How to Get the Best Seat on a Southwest Flight [Complete Guide]

And Do So Without Paying $150+ Extra for Business Class

Whenever you fly, you want to get the best seat on the plane for your money. With Southwest, getting the seat you want is more complicated. That’s because there are no assigned seats on Southwest flights. Rather, as passengers board the plane, they may choose any unoccupied seat.

I'm holding my son Michael on a Southwest flight

My son Michael and I on a Southwest flight last summer

Over time, I’ve given an inordinate amount of thought to how to get the seat you want on a Southwest flight. Here’s a complete guide to scoring your desired seat, whether that be an exit row, an aisle, or a window. (If you prefer the middle seat in the back row near the lavatories, you can stop reading now.) (more…)

How to Get a Spectacular Hotel Room Upgrade for Free

This Approach Has Worked for Me 9 out of 9 Times

The weekend before last, my wife and I stayed 2 nights at the historic Hotel Del Coronado, just south of San Diego, CA. Using Hilton points, I booked a free stay for us in a standard room, which sells for around $350/night. I wasn’t excited about the room. It wasn’t on the ocean, didn’t have a view, etc. But we were upgraded for free to an Oceanfront Tower Resort Suite on the top floor of the hotel. That room sells for over $1,500/night. It was 900 sq. ft. large. And it had the two features that I wanted: a spectacular ocean view and a balcony to enjoy it from.

View from the balcony of our hotel room upgrade

The view from our upgraded room’s balcony at Hotel Del Coronado

The upgrade was a gratuitous gift from the hotel. That said, I took certain steps to ask for the gift. I’ve now taken those steps to try to secure an upgrade on 9 separate occasions in three different countries. In all 9 cases, I succeeded in receiving a free room upgrade. Some of the upgrades, such as the one my wife and I just received, have been jaw-dropping. Others have been more modest, but still extremely meaningful to me, providing larger rooms, connecting rooms, better views, etc. Each upgrade has added substantial value to my family’s trip without costing a penny.

In all 9 cases, I booked the rooms for free using points prior to asking for, and receiving, an upgrade. Most people might be hesitant to ask for an upgrade on a paid stay and would be downright embarrassed to ask for an upgrade on a free room. But I have no shame in asking. And neither should you. Worst the hotels can say is “no.” But that’s not what they say.

Here’s how to get hotel room upgrades—sometimes incredible ones—for free: (more…)

Why Insurance is Never a Good Deal

And 4 Times When You Should Pay for It Anyway

When you purchase a computer, should you buy insurance in case it breaks? Or should you purchase travel insurance for a trip? What about car insurance, health insurance, homeowner’s insurance, or life insurance? You can save a lot of money over a lifetime by answering these difficult questions well.

Building destroyed by Hurricane Irma on St. Maarten island

Properly understood, insurance is always a bad deal. But there are 4 times when you should get it anyway. Let me explain. (more…)

How to Get 23 Months of Free Flights with the Southwest Companion Pass

Act by 10/4 (ideally *on* 10/3) to Maximize the Best Deal in Travel, Worth More than $1,800

The Southwest Companion Pass is arguably the best deal in travel. It allows a companion to fly for free with you on any Southwest flights you book. The pass is good from the time you earn it until the end of the following calendar year. The opportunity has arisen to enable a companion to fly for free with you for 23 months: most of 2018 and all of 2019. But you have to act by October 4, 2017 (and, ideally, on 10/3) to take advantage of this opportunity.

The Southwest Companion Pass works on all Southwest flights.

Following is more about the Companion Pass and exactly what you need to do by October 4th in order to score 23 months of free flights for your companion (and a lot of free flights for you as well): (more…)

How to Decide Which New iPhone to Get

And is the iPhone X worth $1,000 -- $300 more than the iPhone 8?

