Welcome to the next interview in our interview series where renowned mile and point gurus share their insights on having Big Travel with Small Money!
Miles & Points Interview: Hilary from TravelSort
Miles and points collectors know TravelSort, because Lucky of One Mile at a Time writes a weekly column on TravelSort. But TravelSort also has great rates on luxury hotels and I wanted to learn more about how Hilary and her family use miles and points to travel the world!
Hilary & Her Husband In Paris
How and when did you start collecting miles and points?
While I made sure to sign up for the various airline frequent flyer programs early on, I’ve never been loyal to a particular airline, so I always had a few miles here, a few miles there, and not enough anywhere to redeem for a ticket, much less acquire elite status.
My first go at acquiring some status was while working as a strategy consultant at The Boston Consulting Group while on a project up in Canada. Since I was up at the client site Monday-Friday and staying at the nearby Sheraton Four Points, it made sense to sign up for Starwood Preferred Guest and also get the SPG card. I remember not thinking much of the basic rooms, but the rooms improved somewhat once I had Gold status.
This was also my introduction to mattress running—a couple of the other consultants made a point of staying at a different hotel in downtown Toronto every night, but frankly I couldn’t be bothered—we were at the client site until 7-8 pm daily and then working in our hotel rooms until midnight or later, so I really didn’t want to deal with the logistics and drive on top of that.
When I started TravelSort last year, I approached Ben (Lucky from One Mile at a Time) about writing our Business Travel column, given his expertise not only with miles and points but also his personal experience traveling in business and first class on different airlines. Since we pick the topics together and I always review, and sometimes make substantive additions to each post, I’ve learned a great deal over the past year of Ben writing for TravelSort.
Why did you start TravelSort? What’s special about it?
For me and for many travelers going on vacation or a short getaway, the hotel is the most important aspect apart from whom you travel with and the destination (although sometimes the hotel is the destination)! And although I love vacations, I was always frustrated by the amount of time it took to figure out the perfect hotel to stay in.
Now, it could be that I’m pickier than most people, but going to Priceline or Hotwire and finding the cheapest option isn’t for me, and TripAdvisor is polluted by fake reviews and also the sheer anonymity of most reviews, where it can be pretty time consuming to figure out whether or not to pay attention to them.
And as for asking friends, typically the places I’m going are where either no one I know has been there or they have different travel tastes to mine (I don’t, after all, choose my friends based on their travel taste, any more than on their film or music tastes). What I wanted, and what I heard other travelers wishing they had, was a site that would simplify and give me a highly relevant shortlist of hotels I should consider, rather than requiring me to sift through hundreds of choices, many of them poor.
At TravelSort we approach it the way you’d want your travel partner to:
1) We sift out the properties no one would want to stay in (bed bugs, consistently poor reviews from multiple sources, etc.)
2) We prioritize your recommendations based on your travel tastes. So if you prefer elegant 5-star hotels that also have a pool, we’ll automatically sort top picks for you.
If you want a hip boutique hotel that’s pet-friendly, you’ll get a different set of recommendations. We do have some great 3-star properties as well, that offer great value and quality for the price, but our focus is not on the absolute cheapest place you can find in a city—we think Priceline, Hotwire and the like cover that pretty well.
3) We offer a better deal, as typically our prices are lower than Expedia, Hotels.com, and hotel sites. Depending on the hotel and the room type, the savings can be up to 50% off. It’s kind of like having a mini private sale every day, for properties, such as the Four Seasons and Ritz-Carlton, that never appear on private sale sites.
We recently saved a TravelSort Member $2,000 off a family vacation to an all-inclusive luxury resort in Cancun, and their happiness was contagious—I was thrilled that they were able to book their dream resort, instead of having to trade down to a mediocre property.
Unlike many miles/points bloggers, I use our miles and points exclusively for international premium airline travel—I never use them for hotels, because the hotels we like best either aren’t available through points or are incredibly poor value, for example Starwood’s Luxury Collection and other Category 7 hotels.
What’s the one single thing people can do to get more miles?
It’s been said before and I’ll say it again: apply for lucrative credit card bonuses. I applied rather selectively for credit cards and am on track to have earned 450K miles/points this year from credit card bonuses alone, not counting miles and points from actual credit card spend or my husband’s miles/points.
What’s your most memorable travel experience?
