• 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.

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Italy has extended checks on travellers from Spain for another week, but talks between Giorgia Meloni and Pedro Sánchez have opened the way for an end to reciprocal restrictions imposed after the migration crisis in Ceuta.

Italy and Spain have agreed to work towards ending their reciprocal Schengen border controls following discussions between Prime Ministers Giorgia Meloni and Pedro Sánchez at the European Council summit in Brussels. Rome nevertheless extended its restrictions for another seven days on Friday, 16 October, as the two governments consider how to bring their respective measures to an end.

The decision marks a possible turning point in a dispute that has disrupted travel between two of the European Union’s largest countries since the summer. According to the notifications recorded by the European Commission, the restrictions concern air and sea connections between Italy and Spain, which do not share a land border.

The two governments have instructed their interior ministers to consider alternative arrangements over the coming week. Although neither side has formally withdrawn its measures, the agreement to coordinate their removal suggests that both capitals are seeking a way out of an increasingly uncomfortable confrontation over migration and internal European security.

How the Ceuta crisis reached Schengen

The dispute began after an extraordinary influx of migrants from Morocco into Spain’s North African enclave of Ceuta in late July. More than 72,000 people crossed the border, prompting serious questions about the management of the EU’s external borders and the possibility of onward movements into other member states.

Italy responded by introducing checks on passengers arriving from Spain, arguing that the situation created risks for public order and internal security. Rome also raised concerns about the possible movement of individuals presenting security threats, although the extent of any such movement remained disputed.

Madrid rejected the justification and introduced reciprocal measures. What began as an emergency response to events on an external border consequently developed into a disagreement about whether one Schengen member could impose restrictions on another on the basis of anticipated migration movements.

EU Today examined the original Spanish retaliation in August, when the dispute first threatened to turn temporary border controls into an instrument of political pressure.

The wider consequences of the Ceuta incident have raised questions about the vulnerabilities exposed at the EU’s external border and the effectiveness of common European migration and crisis-response policy.

The limits of temporary border controls

Schengen is built on the principle that people can travel between participating countries without routine internal border checks. Member states nevertheless retain the right to reintroduce temporary controls in response to serious threats to public policy or internal security, subject to the requirements of EU law.

The difficulty lies in determining when those exceptional powers are justified. Italy has maintained that the Ceuta crisis warranted precautionary action. Spain has argued that controls imposed specifically on travellers from its territory were unjustified and discriminatory.

These opposing positions matter beyond the two countries. If concerns over irregular arrivals in one member state become sufficient grounds for another to introduce sustained checks, the distinction between Europe’s external borders and its internal travel area becomes increasingly difficult to maintain.

The operational results have also entered the political argument. Italian figures cited during the dispute indicate that nearly half a million passengers were checked during the first month, with 31 refused entry. Those numbers demonstrate that the measures were substantial, but do not by themselves establish whether the original security concerns were proportionate to the restrictions imposed.

Madrid, meanwhile, has maintained that migrants involved in the Ceuta influx had not moved onwards to mainland Spain in the manner suggested by Italian concerns.

Meloni and Sánchez seek a practical compromise

The latest discussions offer both governments a route towards de-escalation without formally conceding their underlying positions. Meloni can present the additional week of controls as a continuation of Italy’s security precautions, while Sánchez can point to an agreement to prepare their coordinated removal.

The two prime ministers remain politically divided on migration. Meloni has consistently argued for stronger border enforcement and deterrence, while Sánchez has defended an approach incorporating legalisation and labour-market integration for migrants already living in Spain.

Those disagreements were also visible during the Brussels summit, where European leaders returned to the question of migration management and the consequences of national decisions for the wider Union.

For Brussels, the immediate concern is whether the two governments can replace competing national restrictions with arrangements that address security concerns without unnecessarily interrupting movement between Schengen countries.

A coordinated end to the controls would not resolve the underlying problems exposed by Ceuta. It would, however, remove one of the more unusual internal consequences of that crisis and demonstrate that political negotiations can still prevent emergency border measures from becoming semi-permanent.

The decisive period is now the coming week. Whether the controls expire as planned will depend on the discussions between the Italian and Spanish interior ministries and their ability to agree practical alternatives.

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