• I booked two separate flight itineraries on different airlines for a family trip to Ireland.
• I realized this was a mistake after the first airline diverted, and the second left without us.
• The fix cost my family nearly $3,000 in new tickets and a day's worth of touring.

I'm a veteran traveler who has booked more long-haul flights than I can count. But earlier this year, I made a very expensive rookie mistake.

While planning a trip, I came across a deal I couldn't pass up: a $317 one-way flight on Icelandair to Ireland with a multi-day layover in Reykjavik. It was essentially a way to take a trip within a trip without paying extra airfare.

The catch? The flight departed from New York, not our home airport in Florida. I'd be in New York a few days early, but my family would need to fly up to meet me. Booking separate itineraries was far from ideal, but I figured a five-hour buffer would be enough.

It wasn't.

A storm in New York canceled my family's JetBlue flight from Florida, and their replacement flight then couldn't land and was diverted to Virginia. Their Icelandair flight to Europe was automatically canceled after they were marked as no-shows.

On the night we were supposed to fly together to Iceland, my family was stuck states away, and I was scrambling to find a solution.

With my family's original flight gone, we had to spend nearly $3,000 to get them back on track and navigate the complicated credit card trip insurance process. Here are 4 lessons I learned the hard way.

Booking separate itineraries comes with a pricey risk

Arriving in the city of your next flight at least 24 hours before may feel a bit extreme, but it's the minimum safety net you need.

Being already in the right location for your flight can be a huge weight off your shoulders. It also allows sufficient time for rebooking should something go wrong with your flight.

My last-minute whim to visit a few friends upstate turned out to be key. Those extra two nights in New York meant I was able to make the flight to Iceland. If I had booked my family of three on a flight the day before our long-haul flight, they would have made it too.

My family made it to New York the next morning and ended up taking a replacement flight to Iceland that evening, getting in about 24 hours later than originally planned. I bought two basic economy tickets for $734 each, and one standard economy ticket with extra baggage allowance for $1,105. In total, I spent $2,573 on new tickets.

The costly mistake made me realize that although an extra hotel night is an added expense and may mean using more PTO, it's a cheap investment compared to the cost of new international flights — and the cost of missed events — if things don't go to plan.

This is especially worth it if you have definite plans right after your arrival, such as a cruise or a concert.

Neither airline has to help in my scenario

When you book connecting flights on a single itinerary, the airline is responsible for getting you to your destination. If you miss that connection through no fault of your own, then the airline will put you on another available flight at no additional cost.

When you book flights separately, you're responsible for making each connection — or buying new tickets if you miss one. And generally, regardless of reason, the airline operating your next flight isn't obligated to accommodate you if you miss it because of a problem with your previous airline.

Our tickets to New York and Iceland were separate, so despite numerous calls to each airline, none were responsible for the missed connection. If you do miss a connection on a single booking, look up alternatives yourself and discuss them with the agent. It's not guaranteed, but they may be able to accommodate you on a partner airline at a more convenient time.

And remember, it's not the staff's fault for the disruption. You get more bees with honey.

I should have read the fine print

I didn't book the cheapest fare, but I didn't read the fine print either.

When things started to go wrong, I was shocked to see there was a $250 change fee per person on my original flight and no refunds. Changing the tickets would have cost nearly as much as the original flight, plus the fare difference.

At the time, it was uncertain when my family would actually arrive in New York and feasibly be able to catch the next flight to Iceland, so we didn't change the tickets. Missing the first flight on this stopover itinerary meant my family was marked a no-show and their onward leg to Dublin was canceled, which is standard airline policy.

While there were other ways to get to Iceland, there were few nonstop flights from Iceland to Ireland — a one-stop meant at least four extra hours of travel — so the best option was to book a new stopover ticket with Icelandair.

When I started booking the new tickets, I noticed that almost every fare class had punitive cancellation and change policies — and this time I was sure to be familiar with the terms of my booking.

I need to better understand my credit card's trip protections

Premium credit cards can have your back when flight plans go wrong, but they don't cover everything.

We used the Chase Sapphire Reserve for Business' trip cancellation and interruption protection for the original Icelandair tickets and were reimbursed $952. The coverage typically reimburses covered unused, prepaid expenses — but not the cost of buying new airline tickets.