Last week, Apple announced three new iPhone models: the iPhone 8, the iPhone 8 Plus, and the iPhone X. (The “X” is pronounced “Ten,” in commemoration of the iPhone’s 10-year anniversary, but probably only “I in X” people will pronounce it correctly.) My first reaction to the X was this well-thought-out response: “I want.” I still do. But I’ve stopped drooling long enough to ask myself the question: is the iPhone X worth its $1,000 price tag? More specifically, is it worth $300 more than the also brand new iPhone 8? At least one person on Twitter thinks maybe not:

Funny picture suggests the iPhone X will cost one human life

In this post I’ll compare the three new iPhone models. My aim is to help any of you looking to get one of them to decide how best to spend your money. (more…)

Last Chance for Merrill+ Card, Worth $500 – $1000

The Generous/Easy Bonus on this Card is Rumored to End “Mid-September”

One of the best credit card offers on the market—the Merrill+ card—will be discontinued by September 18-19 at the latest. The card has no annual fee and comes with 50,000 bonus points. Those points are worth $500 in cash or up to $1,000 in airfare.

Sarah's Merrill+ card

My wife’s Merrill+ card

In this post I’ll cover the basics of the card and how to apply for it. But if you’re interested, you should act fast. A source told Doctor of Credit that the card will be discontinued on September 18 or 19. But another source told Frequent Miler that the card will be discontinued “mid-September,” which means it might not last until September 18. (more…)

Money Can Buy Happiness? It’s About Time.

New Research Reveals a Previously Unexamined Route to Happiness: Spending Money to Buy Time

If you were given $40 on the condition that you had to spend it, what would you spend it on? What type of purchase do you think would increase your happiness?

Man holding money and smiling, symbolizing his happiness

If you’re like 98% of people studied, you wouldn’t choose to spend the $40 on time-saving services such as someone else cleaning, shopping, or cooking for you. But new research suggests you might want to rethink that decision. (more…)

How to Blow $4,000 on a $56 Vacation

It’s All Too Easy to Do

When people go on vacation, they often pay face value. According to Forbes, the average vacation costs $1,145 per person or $4,580 for a family of four. I love family vacations because I like going on an adventure with my wife and kids. But I would never consider paying over $4,000 for a vacation. And I don’t want you to, either.

The three kids and I on the beach during our vacation to San Diego

On my last two family vacations combined, I spent less than $100 total on hotels and flights. Earlier this year, we took a $5,000+ vacation to Cabo San Lucas for $42. Last week, we took a short (2 night) vacation to San Diego for $56. Had we paid face value, the hotel and flights would have cost $4,012.

If vacations are part of your life—or if you’d like them to be—you should seriously consider a total paradigm shift in terms of how much you think they need to cost.

In this post I’ll share how we spent so little on a great vacation. And I’ll show how you can do similarly. (more…)

How to Save Money on Rental Car Insurance

Car Rental Insurance is Confusing and Expensive. But Should You Get It?

You just landed at the airport, ready to start your beach vacation. You can’t wait to change your sweaty clothes for a swimsuit. So you head to the car rental agency to grab your car and be on your way. But first, you must make a series of important decisions that you feel completely ill-equipped to make. Do you want collision coverage on the car? What about liability insurance? Seems expensive. But the agent swears you’d be crazy not to purchase the coverage he’s selling.

Long lines at rental car agencies as renters contemplate what rental car insurance to purchase

Your eyes begin to glaze over. You quickly initial here, here, and there. Depending on your decision, you either just forked over a bunch of cash or waived coverage. Either way, one thing is likely: you don’t have good reasons for the decision you made.

I know, because I’m right there with you. Or at least I was until last week.

Over the past week, I’ve done a bunch of research to try to answer the question: When renting a car, should I buy rental car insurance?

Following is the fruit of my research. It will shape whether I accept or decline rental car insurance moving forward. (more…)

AutoSlash: How to Get the Lowest Price on a Rental Car

And Do So with the Least Amount of Effort

When renting a car, I want to get the cheapest rate possible with the least amount of effort. You, too? If so, you need to use a free site called AutoSlash. I’ve used AutoSlash dozens of times since 2011. On one occasion, AutoSlash saved me a whopping $2,178 (74%) on a 27-day SUV rental. On at least 10 separate occasions, AutoSlash saved me more than 31% off the lowest rate I could find. Due to its considerable savings and ease of use, I highly recommend using AutoSlash every time you book a rental car.

Woman in rental car holding car keys

In this post I’ll explain what AutoSlash is and show you how to use it to quickly save a ton when renting a car.

(more…)