Kip Henley Talks Travel


The RSM Classic - Round Three

We are happy to bring you another edition of Travel Talk. This time we are bringing the caddies into the mix. We are happy to have PGA Tour caddie, Kip Henley. Kip is one of the most entertaining guys on tour. He interacts more with his fans on social media than any other Pro out there.

He is an accomplished golfer who played in multiple PGA Tour events before he started caddying. He has had six wins while caddying on the PGA Tour. Kip currently caddies for Austin Cook. Prior to this, he has caddied for Brian Gay and ViJay Singh, among others.

Kip and his beautiful wife, Sissi, who he refers to as, “The Greens Keeper”,  lives in Chattanooga, Tennessee.  They have two beautiful daughters, Stormi and Darbi.  He is very much a family man and a down to earth guy.

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Fall of 2017, he and his Pro, Austin Cook, got their first win together at the RSM Classic at St Simons Island.

We are happy to bring you the caddie perspective of travel. I hope you all enjoy.


What’s your preferred airline, What is your status with them?

American Airlines, I worked my way all the way up to Platinum Pro after a trip to China. Platinum is huge for upgrades and no luggage fees. Now I’m just a Ruby, which means I turn right when I get on planes, not left. Haha. 

Do you prefer a window or aisle seat?

I love window seats, but you can get caged animal panick attacks, if everyone next to you is asleep on long flights. Aisles don’t work for me, cause I’m fat and everyone whacks my shoulders walking around.

Favorite inflight beverage?

Jack and Diet. Air Maids are slow to let you get over served now in this PC world though. I think airlines are profiling me and only upgrade me on morning flights when they know I won’t drink for free in first class.

What’s one thing you can’t travel without?

I go no where without my own pillow, blanket and fan. I hate hotel pillows and covers and the fan is to drown out slamming door noises in hotels.

What’s the best flight you’ve ever taken?

I actually enjoy overseas flights, if I have a first class cubicle, but the few times I get to caddy in Maui to start the season can’t be beat.

What’s your favorite airport?

Chattanooga! It’s four minutes from my house and you never wait on anything.

What is your preferred hotel brand, and why?

I’m not persnickety about hotels. Give me a solid clean one with a soft bed, a good air conditioner, a fridge, shower and I’m good.  The expensive ones charge you for parking, internet and extra fees. You can have them.

City view or water view?

Water view!

What’s the best hotel you’ve stayed in?

I got to stay in the Greenbriar one year during the toonament and it was a cool spot. I made the wife get on a plane and fly over for the weekend, it was so special.

What’s your favorite travel destination?

Maui! Free money that week in paradise.

What’s your dream vacation?

Me and the wifey love Cancun. Give me a swim up bar and I ain’t going to have a bad vacation.

Do you keep up with your hotel and airline points?

I am the worst points accumulater on Tour.  I have zero hotel alliance. I’m ashamed of my travel. I book everything last second.

Do you have any travel horror stories?

One year we played the Canadian Open on the west side of their country. Coming home I had to drive down to Seattle, fly to Dallas, fly to Nashville, drive two hours home, grab my car and drive five hours to The Greenbrier to work the next morning. Caddying ain’t easy baby!

With as much travel as you do, What are a few travel tips you have learned along the way?

Traveling is easier if your rich.


I hope you guys enjoyed. It was an absolute pleasure having Kip as our first PGA Tour caddie. Here at CaddieTravels we endorse Kip’s view of nothing beats a swim up pool bar! If you want to follow Kip, we recommend following him on Twitter.

The RSM Classic - Final Round

Featured images are courtesy of Getty Images
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