$8000 Trip for under $1000???

Yesterday I wrote about how I got into travel hacking. Today I want to share about a big challenge I set for ourselves for 2020. 

Mandy and I have always loved planning trips almost as much as actually taking them, and travel hacking has taken this to a new level. I decided I wanted a challenge. I wanted to take a big trip next summer, and I wanted it to be as close to free as possible.

We settled on Hawaii. Mandy and I went to Maui for our 5th wedding anniversary. We didn’t have much money so we stayed in a very inexpensive hotel, quite a ways from the beach. We spent a couple of days at Wailea Beach, which is a public beach but is next to the Grand Wailea, a very nice resort. We rented chairs and tipped a waiter 20 bucks, and he treated us as if we were guests at the Grand Wailea. We were pretty proud of ourselves. 

Fast forward 15 years. Now that Southwest flies to Hawaii we decided that we wanted to go back to Maui with the boys, but we wanted to stay at the Grand Wailea, and we wanted to do it for as close to free as possible.  

For those of you who don’t know, Hawaii is a very expensive place. And rooms at the Grand Wailea, which is a Waldorf Astoria resort, go for $600 and up per night during the summer. Those who know me know that I’m not shelling out that kind of money for a hotel room, no matter how nice it is. But (almost) free is another matter.  

Here’s how we did it. 

The first thing I did was to apply for the AMEX Hilton Surpass card. I received 150,000 Hilton points after spending $3000 in my first three months (this has since gone down to 125,000 points). There is a $95 annual fee. You also get automatic Hilton Gold status, which gives you some nice perks. Then Mandy got the AMEX Hilton Aspire card. This one gives you 150,000 points after spending $4,000 during the first three months. This one has a hefty annual fee though: $450. Before you stop reading, know that you get travel credits that bring it down. You also get Hilton Diamond status, which is Hilton’s highest rewards level.

This got us to 300,000 points. After some more spending, and the purchasing of some points, we got to 380,000. What is so special about this number? Well, a room at the Grand Wailea tops out at 95,000 points per night (versus $600 cash!). Another great thing is that if you book four nights with points, you get a fifth night free. So we booked five nights at the Grand Wailea for next June. It would have cost us, with taxes and resort fees, a little over $3200. But it’s going to be free!!!

Getting to Maui isn’t cheap either. That’s where my favorite credit card comes in…the Chase Sapphire Preferred. When you sign up and spend $4000 during the first three months, you get 60,000 points. I’ve had this card for a couple of years now. The great thing about Chase points is that they can be transferred to other airlines and hotel chains. This includes Southwest. We had a lot of Chase points, so we transferred them to Southwest and then purchased tickets to the SF Bay Area, where we’ll spend a few days, and then from there to Maui. Total cost:  $67.20 for security fees. Without points: $3600!

The final piece to the challenge was to book a hotel for our time in San Francisco, another place that is very expensive. I created an account with Hyatt, then transferred 40,000 Chase points to Hyatt and booked the Grand Hyatt in Union Square for two nights. This would have cost me almost $1000.

All of this means that my lodging and airfare for an amazing trip will be covered. We’ll pay for a rental car, food and entertainment. 

I won’t say that all of this has been easy. It’s a bit of work, and there are some areas that can be confusing. But it’s been worth the effort for us. The good thing is that you don’t have to take it to this level. And believe me, there are some travel hackers who make me look like a novice. 

If you’re looking for a place to begin, I highly recommend the Chase Sapphire Preferred card because of the transfer partners. After that I’d go to a Chase Southwest card. If you have a business (and you’d be surprised at what all qualifies as a business), go for the Chase Ink Business Preferred, unless you’re going after the Southwest Companion Pass, in which I would recommend you getting the Chase Southwest Premier or Performance Business Card.

UPDATE (04-02-20)
The current deal for the Chase Ink Business Preferred isn't as appealing as it once was. You now have to spend $15k within the first 3 months. As an alternative, check out the Ink Business Cash Card.

Here are links to my favorite cards. And as I mentioned yesterday, if you are going to sign up for one, it would be awesome if you’d sign up through these links, as it will help both of us out!

Chase Sapphire Preferred

Chase Southwest Priority, Premier, or Plus, and Business Premier or Performance

Chase Ink Business Preferred
Chase Ink Business Cash 

AMEX Hilton Surpass

AMEX Hilton Aspire

Finally, a few resources...

This podcast episode that got me hooked

Favorite website - The Points Guy

Great article on the Southwest Companion Pass

Travel Hacking 101

I first got into travel hacking over fifteen years ago, while we lived in the bay area. We got a Southwest Airlines credit card and began accumulating Rapid Rewards Points. It’s how we afforded to make trips home during the holidays. Ever since then we’ve had Southwest credit cards and have continued to do this.

However, I really got into travel hacking eighteen months ago. That’s when I discovered the ChooseFi podcast and website. From there I learned that the secret to true travel hacking is to take advantage of the bonuses that credit card companies offer when you open a new account. 

One of the things I learned was that the Southwest Companion Pass is the holy grail of travel hacking. I learned that in order to get it you needed to take 100 1-way flights (that wasn’t going to happen) or you needed to accumulate 110,000 Southwest points (that number has since gone up to 125,000). That seemed like a daunting task as well, but that’s where opening new cards comes in. 

You may be wondering what is so great about the Southwest Companion Pass, so I will happily tell you. Once you have it, it allows a companion to travel for free, and this is good for the entire year that you receive it, plus the next year. 

Towards the end of 2018 I started preparing, so to speak. I applied for a Chase Southwest business card and a Chase Southwest personal card. They both required a certain amount of spending within the first few months. I made sure to hit the spending at the beginning of 2019 so that the companion pass would be good for 2019 and 2020. 

Around February, 2019 I received notice that I had the companion pass. Now I could begin using it. And use it we have. The great part is that not only did I have the companion pass, but I also had an additional 110,000 Southwest Rapid Rewards points. This meant that not only did my companion (Mandy) fly free anytime I flew, but we would all be flying free using points.

By the end of 2019 our family of four will have taken trips to Dallas, Denver and Orlando, and Mandy and I will have gone to Chicago. And our total for airfare during this time: $0!

One question that is often asked is how one does this much spending in order to get the bonuses. Some cards require $1000 during the first three months, while others are $3000-4000. That can definitely be a challenge. I have a business that requires a lot of spending, so that has helped me. I've also gotten good at timing large expenditures, pre-paying bills and even buying gift cards to places like Amazon and Kroger. 

I probably don't have to say this but I will anyway...the one key here is that you have to pay off your credit cards in full every month. If you don’t do that, then you shouldn’t travel hack.

Part 2 of this post will be tomorrow, as I’ll share our big challenge for 2020. 

I’ll end this post by sharing a few of my favorite cards. I’ll share more about some of these tomorrow. Note that if you are going to sign up for one, it would be awesome if you’d sign up through these links, as it will help both of us out!

Chase Sapphire Preferred

Chase Southwest Priority, Premier, or Plus, and Business Premier or Performance

Chase Ink Business Preferred

AMEX Hilton Surpass

AMEX Hilton Aspire