“I Love…Introducing My Son to So Many Diverse Cultures That He Otherwise Would Only Read About in Books.”

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Miles & Points Interview:   BaldThoughts

Lee writes BaldThoughts to share his tips on traveling for (almost) free and personal finance.

And he’s giving away a $25 Amazon gift card along with 2 United lounge passes on his blog!

Bald Thoughts - Interview With Lee

Lee’s Son, Timmy, Flying Iberian Business Class From Paris

How and when did you start collecting miles and points?

I’ve been using the Chase Southwest card and American Express Starwood cards for about 10 years.  For a long time, I really thought that I had travel dialed in and life couldn’t get any better.  My wife and I have been traveling together since shortly after we met in 2006.

For several years, we would travel at least once a month and it seemed like we were gone more weekends than we were home.  Anna always talked about traveling internationally, especially to visit France, but I always changed the subject because Southwest doesn’t fly there, and I thought it would be incredibly expensive.

I read a few blog posts on Million Mile Secrets and other sites in January 2012 about the now-defunct Citibank American 2-browser trick, so I tried it and earned 100,000 miles.  From that point on, I knew I could make her dream of international travel a reality!

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

For 2 people who work full-time, have limited amounts of vacation, and are raising a curious 3 year old, our family travels a lot.  Mostly, we do long weekend trips so that we can stretch our limited vacation time across as many trips as possible.

I originally created BaldThoughts to talk about our travels, personal finance, and attending professional sports events.  Although these topics are loosely related, I split these topics into 3 sites…BaldThoughts, BaldFinance, and FlyToTheGame…so that each could focus on 1 of my passions — travel, personal finance, and sports, respectively.

Bald Thoughts - Interview With Lee

Go Seahawks!

Our friends, family, and co-workers think that we spend a lot of money traveling.  But we use the Southwest Companion Pass, AMEX Starwood Points & Cash, and our timeshare to explore US cities and attend professional sports events since 2007.

Our flights and lodging generally cost less than what another couple would spend on a night out to dinner, a movie, and drinks.  The biggest expense we incur is buying the professional sports tickets!

Most travel bloggers think that timeshares are a 4-letter word, but we love our timeshares – Worldmark by Wyndham and Diamond Resorts.  On BaldThoughts I write stories that describe how we incorporate both hotel points and our timeshares into our travel experiences to get the best of both worlds.

Bald Thoughts - Interview With Lee

Diamond Resorts Avila Beach, Timeshare June 2012

The biggest benefit of timeshares that we love is that our friends and family can join us on our adventures and we’re all staying in the same unit so the kids can play while the adults enjoy real conversation over a “home cooked” meal.

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

Credit card sign-up bonuses are the obvious #1 way to get more miles.  However, you need to have a long-term strategy with your applications.  Have an idea of where you want to go.  And consider which cards will get you the miles and points to get there the easiest and will use the least amount of miles and points.

Once you’re on your way, I suggest diversifying your balances with other cards so that you have options.  Flexibility is key in making your travel dreams a reality since award space may not be available on your preferred airline during the time you wish to travel and not every chain has a hotel in the city that you’re traveling to.

Bald Thoughts - Interview With Lee

NHL 2012 Winter Classic in Philadelphia

What’s your most memorable travel experience?

I’m lucky to have shared so many memorable travel experiences with my wife, and now my son.  For example, we were married at a winery in Solvang, California, which is the 1st place we traveled together during a weekend stay at our timeshare.  Life came full circle for us.

Bald Thoughts - Interview With Lee

Our Wedding at Winery in Solvang, California

However, making Paris a reality for her in April 2013 has been my greatest travel accomplishment.  I used the 100,000 American Airlines miles, 50,000 from Fidelity, and transferred the rest from Starwood to book 4 tickets for us to travel from Los Angeles to New York (3 day stopover for New Jersey Devils game) and on to Paris.

We traveled off-peak so it was only 20,000 miles each in coach there, and 50,000 each for Business Class coming back.  We were gone for 2 weeks and used a combination of hotel points and our timeshare to stay in NYC and Paris for free.

I’ll never forget climbing the Eiffel Tower with Timmy on my shoulders and watching him giggle uncontrollably as he chased the pigeons outside the Louvre.  Timmy was recently featured in a CNN article talking about what age is too young to travel with a child.

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

Most of my friends and family still don’t comprehend how we travel so much.  Even though I share with them how I earn miles and points to travel, they probably think I’m exaggerating and am just paying for our travel.

Although I love to travel, the frugal part of me wouldn’t allow such extravagance if we were paying cash for our travel experiences.

A few friends have started to convert into the miles and points game.  One family just earned their 1st Southwest Companion Pass in February and booked tickets before the March devaluation to join us in Orlando.  We’ll be staying in a 2 bedroom unit using our timeshare, which means we’ll have plenty of great bonding time and will save a ton of money on food and drink with the full kitchen.

If his family of 4 was going to buy these tickets, it would have been over $1,700 just for the flights!  Instead, with 2 credit cards, the flights were $40 for taxes and fees, with enough points left over for a weekend adult getaway to Las Vegas.

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

The best tool is AwardWallet, which helps me track our family’s miles and points and makes it super easy to log-in to verify points received and to book travel.  The best trick is really a benefit.  The Southwest Companion Pass allows me to stretch my points so much further because Anna flies for free wherever I fly.

Ever since our son turned 2 years old, and we had to start buying tickets for him, that really started putting a crimp in my Southwest points balance.  Having the Companion Pass means our family of 3 only needs to redeem points for 2 tickets.

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

It’s always a nice surprise when you get unexpected points from dining.  We generally only eat out when we travel, so we pick places that look interesting and have no idea that they would participate in the airline dining programs.