The Galapagos Islands. Right before my son turned 2 (so that we didn’t have to pay for his airfare), we took a family trip there, visiting the various islands in the archipelago with Lindblad Expeditions. There’s something magical about being able to be side by side with all these animals and birds, from the Blue Footed Booby to playful sea lion pups frolicking right next to you or swimming right up to you while snorkeling.
While a cruise with Lindblad isn’t cheap (and unlike the flight to Ecuador, you can’t redeem points for it), it was well worth it to see the islands with their expert naturalists. I know we’d never have seen all the wildlife we did, especially the marine life, such as Galapagos penguins and sharks, without our guides. It may not be the most conventional family trip, but there were other kids on board, the crew was incredibly friendly and accommodating to the kids, and this is truly a once in a lifetime kind of experience worth saving up for.
One tip if you go with kids though: either go when they’re small enough so you can carry them on your back hiking (which is what I did) or wait until their 6 or 7 and can do the hikes themselves.
Visiting the Galapagos Islands
I’m also incredibly excited about our family trip to Bali next summer! We redeemed 300K BA Miles (from our BA Visa and Chase Sapphire Preferred credit card signups) for two Cathay Pacific First Class tickets via Hong Kong. Just for fun, I looked up the retail price for the tickets, and they go for nearly $20,000 each.
So the British Airways Visa annual fee of $95 and 2 credit card bonuses got us each a $20K first class ticket to Bali. Now, naturally we’d never pay anywhere close to $20K a ticket to fly to Bali, but we would pay a few thousand for these tickets so it’s still an amazing ROI simply for applying for a couple cards and spend we’d make anyway. We’ll also be staying in some pretty amazing TravelSort hotels (which aren’t available through miles or points) at great discounts.
I’ve been to Bali before on my own, but am looking forward to experiencing all the great outdoor activities, friendly people and beautiful spots with my family.
What do you have to do differently when you travel with a child?
With very young babies, there’s a good deal of gear that accompanies you, and you have to look at a “vacation” as more of a “change of scenery” simply because it is pretty exhausting (at home or when traveling), especially before they start sleeping through the night.
As a 1-2 year old toddler, my son was at the most challenging stage for long plane flights, because he wasn’t yet ready to watch any children’s programming so my husband and I needed to read and entertain him most of the flight—we even brought his favorite magnetic blocks (which is where the extra space in business class really helps). Once at the destination though, he was fine.
More recently, now that my son is almost 4, he’s been a lot of fun to travel with—he’s curious about how the plane flies, what’s inside the engines, where the other planes are flying to, etc. At the destination, the key thing is to ensure that there’s plenty of fun and outdoor things for them to do at the destination, since young children have so much energy to burn. Go with the flow and enjoy getting to know some foreign parks and playgrounds!
Feeding The Ducks in Jardin Du Luxembourg
If you enjoy international and/or luxury travel, don’t think that it has to end just because you have a child. In addition to the Galapagos, we’ve taken our son to France, both times in business class, and have for special occasions dined as a family at Michelin starred restaurants, and been made to feel welcome.
We’ve always been ready to whisk him outside (at the restaurants) or to the coach galley area (on the plane) if he’d been disruptive, but have never had to. Although kids in first class or a fancy restaurant seems to be a contentious topic, it really shouldn’t be, as long as the child is as quiet and behaved as an adult.
What do your family and friends think of your miles & points hobby?
My husband at first thought I was a little crazy, but he’s come round to it, especially as he simply is too tall (6’5) to fly coach comfortably anywhere. He still wishes for a teleportation device, but using miles and points for first class travel is the next best thing.
I’ve also mentioned it to other friends and relatives, and many of them are interested (or just being polite 
), and some have started reading our posts on the TravelSort Blog.
Is there any tool or trick which you’ve found especially useful in this hobby?
Persistence: I probably spoke with about 10 different people at American Express in order to confirm the 75K bonus for the American Express Premier Rewards Gold card, and another couple of folks, including their Twitter team @AskAmex just recently to clarify when the remainder of the bonus would post, since only part of it had posted even after I had met the required spend.
Planning ahead: Since we had a pretty specific window for when we could take a vacation in 2012, I made sure to start searching the British Airways Executive Club for first class availability on Cathay Pacific within a day of that availability coming online.
If you’re more flexible, either with dates or with routing (say, adding a segment up to Canada) it doesn’t matter as much, but given our dates, wanting to nail a direct flight from New York to Hong Kong, and the fact that Cathay releases 2 seats at a time, we needed to book our flights a full year in advance. There are some travel deals that you can nab at the last minute, but a first class award seat on a popular route isn’t one of them.
