Is trip cancellation worth it? Navigating this uncharted territory at the last-minute.
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I’ll start by saying that life is too short and too precious to be devastated by a change in travel plans. Even as a travel enthusiast who ranks opportunities to explore the world very high on my list of values and priorities… the people I love rank way higher. ❤️
The Anticipated Trip
Italy was the number one destination for revenge travel after COVID. The crowds came en masse during the spring and summer of 2022 and into 2023. Despite enjoying living life a little differently than the masses… I was right on trend with a 5-week trip planned for Bella Italia! I’m a committed shoulder season traveller, so felt okay departing in October with an itinerary that took us a bit off the beaten path.
This trip went from a vague dream to an exciting reality when we committed to the airfare 8 months prior. I visited Italy as a teen and have been excited to introduce this beautiful country to my husband. Among these vague dreams also linger hopes to co-own a little Italian getaway with friends someday. This was going to be an opportunity to test the waters.
I’m solidly in the slow travel camp. I don’t believe you “do” Italy in a single trip. The regions are diverse and the number of treasures to explore is many. Instead, our off season itinerary carved out 3 small special areas of focus: hiking in Tuscany (with some fly fishing thrown in as we rested our feet); travelling down the Adriatic Coast to explore Puglia; and staying put for a deep dive into Rome.
Planning and anticipating a trip is exciting. Research suggests that it can be almost as rewarding as the trip itself and that people are happiest when they have a trip in the works.
But life is life and sometimes unexpected events force us to cancel our carefully arranged adventures.
I am sure you know dozens of people who had to cancel their travels in 2020 and 2021 due to COVID-19. I have a school principal friend who tells a heart-wrenching story about that crazy week in March when the pandemic began its voracious and uncertain path in changing our world. She was at the high school in the wee hours of the morning meeting a group of students laden with backpacks and suitcases ready to depart on their Spring Break school trip to Central America. My friend was greeting them while simultaneously on the phone with School District administrators wrestling with the decision to cancel this trip or not. Sadly those students, along with millions of people, stayed home that year.
OK, Let’s Cancel!
Trip cancellation at the last minute can be a daunting process, encompassing various logistical, financial, and emotional challenges. I hope that sharing my experience of navigating through the complex web of cancellation decisions might be helpful if you find yourself in a similar place. I have drawn from my lessons learned to show how to consider the possibility during your trip planning process.
Once the decision was made, the first thing I did was make a checklist of everything I had already booked, and how much I paid, noting any cancellation policies and deadline dates. In hindsight, it would have been even easier if I had done this when I was booking each one. I’m pretty organized and had all my travel emails tagged, some things printed out, and all bookings listed in my planning app, but not all these pieces of information were centrally listed.
Trip Cancellation: Accommodation
I am known to be resourceful when it comes to curating accommodation. Everyone is different, but my planning approach is to balance amazing locations with affordability. I don’t place a high value on luxury accommodation and instead focus on comfortable, clean, convenient, and, where possible, unique and special. This trip was no exception. I hunted down special places that fit our needs and found them using Airbnb, Avion Rewards, Monastery Stays, and Home Exchange. I also use More Rewards, VRBO and Booking.com but didn’t on this trip. It turned out that my accommodation was, for the most part, easily refundable.
Airbnb Bookings
When I look on this site during the planning phase, I filter for places that offer free cancellation. When it came time to cancel, it was easy peasy. Just make sure you check the cancellation description on each listing. Ours all offered 100% refund up to 14 days before.
The only odd thing is that since all my refunds came as a credit back to my credit card, I can’t simply restore my travel savings account. Credit is as good as money - I’m not complaining - but it sits there on my card balance until I spend it since I pay off my credit cards religiously.
Avion Rewards
I often use travel rewards for short stays of 1 or 2 nights. For this trip, there was one night when we arrived in Rome before heading by bus to Siena and then two nights in Rimini on the Adriatic Coast at the beginning of our train journey south to Puglia. No cash was paid, the bookings were only points.
Cancellation was an easy click online. All points were refunded and ready to spend later. I imagine every rewards program is different, check yours for cancellation policies before you book!
Monastery Stays
On our last 2 nights in Rome, we chose to stay in a convent just outside the Vatican. I like to stay in unique accommodations when I can. Much to my husband’s chagrin I get excited about very non-luxurious, ridiculously memorable options! For example, we’ve stayed in a jail in Ottawa, a crazy loft overlooking a cathedral in Bruges, and a park bench in Greece. To be fair, the park bench was free and a whole level below non-luxurious!
To book the convent room, we paid a deposit that we lost. The unpaid balance was fully refunded. In a way, I’m totally okay to “donate” these few bucks to help keep these incredible buildings open for affordable and unique accommodations.
Home Exchange
We had 11 nights arranged through Home Exchange.
Home exchange is a phenomenal travel option. Check it out here. Membership supports traditional “reciprocal exchanges” when you go to someone’s house while they stay in yours, but it also has a GuestPoint system that sort of works like currency. When people stay in my house I earn GuestPoints instead of having to reciprocate the exchange. I can then build a bank of GuestPoints and use them to visit a different person’s house at a different time.
