Dublin, a Mercedes, and the Trip That Changed How I Plan: Hear My Personal Travel Mistakes

Amanda and I were going to celebrate our tenth wedding anniversary in March 2023 by taking our first overseas trip together. We aren’t wealthy, so we put aside money each month and saved our airline miles until it was possible.

We knew that we wanted to see Scotland, but also needed to make the budget work. After researching multiple routes, we found a very affordable multi-city one that involved flying from Dulles Airport to Heathrow, spending a couple of days in London, taking a train to Edinburgh, road tripping around Scotland, then flying from Glasgow to Dublin for a day or two, then back home via Heathrow.

It was ambitious, but we had about two weeks for the vacation.

I have trouble sleeping on planes, and the red eye flight to London did me no favors. Awake the whole time, I was exhausted when we landed at Heathrow in the early morning the next day. We then took the tube to our hotel in Fulham—not realizing the connections we had to take on the Underground, dragging our luggage the whole way.

Finally arriving at our hotel, we crashed for a few hours and got back out to see some of the city before the day ended. Two days in London together was fun, but also exhausting by the time we boarded the train to Edinburgh.

Did You Know? My background is in history, defense and foreign policy analysis, and international humanitarian work. That means I've spent years studying countries, cultures, people, and risks. That knowledge goes directly into every itinerary I design.

Arriving in Edinburgh around 11:00 at night, we decided to walk to our hotel in Old Town, as it didn’t seem far. If you’ve ever been to this beautiful city, you probably know what I’m about to say…

Both us and our luggage were not prepared for the cobblestone streets, steep hills, and stone steps. Exhausted, we checked into our hotel, which also had an outdoor bar with live music. Without a doubt it was a great welcome to Scotland, but when the music still rages at 1:30 am and you’re trying to sleep…it affects you.

Then came the Mercedes.

At Edinburgh Airport’s car rental center, I was tired and impulsive. We had booked an all-wheel drive mid-size SUV—the type of vehicle we drive in the U.S. and one I deemed a smarter choice for Scotland’s early-March weather in the Highlands. However, the rental agent said they upgraded us to a Mercedes at no extra charge, to which I impulsively responded, “sounds great!”

Don’t get me wrong, a new Mercedes was a great drive on the UK highways. But it became apparent it might have been a poor choice when it snowed on the Isle of Skye and we had to abandon one of our planned outings because the Mercedes couldn’t handle snow-covered, rough road conditions. Further along in the trip, a rock came up under the very low car and caused about $300 in damage (thankfully I had purchased rental insurance, and it was entirely covered).

My biggest regret on this Scotland trip was trying to see too much in the amount of time that we had. We were in a new place every one or two nights, which can be exhausting over two weeks. More time could have been spent exploring on foot rather than driving to new places every other day.

Unfortunately, our last few hours in Scotland were tiring and stressful. We returned the rental car at Glasgow Airport and waited for our short flight to Dublin. And waited. And waited.

A weather system had moved in and delayed our evening flight by several hours. Now, instead of arriving in Dublin around 9 pm, we wouldn’t land until after midnight. After finally landing in the middle of an intense storm (the only landing where I’ve been scared), we got an Uber to go to the hotel.

It quickly becomes apparent to you that you’ve chosen the wrong lodging when the Uber driver looks nervous pulling up. At nearly two in the morning, the street in front of this hotel had homeless people and some shady figures right outside. It was not well lit.

Did You Know? The Voyager Package includes a Neighborhood Brief for every accommodation location on your trip. This is a detailed half-mile snapshot of the neighborhood or block around your lodging that includes walkable locations (health facilities, pharmacies, police stations, grocery stores, gas stations); wildlife briefing (if in rural areas); and safety & security overview (including streets to avoid).

We were let in through the locked glass doors by the night manager, who was not exactly the epitome of customer service. It was a relief to leave the lobby and get to our room around 2 am…until it wasn’t.

The toilet hadn’t been fully flushed since the last guest to use it, and the noise outside was going to prevent a peaceful night of sleep. We were too exhausted to move rooms.

We slept until early afternoon, and ended up seeing only one attraction until it was time to go back to the hotel, pack, and prepare for our flight early the next morning.

It was the most miserable point of our ten-year anniversary trip. But sadly, not our last mistake.

We flew back to Dulles and…waited in the immigration hall for two hours…slowly shuffling through a crazy long line with crying children.

Then we had to drive to southern West Virginia to pick up our dogs at my in-law’s. A several-hour drive after a transatlantic flight was not a smart idea. It was brutal.

Despite all of this, our time in Scotland was incredible. So much so that we returned two years later and brought my mother along.

I post this to give you a glimpse into the mistakes I made when planning this trip. I would have gladly paid an expert almost any amount to have avoided most of that and experience a more seamless journey. You can never plan an entirely risk-free or problem-free trip, but you can certainly mitigate most problems.

This is where Twelve Tine Travel comes in. Our package prices reflect the depth of research behind them, research you simply won't find in a generic itinerary template or a budget planning service. And unlike traditional travel agents, Twelve Tine Travel earns nothing from the airlines, hotels, tours, or restaurants we recommend. No commissions, no conflicts—just a plan built entirely around you and your travel preferences.

Here’s the reality: every mistake or bad experience in this post could have been foreseen and avoided had I hired professional services like Twelve Tine Travel.

Click here to see a video from our most recent UK trip—where the only bad experience on the 15-day journey was catching a cold.

Knowing what I know now, I would have gladly budgeted a percentage of my trip to bring in an expert and end up having a completely wonderful (and less exhausting) wedding anniversary.

You’re already spending hard-earned income to travel internationally, what's a small percentage more to protect the entire investment? If the experience and memories of an overseas vacation or honeymoon are truly important to you, why not make it the best it can be rather than hope it will be the best it can be?

If you would like me to plan your next overseas vacation (or you know someone else who would), check out our packages here. For any questions, just contact us through our site.

I look forward to designing something extraordinary for you.