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I’m really excited to announce a new team member to Travel Freely!


Few people have navigated the world of points and traveled the actual world like Caroline Lupini. She is an incredibly experienced free traveler. Her knowledge and experience with points and miles is almost unparalleled.


Caroline is a travel writer who has spent years combining her knowledge of points with her love of travel. Truth is, she’s more likely to be on an adventure than at home (in Boulder, CO). Unlike many advanced rewards travelers, Caroline has an amazing ability to explain the world of points and miles to the average person. That’s why I’m so excited to bring her on board.

Last year, she traveled over 100,000 miles. In total, she’s been to 81 countries. While traveling, Caroline has also written for some of the most popular media outlets, including USA Today, Business Insider, and a speaking role at the New York Times Travel Show.


I’m glad I made it out to Alta anyway! With 8″ of fresh powder, it’s probably the best ski day I’ve had all season.


I got to know Caroline over a few fancy lattes in downtown Denver (when she was in town). The first time we met, she said she had been at home too long and was starting to get the travel itch. She had been home for 8 days!

It’s so exciting to have Caroline joining Travel Freely to share her wisdom with us. She’ll have a monthly feature called “Travel Freely with Caroline” where she’ll offer tips and advice on how to navigate the world with points and miles. She will also be sharing some videos about her travels and points strategy via our Facebook group. It will be fun to get her advice while she is traveling around the globe.

I asked Caroline some questions to share with you all as she gets started with Travel Freely. Here’s what she had to say:


What’s your favorite country or city in the whole world to visit?

It’s so hard to pick a favorite because I love something about everywhere I have visited so far. That said, I’m really interested in traveling to the Middle East and really enjoyed my visits to Iran and Iraqi Kurdistan. I also love Japan. Overall, I enjoy exploring off-the-beaten-path places the most and helping people discover new places the would like to travel.


Jameh Mosque of Yazd – I seriously loved all of the mosques in Iran. There are so many and each features something unique.


What got you started in points and miles?

That’s a funny question because I’m really not 100% sure. I went on a trip to Europe in 2011 and when I returned I knew I had to figure out a way to be able to afford to travel. I assume I came across The Points Guy, FlyerTalk, and/or BoardingArea while I was researching online and the rest is history! I honestly remember not knowing this world existed at all and then spending many many MANY hours each day scouring the blogs and forums and learning how to travel for so much less than I ever thought was possible.


What has been your favorite trip on points and miles so far?

I have a really flexible travel schedule, so I can usually wait for fare sales when I’m booking flights. Usually, when I do redeem miles, I prefer to splurge for business and first class (or getting to places that are otherwise really difficult and expensive to get to). Probably my favorite flight redemption was the first time I ever redeemed miles for a premium cabin. I used United miles to fly both Thai and Lufthansa First Class back to the US from South East Asia after backpacking for 6 weeks!


At the Musandam region of Oman. Did you know that Musandam is sometimes referred to as the Norway of the Middle East?


What is your best advice to beginners with points and miles?

Learn the basics first. Points and miles can get so complicated, and most of the airline and hotel programs are not making things easier as time goes on. Start with a couple of good credit cards (I recommend Sapphire Preferred or Sapphire Reserve and Chase Freedom Unlimited) and work on understanding how to value your points both through Chase Travel and when you transfer to partners. It will take time and effort, but it will be worth it!


What is your best advice to experts with points and miles?

USE YOUR POINTS! I need to take this advice too! We see devaluations happening all the time, so your points are not going to be worth as much in a year as they are now. If it’s a borderline value case, probably just use your points anyway!


Would you ever consider running with the bulls in Pamplona, Spain?


What makes you excited about Travel Freely?

It’s so much easier to track my credit cards than my old spreadsheet! I love that I get annual fee reminders in my email and that I can see how many points I’ve earned since I started with this hobby.

Your next vacation could be free with TRAVEL FREELY.