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Spontaneous Travel
Cuba Setback to South East Asia Success
We woke up early one Saturday morning in February with expectations of strolling through the classic streets of Havana later that afternoon. What we didn’t know was that 15 hours later we would be en route not to Cuba, but to the other side of the world. How did this happen?
With our bags packed and mind set on Cuba, we arrived at the JetBlue terminal at JFK 3 hours ahead of our flight. Step one was to purchase the tourist visa from the special downstairs counter.
Jumi handed over her passport, but was told “you can’t board the plane.” Having a Philippine passport, she was denied the chance to buy a visa. Apparently, a new rule was just implemented: she needed to purchase one from the Cuban embassy in Washington, DC! We had no advance knowledge of this and frustration rapidly set in. Damn. It was really heartbreaking.
We had booked most of our accommodations and already set our minds on spending a week basking under the Cuban sun, cigars in one hand and rum in the other.
A few calls to JetBlue we really wouldn’t be able to go and the reality that we would miss out on this trip hit hard. Fortunately, we would be able to recover the value of our ticket prices as travel credits for future JetBlue flights within the next year, though we wanted more than just travel credit. We had already taken off the whole week and there was no way that we would be strolling back to our workplace, tails between our legs.
As the minutes passed, we both started to accept the fact that we were not flying to our intended destination. Without talking to each other, we sat down and turned to our phones. We decided right there that we would not be leaving JFK unless it was on an international flight.
Skyscanner was our website of choice. We tinkered with the “Search Everywhere” function, with maximizing our time with the best value being the goal. Mexico at $450 was the cheapest international destination, but did we really want to spend that with deals routinely in the $200’s? And also, we have been to Mexico and would love to visit other parts, but not yet.
Peru had long been high on our list, but the scheduling would have had us leaving on a Sunday evening with an overnight layover in Mexico City and only 4 days to spend in Lima before returning home. Clearly, the value here was also lacking, so we broadened our search.
Thailand came to mind. Manila popped up with excellent value on Cathay Pacific, but we were already set to visit the Philippines in less than a month. However, this planted the seed for what would be a tremendous 180 on our original plans.
The plane that we were supposed to be on was already on it’s way to our intended destination when we finally figured out and booked a round trip ticket on the day of that would take us to the other side of the world — not to Poconos or Atlantic City, but Hong Kong, Singapore and Malaysia.
We’d be leaving in just 10 hours and returning to JFK the following Sunday evening – perfect! Cathay Pacific is one of our favorite airlines to fly with, and we were impressed with the value on an extremely last-minute itinerary to a destination so far away. The feeling once we submitted our payments and received confirmation will be one that we will never forget!
Since we are not into planning and have mastered the art of procrastination in travel, we only had 10 hours until our flight time and spent it happily mapping out where to eat and what places to explore. We boarded the plane while we booked our first night’s accommodation (thanks to AirBnB). Twenty plus hours later and we said hello to Singapore.
Booking our most spontaneous trip ever gave us a whole new perspective on how to handle setbacks in traveling. With the phenomenal resources available, particularly Skyscanner and Google Flights, it was much easier to handle than you would ever expect.
Don’t just give up and throw a fit without throwing a fight!
Have you ever had to change your travel plans on a whim and book a spontaneous trip?
How was your experience and how did it work out? Would love to hear about it. Leave a comment below 🙂
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Thanks for sharing this story! I think most people have no idea how hard it can be to travel if you don’t have an American passport. Good for you for making the best of an unfair situation. Hope you had fun in Singapore!
Thanks, Emily! Appreciate the kind words.
You’re right – the number of countries with visa requirements can be daunting. We have to limit ourselves to certain countries while traveling together for now, but it just means there will be plenty to see down the line.
We enjoyed the brief amount of time we spent in Singapore and had an awesome time in Malaysia!
Wow! I’m so impressed with how you guys bounced back from that setback! I want to believe I would have that tenacity, but also feel like I would’ve been so disheartened. I’ve never had a travel setback like this one but now I know that if the situation arises to never give up! Cheers!
Thanks, Christina! As disheartening and frustrating as it was, we had to do whatever possible to avoid just staying back with nowhere to go.
Glad that our story was able to provide you with some inspiration! There is always somewhere you can go in that situation if you really try to make it work.