Trip delay coverage doesn't either, but it can cover other expenses for covered trips. However, credit card policies vary — and this is where I went wrong.

We booked the flights to New York on an American Express Business Platinum Card but used a different card for the return flights. That meant the Amex trip-delay protection did not apply: its terms require the full round-trip fare to be charged to the eligible card.

I had split the flights across cards to preserve Chase's bag-delay protection, but I didn't realize I was giving up the Amex protection in the process, so the $103 spent on dinner after the diversion wasn't covered. For future trips, I'll use only one credit card with good travel protections for all my trip expenses to reduce complications.

Airlines may also provide some compensation for flight disruptions. In our case, my family was reimbursed for a hotel stay ($185) on the night they were diverted. When delayed, I always keep receipts of all my added expenses to submit to the appropriate parties.

Overall, although our vacation had a rocky start and cost more than we planned, we had a great trip and are glad we pushed through it.

Missing a flight always seems avoidable in hindsight, and some things are beyond anyone's control, but with a few precautions, we can travel more confidently. Next time, I'm booking the extra hotel night.

• Visiting Utah in the winter isn't for everyone.
• I learned that the hard way in January 2025.
• My first mistake led to the rest.

Gazing out my window at the snowcapped mountains on the train to Utah, I had no idea that I'd already set myself up for regret. Some mistakes were set in motion before I'd even left my apartment.

In January 2025, I flew from my home in NYC to Denver and hopped on a 15-hour Amtrak train to Utah's Silicon Slopes — a tech hub lining the Wasatch Front that includes Salt Lake City, Park City, and the surrounding suburbs.

I spent three days exploring Utah's pocket of luxury amid ski season and left with four regrets.

My first mistake was booking my trip in the peak winter season as a non-skier.

As a first-time visitor to Salt Lake City and Park City, I thought seeing the mountains blanketed in snow would be awe-inspiring — and it really was.

I knew winter would be a popular time to visit Utah since it's a ski hub, but I underestimated how busy it would be. Park City was packed with winter sports enthusiasts.

Skiers and snowboarders crowded the sidewalks lining congested streets in downtown Park City, all suited up — some with gear in tow.

I stopped by the slopes at Deer Valley Resort and spotted long lines of skiers waiting for lifts. I waited in line to ride a funicular up and down the mountain.

Maybe seeing the snow was worth the crowds — I won't know for sure until I visit during another season. But had I realized I'd be visiting during the busiest time of year, I would have pushed my trip to the spring, during the shoulder season.

I didn't pack enough clothing.

Overpacking is a rookie mistake when traveling, so I go to great lengths to avoid stuffing too many outfits into my bag. But this time, I overcorrected.

When packing for a trip that's less than a week long, I typically only bring layers I can wear all at once when needed or mix and match. Since I was traveling in winter, I brought a couple of extra shirts, one additional pair of pants, and zero extra outer layers.

But in January along Utah's Wasatch Front, when temperatures ranged from 24 to 44 degrees Fahrenheit, I needed to wear most of my layers daily.

After bundling up for a flight and a train ride, I felt desperate for fresh layers when I arrived in Salt Lake City.

Doing laundry at the hotel was another mistake.

What do you do when you need clean clothes on the road? Utilizing the hotel's laundry services seemed the most straightforward solution, but I regretted it.

That night, I stayed at the five-star Grand America Hotel, where laundry services were top-tier. My shirts and sweaters were returned to me on hangers, each in an individual hotel-branded bag. Smaller items were wrapped in paper in a cardboard box.

I felt like I was opening a present as I sorted through my clean clothes. It excited me — until I saw the receipt.

I paid $115 for three shirts, two pairs of pants, one hoodie, six undergarments, and one two-piece blazer. It was certainly the most luxurious laundry service I'd ever experienced, but for the same money, I could have bought a whole new outfit — and what a great excuse it would have been to treat myself.

I should have made time for winter activities aside from skiing and snowboarding.

I didn't consider other winter activities I could have enjoyed besides skiing and snowboarding.

I wish I'd taken time to tour Utah Olympic Park in the snow and get a feel for what it was like during the 2002 Winter Olympics.

After my trip, I learned that Park City offers mountain-top snowshoe yoga classes, which I would have loved to try.

Next time I travel to the Silicon Slopes, I'll pack enough clothing and make use of the season's offerings.