How To Travel Like A Pirate! An Interview With Senior Editor Jessica Bisesto

A deal by , 28. Jun. 2018 9:06 am


Jessica Bisesto

Job Title

Senior Editor for the US. I research, write, and publish travel deals and articles and lead a team of in-house and remote editors as we search the web for the latest and greatest in the world of travel.


I’m from San Diego, California but never felt completely at home there. I lived in Vancouver, Canada for a year before heading to sunny Costa Rica, where I spent 4-5 months exploring the country. I returned to California for almost two years before booking a one-way flight to Hong Kong, which was the starting point for my 8 month solo backpacking trip through six countries in Southeast Asia. Once I’d had my fill of Asia, I booked a one-way flight to Montreal and stumbled down to Boston where I’ve been ever since.

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Jess in Buenos Aires, Argentina

How many countries have you visited?

29 so far and I’ll be hitting several new ones this summer

What is your favorite place you’ve traveled so far and why?

It’s a two-way tie between Greece and Vietnam. Both countries have friendly locals, delicious food, affordable prices, and it’s easy to get around. There is so much to do and see in both destinations, and the mixture of history, culture, and scenery can’t be beat.

Where are you traveling in July? Why did you choose those destinations?

So I’ve booked a one-way flight to London where I'll spend three days before heading to Warsaw. I’ve always wanted to visit Poland, and once I saw the Rolling Stones tour was running through Warsaw, it was a done deal. I’ll spend a few nights in Warsaw, before heading to Berlin. I haven’t quite made up my mind on where I’ll go after Berlin, perhaps I'll swing back through London or Budapest.

What are 3 tips you have for someone looking to plan a vacation on a budget?

1. Be flexible, whether it’s with your dates, destination, departure airport, or type of accommodations.
2. Book the most basic fare; check the carry-on requirements so you won’t have to pay extra to check a bag and bring your own snacks and reusable water bottle.
3. Eat like a local; skip the expensive, touristy places with inflated prices and enjoy some street food or a meal at a place where you might be the only tourist in the restaurant.

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Jess in Yangon, Myanmar

What’s the most underrated travel destination?

Ho Chi Minh City. If you’re looking for a cheap place with excellent food, vibrant nightlife, lots of things to do and see, and an easy place to use as a headquarters (whether you’re exploring more of Vietnam, or flying to nearby countries), HCMC offers something for everyone.

What song/album/artist gets you in the mood to travel?

I’m a huge Third Eye Blind fan and so many of their songs are just perfect for boarding a flight (especially alone), riding a motorcycle in a foreign land, and genuinely embracing the good, the bad, and the unknown.

Some people like to plan everything down to the tiniest detail when they travel, and some prefer to be completely spontaneous. Where do you fall on the spectrum?

I’m somewhere in the middle. You can’t plan every detail because what if you get to a place you only intended on staying for two nights and you fall in love with it, or meet really cool people, and decide to stay longer… now your entire itinerary has been thrown off! I always research things to do and places to eat so I have an idea of how I’d like to spend my time in a place, but I keep everything else as flexible as possible.

You’ve been gifted an all-expenses-paid trip anywhere in the world–where do you go?

Anywhere in the South Pacific (Tahiti, Vanuatu, Kiribati, Fiji) that offers overwater bungalows with glass floors

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Jess in Athens, Greece

What was your most memorable/unique travel experience?

It was sunset and I was walking with a new friend on the beach in Hoi An, Vietnam and we were flagged down by these local fisherman. We ended up helping them cast out fishing nets, before pulling them back in and carefully removing fish and other ocean critters that were then placed on a fire pit to cook and eat. Since we didn’t speak Vietnamese, and they didn’t speak English, there were plenty of smiles and hand gestures to go around. One of the locals pulled out a bottle of whiskey to share and we all sat in a circle in the sand eating fish with no utensils.

What kind of trip/destination would you recommend for someone who has never traveled outside the US?

Head to Costa Rica! Beaches, mountains, jungles, volcanoes, and a defined bus system that makes it easy (and cheap!) for people to get around. The locals are friendly, many speak English, and there’s plenty of other backpackers around so you’ll never be lonely or bored. Flights are usually cheaper and shorter than going to Europe or Asia, which can even help people feel a bit closer to home.

Fill in the blank: When I travel to a new city, the first thing I like to do is ______

Get a lay of the land

Fill in the blank: When I discovered _______, it made travel so much better

The eBag. It's a carry-on sized backpack that’s been designed as a suitcase—it’s lightweight, has ample pockets to aid organization, and is easy and comfortable to wear.

Fill in the blank: I know a lot of people love _________, but I hate it.

Checking bags

How To Travel Like A Pirate! An Interview With Senior Editor Jessica Bisesto

Jess in Thailand

What was your longest trip?

8 months across Southeast Asia

What was your shortest trip?

4 days in Iceland

Tell us about a time when you felt like a pirate on your travels?

I’ve booked a few error fares ($350 round trip from Boston to Buenos Aires, $700 Boston to Sydney, etc) and severely discounted flights ($180 round trip to Dublin, $200 round trip to Reykjavik, $200 round trip to Amsterdam) since I’ve been at TravelPirates. I always get this rush of adrenalin when I’m typing in my credit card numbers to buy a flight that’s at such a cheap price I feel like I’m stealing!

Do you want to travel like a pirate, too? Our deal hunters are hard at work to find you the best deals on trips all over the world—check them out here!

How To Travel Like A Pirate! An Interview With Senior Editor Jessica Bisesto