I recommend that the 1st thing you do with your new cards after activating is to register them with 1 of the airline dining programs.  You never know when that restaurant with the tasty food will also provide some tasty airline miles!

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

For the 1st couple of years of traveling on Southwest, I didn’t realize that the Companion Pass was good on award flights.  So, we only used the Companion Pass when I bought a ticket, and used 2 award tickets whenever we didn’t pay cash.

I also wish I knew about applying for lots of credit cards to get the sign-up bonuses.  I’ve always maintained a solid credit score, and that’s 1 asset I wasn’t capitalizing on until I started focusing on miles and points in January 2012.  Until that point, I earned Southwest and Starwood points with my monthly spending and having my Dad put his business expenses on my cards.

What would your readers be surprised to know about you?

In my “free” time, I like to run obstacle course races like Tough Mudder and Spartan Races.

The toughest challenge was the GORUCK Challenge.  We started at 9:00 pm and covered 23 miles and several team and time challenges over 13 hours.  We each wore a backpack with 6 bricks, food, and water (about 45 pounds total) throughout the night…with the caveat that our backpack could never touch the ground.

Bald Thoughts - Interview With Lee

Showing Some Grit in the Spartan Sprint Charlotte, North Carolina

Any parting words?

My wife often says that I book too many vacations for our family, but I disagree.  Like most families, we’re busy with work, her MBA program, and normal life responsibilities, so booking vacations ensures that we get to spend time together.

I love exploring the world with my 2 favorite people and introducing my son to so many diverse cultures that he otherwise would only read about in books.

There is no better time to travel than now.  Some other “fire drill” will always come up and your responsibilities will be waiting for you when you come back.  But children will grow up faster than you realize and they’ll reach a point where it’s no longer cool to hang with Mom and Dad.  Show them the world now, while you can.

Lee – 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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8 responses to ““I Love…Introducing My Son to So Many Diverse Cultures That He Otherwise Would Only Read About in Books.”

  1. Timeshares might work out for those who travel domestically and flexible on dates, but we have found it way too difficult to utilize and expensive as we can only go at a certain time and travel internationally; there are limited numbers of properties and hardly any in cities in Europe and Asia where we travel, they come with restrictions in how many people can stay as most unites are smaller, you have to secure flights way ahead in advance using miles and points while your timeshare reservation is most likely on request for months and keep paying fees. I am not challenging your opinion about timeshares (in face, I am happy that you find it rewarding for you and your family); however, it is my honest thoughts even after having used up all our Diamond Resorts points so far at some at a property (couldn’t call it “resort”) in Spain. It takes so much work and stress to get what you want outside of US or even in US where there is a low supply and a high demand unless you don’t mind going when and which property they tell you to go… 🙁

  2. Really great guest post today, although it was probably the first time I read the words “love” and “timeshare” in the same sentence. 😀

    My only question is about your constant reference to the Southwest Companion Pass. It is only good for a calendar year plus the rest of the year in which you earned it, isn’t it? Have you some trick to stretch this longer?

  3. Daraius, thank you for this great opportunity to share my travel experiences with your readers. I welcome everyone’s feedback and questions, and I have enjoyed the conversations I’ve already had with readers who have contacted me by phone, email, Facebook, Twitter, and comments on my blog posts. Thanks for having me as this week’s interview!!! Have a great weekend everyone.

  4. @Emily – I totally understand your frustrations with timeshares. Just like with a hotel chain, there are some amazing properties, and some major lemons. The first several years I owned mine, I had trouble committing to the vacation and didn’t use it. In fact, my family used them several times before I ever did. I see the limitations of timeshares the same way I see the limitations of airline miles and hotel points… you have to learn the ins and outs of the programs you have to maximize your value and enjoyment. Each way of travel is not for everyone, but when you learn some great tips and tricks, a whole new world opens up for you!

    @Anne – the Companion Pass, to me, is the best perk out there for domestic and limited international travel (now that Southwest is taking over the AirTran routes to Mexico and Caribbean). When you earn the Companion Pass, it is available for you the remainder of the current year and all of the following year. If you haven’t earned it already, the best time to earn it would be in the 1st Quarter of the year, that way you will have it for approximately 21-24 months! Daraius has some links to the 50,000 point Chase Southwest card or you can email me and I will give you my promo code. The sign-up bonus DOES count towards the 110,000 points needed to earn the Companion Pass.

  5. Daraius, thank you for including a guest post about my husband, Mr. BaldThoughts. Yes, I’m the one who has from time to time complained about taking “too many trips”. With more than a full plate, I have been known to turn down some fun on a few occasions. However, the majority of the time, I’m eager to jump on the fun traveling bandwagon. We’re fortunate to own two timeshares, and thus we’re afforded a significant amount of flexibility. We have stayed at more than a dozen locations with several being oversees. My two favorites are distinct and both appeal to me on a higher level. Who can resist the appeal of a first class resort in Cabo or the quaint charm just outside Paris? All I can say is I look forward to our next adventure!

  6. All,

    I love this post! My wife and I run a millennial couple travel blog, and we joke that the two to tango will hopefully soon be three to tango. So more and more, we read about other couples who push aside the conventional wisdom that you can’t travel with a child, and take inspiration from those that are out and doing it. Darius, thanks for allowing the guest post- it was great! Lee, you’ve got a new follower over here! =)

  7. Patrick, I’m glad that you and your wife look forward to traveling with your future children. Travel is great for the soul, but is that much better when you see your children experiencing things you love for the first time. Sure, it’s not always rosy, and always pack more juice, snacks, and diapers than you think you need, but the reward is worth the effort. Thanks for the positive comments!

  8. Pingback: Check out my interview with Million Mile Secrets | BaldThoughts