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How to Pay for Travel During Teacher Vacations and Summers by Travel Hacking

Jackie horseback riding in the mountains around Puerto Natales, Chile (near Torres del Paine National Park), Patagonia!
Jackie horseback riding in the mountains around inuerto Natales, Chile (near Torres del Paine National Park), Patagonia!

Teaching Traveling: Curious how to earn free travel by credit card travel hacks?

Welcome to expert, Jackie Sills-Dellegrazie. Jackie, tell us a bit about your background.

Jackie: I’m originally from Connecticut, but I moved to New York City 20 years ago. Before becoming a teacher, I worked as a singer and actor in musical theater. My first paid musical theater job traveled around North America. What could be better, right!?

I was getting paid to perform and travel around in a van with my cast mates. Think Road Rules, without the MTV! Over the 6 months, I was able to visit all 48 continental states and parts of Canada.

I’d never really traveled much as a kid and although this experience didn’t launch my musical theater career, it ignited my desire to travel! Seeing the vastness and diversity of the United States and Canada opened my eyes to the wider world and left me wanting to see more.

In between musical theater jobs, I’d always end up teaching something: ESL to adults, private classes for babies and toddlers, tutoring, etc. Eventually, I used my B.A. in English and M.A. in Reading and got a full-time teaching job as a 2nd grade teacher.

My husband and I (or sometimes just me!) use all our vacations and summers off to travel! Currently, I teach English at a bilingual French school to 1st, 3rd, and 4th graders. The school is very international, with children speaking both French and English, as well as other languages they may be studying or speaking at home.

I also have a travel blog called The Globetrotting Teacher in the hopes of inspiring others to travel and by teaching them how to use miles and points to pay for their travel expenses.

Elephant Nature Park, Thailand, with the elephants and one of the rescued dogs named Ahn.
Elephant Nature Park, Thailand, with the elephants and one of the rescued dogs named Ahn.

TT: Nice! Tell about some of the interesting travels you have undertaken.

J: This year, I took 2 amazing solo trips! In April, I spent a couple weeks exploring and hiking in Patagonia. I’d always seen incredible photos of the landscape and knew I had to get there! I hiked up to the glacier-fed lake at Mt. Fitz Roy in Argentina and ice-trekked onto Perito Moreno Glacier.

I had to pinch myself as I tried to take in the stunning natural beauty of Chile’s Torres del Paine National Park. I finished my adventure by taking a 12 hour bus ride through the Tierra del Fuego to reach Ushuaia, Argentina, nicknamed “el fin del mundo” or “the end of the world” because of its position as the southernmost city in the Southern Hemisphere!

This summer, I spent almost a month traveling in Thailand and Cambodia! I visited famous temples in Bangkok, ate delicious Thai food, and marveled at the chaotic vibe of the city. I watched the sunrise over Angkor Wat and spent several days exploring the temple ruins of Angkor Archaeological Park in Cambodia.

A major highlight of my trip was in northern Thailand, near Chiang Mai. I spent several days at Elephant Nature Park, a sanctuary for elephants that have been abused or mistreated from working in the tourism and logging industries. I was able to walk amongst them, feed them, bathe them in the river, and witness their everyday life.

Traveling solo is such an incredibly empowering experience. You decide what you want to do or if you want to change something. You end up really listening to yourself and refining your understanding of who you are.

I’ve a keen sense of when that little voice in my head is giving me a legitimate warning versus the self-doubts that try to push you back from something new and exciting. While I love and prefer to travel with my husband, I loved my solo travels and would highly encourage others to give it a try.

 Pete and Jackie in a London selfie.
Pete and Jackie in a London selfie.

TT: Awesome. How did you use credit cards for free travel by travel hacking?

J: I could never travel as much as I want to just by getting paid a teacher’s salary and contributing to normal monthly expenses. I found out about travel hacking years ago and I was hooked. I’ve learned how to maximize rewards credit cards and use things like airline and hotel dining programs and shopping portals to earn miles and points that cover many, if not all, of my major travel expenses.

In the past 11 months, my husband and I (or just me!) have spent time in London and the English countryside, Turks and Caicos, Chile and Argentina to explore Patagonia, and Southeast Asia to sight see and volunteer in Thailand and Cambodia.

