Saturday, December 14, 2019

$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.

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!



Finally, a few resources...

This podcast episode that got me hooked
Favorite website - The Points Guy
Great article on the Southwest Companion Pass

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