“Make the Most of Every Opportunity and See as Much as You Can of This Beautiful Planet”
Signing up for credit cards through partner links earns us a commission. Terms apply to the offers listed on this page. Here’s our full advertising policy: How we make money.Welcome to the next installment of our interview series where folks share their thoughts about Big Travel with Small Money!
Miles & Points Interview: When2Trip
Jamie & Hemali write When2Trip to share some of their favorite travels and can’t-miss mountain hikes. They categorize their experiences and detailed itineraries by location and best time to visit to make it easy for the readers to plan their next vacation. You can also follow them on Facebook!
How and when did you start collecting miles and points?
We started traveling extensively internationally and domestically within the US since we met in 2010. Before we knew better, we simply paid cash for all our flights and never joined a single stinking frequent flyer program! We finally began collecting miles & points during an incredible travel opportunity in 2014.
We were able to visit 8 countries across 4 continents over the course of 3 months. It wasn’t until the 3rd or 4th city on this trip that we recognized each friggin’ hotel had their own “fake” currency of loyalty points to accrue. A recurring nightmare for the both of us is repeating the time we horribly wasted 3 weeks worth of Starwood hotel points in Hong Kong because we foolishly opted for a tiny, cramped (but furnished) extended stay housing.
This was our longest stop for this trip. And since we love to cook it felt logical to have a small, stocked kitchenette. Unfortunately, even the best chef might have had a tough time whipping up a home cooked meal with only one set of plates and 8 spatulas and a wine glass (no pots or pans offered). The lone wine glass was used extensively, and shared between the 2 of us.
Why did you start your blog? What’s special about it?
We began the blog to keep our favorite trips fresh in our minds, and to inform our friends and family that reaching exotic natural areas and remote hikes isn’t all that intimidating. Most people we know think a safari in Africa is only for photojournalists or people named Rockefeller from the 20th century. Just the exotic name “Zanzibar” would elicit confused looks from colleagues.
Writing down how we thoroughly enjoyed these destinations, and how to reach them with relative ease (so long as you’re not afraid to fly) has been enormous fun and will hopefully spur other travelers to find their favorite trail or vista.
Another frequent question we get from friends is where to visit at certain times of the year based on their industry-specific work schedules or remaining vacation days. You won’t have a great trip to Machu Picchu hiking the Inca trail in February or March due to the rainy season. And if time is on your side in the spring then Japan is a worthy destination for the elusive cherry blossoms.
To make this process easier, we have made it simple to search by the best time of year to visit and type of activity (e.g. beach, adventure, etc.). We are still starting out with this categorization so you will see a more holistic list of places over next few weeks.
What’s the one single thing people can do to get more miles?
Read, read, and read! The one thing people can do to maximize the points & miles hobby is to learn the rules of the credit system (the US system being most lucrative) and use it to your advantage. In our opinion, there’s really no point in shortcuts to this hobby (sorry, we know that no one wants the advice of “do your homework”).
Sure, someone can spoon-feed you every detail, instruct you when and where to apply for a given card, or mail in a postcard for a billion-mile giveaway sweepstakes. But you will get much more from it by optimizing your own strategy for your needs. ESPECIALLY when it comes to redeeming points and miles.Always take a results-oriented approach to earning points & miles. You could certainly sign-up for a Chase Hyatt credit card just because you received a lucrative offer in the mail, but will your next few destinations even have a Hyatt hotel? And those points may devalue by the time you even get around to using them.
What’s your most memorable travel experience?
We definitely cannot pick one single travel experience as the most memorable – viewing the sunrise on top of Kilimanjaro, over-water bungalow in French Polynesia, hiking the Inca Trail, Moai statues in Easter Island, trekking in Patagonia & New Zealand, hot air balloon ride in Cappadocia – it’s like choosing your favorite child (we all know who it is, but don’t tell the others).
What do your family and friends think of your miles & points hobby?
As a teenager turned responsible adult (FINALLY), Jamie’s parents are shocked the only life lesson he inexplicably absorbed early on was how to use a credit card (use like a checking account, pay full balance early each month). His parents have been stashing points & miles for years, and having recently retired they are eager to use them up as well! All the years of grief and grey hairs that Jamie caused as a youngster now can melt away as we explore destinations together on fantastic far-flung journeys.
This hobby may have been more challenging without a fairly clean credit history, but no one should be dismayed if their FICO is low. Simply read the how-to guides for removing negative items on your credit report, and pay attention to what factors affect the scoring system.
Is there any tool or trick which you’ve found especially useful in this hobby?Spreadsheets! Boring ‘ol spreadsheets – just take notes and save your work. Staying up till 4:00 AM to plot flight connections for the least number of miles can all blur together if you don’t take screenshots and save some notes.
As your flight redemptions get more in-depth and convoluted, using websites like expertflyer.com will become very useful. Also, even in this industry we don’t see many people take advantage of Round-the-World flights. With our last Round-the-World flight, we went to 13 countries (14 legs) across 5 continents for ~$7,000.
What was the least expected way you’ve earned miles or points?
A very unexpected point accrual was in Madrid – our hotel room was directly above an event space at the Westin and a wedding reception went past the stated cutoff time of midnight. Our water glasses vibrated on the fancy, marble bedside tables and the music just wouldn’t stop. We called the front desk a few times, but the party persisted until 3:00 am.
We never got irate with the overnight staff, but just laughed at our fate, and watched crappy late-night programming on local TV. As we departed bleary-eyed and tired for our early flight the next day, the staff apologized with an additional 15,000 Starwood points. We were going to be sleep deprived from our next day of travel regardless, so the hotel points were a pleasant surprise!
What do you now know about collecting miles and points which you wish you knew when you started out?JUST ENROLL AND COLLECT THEM, DAMMIT! Don’t worry about getting too sophisticated when you start, but make sure your names and spellings match ID cards (Hemali changed her maiden name – dozens of bank & credit card accounts). Airline & hotel loyalty programs were the worst and least responsive organizations to deal with regarding the name change process.
What would your readers be surprised to know about you?
Readers may be surprised to know that Jamie hiked 90% of the 2,000-mile Appalachian Trail in one summer, but stopped early to brew beer in Asheville, North Carolina. Hemali also hiked the 100-mile wilderness section (in Maine) of the trail with Jamie. She forded the raging Big Wilson River only using a rope, and without knowing how to swim!
As a real estate professional, Jamie’s passion for utilizing the US credit system for travel has a huge crossover benefit of being able to help his clients prepare for home buying and renting in New York City.
Any parting words?Travel doesn’t have to cost a fortune anymore. There are INCREDIBLY cheap flights and hotel stays to earn with a bit of effort and researching. Make the most of every opportunity and see as much as you can of this beautiful planet. Jamie & Hemali – Thanks for sharing your thoughts on having Big Travel with Small Money!
If you’d like to be considered for our interview series, please send me a note!
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