I had booked places in Sansepolcro and Matera, Italy using GuestPoints. From a policy perspective, cancellation can be a bit tricky since the host can choose whether to keep your points if you unexpectedly cancel, or return them to you. In Sansepolcro, we were going to stay in the vacation home of an Italian woman. When we booked her place, it generated GuestPoints for her to plan her own getaway. When I cancelled she messaged me with her conundrum that she wanted to return my points but she had already committed the points for her own travels. It was last minute and I certainly understood her situation. The Home Exchange company was awesome when I contacted them. They compassionately allowed my hosts to keep their points and also fully reimbursed me for my points.
Trip Cancellation: Airfare
For this trip we were flying WestJet using a companion voucher, some WestJet points and a bit of cash. To be honest, I typically choose the cheapest options with the least flexibility when booking flights. I might reconsider this habit next time. Fortunately, my frugal choice of the least flexible option had a cancellation fee - so I lost a few hundred dollars in the transaction.
WestJet made it very simple to cancel online - a simple click. I was refunded everything (minus the fee) as a WestJet credit. While it’s not cash in my pocket, as long as I don’t let this credit expire, it now feels like a fun pot of travel gold waiting for the next adventure in the next 12 months!
Trip Cancellation: Tours
My husband and I don’t typically book travel tours but for this trip, we were thrilled to work with a company that offered a one-week walking itinerary. The package included all of the hotel bookings, walking trail details, GPS information, in-country support if we needed it, and luggage transfers from hotel to hotel so we didn’t have to carry our backpacks.
On Foot Holidays is a small company out of Salisbury, UK and they showed nothing but compassion and efficiency with our last-minute cancellation (no affiliation). We were bound by their policies, though, which we had been aware of and accepted months ago. The company had already pre-paid all of our accommodation so much of the money paid was already out of their hands. As per the policy, we received a 10% refund and all the documentation required to pursue recovering the rest through the cancellation insurance of the associated credit card.
Trip Cancellation Insurance
We’re now in new territory as we have never bought cancellation insurance. We knew, however, that one of our credit cards had the benefit of providing trip cancellation insurance. To be honest we hadn’t really read the fine print but figured if we needed to cross that bridge, we at least had an option to investigate. Here we were, crossing that bridge!
I work hard to create affordable itineraries in which things are either refundable or economical enough that we would be fine if we had to walk away for any reason. But that doesn’t mean I want to leave money on the table! Since the walking tour package cost a chunk of cash, getting that back felt like pursuing a trip cancellation claim was well worth the effort.
We did a deep dive to read all the fine print of this “free” trip cancellation insurance with our TD Visa Credit Card. Check yours as I imagine they are all different! We thankfully met the criteria:
75% of the cost had to be charged to that card.
The reason we were cancelling was listed as a valid and supported reason.
We had all the necessary documentation as evidence.
I had a vision of insurance people as greedy, evil goblins trying to trip you up so they could avoid paying out claims. And while that might be true in some cases, it wasn’t in ours. We called the number provided in the fine print and talked with a very kind woman who after a short conversation approved initiating a claim as long as we uploaded all the documentation into their online portal within 90 days. As of today, we have not completed this yet but I am a serial optimist and have no reason to believe that it won’t “work.”
The insurance company’s maximum claim amount was a titch less than our tour costs - so we will be, in the end, out a little bit of cash. Next time, in planning, I’d compare my non-refundable costs to the maximum amount able to be claimed by “free” insurance with my credit card. If the difference is larger than what is comfortable, I’d fork out extra for more insurance. With some credit cards, this might simply be a top-up, or it may require purchasing a separate policy.
Trip Cancellation: all the other little things.
For us, this included:
a bus ticket (using the Flix Bus app) which was fully refunded with a simple click!
travel medical insurance which was fully refundable up until the departure date. It was a quick and painless phone call to the provider! We used the medical travel insurance that is included with one of our credit cards and had simply topped it up given we were staying in Europe longer than the “free” coverage.
In another situation, it may also include train tickets, tour tickets, and car rentals. A little note that Get Your Guide has a great cancellation policy with a full refund up to 24 hours in advance for most experiences. We hadn’t yet started booking these experiences.
Dealing with Disappointment
Cancelling a trip can bring about a range of emotions, leaving us or other people feeling frustrated, disappointed, or guilty for the disruption in plans.
By flexing your resilience muscle, feeling some compassion for yourself and others, and finding the positive in the situation, navigating the emotional side of cancellation can be as smooth as the practical and financial side.
Allow yourself to acknowledge and process your emotions. It's normal to feel upset or frustrated, but don't dwell on these feelings for too long. The first thing my husband and I did was change our language. We were cancelling our bookings but POSTPONING our trip. It softened the edges of our disappointment considerably.
While cancelling a trip can be disappointing, use this newfound time for other high-priority purposes. Engage in activities that bring you joy, such as being with friends and family or exploring your local area. Let other things you value get some attention until you can pack your bags again.
Is trip cancellation worth it? Should you buy trip cancellation insurance?
We each have to make a personal decision about risk (financial and emotional) when it comes to preventing losses if the unexpected thwarts your travel plans.
My recent experience validates that there are many things you can do in the planning stages to mitigate losses if you have to cancel a trip. I have learned to check my existing options and run the numbers ($) before buying a policy. Ultimately, embracing flexibility and maintaining a positive attitude will always help ensure a smoother journey through the cancellation process
What tips do you have? Please comment below!
