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Booking a Dream Trip to the Cayman Islands on Points - Part 2

travel hacking Mar 13, 2026

If you haven’t read the first newsletter in this series, you can read it here.

Ok, back to planning a dream trip.

So you’ve got your flight & hotel booked, what next?

Well, the Caymans is super expensive.

Here are some of the other costs you’ll incur:

  • Resort fee at the Kimpton of ~$100/day (this includes a number of fun activities the resort offers)
  • Food - this is expensive pretty much everywhere you go
  • Transportation - we use the public taxis and they’re relatively affordable (first time we went we did activities around the island but second time we just hung out at the resort because it’s so amazing)
  • Activities - they have many excursions & other activities on the island

Here are some of the ways you can cover these costs as well:

  • Redeem some of your Chase points for cash (easiest) and if you don’t have enough, grab another Chase card in the process and get the welcome bonus
  • Use travel credits you may have
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Booking a Dream Trip to the Cayman Islands on Points - Part 1

travel hacking Mar 06, 2026

My wife and I just returned from a couple’s trip to the Cayman Islands (the picture above is from our balcony).

We went for the first time in 2024 and took the kids. I wrote about that trip here.

While we’ve traveled to many amazing places, my wife thinks the beaches at the Caymans are the best she’s seen, so she was eager to return.

I want to spend the next two newsletters explaining how we booked this trip with points & how you could do the same.

The cost of this trip, if you were paying cash, is likely more than you would be comfortable paying. It certainly would’ve been for us. But points allows you to splurge in ways you likely wouldn’t do otherwise.

Let’s start with flights.

Flying to the Caribbean can be expensive. One of our flight attendants told us that they get paid for an 8 hour trip on only a 3 hour flight because of where we’re going. That’s why they like to fly this route.

American Airlines has a direct flight to the Caymans from our

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Check For Retention Bonuses Before Canceling

travel hacking Oct 24, 2025

My wife’s AMEX Gold card had a $325 annual fee posted to her account today.

She got this card last year because it had a great welcome bonus & was well worth the $325.

Whenever an annual fee hits for a subsequent year, I always consider whether it’s worth keeping the card for another year or just canceling (you typically have 30 days after the annual fee hits to cancel the card & request a refund of the fee).

In order to make that decision, I check to see if there are any “retention offers” to keep the card.

Retention offers are additional bonuses the credit card company will give you to incentivize you to keep the card for another year.

They won’t always have these, but knowing whether you qualify will help with your decision about canceling.

After checking with AMEX this morning, they offered my wife an additional 20,000 points (~$200 in cash value or ~$400 when redeemed for travel) for $2,000 in spend over a 3 month period.

As you can see, it’s basically another welcome b

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Earning American Airlines Platinum Status

travel hacking Sep 12, 2025

My latest Travel Hacking pursuit has been earning American Airlines Platinum Status primarily with spend on a credit card & shopping through their online portal.

American Airlines has a hub where I live, so it’s the airline that usually has a non-stop route to most of the places we choose to travel.

And, without status, you’re paying for bags, boarding at the back of the line, and not getting any free upgrades.

American Airlines grants status based on Loyalty Points earned over the course of a year. You can earn these loyalty points in a variety of ways:

  • Flying
  • Shopping through their online portal
  • Rental cars
  • Hotels

Among others.

I don’t fly enough to earn status with AA, so I knew I’d have to go about it a different way.

My goal was to achieve their second tier of status because I thought it had the best benefits for the effort I’d have to spend to get there.

Gold is their first tier & you have to earn 40,000 Loyalty Points to achieve it.

Platinum is th

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How I Got Started in Travel Hacking (and Unlocked $40,000+ in Free Travel!)

travel hacking Jun 20, 2025

Ministry is incredibly rewarding, but let's be honest about the financial reality many pastors face. Recent research shows that one-third of pastors don't even use all their vacation days, often due to financial constraints rather than lack of time. Today's guest post comes from Tim Walker, a pastor who discovered how travel hacking transformed not just his family's ability to travel, but became a legitimate tentmaking opportunity. His story proves that with the right strategy, ministry leaders can break free from the paycheck-to-paycheck cycle and create the margin they need for rest, family time, and ministry effectiveness. Whether you're skeptical about travel hacking or wondering if it's actually legitimate, Tim's transparent journey from financial struggle to earning over 3.5 million points will give you the real story. Over to Tim ...


For many years in ministry, my family barely made enough money to live on, and our paycheck-to-paycheck life meant that we never made enough mon...

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A 6 Month Travel Hacking Update

travel hacking May 30, 2025

It’s been 6 months since I’ve given an update on my tentmaking adventures, so I wanted to start with an update on Travel Hacking.

