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- I just booked a $10,000 Carribean trip for $190 out of pocket.
I just booked a $10,000 Carribean trip for $190 out of pocket.
No, actually. I did.
I’m here to report the excellent news that I booked more travel for my family.
The goal of this newsletter is to:
Educate you.
Inspire you.
Sell to you make you laugh.
Today, I will do all 3.
Yes, I booked a $10,000 vacation using points & miles and paid just $190 out of pocket for flights & hotels. Absolutely wild!
Here’s the full breakdown:
But first, my cohort!
I mean I have to mention it.
My cohort has 10 spots left and is going to be SO GOOD.


You can register here. Email me if you’d like more information.
My $10k trip to the Caribbean.
Wednesday night, during dinner, I said to my wife, “What if we went to St. Kitts"?”
I expected her to say, “Honey, we just had a baby, I don’t have energy to even think about that right now.”
BUT she said, “I’d do that!”.
What a woman.
I’d been looking at the Park Hyatt St. Kitts for a client that afternoon, and my wheels were already turning.
To make a long story short, but 9pm that night we had the trip booked.
The details:
We’re staying 5 nights at the Park Hyatt St. Kitts one of the best Hyatt properties in the Caribbean.
Look a this place…

We’re paying 35,000 points per night. The cash price is a little over $1,500/night.
I have never stayed in a hotel even close to that expensive. This is a whole new level for us.
Even better, a friend gave us his Guest of Honor award which will let us enjoy Hyatt Globalist status for the whole trip!
That means:
Possible suite upgrade.
Free breakfast ($55/person, ouch!)
No resort fees.
4pm checkout.
This is going to be so cool.

Our flights:
This summer, I was flying American Airlines and heard about an amazing deal to get 70,000 points from their $95 annual fee card after spending just $1.
I had already transferred my Bilt rewards over to American, so I’ve been sitting on 100k AAdvantage Miles waiting to strike.
I found flights to St. Kitts (which is not the easiest place to get to) for 27,000 points per person roundtrip. Not the best I’ve seen, not terrible.
We used 81,000 miles + $190 in fees to get 3 of us roundtrip tickets.
The cash price was about $2,300 for those tickets. Solid 2.65 cents per point redemption.
If you don’t know where St. Kitts is by the way…

How I earned the points:
You’ll be annoyed by this. But the majority of the Chase points that I transferred to Hyatt were earned through referrals on my wife and I’s Chase Ink Unlimited cards.
I already shared how I earned those AAdvantage miles. And I still have some left for another trip!
The numbers:
So, I used 175,000 Chase points transferred to Hyatt for 5 nights @ $1,500 night.
175k points for $7,500 of hotels.
I used 81k American miles for $2,300 of flights. I paid $190 out of pocket for taxes & fees.
So, that’s 256,000 points used for $9,800 of travel! With the $825 of free breakfast we’re going to get (yes, $55×3 for 5 mornings), that gets us over $10,000.
$190 out of pocket for a $10,000 trip.
This is why I started Go Somewhere. To help more people do this kind of things.
This is what I’m preaching - you can do this!!!
I’m a normal guy, I’m nothing special, and I’m doing some pretty cool stuff.
If you want to book a strategy session with me, do it here.
I can’t wait.