So happy to hear that you didn’t just cancel your trip altogether but must have felt like a right sucker punch at the time, hearing that you couldn’t go to Cuba. I have been in situations over the years that I had to change travel plans and end up at another destination but nothing like this like. Props to you for using your traveling nous to figure out somewhere else to go 😀
Hi Amit,
It was definitely a sucker punch for the first 45 minutes or so. It ended up being all for the best, as Southeast Asia is our favorite part of the world to travel in.
What were some of the other situations that you had to change travel plans before?
Thanks for the props! Definitely a life-changing experience for us.
No matter how much you plan, something can always happen. It’s great that you’re so flexible and were able to have a great vacation in Southeast Asia instead. Cuba will still be there for next time:)
Hi Jennifer,
Absolutely. Fortunately, everything was able to break our way with overcoming it. You’re right, we can always go to Cuba in the future!
Thanks for reading!
I’m completely blown away by this story! It seems so exciting and makes me want to book a spontaneous trip this weekend! Can’t wait to read more about this amazing trip!
Thank you! Glad it inspired you – we hoped that the story would be a motivation for anyone with travel plans that hit a snag. Any spontaneous destination in mind?
I’ve never had to change plans at an airport like that last minute. Phones are so handy for that! What a story! Just goes to show that being flexible is a great trait, especially when traveling.
Hi Lara,
We never would’ve expected to have to do that either. Phones are a game changer for it – couldn’t imagine how it would’ve been back in the day. Glad you enjoyed the story and hopefully it inspires you if you are ever in a similar bind!
Wow, what a change of plans! Good for you guys on setting your mind to it and booking an amazing trip so quickly. Love it! We had a trip to Key West canceled earlier this year…leaving the airport to go home when you thought you were going on vacation just plain sucks. So glad you still got to go on a great trip.
Hi Katie,
Sorry to hear about the canceled Key West trip. What happened? We were fortunate to be able to find a good deal at the last minute that was worth all of the extra hours of flight time. Thanks for reading and happy holidays!
Talk about going with the flow! It’s a quality I need to work on but you guys seem to have to down. We use Skyscanner as well but it sounds like in this case it was the perfect situation for it. Happy everything worked out!
Hi Angela,
Beforehand, the only “go with the flow” situations we had experience with were leaving a few days open on trips to figure out the weather. Skyscanner is a gem and it was perfect for this situation! Hope our story inspires you to go with the flow if something like this arises. Thanks for the kind words and happy holidays!
It’s not in my nature to be spontaneous – especially with the kids. I am a planner and not only do I have plans made well in advance, I plan out our days before we ever even leave.
That makes a lot of sense when you have kids in the picture. Certainly not as easy it would be if it was just two of you.
I would have been so disappointed to find out I would not be going to the destination I had dreamed of and packed for. I love your positive attitudes and how you turned an unfortunate situation around and were able to book another amazing destination.
Thank you! We were crushed initially, but we soon realized that we had to make the best of it. Fortunately, we were also packed for SE Asia climate-wise.
What an interesting travel story. Don’t think I have ever heard anything like what you went through. Glad you still enjoy traveling.
Thank you! Oh absolutely – if anything, it made us enjoy traveling even more since it was a pitfall we overcame.
I’m so glad everything worked out in the end! It would be frustrating to not be able to go to the place you intended, but at least you got to travel to other places that you were curious about.
Thank you! It really did end up working out for the best
What a great way to salvage a potential bummer of a situation! I love to travel, and love doing all the planning and researching. Sounds like you had a blast!
That’s awesome that you love to travel and do all the researching that goes along with it. Gotta love seeing all the hours turn into reality when you gaze at that beautiful sight or feast on that delicious meal. We really did have a blast!
I am surprised noone told you about the requirement before you left, it seems important. It’s good that you found a place you both wanted to go so you could enjoy your time off. For me I probably would have traveled to DC and gotten the problem handled if possible.
Yeah it was odd that we didn’t get an e-mail from the airline about it. Even if we had gone to DC to handle it, who knows how long it would have taken to process the visa. Usually, that type of stuff takes a while.
What an amazing story. I loved how you made the most of such a disappointing situation. Thanks for sharing, we travel Europe a lot, and this is a great reminder to stay positive even when things go sideways.
Glad you enjoyed the story! It was really a defining moment for us as travelers. Our intention with sharing it was to give hope to others who may encounter a similar situation.
If there’s one thing that I learned, it’s that nothing ever goes as planned when you travel. I think it’s awesome that you learned so much from this experience and that you never let the bad things get in your way of having a great time.
