vacations are meant to be fun! 

PS! We’re on instagram!