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 🙂