My husband and I have done a lot of traveling. We’ve also lived through an awful lot of experiences in those travels. Travel can give you the highest of highs (hot-air ballooning over Love Valley in Cappadocia is an experience I’ll never forget), and in the next breath, bring you down to the lowest of lows (anyone else out there hurled on a Moroccan road side in the middle of the night?).

So why do it at all? Is it worth it? Are the high points really so good that they cancel out the lows? The short answer: YES! Here are some of the luckiest things that ever happened to us in all our travels, whether solo or together. Some were written by yours truly, and some have been written by my husband and favorite travel buddy, Steve!

Room Upgrade at Hotel Sacher Salzburg

Whitney

We’ve had hotel room upgrades before and since this particular experience, but the upgrade in Salzburg had timing on its side. We had recently returned from a less-than-perfect trip to Morocco, and honestly, I was not ready to get back to traveling yet. We’ll just say my travel confidence was low.

Once we arrived (we walked from the train station to the hotel in the rain, by the way), our luck completely turned around. Not only did we score an upgraded room with a truly epic view from an actual balcony, we received a welcome bowl of fresh fruit and two of their personal-sized, signature Sacher tortes! The whole trip far exceeded our expectations, and I will always treasure that experience as one of my favorite travel memories!

Get the details: Staying at the Hotel Sacher Salzburg

$300 Voucher to Take a Different Flight, but Got on My Original Flight Anyway

Steve

Like many frequent travelers, I like the sound of a generous travel voucher in exchange for my willingness to take the next available flight. But I am typically too eager to get to my destination on the outbound flight to take advantage of such offers because I am keen to see family, excited about a new leisure destination, or have a work commitment.

I have more flexibility when returning to home, but when the time comes, I generally just want to get home. On one particular occasion, however, I was flying home from a business trip in the Nashville area, back to my base at Dulles International (IAD). 

After a few unmotivating announcements seeking volunteers to “possibly” get a voucher “if needed,” the gate agent escalated to saying that she “required” volunteers, and that we could not take off, and would not board, without volunteers, due to weight and balance issues. The next available flight was the next morning, but I had no other plans, so I volunteered, and got a $300 voucher in my hand. Even better, when the weight issue was resolved, I was able to board anyway, and got home as originally planned, $300 richer!

Related: The Benefits of Airline Loyalty

Business Class Upgrade from BKK to VIE

Whitney

I’m about to blow your mind: Bali is overrated! At least it was in our experience there. The best part was definitely leaving… For more reasons than one!

After a somewhat disappointing trip, we braced ourselves for a long drive to Bali’s airport, followed by a series of long flights home. The entire journey was going to take more than 24 hours, including 4.5 hours to Bangkok (BKK), 12 hours to Vienna (VIE), 1.5 hours to Frankfurt (FRA), and finishing out with 9 hours to our home airport.

We ate our fill in the Thai Airlines Lounge at BKK, took food with us for the 12 hour flight in economy, and told ourselves we could do it. Then, our boarding passes didn’t work when we got to the gate and attempted to board our flight. I was mad about it, but we stood off to the side until the gate agent figured out what the problem was…

We had been upgraded to business class! We didn’t expect it at all, and we hadn’t received any notifications about the upgrade as we normally would. But sure enough, we boarded our Austrian Airlines flight, watched movies in comfort, ate dinner and breakfast in style–served by a chef in a real chef’s hat!–and most importantly, we slept a full eight hours each. It. Was. Bliss.

More here: The Hidden Benefits of Business Class

$125 Vouchers for No TVs

Steve

This one was a quick, easy win. I had monthly travel to Orlando, merely two hours of flight time from IAD. On one occasion, United Airlines was using a larger aircraft, a 767.  When I boarded, I saw TVs on the seat back in front of me, but quickly realized mine was not functioning. I could tell some others around me had the same issue, but folks in other sections did not have this problem. Oh well, the flight was full, the time in the air was short, and I could view entertainment options on my phone in the meantime. 

Before the gate even closed, however, a flight attendant came by to acknowledge that the TVs did not work, and said he would take care of us. That sounded nice and pro-activate, so I was favorably impressed, but did not expect much, maybe a free snack or drink (which I get anyway as a 1K Customer with United). 

