Guest Post: An Inconvenient Truth About DIY Travel Planning

A story about a family vacation gone wrong.

When most people think about traveling to Portugal, the things that come to mind include beautiful beaches, romantic architecture and an iconic culinary experience. For me, I think about running through airports, bruised rental cars and expecting the un-delightfully unexpected. My name is Chris, and this is my story.

It all started in the summer of 2019. My wife and I were planning our fourth trip abroad with our two-year-old son, excited at the prospect of sharing memories in the beautiful cityscapes and countryside of Lisbon, Lagos and Porto. We’re no slouches when it comes to pursuing adventure with our toddler, Austin, who has already been to 8 countries, not including the USA of course. You could say we’re a bit enthusiastic about our family vacations, but after this last trip, I think we’ll be reconsidering a few things.

In this article I’m going to detail where it all went wrong, and what I would do differently so you can learn from our mistakes.

Our bags were packed snugly in our mini Cooper as we embarked to Newark Liberty International Airport that fateful Sunday. We arrived 3 hours early for our international flight and searched diligently for our airline, Brussels Airlines. The airport staff sent us on a wild goose chase back and forth from gate to gate – which is incredibly time consuming with a toddler, luggage and a pregnant wife. Did I mention my wife was 4 months pregnant?
Long story short, by the time we figured out Brussels Airlines operates as United Air, it was too late. That was the first flight I had ever missed.

This dramatic event could have been easily avoided if only we had someone who could have told us this crucial piece of information ahead of time.

Incidents like this can be avoided with Tenon Tours. They offer flight assistance and notify travelers of anything that will impact their travel. They also provide a 24/7 hotline for emergencies, and would have been able to point us in the right direction should we have still needed their assistance. Lastly, because all your travel documents are stored in their mobile app, you have everything you need in one centralized location.

Persistent not to let this blunder ruin our trip, we arrived extra early the next day to catch our flight. One red-eye, two melatonins and three Scotch whiskies later, we arrived in beautiful Porto, Portugal. We gathered our luggage and set out on our next adventure: finding the rental car company. We had a great deal on the rental car ($100 Euro for 10 days). The only problem was, we couldn’t find it once we arrived. “Where’s the damn rental car agency?” we muttered countless times as we wandered past the rental companies that riddled the airport. After what seemed a jet-lagged eternity, we located our rental company with the help of a taxi driver. We only had to cross the major cobblestone road across the street from the airport, which wasn’t easy when traveling with three bags, a car seat, stroller and a cranky two-year-old.

The rental vehicle was actually pretty nice despite costing twice as much as our original reservation, but I suppose that’s how business is conducted when you lose a day on the reservation. We hurried through the paperwork so we could get on with our vacation. I inquired about the insurance, to which the rep assured me that we had adequate coverage. We learned a valuable lesson in insurance coverage while gliding down a cobblestone road after our excursion to the beautiful castles of Sintra. I still have no idea where that rock came from, but it glanced the side of our rental car and impacted our bank account by about $1,000. Unfortunately, our definitions of “adequate” are starkly different as I found out in our epically poetic venture abroad.

Pro Tip: Many credit card companies offer additional insurance for rental cars if the reservation is booked on the card. Always inquire about these benefits ahead of time so you can be prepared.

Licking our wounds and determined to enjoy our annual family vacation, we ventured to the beautiful beach town outside of Lagos. We had read a few travel books which detailed several boat excursions available to explore the coast and caves throughout the waters. Allegedly, one could arrive without a reservation and hop aboard any number of boats for an exploration. So, we arrived at the destination, which was crawling with sightseers who had the same precipitous assumption as us. After scaling what seemed a half mile steep terrain to the coast (with my pregnant wife by my side and two-year-old on my back), we waited 20 minutes for the first boat to arrive. We soon found out that the boats come every 45 minutes. Unfortunately, the area wasn’t exactly “kid friendly” and it was apparent that our jet-lagged toddler was not going to last to see the venture through. Sadly, the boat excursion did not happen, but could have been easily avoided with some guidance and oversight.


Don’t get me wrong, it was a delightful trip despite my dramatic synopsis. We had a wonderful time, but the hiccups throughout the journey tarnished what could have been an even better family vacation. When it was all said and done, our trip cost us 25% more than we had originally budgeted, not to mention the cost of “loss of enjoyment.”

I wish you all the best of luck in your travel planning and adventures abroad. Plan for the unexpected and don’t make the same mistakes I made. Happy travels!


Note from the team

Our mission with By-Your-Side Service℠ is to provide you with peace of mind. Travel can be unpredictable, and we want you to be prepared. Tenon Tours provides insight, travel tips, recommendations on your destinations and is available from planning to traveling.


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