“We Always Stay at 2 Hotels Each Trip – It Feels Like 2 Trips In One!”

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Welcome to the next installment of our interview series where folks share their thoughts about Big Travel with Small Money!

Miles & Points Interview:  MilePro

Tim writes MilePro to help readers travel smarter.  Like a pro!  And also to provide the tools and techniques that allow anyone to travel much more than they would otherwise be able to.

You can also find him on Instagram, Pinterest, Facebook, and Twitter!

How and when did you start collecting miles and points?

As someone who has traveled most of my career as an Account Executive in the Technology Industry, I have been collecting miles & points for a long time.  But it wasn’t until I was planning a Caribbean trip for my family about 8 years ago that I took notice and realized how valuable they truly are.

At the time, my kids were 4 and 6 and we were planning our first trip as a family.  I went to a Travel Agent to look into options and was shocked to find out the trip would cost close to $10,000.

I hadn’t added up the costs of flights for 4, hotel, rental car, etc.  It was quite a shock!

I realized if I wanted to have a life of great travel, I was going to need to focus on getting the most out of my miles & points.

We ended up going to Puerto Rico, with my frequent flyer miles and hotel points.  We used Delta SkyMiles for the flights and a combination of Marriott points and Starwood points to stay at the Ritz-Carlton San Juan and Westin Rio Mar.  As a general rule, we always stay at 2 properties on any trip – this provides 2 completely different environments and feels like 2 trips in one!

It was an awesome trip at a fraction of what the travel agent originally quoted.

Why did you start your blog?  What’s special about it?

Not long after the trip to Puerto Rico, I decided to start a blog.  The name of the blog was TravelFreeFaster and it was doing well for a while.  Well enough that I hired a programmer to automate the credit card feeds coming in from an affiliate program, so I wouldn’t have to manually update them (it was much easier to be a credit card affiliate back then).

That was the beginning of the end of that blog.

I learned 2 important lessons from my experience hiring a developer.

The first is to check the background of any developer you hire (he took several months and totally screwed up the site, rendering it useless).  The second is to back up your database (I lost the entire site in the process and did not have a good back up to restore it).  Needless to say, that put an end to the TravelFreeFaster blog.

At the time, I was busy with work and kids’ activities, plus I was discouraged from all the effort that went down the drain.  So I took a break from the blogging world.  However, I have been inspired again and am planning on sticking with it!

MilePro is different from many of the other “miles and points blogs” because I am more of a business traveler, which brings a slightly different perspective.  My vision is to help people “Travel like a Pro,” which means helping them pick the best loyalty programs, achieve elite status, maximize promotions, and get the best rate possible on hotels and flights when you have to pay for them.

To do this, I put together profile pages of each program so you can, for example, visit the SPG page to make sure you are up to speed with the latest SPG promotions and any special offers they have for paid stays.

What’s the one single thing people can do to get more miles?

Leveraging the right credit card is an important part of any miles & points strategy, but one area that many frequent travelers overlook are promotions.  In particular, the hotel chains are always running great promotions.

For example, I recently signed-up for a targeted promotion from Starwood called “Stay More, Get More”.  This promotion provides the ability to earn Starwood Preferred Guest elite status twice as fast because each stay will count as double toward SPG elite status.  With this promotion, you can earn Starwood’s top tier Platinum Status in as few as 13 stays.  As a result, I just locked in Platinum status for 2017!

The hotel companies come out with new promotions every quarter.  Airlines and rental car companies have them as well, although not to the extent of the hotel promotions.  My advice is to stay on top of them and make sure you register, or you will miss out on some great offers!

What’s your most memorable travel experience?

When it comes to memorable travel experiences, I put them into two categories – family travel with the kids, and luxury travel with my wife.

A couple of years ago my wife and I decided sharing experiences together is the best gift we can give each other, so every year our anniversary gift to each other is a great trip somewhere new.  To date, we have taken anniversary trips to Aspen, Napa Valley, Paris, Tuscany, Punta Mita and Vancouver.

My favorite was our anniversary trip to Tuscany, where we spent a couple of days in Florence at The St Regis, Florence and then ventured to the Tuscan countryside, to a beautiful boutique hotel called Castello del Nero.  We walked the cities of Florence, Siena, and San Gimignano; rode Vespa’s to Monteriggioni, toured a winery, ate great food, and drove through the Tuscan countryside.  It was definitely a trip to remember!

There are also 2 trips with my kids that really stand out.  Both were birthday trips and both were just with me (although I have to give my wife all the credit for coming up with the idea)!

For my daughter’s 11th birthday, I took her on a trip to New York City.  She had always wanted to go there, so what better excuse than a birthday!  We stayed at the Ritz-Carlton Central Park – the perfect location for our journey.