Instead, after take-off, he came by with his iPad to fill out a customer compensation form, indicating that the TV issue seriously impacted our flight, and gave us two options: Reward miles or a $125 e-certificate. I took the e-certificate happily. Even better, Whitney was with me on the flight, so we each scored $125 for a trivial inconvenience! We used the e-certificates for fun flights later that year.

Keep reading: How to Be Your Own Travel Advocate

Miraculous Athens Business Class Seats

Whitney

A trip to Greece was on my bucket list for a long time, and this particular trip was intended to celebrate Steve’s happy birthday, so it was extra special. Getting there in a reasonable amount of time, at a reasonable cost, however, was notably challenging in early 2022 (as with all world travel throughout 2022). So, we booked super expensive, economy class seats, applied for upgrades, and hoped for the best.

Upon further thought and the dwindling likelihood that we would get the upgrades we requested, we decided to pay just a little more and book into Business Class, but with a connection in Rome (FCO). Our connecting flight on Aegean Airlines was cancelled, so we re-booked, still in Business, but still with a connection, even though there was Business Class available on the non-stop from our home airport to Athens (ATH).

A couple of weeks later, our connection on United Airlines was cancelled, and we were automatically rebooked on a longer itinerary with two connections, considerably reducing our time in Athens itself. So, we called United to try and get on a different itinerary. I thought there was no possible way that we would get the Business Class seats on the non-stop flight to Athens, but that is exactly what happened!

Long story short: We got two $19,000 non-stop, Business Class seats at a massive bargain, all because our flights were cancelled! That’s good luck!

Also this: The Best Way to Spend 36 Hours in Athens

Unexpected Operational Upgrade from NRT-IAD

Steve

We are willing to do a lot of research to find upgrades or great prices to fly in Business on ultra long-haul flights. But on this trip, I was dropping my wife off in Southeast Asia to meet some friends at Angkor Wat, and we did not have much control over destination or schedule, so we ended up in economy on the way to Bangkok (BKK). After a couple of days enjoying Bangkok, we tearfully parted ways, and I boarded my plane for Narita, Japan (NRT). 

I was mentally prepared for at least 14 hours in economy as I walked to my gate for the flight onward to IAD. I heard my name called at the gate, which is generally not a good thing. I thought that probably some poor planner wanted me to change seats so they could sit with friends. But that was not the case this time. 

The gate agent handed me a boarding pass for Business Class for the 14 hour flight!  This was an “operational upgrade,” the kind a status passenger may get when economy is overbooked, but Business is not.  Hugh score! (Note: Whitney schlepped it in Economy on the same flight a week later.)

Read next: How to Know If Airline Loyalty is Worth It for You

$1,000 Voucher for Taking a Connection

Whitney

How much is a little inconvenience worth? For me, taking a connection instead of a non-stop and getting to Dallas to visit a friend a couple of hours later than anticipated was worth $1,000! My original, non-stop flight to Dallas was oversold, so the gate agent started offering vouchers to passengers willing to take a different flight or a connection. My plans were a little bit flexible, and it seemed like a good deal to me, so I took it!

Even better? I was able to get on an earlier flight to make a connection in Houston, and when I arrived and looked at my seat assignment, it was for First Class! Woohoo!

Get the whole story: Why You Should Do Your Airline a Favor

Our Meet Cute in Prague, Czech Republic

Steve

In May of 2012, I was traveling with a group of friends to Prague to run the Prague Marathon. I thought that would be a fun, fit way to celebrate my birthday! While I don’t run marathons to compete, I do train seriously and attempt a to make a good time without injuring myself. To keep things simple, my friends and I booked the Hilton hotel on the Club Level, which includes some meals and snacks, so we would not have to spend time searching for appropriate marathon food in a foreign city. 

My friends let me know that a friend of theirs, Whitney, was taking a train to Prague from my nearby country, and when she arrived, we would be doing some touring in Prague. This friend turned out to be beautiful, sweet, cute, quite young, and had hobbies that included travel and fitness, just like me! But I was not thinking of making a connection because I had not previously anticipated her arrival, she appeared much younger than me, and I was primarily focused on making the most of my six months of marathon training.

