Itinerary Boss

Itinerary Boss Travel help for busy professionals & business owners: turn everyday spend into points & miles for paid for trips. šŸ‘‡ Grab the free points guide!

The couple behind us paid $11,248 for their seats.Ours were $304Ā They were part of a luxury $19,000+ honeymoon we covere...
08/26/2026

The couple behind us paid $11,248 for their seats.
Ours were $304
Ā 
They were part of a luxury $19,000+ honeymoon we covered on points.
Ā 
Five star luxury stays across Bali and Thailand.
Top lie flat business class Qatar Airways

558,000 points total for the trip

Those same 558,000 points redeemed poorly are worth $3,348-$5,580

Thatā€™s a $14,000-$15,000 difference of wasted money.

If youā€™re redeeming for:
- booking through portal
- statement credits
- cash back
- Amazon

Thatā€™s what I mean by poorly.

Thatā€™s the whole reason my company exists.

To simplify and get you these type of results with the people you care about.

Comment ā€œSeatsā€ if you youā€™re looking to save $10,000 on travel every year from the money youā€™re already spending.

Kotor Bay šŸ‡²šŸ‡Ŗ you are one of my favorites 48K total points for 3 nights saving $1,971
08/21/2026

Kotor Bay šŸ‡²šŸ‡Ŗ you are one of my favorites

48K total points for 3 nights saving $1,971

Turkish Business Class didnā€™t disappoint as expected. $4,260 cash saved vs. cashing those same miles out for $430 statem...
08/19/2026

Turkish Business Class didnā€™t disappoint as expected.

$4,260 cash saved vs. cashing those same miles out for $430 statement credit.

That's the mistake that 99% of people make and on 500,000 points that becomes a $20,000 mistake, being lost every year.

If you are spending over $15,000 a month in your business or personal. That's exactly why my company exists.

Comment "SEAT" if you Have over 500,000 points and wanna save over $20,000 on luxury travel this year

Heading over to Europe for almost a month āœˆļø43K Capital One Miles for this $4,260 lie flat seat.Business is going great ...
08/14/2026

Heading over to Europe for almost a month āœˆļø

43K Capital One Miles for this $4,260 lie flat seat.

Business is going great so Iā€™m taking a little sabbatical, something Iā€™ve wanted to do this since college.

First 5 people to comment ā€œEUROPEā€ before I land in 9h 25m at 4:25 PM EST get a free 15-min card audit call.

This ends when I land

08/13/2026

Donā€™t miss out on luxury flights and hotels by not having a simple strategy in place

08/07/2026

Quick clip to help get you over a big fear and misconception weā€™ve all been taught by people who donā€™t know what they are talking aboutā€¦

08/06/2026

The simple right card + payment structure in place pays for luxury vacations every year

08/05/2026

Having the right card + earning points on every dollar you spend is the simple way to win in this game

07/28/2026

In 2014 right after I graduated college, I opened my first travel credit card. Zero dollar annual fee. Zero strategy.

My cousin told me: hey, you should start earning points.

That was it. No travel goal. No system. No idea how to leverage points. Just a first step.

12 years later that first step led to business class to Japan, South Africa, Bali and Thailand. Every flight covered by points. Every big trip and everything domestic.

It's just like investing. Just like building a habit.

You don't have to have everything planned out. You don't have to read 1,500 blogs and get overwhelmed.

You just have to start.

That's what we help with ā€” 12 years of experience, every mistake made, so you don't have to spend 12 years figuring it out yourself.

Follow along and we'll show you how to get started with the right cards for your specific goals.

In 2016 someone sent me a Venmo request for a group trip.I paid it on my card instead and collected from everyone else.T...
07/28/2026

In 2016 someone sent me a Venmo request for a group trip.
I paid it on my card instead and collected from everyone else.

That one decision accidentally started a system that's funded ten years of epic group travel.
Annual snowboarding trips to Whistler, Park City, Tahoe, Jackson Hole, Big Sky and all over Colorado.

International trips to Germany, Amsterdam, London, Spain, Croatia, Hungary, Czech Republic. Greece, and Carribebean

Still running in 2026.
Every one of those trips had 6-10 people.

Every dollar they spent ran through my card first.
Every point went straight into my balance.
They got convenience.

I got a decade of points and learnings on other people's spend.
You're probably already organizing trips for your friends or family.

You're just not getting paid in points to do it.
A decade of being the one who books means a decade of points accumulating on spend that was never yours to begin with.

Comment "GROUP" and I'll show you exactly how to set this up for your next trip.

Address

Charlotte, NC

Website

,

Alerts

Be the first to know and let us send you an email when Itinerary Boss posts news and promotions. Your email address will not be used for any other purpose, and you can unsubscribe at any time.

Contact The Business

Send a message to Itinerary Boss:

Shortcuts

Share

Category