Get your spouse or partner on board: If you have a travel partner, make sure they’re “pulling their weight” in terms of applying for credit cards, using the appropriate cards to get double or triple points, etc. And once you’re paying for a seat for your child, make sure they have their own frequent flyer accounts (or are part of your household account, for British Airways).
What was the least expected way you’ve earned miles or points?
I’m definitely a latecomer to the mileage malls. I never expected to be able to earn miles for clicking through to Amazon from the US Airways Dividend Miles Mall, although sadly they’ve recently reduced it from 1 mile/$1 spent to just 0.5 mile/$1 spent.
What do you know now about collecting miles and points which you wish you knew when you started out?
I wish I’d realized earlier how easy it is to collect the various credit card bonuses, with spending I would be making anyway. As with many other travelers, I’d had this idea that having too many credit cards was somehow bad, even though I’ve always paid everything off and never carried a balance.
It’s also good to know that, while you can of course spend a ton of time obsessing over your miles and points strategies and tracking down every last deal, you don’t have to.
There is no shame in simply following a few bloggers or sites that are useful to you. I think sometimes people get scared off by the “nerdiness” of some of the miles and points collectors, or think that it’s only for young single guys with a lot of time to travel and master the art of mileage running.
While there are definitely tricks of the trade, it’s not rocket science, and at TravelSort we aim to not only provide some useful tips for experienced miles and points junkies, but also make it more accessible to people who might be new to the miles and points game.
What would your readers be surprised to know about you?
Even though I’m originally from Hawaii, I’ve spent over six years of my life studying and working abroad, in Japan, the UK, Norway, Russia and Kyrgyzstan. I speak French and Russian and read Norwegian, and have been pressed into some impromptu translating at various times for fellow passengers who spoke only French or only Russian.
Oh, and I’m one of the less than 1% of Americans without a TV (by choice)
Any parting words?
This may sound like heresy to some, but don’t let miles, points or loyalty programs get in the way of what works for you, whether it’s taking a JetBlue flight that’s direct or leaves at a more convenient time, or trying that Four Seasons or Aman Resort you’ve always dreamed of.
If you find yourself eating out at mediocre restaurants for the points or regretting a miles-driven purchase you made, it’s time to reassess. Miles and points should be additive, and will hopefully not only save you money, but also enrich your and your loved ones’ lives with some amazing trips and experiences.
Hilary – Thanks for sharing your thoughts on having Big Travel with Small Money!
So check out TravelSort if you’re looking for great hotel deals and miles and points tips!
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I have earned and redeemed millions of airline miles and hotel points to travel the world for free. Now I'm blogging to help more people do the same! 
Disappointed that you need a facebook account for TravelSort.
Hi Aiden, you don’t need to log in to see the TravelSort Blog at http://travelsort.com/blog with our miles and points tips, travel guides and reviews. For the hotels, we do require you to log in because the hotels don’t allow these lower rates to be generally visible or searchable. We use Facebook Connect because it allows us to better personalize your experience and provide more relevant recommendations.
Not a good first impression. Read the story and went onto TravelSort immediately. Have two nights in December booked at the Andaz Wall Street. TravelSort price for those dates was $325 per night. Rack rate is $225 and Senior or AAA rate is $203.
Shows me there really is no site you can take to the bank. Need to always check multiple sources.
Steve, I can’t speak to your specific dates, and there may be some where the Andaz has the better rate, but there are several December dates I just checked where the Andaz has no availability and we have availability, or where the cheapest Andaz room is a suite, for $766 incl. tax, and our rate for a double is <$450 incl. tax.
It's also the case that our best discounts are for 5-star hotels (Andaz is 4-star) and for the higher room categories, where we do save our members hundreds if not thousands of dollars, depending on the hotel, room type and length of stay.
I agree with you that it bears doing a quick price check on a few sources; but for most hotels in our collection, especially the 5-star hotels, we do have the best tax inclusive rate.
Thinking of taking family to NYC in December, after Christmas, and amazed to see Ritz Central Park for under $600 per night on TravelSort. Best I could find on Ritz site and Kayak: $1000 a night for same nights. Some serious savings.
Vik, glad you found some great savings on the Ritz-Carlton! Hope you and your family have a great trip to NYC. Let me know if you’re looking for any family-friendly tips; I wrote a post on NYC with Kids http://travelsort.com/blog/new-york-city-with-kids and live here with a 3-year old, so happy to make some recommendations if you’d like.