Whitney, like me, was an early riser, so, by chance, we had breakfast together each morning at the Club Level before the others arrived. With no pressure, we had delightful, wide-ranging conversations. We officially started dating that fall after overcoming calendar obstacles, got engaged in Switzerland in 2013, and married in May of 2014, just under two years from the day we met! Whitney remains my Miracle more than 8 years into our marriage.

We’ve been together ever since! The Secrets to Happy Couple Travel

Dan Crenshaw Book Signing in Coronado

Whitney

I have kind of an eclectic taste in books. Favorites range from cheesy Christmas stories to murder mysteries, and from military books to historical fiction. I happened to hear about the Dan Crenshaw book, Fortitude, that came out in 2020, and I picked up a copy at the library.

I’m a huge fan of comeback stories and people who make the most of their lives in less than ideal circumstances, and Dan Crenshaw definitely fits that bill. For those who don’t know, Dan Crenshaw is a Navy SEAL who lost his eye to an IED in Afghanistan in 2012. He later went to Harvard Law School, and is currently serving in the U.S. House of Representatives.

Anyway, while I was reading the book, I was also getting ready for a trip to Coronado Island, California. That happens to be where SEALs train, which was purely coincidental. A further coincidence was that Dan Crenshaw was going to be there the day we arrived, because he was having a book signing on Coronado! So, I ordered my own copy of the book on Amazon, it arrived the day before we left for the trip, and I got to meet him at the book signing! How’s that for luck?

Read on: The 10 Essential Blog Posts All Travelers Need to Read

Upgraded Suite in Waikiki!

Steve

Once upon a time, Hilton conducted a revenue enhancement exercise wherein one could offer to pay a small supplement such that if an upgraded room became available at check-in, they took the fee, and you got the better room. The gamble was that not only was the upgraded room not guaranteed, but you also did not get to know what made it “better” such that it was worth it to you. 

On my first trip to Hawaii, for business, my employer at the time indicated that we could book the Club Level, so I did. At booking, Marriott offered a chance at a further upgrade for a negligible amount, so I agreed. When I checked-in, I scored the upgrade.  

But this was no ordinary suite. It had two bedrooms, two bathrooms, a full kitchen, a dining table seating eight, three TVs, and many other amenities I had never previously associated with a hotel room. Obviously, this gigantic penthouse extravaganza became the gathering place for the team on our business trip!

More here: The 10 Best Things to Do in Waikiki

Helicopter Tour with Faraway Friends

Whitney

There are some things that happen in life that you cannot make up, y’all. I try to find something unique and special for Steve and me to do on our anniversary trip every year, and in 2018, it was a helicopter ride over Mau’i and Molokai in Hawai’i. One problem: At least four passengers were required to for the tour to even happen, and no one else had signed up except just the two of us. We wouldn’t be able to fly unless two more people signed up.

And as it turned out, our friends Ron and Jane, the couple who did our pre-marital counseling four years earlier, just so happened to be on Mau’i at the same time! I had seen their photos earlier in the week on Facebook and messaged them to see where they were and if we could see them. So, when I got the phone call from the helicopter company to tell us we needed to find two more people, we asked Ron and Jane!

We got to see our friends who had actually moved away after we got married, we got to take our special helicopter tour, and it was almost too good to be true! How’s that for luck?

Unforgettable: Our Epic Helicopter Tour Over Mau’i and Molokai

80s and Sun in Miami Beach When the Rest of the Country was in a Tundra! 

Steve

Do you happen to remember that Presidents’ Day weekend when a cold front overwhelmed virtually the entire USA, making headlines with freezing temperatures and power shortages in Texas, and even several inches of snow in Houston? Almost the entire nation was 20 to 30 degrees below normal (in February!), but not Miami Beach!

Whitney loves sunshine and warmth, and I love a break from the cold in the depths of winter, and we sure got it on that trip. Every time I saw the actual weather or future forecast, I had to comment to Whitney how remarkable it was that it was 87 and sunny day after day in Miami Beach, while it was 60 degrees colder in another part of Florida.  The cold front dipped far south, but Miami held it at bay. We came home with nice, healthy sunburns as the D.C. area emerged from negative-degree windchills!

Read next: The Top 10 Places I Could Visit Again and Again

Want more? Get all our best travel anecdotes on my dedicated Travel Tips Page!

Love this post? Pin it for later!