All of these flights have been “paid” for with miles and points! Most of our accommodations have been “paid” for with points!

This fall and winter, we’re looking forward to a few shorter hiking and skiing getaways. We also plan to visit Prague, Vienna, and Budapest, again, having gotten our flights and hotels with miles and points!

This is one of the main goals of my blog. Miles and points websites can sometimes seem confusing to someone just trying to figure out the basics. As a teacher, I’m used to breaking things down into smaller pieces. On my blog, I try to show simple steps others can take to earn miles and points to travel more.

I think travel hacking is perfect for teachers. We’re organized, dedicated, and ever-conscious of our salaries, not to mention, the many professional development and teaching opportunities abroad that so many of us would love to take advantage of if only we had the means!

Sunrise over Angkor Wat, Cambodia.
Sunrise over Angkor Wat, Cambodia.

TT: Love it! Tell us one moment from your travels that was particularly powerful.

J: The days I spent at Elephant Nature Park in northern Thailand were incredibly impactful. Seeing the resilience of the elephants, having experienced early on in their lives a horrific process known as “the crush,” where an elephant’s spirit is broken so they can be ridden by tourists, trained to do tricks, beg in the streets, or work in logging, was so humbling.

Aside from hearing their tragic stories and helping to prepare their food and feed them, you get to observe the elephants actually being elephants! The sanctuary felt as if it was overflowing with joy as the elephants socialized with their adopted herds, roamed freely, splashed in the river, and rolled in the mud. When you see such unbridled happiness and affection, it’s infectious.

It’s also a reminder that people and animals share this planet. Our choices matter and I want to be the type of person who helps bring about love and respect between animals and people. It was a really powerful experience and I’m so grateful to have spent some of my time in Thailand there.

Elephant love at Elephant Nature Park, Thailand.
Elephant love at Elephant Nature Park, Thailand.

TT: How have your travels impacted you as a teacher?

J: Traveling has given me the chance to see different places, where I’ve learned about history, culture, food, and different ways of life. Through these first hand learning experiences, I’ve learned more than I could’ve ever learned from a Google search or a classroom lecture.

This type of learning informs my teaching. I’ve been fortunate to mostly work at very progressive schools, where teachers are encouraged to get out of the classroom as much as possible with their students to foster firsthand learning experiences. My students love exploring the culture and history of New York City. Sometimes we visit world famous museums like the Metropolitan Museum of Art.

Other times we walk through city parks looking at trees that are hundreds of years old to get a sense of what Manhattan might have looked like long ago. Traveling and seeing the impact on my students further confirms how important experiential learning is.

My travels have also brought about broader thinking. Not just about different perspectives and cultures, but also pedagogically, when thinking about teaching skills versus concepts.

While there’s always a balance to maintain, and certainly skills like reading and multiplication facts are important, I’ve witnessed how remarkable it is when a student can synthesize what their learning and draw their own conclusions or when a student can come up with 3 different strategies to solve the same math problem. I believe these larger concepts become assets for our students as they grow and prepare to enter our global and technological world.

Perito Moreno Glacier in Patagonia, Argentina.
Perito Moreno Glacier in Patagonia, Argentina.

TT. So well said. How have your travels impacted you as a person?

J: Travel is empowering, not only from the confidence you gain, but also from the many things you learn about the world and yourself. I have a better sense of what I want and how to work to make it happen. I’m eager to try new things, with less and less worry over whether or not something is a mistake. When something doesn’t go as planned, it forces you to think on your feet and be in the moment. It’s so much more interesting than monotony.

It’s cliche, but traveling has put in perspective how lucky we are to live in a first world country. My basic necessities are easily met every single day. As a woman, I have an education. I have the choice to decide how I want to live my life. These are privileges in many parts of the world. I’ve never been overly materialistic and traveling has only made me want to live more simply.

I’ve also learned to turn off the news. It’s not that I don’t want to be up-to date on current events, but the typical news broadcast is 100% fear based. Travel has reinforced HOW MANY really kind and helpful people there are in the world. It’s easy to think the actions of a country’s government represent the mindset of its people. I know I’m not the sum of my government’s viewpoints and decisions.

I wouldn’t like to be judged by my fellow humans based on what politicians and leaders do and don’t do. People think and live differently around the world. My travels continuously make me more aware of, open to, and interested in these differences.