I’ve planned some pretty cool trips over the past 6 months & have earned just over 1.1 million new points & miles in the process.

I’m earning most of these points by completing a minimum spend for welcome bonuses on new cards. Instead of optimizing our usage of our cards for various categories like groceries, restaurants, travel, etc, we are typically trying to work on hitting the minimum spend for a new welcome bonus. This is by far the best way to earn the greatest number of points in the shortest amount of time.

Here are the bonuses we’ve worked on since the last update:

  • American Express Business Gold - 200,000 points
  • American Express Business Platinum - 250,000 points
  • Capital One Business Spark (x2) - $4,000 or 400,000 points
  • Citi AA Executive - 70,000 points
  • IHG Business - 200,000 points

We planned the following trips (u

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Chase Ultimate Rewards vs American Express Membership Rewards

travel hacking Oct 31, 2024

Chase vs American Express.

Honestly, both are fantastic!

I recommend people start with Chase cards first because of the 5/24 rule.

But once you’ve maxed out your Chase cards, AMEX is a great place to go next.

While Chase UR points are still the most flexible in my opinion, AMEX MR points are a close second.

Unlike Chase, AMEX has cards like the Blue Business Plus card that get 2x on everything (up to $50,000 in purchases).

But unlike AMEX, Chase allows you to transfer points back & forth from your spouse.

Instead of choosing between them, I get both, but I prioritize Chase if I’m under 5/24.

And once you get an AMEX card, they’ll start sending you additional offers in your account.

I recently got an offer for up to 99 employee cards where they’d give me 15,000 MR points for $4,000 in spend over 6 months. Wow!

I went ahead and got 5 employee cards (they can be in your name) and plan to get 75,000 MR points in the next few months.

Also, AMEX right now has the ability to tr

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An Update on our 500,000+ Points Journey

travel hacking Oct 02, 2024

I wrote a newsletter a few months ago talking about the opportunity to earn over 500,000 points in just a few months.

Chase was running an all-time high bonus on the Chase Ink Business Preferred card of 120,000 points & an all-time high referral bonus offer of 40,000 when you referred that card to a friend.

Our original plan was to get one card for me and one for my wife & then refer as many people as we could.

What we didn’t know at the time is that Chase would approve both me & my wife for TWO of the same card in a short period of time.

We just finished hitting the 4th welcome bonus, so here’s how all the points stacked up:

My wife referred me to the card = 40,000 points

We hit the welcome bonus on my 1st card = 120,000 points

I referred my wife to the card = 40,000 points

We hit the welcome bonus on her 1st card = 120,000 points

My wife referred me to my 2nd card = 40,000 points

We hit the welcome bonus on my 2nd card = 120,000 points

I referred my wife to her 2nd car

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An Exciting Merger for Points Enthusiasts

travel hacking Sep 26, 2024

A merger between Hawaiian Airlines and Alaska Airlines has been in the works for awhile.

Everyone was unsure whether or not the merger would make it all the way through or if the Department of Transportation would object.

About a month ago, AMEX was offering a 20% transfer bonus on points transferred to Hawaiian Airlines, one of their travel partners.

Travel Hackers online were discussing whether or not Hawaiian Miles would transfer 1:1 to Alaskan Miles if the merger went through. Hawaiian Miles are not worth much and easy to earn, but Alaska Miles are very valuable and very hard to earn.

Alaska Airlines is part of the One World alliance, so you’re able to book American Airlines flights at great point redemption rates.

This potential merger provided an opportunity for Travel Hackers with many points to put some at risk by transferring to Hawaiian, hoping Alaskan would honor the points if the merger were to go through. But no one was sure, so it was definitely a risky play.

I

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I Got Denied Twice And Then This Happened

travel hacking Aug 29, 2024

I’ve been talking a lot about the all-time high Chase Ink Business Preferred bonus (here & here). Apparently, everyone else is too because I get emails on a regular basis talking about how great it is.

Well, we decided to try something that we haven’t done before & we weren’t sure if it would even work.

Here’s a little backstory:

  • When the big Chase Ink welcome bonus first came out, I wasn’t sure I’d be able to get it. Why, you might ask? Because I was already at 5/24. Technically, Chase shouldn’t approve me for any more of their cards until I drop back down under 5/24.
  • I thought I would try anyway since the bonus was so great, and to my surprise, I was instantly approved! What?!? It’s not common that they’ll violate their 5/24 rule, but I’ve read online that sometimes they may still let you nab a business card. It’s rare, though.
  • Once I hit the minimum spend, we immediately had my wife apply for the same card. We applied under the same exact business name, but she wa
  • ...
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