Thanks for interviewing Hilary. An amazing read. I read her blogs with great interest. What surprised me the most was “Oh, and I’m one of the less than 1% of Americans without a TV (by choice) “. Wow! this is so hard to believe but I am waiting very patiently for the time when her son enters the teens and see what she does then. I wish I can at least cut down some of my TV time if not all.
Thanks Shami, so glad you enjoy our posts! Actually we do allow our son to watch up to 30 min./day of Blue’s Clues or Thomas the Train (via computer). We just didn’t want him to get into the habit of passive entertainment, when he could be enjoying reading a book with us, building with blocks or doing something more active and creative. Hopefully he’ll continue this into his teens, and find some like-minded friends, but you never know, and I doubt I’ll have much influence by that point!
I agree with Shami. This is a really interesting read, and though I do not know Hilary personally, I connected with her on many levels!
One, I have been using my miles and points for international premium air travel. I just redeemd for my second first class flight to Singapore from Toronto, via Hong Kong in the past 2 years.
And most importantly, though we have given in and bought a TV 3 years ago, for 7 years prior, we had no TV by choice, and it was the best thing I could have ever done for myself. There’s so much to do in the world, that there just isn’t enough time to vegetate in front of the TV! And I am passing on the same philosophy to my 18 month old son.
Thanks so much for sharing your life, Hilary. I will look out for you in your blog.
Thanks Denise, so glad you enjoyed it! Fantastic to be able to give your family incredible travel experiences, and expose your son to the richness of other countries and cultures. It’s amazing how much kids take in and remember, my son still talks about what he liked on the Galapagos trip (almost 2 years ago, and he wasn’t quite 2) and also about what we saw and did in France. So your son may well be talking about Singapore for years to come or even count it among his earliest memories
D, good job. Best interview so far.
Thanks Ed, and thanks Daraius for interviewing me!
@Hilary We also down own a television in our home. Best decision we ever made. Have a 11 year old son and 9 year old daughter. My son loves to travel and enjoys the outdoors. My daughter is the same. They never miss tv and honestly neither do I
David, glad to have company! Usually get strange looks from folks if it comes up in conversation. We’re also outdoors in Central Park as much as we can be, though I have to say it’s just not the same as growing up in Hawaii, where as a kid I practically lived outdoors.
So true that miles and points collecting isn’t just for young single guys who travel a lot for business.
That’s awesome that you have successfully traveled so much with your son. It’s always good to share the news that having children doesn’t have to mean the end of your traveling days (though some do travel better than others). Thanks for sharing!
Thanks Mommy Points, love your blog and following your family miles and point adventures! I think at this point my kid travels better than I do–he falls asleep more easily en route and seems less jetlagged
Great post. Travelsort is one of the sites I check daily. Two questions from the interview.
1) You said you don’t use points for hotel stays. So do you convert all the hotel points to airline miles? The conversion rate may not be good for some.
2) Did you all take biz class when you travelled with your son? Sometimes it’s difficult to get three (four for my case) award ticket in biz/1st. For your Bali trip, you only got two 1st class on CX, what about your son?
Allen, so glad you enjoy our posts! Great questions; in terms of hotels, the only chain hotels I stay in are SPG so I convert those in 20,000 increments to get the 5000 bonus for each 20K. My most recent transfer was to Aeroplan, for a first class Lufthansa ticket to Europe.
And nice catch on Cathay; Geneyem asked the same question in the comments to my post on that, http://travelsort.com/blog/time-to-redeem-british-airways-miles-for-cathay-first-class I actually booked the 2 first class tickets for my husband and son and I’ll either pay for or redeem for a coach class ticket for me, which I hope to not have to use a lot, since the first class seats are very private and my son is going to want either my husband or me to be sitting there with him. We’ll see how it goes next summer, and I’ll report back
Hi Hilary, I can’t figure out how to look up hotels on TravelSort. I must be doing something wrong… I only see 6 hotels in total.
Who says woman don’t sacrifice for their family? This is a living example people . OK, just kidding but I must admit a smart move. Hopefully Hillary will spend more time in first class then economy and I must say practical planning under the circumstances.
Thanks Shami
Jenny, we’re still building out TravelSort Hotels and adding more cities and hotels to the site, although we are being pretty selective about which hotels we include based on quality/value. We have access to more than are currently up on the site, so just let us know at concierge [at] travelsort.com which city and type of hotel you’re searching for, and we’ll be happy to help.