Cruising the Beagle Channel off of Ushuaia, Argentina.
Cruising the Beagle Channel off of Ushuaia, Argentina.

TT: What advice do you have for teachers who are dreaming of travel, or travelers dreaming of teaching?

J: It’s easy to say, “If you want to travel, just do it!” Life sometimes does everything it can to make a decision to travel seem near impossible, be it work, money, or family responsibilities. But, it’s so important to be true to what you want, trust yourself, and go for it! I’m continually inspired by 2 quotes. The first is by author, Anna Quindlen.

“The life you have led doesn’t need to be the only life you have.”

It’s so simple, yet so powerful. No matter what your life is like right now, you can create the life you want. Think of a place you’ve always wanted to see and devise a plan for how to make that trip a reality. Whether that’s using miles and points like me, or setting aside a small amount of money each paycheck, or selling stuff you aren’t using or don’t need, you can reach your travel goals. When you make decisions about what you want and stick to them, you start to cut out all the things that get in the way.

The 2nd quote is by another author, Ray Bradbury. (I am English teacher, after all!)

“Stuff your eyes with wonder, live as if you’d drop dead in ten seconds. See the world. It’s more fantastic than any dream made or paid for in factories.”

You’ll never regret making the decision to travel. Even if it doesn’t work out as you planned, there will always be incredible value in the experience. More than that, though, “stuffing your eyes with wonder” is even more thrilling and awesome than it sounds! When you fulfill a travel goal, there isn’t a single store-bought possession that can compare.

Some of my favorite travel planning resources are:

Pinterest and Trover are great places to start if you’re looking for travel inspiration and ideas. Google Flights is fantastic for finding great airfares. Use their “explore map” feature to look at prices for anywhere in the world departing from your home airport. I also subscribe to The Flight Deal and use the Hopper app for updates on and when searching for the best airfares.

If you’re interested in learning more about using miles and points for personal or professional development travel, I’d love for you to check out my blog, The Globetrotting Teacher. Of course, stay up-to-date with new posts on There’s such fantastic information and inspiration for teachers who want to travel and travelers who want to teach!

I want send out a big thank you to Lillie Marshall for giving me the opportunity to share my travel thoughts and experiences on Teaching Traveling!

Stunning landscape in Torres del Paine, Patagonia. Where will YOU go next?
Stunning landscape in Torres del Paine, Patagonia. Where will YOU go next?

TT: Thanks so much, Jackie! Readers, what questions or comments do you have?


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Monday 16th of November 2015

So inspired by your love for traveling and what each and every adventure has taught you. I only WISH I could visit all the wonderful places you have been to. Your courage, tenacity and passion for for traveling shines through in this article. I wish you many, many more inspirational travel experiences!


Monday 16th of November 2015

Thanks so much, Lisa! It's never as difficult as it seems to get out there and explore. You just need to make the decision and take the first step to make it happen.

Joanne Dellegrazie

Sunday 18th of October 2015

Hi Jackie, your pictures show an amazing experience , wish I could have gone with you. As far as doing it solo, I'm not sure if I could, but I certainly give you so much credit for doing it. Your information for traveling with little or possibly no cost is very well taken and I will definitely look into it. Enjoy your rewarding travels along with Peter. Love you!

Chad Ferris

Saturday 17th of October 2015

I've been following the travel hacks since its inception and have already used Jackie's tips for TWO vacations with my husband. Points are magic and can add up quickly when you're smart about it. Thanks for the great interview and we look forward to more!! Keep it up!!!


Thursday 15th of October 2015

As your beginnings were in musical theatre, you probably have an eye for remarkable performances. Any customs or traditions you'very seen in your travels that took your breath away?

Jackie | The Globetrotting Teacher

Friday 16th of October 2015

Hi Sonia, I've seen observed some of the customs of the monks while in Thailand. It's such an interesting way of life!

Kerri Fox

Thursday 15th of October 2015

I enjoyed reading this interview. It is amazing how much you can do with using points and there are so little people not educated enough about what their credit cards can do, including myself! You have always been a friend I look up to and traveling alone is just another reason you are so great! Keep traveling and giving everyone inspiration to travel more and explore their options to do it cheaply.

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