How To Travel Like A Pirate! An Interview With Travel Deal Hunter Molly Cowen

A deal by , 1. Aug. 2018 6:14 am


Molly Cowen

Job Title

I’m an Editor/Deal Hunter for the U.S. market. I research flight, hotel, and vacation deals and publish these for our audience.


I grew up in Wilmington, a coastal town in North Carolina, and fell in love with traveling from a young age on family trips. I went to college in North Carolina and studied abroad in Dublin, where I first experienced solo travel (and couldn’t get enough of it). After graduation, I left on a solo 5-month backpacking trip through Eastern Europe and Germany, where I gained a lot of experience in budget traveling. I spent the next few years working in Boston, New York, and various areas around Europe, and eventually started working with TravelPirates in Boston!

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Molly hiking in Howth, outside of Dublin

How many countries have you visited?

30 countries.

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

Bay of Kotor, Montenegro. I went in with no expectations and was absolutely stunned by the dramatic scenery, delicious (and very reasonably priced) food, fascinating history, and friendly locals. If you love hiking, relaxing at the beach, and under-the-radar destinations, definitely add Montenegro to your list.

Where are you traveling in August? Why did you choose that destination/month?

I’ll be in Montreal from August 2 – 6 for Osheaga Music Festival. This Indie music festival is on an island and takes place over three days. I’m not only excited to see the musical acts, but also to enjoy Montreal! I love Montreal because it’s in easy reach of Boston, yet has a vibrant French-Canadian culture and tons of history. I can’t wait to explore the beautiful Old Town and check out some of the area’s trendy bars and restaurants.

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Molly on the coast near Lagos, Portugal

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

1. Flexibility. The cheapest prices often only fall on certain days, so being open to these dates is essential. Also, don’t be afraid to get creative with different combinations of origin/destination cities. For example, maybe a flight to Europe from NYC is $300 cheaper than Boston, yet the bus from Boston to NYC is only $20. If you’re willing to take that bus you’ll save up to $280!

2. Limit your spending. Save money by cooking whenever you can, taking public transportation, and staying in budget accommodations like hostels or Airbnbs. Of course there’s always room for an occasional splurge, but just be sure to balance it out.

3. Pack light. If you’re able to pack just a carry-on, you’ll save tons of money on checked bag fees, and your increased mobility will allow to to make transfers on public transportation. Plus, there’s less temptation to shop when you know you have limited packing space!

What’s the most underrated travel destination?

The Balkans—my personal favorite countries were Bosnia & Herzegovina and Montenegro! You’ll find friendly people, lower prices, and breathtaking scenery.

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

I’m constantly listening to music while traveling so this is a tough one! Some of my favorite and most cliche travel songs are “Strangers” and “This Time Tomorrow” by The Kinks, “Across The Universe” by The Beatles, and “Vagabond” by Wolfmother.

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 very much on the spontaneous end! I’ve found some of my favorite travel memories have come from last-minute opportunities. For example, when I arrived in Croatia I thought my Balkans journey would end there, but then I ended up tagging along with some friends from my hostel to Bosnia. This led me on to spend two more months traveling the Balkans. Of course, planning is often needed for shorter trips, but I like to still leave a few days open to figure out as I go. You never know who you’ll meet or what you might stumble upon!

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Molly at Buzludzha in Bulgaria

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

New Zealand! It’s at the top of my bucket list for its natural beauty, but flights and tours often come with a big price tag.

What was your most memorable/unique travel experience?

My first solo traveling experience was Paris, and I was absolutely blown away by the city. I was there for a jam-packed three days in December, and couldn’t believe my luck that I had most of the tourist attractions practically to myself. One afternoon I went to go see the Paris Catacombs and was shocked when there was no line and there were no other tourists in sight. I ended up having one of the spookiest but most memorable tours of my life walking through the catacombs completely alone. It was incredible, but I still get chills thinking of it!

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

I would definitely recommend Dublin. This city is a manageable size, is full of incredibly friendly people, and it doesn’t hurt that it’s English-speaking! There’s plenty to do with museums, parks, and a lively nightlife scene. There are also tons of day trips to castles and picturesque seaside villages within easy reach. Another advantage—flight prices to Ireland have reached all-time lows!

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Molly at Spreepark in Berlin

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

Go on a free walking tour. This helps me gain insight into the city and get my bearings so I can map out the major sights I want to see during my visit. The guides are often passionate about the city and are usually happy to provide recommendations on sights, restaurants, and bars. Just be sure to tip as these tours are tip-based!

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

The app maps.me. Especially when you’re solo traveling, there’s no worse feeling than being completely lost in a new area. This app allows you to download a detailed map for the cities/countries you visit, so even when you accidentally close Google Maps you’re completely covered. I can thank this app for helping me find my destination more times than I can count!

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

Eating out every meal. This might sound crazy, but I really enjoy visiting local markets and cooking at my hostel. Of course, I usually won’t leave a country without eating at least one meal of the local cuisine, but I find myself most relaxed when cooking the majority of my meals. Plus this allows me to save money and stay healthy over long periods of traveling.

How To Travel Like A Pirate! An Interview With Travel Deal Hunter Molly Cowen

Molly in Mostar, Bosnia

What was your longest trip?

Five months backpacking in Europe.

What was your shortest trip?

One day in Belgrade—where I did a city tour and then had to sprint to the bus station to catch my bus. I definitely intend to go back one day and see more of the city!

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

In Bulgaria, I stayed at a hostel in Veliko Tarnovo that hosted tours to Buzludzha, an abandoned communist monument. We ended up off-roading through the mountains to a remote area in the Bulgarian countryside, where we had to (likely illegally) climb into the UFO-shaped amphitheater. It was unbelievably worth it to see the crumbling structure full of Stalin and Lenin mosaics, communist slogans, and vacant meeting rooms. I would highly recommend it to any adventure junkie!

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 Travel Deal Hunter Molly Cowen