Thanks for your clarification. Glad that you have one kid. What will you do when you have a son and a daugher like me? Even if I had the miles to seek four award ticket, it is unlikely to get them on one flight. TIME recently ran a cover page on Favoritism. I don’t want to be accused of something. -:) So coach-for-all is the practical choice for me right now. Enjoy your trip and looking forward to your trip report.
Thanks Hilary! I’ll do that.
I hear you Allen! It can be really tough to get enough reward tickets, especially all in biz or all in first. BA tends to have a lot of availability, but there are high fuel surcharges/fees on BA metal. We also sometimes split up for purposes of award travel, with my husband taking a different flight from my son and me. Not ideal, but we’ll be doing that when we visit family in Hawaii next year. Unfortunately we’ll only have the one kid, as we’re older parents, and just wouldn’t be able to keep up with more than one high energy munchkin!
Hilary,
Requiring Facebook for authorization into your site is pretty frustrating for me too. I’m a 33 year old man and have no use for Facebook, never have, never will. I find it intrusive and distracting, but mostly unnecessary, especially when it comes to finding the best travel deals for my wife and I!
Sounds like you’ve got something cool brewing, but the Facebook requirement just makes it unusable for the small percentage of us that don’t leverage that platform.
Hi Tim, thanks for your comment and feedback. A key part of our value in addition to the deals is saving people time in their hotel search and personalizing hotel and content recommendations, and so far Facebook Connect coupled with the profiles Members fill out has been the best way to do that. But we do recognize not everyone uses Facebook, and we’ll be revisiting the registration/login process after we finish developing our iPhone app. As a startup, we have a pretty small team and lots of work still to do, but we are taking into account your and others’ feedback.
Hey Hilary,
I appreciate your response. I’m a daily watcher of this site, so if and when you guys offer a different authentication schema, please get it posted here!
Best of luck with your site until then.
-Tim
hey hilary, that galapagos sounds like a really neat vacation, is there a trip report anywhere about flights, and sights and things you did over there? (especially what’s doable with kid/s)
Hilary has written two very nice reports here. However my understanding is the trip was very expensive. I wish she could elaborate a bit more on expenses.
http://travelsort.com/blog/traveling-with-kids-to-the-galapagos
http://travelsort.com/blog/galapagos-adventure-stunning-wildlife-fearless-and-up-close
@Tim, will do! We’ll also post here when we have our iPhone app ready, would love feedback
@arye, Shami beat me to it, thanks for posting the links to our Galapagos posts! While I didn’t detail our flights there, we used AA miles for awards from NYC to Guayaquil (GYE) via Miami. There are several tour operators but I was very happy with Lindblad, we chose them especially for their naturalists, reputation for being one of the most responsible operators in terms of environmental impact and sustainability (they are partnered with National Geographic), and for being family-friendly. While it’s possible to go on your own to the Galapagos, it’s much harder to cover as much ground or get access to some of the best areas since it’s a national park and they strictly limit the numbers of visitors that can be anywhere at a given time.
Although I carried my son on the hikes since he was <2, there was a 6 year old (and some older kids) who did most of the hikes and also participated in all the snorkeling and zodiac boat trips. I'd be leery of taking kids <6 if you're not able to carry them on the hikes though. The boat itself was a big highlight for our son–he pretty much explored every inch of it with us, and loved the round porthole and nooks and crannies of our cabin.
To Shami's point, yes, it was pretty expensive; it was something around $4500/person (since our son was <2 he was free) for our 7 day expedition almost 2 years ago, including all meals and activities, plus there's the airfare from GYE to Baltra Airport in the Galapagos. I also just checked and seem to only see 10-day and 16-day expeditions now, so they may no longer do 7-day expeditions (probably due to new regulations limiting visitors and stopping boats visiting the same island more than once in 14 days), making it more expensive. 6-7 days I think is the minimum one should allot in any case; we would have been happy to stay another few days, the wildlife and snorkeling were that spectacular. It really is an incredible experience if you enjoy wildlife, snorkeling and nature–hope you get a chance to go!
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Just wanted to alert Tim and others who wanted an email/password login to TravelSort Hotels that it’s now possible to use an email/pw when requesting membership, and to create a password if you previously used FB to login: http://travelsort.com/users/sign_in
As always, there’s no need to login to read the blog. We’re also on our last couple weeks of a luxury travel giveaway, recent post here: http://travelsort.com/blog/week-4-win-luxury-travel-from-travelsort