Hi, I’m Jackie Sills-Dellegrazie, the founder and author of The Globetrotting Teacher. I’m thrilled that your World Wide Web travels have landed you here!

On The Globetrotting Teacher, you’ll find in-depth travel itineraries and travel guides, travel-tested tips, and expert miles and points guides all based on my own first-hand travel experiences.
I can’t wait for you to explore the site more whether it’s for travel inspiration or to plan your own fabulous trip!
About The Globetrotting Teacher
I started this blog in 2015 completely on a whim (“Hey honey, I think I’m going to start a blog today!”) with just a fierce love for travel, miles and points expertise, and absolutely zero clue how to build or run a website.
At the time, I was an elementary school teacher who used every last vacation day to travel across all 48 continental states and internationally. None of which would have been possible without the help of using points and miles to book award flights and award nights. (We all know what teachers make, right?!?)
But after 15 years of teaching and a travel blog that was growing faster than I could manage with a full-time job, I set off on my own field trip, so to speak, to earn another (albeit self-taught) “Masters Degree” in the world.
So far, this adventure has taken me to 5 continents and 45 countries…sometimes with my husband or family and many other times as a solo female traveler. And, along the way, I’ve also learned how to run a successful online business.
Deep down, I’m a teacher at heart. And I wanted The Globetrotting Teacher to not only be about my trips and how I made them happen, but I also wanted to teach others how they could make their travel dreams a reality, too.

On the site, you’ll find travel-tested guides and itineraries, expert travel tips, and travel gear guides to help you discover new destinations, actively plan your own trips, & travel the world confidently. If you’re headed to New York City, I’m a 25+ year local who’s got you covered! No matter what your travel plans are, you can trust that each travel guide is based on my own first-hand travel experiences.
Using my points and miles know-how, I can also teach you how to make more travel possible for a lot less than you ever imagined with the help of credit card points, airline miles, and hotel points. I travel regularly throughout the year and use miles and points almost exclusively for every flight I take and many hotel nights.
This traveling and blogging journey has also included building a digital course called Booking Award Flights Made Easy to help others redeem their miles and points for awesome travel experiences, working on a new travel website, Discover Northern Italy, and building a shop to showcase my travel guides and resources.
When I’m not traveling, I’m either in New York City where I work and live with my husband and love, Peter, or we’re off in northern Italy on our newest adventure…renovating a 200-year-old-house!
My goal with The Globetrotting Teacher has always been to inspire and teach others how to travel more for less because travel can open minds and hearts. These expressions may be cliche…”Not all classrooms have four walls” and “Travel really is the best teacher.” But they are 100% the truth.
I’m beyond grateful for the opportunity to share my passion and travel knowledge with more than 10 million visitors who come to this site since it started; it’s both humbling and a responsibility that I take seriously.
I truly hope The Globetrotting Teacher will become your go-to for trusted travel guides and advice!




Jackie Sills-Dellegrazie + The Globetrotting Teacher In the Press
Here are just a few of the various outlets that have featured me as a travel expert.
- “37 Ways to Game the Airlines: How to Get Free Flights, Travel Perks, and More” [Forbes]
- “7 Must Know Tips for First Time Flyers” [Nerdwallet]
- “How to Curtail Currency Fees When Paying for Stuff Abroad” [News Channel5 Nashville]
- Travel Expert Podcast Interview, Season 1 Episode 11 [Transparency in Teaching Podcast]
- “How to Snag Credit Card Rewards Flights, Even During Peak Season” [USA Today]
- “How to Pay for Traveling During Teacher Vacations and Summer by Travel Hacking” [TeachingTraveling.com]
- “5 Signs You Need to Visit Romania Immediately” [Romania Tourism]
- “5 Reasons Why Flagstaff Needs to Be Your First Solo Trip” [Discover Flagstaff]
- “How I Ended Up on My First Solo Trip” [Ottsworld.com]
- “How to Set Travel Goals with Credit Card Rewards” [USA Today]
- “What ‘Worldwide by easyJet’ May Mean for Travelers” [HuffPost]
- Past Miles and Points Speaker at Women’s Travel Fest [Womenstravelfest.com]
Keeping in Touch
Questions, thoughts, ideas? Feel free to reach out! I love chatting with readers about their travel plans and aspirations, and I’ve made sure there are plenty of ways you can stay in touch.
- Comment on My Posts: I love hearing your travel questions and stories. I reply to every comment.
- Social Media: Follow my adventures and message me on Instagram, Facebook, Threads, and Linkedin. And check out what I’m sharing on Pinterest, YouTube, and TikTok. Or request to join Travel Hacking Study Hall, a miles and points Facebook Group I started to help others learn how to earn and use their travel rewards.
- Email Me: You can reach me directly at [email protected]
- Join the Newsletter: Along with 6,000+ other passionate travelers, get travel guides, inspiration, and tips delivered directly to your inbox.
Ilook forward to hearing from you! And for more ways to get in touch, visit my Contact page.