Absolutely – you have to be ready for anything to go sideways! It was a much needed setback that we needed in order to overcome it and emerge stronger as travelers. Flexibility is key!
Wow, that would have been so frustrating to find out last minute. You turned it around by creating a whole new adventure to go on, which I think is great!
It was very frustrating at the beginning, but it turned out to be an incredible adventure!
I would have been extremely frustrated too, but glad to know that everything worked out well for you! I guess it is a blessing in disguise too, because you were able to visit three countries instead of just one!
Great point. It really was a blessing in disguise, as we never had Singapore or Malaysia on our immediate radars. Both were great, Malaysia in particular!
I would have been so incredibly frustrated. Traveling is so stressful and overwhelming and it is sometimes so hard to just get where you want to go so you can relax. Happy you still had a fun adventure!
We certainly were at first. It can be very stressful at times, but encountering situations like this help address them better and less stressfully in the future. Definitely helps develop a thicker skin! Thank you!
You handled the situation really well. I’ve had to switch up my travel plans a time or two and it can really ruin the entire trip if you let it. Like the time I had to spend 8 hours in a DC airport due to weather delays. OMG, it was the worst. Fortunately, I was traveling with a friend and we made the best of it.
Thank you! Those weather delays can be a nightmare – glad you were able to make the best of it with your friend!
You handled that really well. I would have been so frustrated! I get my heart set on travel plans.
Our hearts were set on it too and we were frustrated at first. But then, our fight response overcame the flight response and handled it as best we could!
Oh I am glad you guys got to enjoy your trip anyway. You handled that situation with such poise and grace!
Thank you! It was a necessary moment for us to develop more grit as travelers and continue to be flexible when setbacks occur.
I’m so very glad that things worked out for you. You handled this all so very well. Sometimes spontaneous can work out best.
Thank you! We totally agree – being spontaneous can be even more memorable than meticulously planned experiences.
It was a nightmare for me when Cathay Pacific cancelled my flight because I was traveling alone and terrorism was everywhere. They didn’t want me to travel by myself. A refund was given to me and understood how cautious they can be.
Oh wow! That is scary to think of a situation like that. Fortunately, they were able to refund you. We have flown Cathay a lot and have had nothing but good experiences.
Oh wow, I’ve never had to deal with travel flight plans yet. My sister was recently delayed and let me tell you, she was not happy. She should have used that time to plan her trip and just relax.
That’s good that you haven’t yet. Hopefully our story can help if and when you do encounter any sort of flight setback.
Not everyone knows that there are also setbacks when travelling. Good to learn that inspite of what had happened. You still manage to have a good vacation. Enjoy!
Couldn’t agree more! Traveling isn’t all sunshine and positivity – there are very real setbacks, risks and situations that could put a damper on things. But that is all part of the experience and helps build character. Thank you!
Nice story! Yes, I changed my plans and stayed in Sevilla, Spain for a long weekend alone, when my cousin and his girlfriend changed their minds at the last minute! looking forward to reading about your SE Asia adventures!
Thank you! Glad you were also able to overcome your travel partners changing their minds. Sevilla must have been awesome!
Thank you for this inspiring story! I would have done the same (never leave the airport!!) but I know most of the people would have been discouraged! I can’t imagine your families’ and friends’ faces as soon as they saw your Facebook /Instagram first photo from the other side of the world
Thanks for reading! Glad you are on the same wavelength as us – friends and family were definitely shocked when they found out!!
A good example of making the best of a bad situation. There are a couple good things to learn from this. Firstly plan, plan, plan, research, research, research, backup plans are always a good idea. We all love planning for the best case scenario, but rarely have the resources at the ready if things go wrong. Great to hear you were ready to pull together your resources and remedy this bad situation with a fun alternative.
Thanks for sharing. Keep travel blogging. Adventure is better shared with friends!
Thank you! Backup plans are important, even if they are buried a bit in the back of your mind.
So sorry to hear that that had happened!!! But then again I guess things happen for a reason and seems like everything worked out in the end anyways. Spontaneous trips are the best and it’s great that you guys turned an unfortunate event into an even more adventurous one!
Thank you! Things can happen for a reason and we have zero regrets about how it played out.
Passports definitely play to a disequilibrium in world travel, in large part reflecting the geopolitical and historical state reached in the 21st century – best summed up as a polished turd. Privilege is handed to ‘strong’ passports, so its great to read that you bounced back in the face of a crappy situation!
Unfortunately those passport situations are definitely a mess. Thanks for reading!