Our Top Trips of 2019

To kick off the new year we asked our network of Flashpacker Chronicles contributors to put together their Top Trips of 2019. These first hand, personal stories from three unique travelers will inspire your adventures in 2020 and give you an idea of what we loved from this past year.


Top Trips of 2019 - Castelnuovo Calcea, ItalyI was living abroad in London, United Kingdom when my friend who was also overseas wanted to meet up somewhere in Europe. She’d been doing an internship program in Rome and she wanted to do some traveling around the country and I was available to join her.

This trip ended up being one of the best of 2019 but also probably one of the best of my adult life because of how random and spontaneous it was. I looked up the cheapest flights from London to Italy and she looked up trains out of Rome to nearby cities. We ended up picking Turin (Torino) and both met up in a city neither of us had heard much about.

The flight was about 80 euros round-trip and we’d booked an Airbnb for about $50 each of us. We were happy to spend a bit more on accommodations since we were two people and wanted comfort over convenience. Since Turin was a less-traveled city, we were able to save on meals out and drinks.

We spent two days in one of the central neighborhoods, La Hermosa, near a market and there was live music and dancing in the streets every night. We then moved to another major neighborhood, San Salvario, for another few days to explore a different area.

Part of doing this trip was to get away from big-city life and since we had no set plans we decided to check on Airbnb if there were any getaway homes we could reasonably afford. We ended up booking a beautiful cottage home on an Italian vineyard in Castelnuovo Calcea, just a few hour train ride away. It was also the off-season, so prices were more affordable.

We communicated with the hosts beforehand, Carlo and Rosella, who were an older, retired couple. Since they usually hosted big family gatherings in their home, and, again, since it was off-season, they offered to include their home-cooked meals into the price of the rooms instead of for an additional cost, which is what they usually do.

We drank wine from the vineyards literally just a few feet away and ate food cooked from their garden — fresh ravioli, vegetables, home-made Tiramasu.

Honestly, the whole trip was really affordable and we ended up having the experience of a lifetime just by going slightly off the beaten track.


I have been in enterprise software sales for a number of years where I was very fortunate to work remotely. As long as I could work North American hours and be able to travel to US or Canadian cities on relatively short notice it didn't matter where I was. For a few years I became very comfortable living and working on the road in North America. My girlfriend also works remotely so we would regularly spend long weekends or full weeks in different US & Canadian cities. We enjoyed about 1.5 years of domestic (Canada & US) travel being on the road 2-3 weeks a month. At the end of 2018 we decided to quit our jobs and take a year off to travel full time.

My top trip of 2019 was our 7 month Southeast Asia adventure. January 2019 we kicked off ten months of full time travel with a first class flight from Atlanta to Seoul paid for entirely with credit card reward points. After a week in Seoul we landed in Bangkok where we began 7 months exploring South East Asia. From 3 days in Brunei to over 2 months in Thailand we experienced nearly every South East Asian nation.

The first few months were fast-paced, covering lots of cities. We gradually slowed down preferring to spend 5-7 days minimum in cities we liked and doing more activities like day trips or excursions.

We had saved up so that we could do it in our own style (flashpacker style it turns out) and we very quickly realized how much more enjoyable the trip was when we didn’t stress over our budget, even if it meant cutting a few months off the total trip.

We both agreed our favorite country overall was Thailand and Vietnam had the best food. Bali was the biggest disappointment and Myanmar was the most unique.

Top Trips of 2019-Southeast Asia

Our top 5 experiences:

5: Relaxing over 2 weeks on the 3 Gili islands off Lombok, Indonesia
4: A 3 day motorbike tour of The Loop in Northern Vietnam
3: 2 weeks in the most pristine waters we’ve ever seen on the Maldives
2: Getting our scuba certifications in southern Thailand
1: A week long Muay Thai camp in southern Thailand

Our bottom 5 experiences:

5: The unsafe and uncomfortable Asian discount airlines that temporarily ruined flying for us
4: Doing a 10 day silent meditation retreat in Myanmar
3 The week a wave of pollution came down from China and made it unbearable to go outside
2: The inevitable food poisoning every couple months
1: The trains and buses in Vietnam (old, dirty, noisy, smokey, uncomfortable, and dangerous)

After more than half a year in Southeast Asia we decided to end the trip with a few months in Western Europe before heading home.


I’ve been working remotely for about 5 years in digital marketing and have recently fully adopted the digital nomad life when my wife joined me in the remote working world. We love to travel, but until recently were stuck to the usual 2-3 weeks of paid vacation from her job. Since leaving that job we’ve found a new freedom in location independence that we’ve jumped full-on into.

Our first big trip since becoming digital nomads was a 6 week trip to Spain from mid-August to the end of September. This was going to be a bit of a proving grounds. Despite everyone in our company working remotely, everyone was still within 15-20 miles, on east coast time and generally available for in person meetings. In order for this trip to be a stepping stone for further travel adventures, we’d need to continue to excel at work and be available for collaboration and meetings with clients. In general, our adventures abroad needed to avoid being disruptive to everyone else in the company so that we’d be able to take future extended trips to faraway places.

Top Trips of 2019-Grenada Cathedral of the IncarnationSpoiler: This trip was a HUGE success, and even one of the catalysts for the launch of Flashpacker Co. I’m sure I’ll write about that in more detail eventually.

We were able to overlap significantly with our coworkers by working 1pm - 9pm (Spain time), exploring every morning and enjoying the vibrant nightlife each night. Each of our affordable Airbnbs all had great wifi and we were able to make and receive calls easily with our international phone plan (bad idea, I’m sure I’ll write about that in the future as well).

As for the trip, we spent 6 weeks in 6 cities. WAY too much to cover here. But, I will spoil you all with my clear favorites.

Near the end of the trip we were lucky enough to spend a 3 day weekend in Granada then a full week in Seville, Spain.

First Granada. What an incredible place. Cobblestone streets, beautiful city views, lively squares and beautiful bright colors abound. The city is alive. There were musicians, art and delicious food literally everywhere. We were lucky enough to run into a festival and see a bit of the deep culture and history of Granada. The Cathedral of the Incarnation and its square are gorgeous and if you plan on seeing the city, you HAVE TO go to the Alhambra. There is an entry fee, but a guided tour is well worth the money. The history, architecture, art and amazing views are priceless. Lastly, if you find yourself in a bar or restaurant, Granada is world-famous for its tapas. So famous, that Granada is known for the tradition of providing free tapas plates with each round of drinks. Let the food and drink flow!

But Seville. Seville was the kind of place that was really, really difficult to leave. We stayed in an AirBnb on the edge of a local neighborhood and the food and bars were lively (and cheap!) every night. We spent every night that we were in Seville sitting outside enjoying the buzz and entertainment of the city over tapas and many, many pitchers of Sangria.The gothic cathedral in the heart of the city is the largest in the world and does not disappoint, and the Alcazar somewhat hidden around the corner is another unbelievable stop for culture, art and architecture. Seville was full of life and energy, but also not too big and intimidating. If you make it into Spain, it is a must-visit.

Top Trips of 2019 - Sevilla, Spain

What Will be Your Favorite Trip in 2020?

Hopefully these trips have inspired you to get out and travel in 2020. Sign up for our newsletter below to get updates on all our best travel tips, destinations, gear guides, and sales!

Back to blog

Leave a comment

Please note, comments need to be approved before they are published.