Here's how to win at travel, according to the founder of The Points Guy

We all love a vacation, but hate the headaches that come with the travel.

Luckily, Brian Kelly, travel expert and founder of The Points Guy, has a new book out called How To Win At Travel to help you navigate all the turbulence.

He spoke with Larry Mantle, host of AirTalk, LAist 89.3's daily news program, to share some quick tips, from finding cheap flights to dealing with those dreaded customer service calls.

First things first. How do I find the cheapest flight?

The short answer: Google Flights.

“That's where you find the deals,” said Kelly. “It's not about searching for airfare at 2 p.m. on a Wednesday. That advice is so outdated.”

He recommends people use Google Flights’ explore feature to view all possible flights offered for their destination of choice within their preferred time frame.

“Google Flights is not like an online travel agency where you buy your ticket with them," Kelly said. "It's a search engine. And what I love about Google Flights is it pulls in flexibility."

So, I found a flight. How do I use my points?

Kelly recommends the website Point.me.

“It's basically like what Google Flights is for paid tickets for using your frequent flyer miles. It's especially useful if you have credit card points that transfer to a lot of different airlines,” he said.

Point.me will let you know what airlines you can transfer your points to so you can book flights at a lower cost.

To insure, or not insure

“ I recommend travel insurance for the big ticket trips when you've got to make non refundable deposits on cruises, on villas that you're renting, on personalized tours,” Kelly said.

And steer clear of insurance offered through the airline itself, he added.

“When you buy it through airlines and hotels you're not even getting insurance," he said. "You're getting what's called travel protection, and it's highly overpriced with really terrible coverage."

Kelly uses InsureMyTrip, a marketplace where you can compare and contrast different policies and prices.

For international travel, Kelly said to find policies that cover all medical and evacuation services.

“Even though most health care systems are cheaper than if you got sick in America, if you need to be medevac'd, that's hundreds of thousands of dollars, and you're really gonna wish you got that $300 yearly policy,” he said.

But for every day trips where you’re spending only a couple hundred dollars on a flight, no insurance is necessary.

“Nowadays, the airlines let you change [flights] pretty easily and get vouchers. Credit cards also have flight delay and cancellation coverage, so I use my credit card coverage for the smaller ticket trips,” Kelly said.

I’m on my trip, but I didn't get what I paid for

Kelly calls this the contract of carriage: what you’re owed when something goes wrong.

“Unfortunately, in America, we don't have great consumer protection," he said. "So a lot of the time when something goes wrong with the flight, the airlines don't really owe you anything."

But that doesn’t mean you can’t get something back. It’s all about how you ask.

Kelly said the biggest mistake is to take out your frustration on frontline employees, the very people who could actually help you.

“Frontline employees are under pressure from the airlines to not give out any freebies, so if you want that person to help you, rebook you, give you compensation, your best bet is to be nice,” he said.

Kelly also employs the strategy of HUCA: hang up, call again. If you’re on the phone with an agent who isn’t helping you, you may get another employee more willing to listen or who has more seniority the next time around.

He also recommends messaging senior managers and CEOs on LinkedIn.

“But keep it short and sweet. To the point. Be nice,” said Kelly. “You'd be shocked at what you might get.”