We went to a play, took a horse carriage ride around Central Park, checked out the American Girl Store, shopped in SoHo, went to Ground Zero, and ate great food, ranging from her first street vendor hot dog to the trendy French restaurant, Balthazar.

Just 4 months later, it was time for my son’s 13th birthday.  For him, we went to Punta Cana for some golf and sun.  We stayed at the Westin Punta Cana, where the staff was as friendly as any place I have ever been!

This trip took an unexpected twist – we went scuba diving.  This was the first time my son had been scuba diving and he absolutely loved it!  What was meant to be more of a golf trip, quickly turned into a golf and scuba trip.  Both were essentially right on the resort property, so we could alternate between the two each day.

To this day, they both consider these to be two of their favorite trips.  They are now both teenagers (13 and 14) who really don’t want to be seen with their “uncool” parents, so it is always nice to think back on these trips when, in their eyes, I was the coolest dad in the world!

As a family, we have traveled to London, Hawaii, Costa Rica, Mexico, St Martin, St Barts, Puerto Rico, Grand Cayman, and Canada, all because of our miles & points!

These trips have strengthened our relationship and provided me with great memories of experiencing new cities and countries with the three most important people in my life.

What do your family and friends think of your miles & points hobby?

To be honest, I don’t talk about miles and points with them too much, other than my Dad, because he is in the hotel business and relates to a lot of this stuff.  They all know I love to travel and we talk about that, but not too much on the miles and points side.

Believe it or not, most of them don’t even know I have a blog…I probably need to open up a little more 🙂

Is there any tool or trick which you’ve found especially useful in this hobby?

As far as tools go, I love Award Wallet to track my miles & points, especially the expiration feature so I don’t lose any of them due to inactivity.

I don’t know if you would call it a trick, but understanding the airline alliances and leveraging partner airlines is one thing that I find incredibly useful that I don’t think most people fully understand.  In particular, I love British Airways Avios points for short-haul domestic flights on American Airlines, as well as their household account feature, which lets me link and treat my entire family’s accounts as one.

If there was one program I think people need to get to know, it is the British Airways Avios program.  Even with the recent devaluation, it is still a great way to fly domestic for the least amount of miles!

What was the least expected way you’ve earned miles or points?

This one goes back a little while, but it is a good one and shows the value of being aware of promotions.

In 2010, when the Delta and Northwest merger was complete, Delta put out a promotion called “Together We Fly”.

For this promotion, you had to assemble a team of 4 with a team captain who had to be based in one of Northwest’s former hub states – Michigan, Minnesota, Tennessee, or Washington.  If the “team” flew 25,000 miles during the promotion period each member received 20,000 miles.

I am based in Michigan and work in the technology consulting business, so I work with people that fly every week.  I set up myself, my wife and my two kids, each as team captains and recruited an additional 12 people from my company to join the 4 teams.

Even though I work with a bunch of road warriors, none of them were aware of this promotion – getting back to my original point of how important promotions are and how unaware most people are of them.

All 4 teams easily hit the 25,000-mile mark within the time period without doing anything other than what they already planned to do from a flight perspective.  This promotion netted 80,000 easy Delta miles for my family and another 240,000 for my coworkers.  That was fun!

What do you now know about collecting miles and points which you wish you knew when you started out?

I wish I paid closer attention to expiration policies.  I have lost several hundreds of thousands of miles & points over the years because I took a temporary break from a particular program, and lost the entire balance due to inactivity!

What would your readers be surprised to know about you?

I think a surprise for the readers may have more to do with the domain my blog sits on than me personally.

Those that have been in the miles game for a while probably know that Award Wallet was not the first mileage manager out there.  One of the first mileage managers was actually a desktop application, with a monthly subscription fee, called MilePro.  It sat on my very domain, milepro.com.

InsideFlyer showcased it in an article ranking the top mileage manager programs back in 2003.  MilePro was 1 of the 7 programs featured, most of which are now gone (actually they may all be gone).

I just love the history that my domain has in the “miles & points industry”.  I should probably call Randy Petersen and have him do a “Where Are They Now” feature on these mileage applications. 🙂

Any parting words?

The gift of travel is one that keeps giving back.  Too many people don’t explore the world because they think it is cost prohibitive.  It’s not when you use miles & points!

I am personally not a big fan of the more extreme things people have done to earn miles, like buying pudding cups or purchasing coins from the US Mint.  I don’t change any of my behaviors to earn points – I just make sure I am using the right credit card and have registered for all the promotions.  Those 2 things alone have provided access to some of the most beautiful places in the world!

Tim – 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!