Extra nights in cushy hotel suites, free premium air travel and even stays on private islands. Loyalty points and frequent flier miles, when strategically collected, can fund trips well beyond a traveler’s usual expectations and budget.

But it isn’t easy to get these deals. Luckily for us, there’s an entire universe of experts who share their savvy in booking award travel, and at the forefront is Brian Kelly, who founded the travel website The Points Guy in 2010.

For Mr. Kelly, 41, it started with the childhood challenge of booking travel for his family. At 12, he planned an entire vacation to Grand Cayman for his family of six, booking all of the flights with miles earned by his father. This successful trip laid the groundwork for his career as travel expert, he said. Deals still dictate his travel.

In his new book, “How to Win at Travel,” Mr. Kelly shares advice on everything from understanding points and miles to handling flight disruptions and flight anxiety.

He shared some of that advice with The Times, discussing how to strategize purchases with credit cards (he has 29!), flying with children in business class and the evolving world of award travel.

This conversation has been edited and condensed for clarity.

I love solving the puzzle. Yes, it’s a little bit difficult, but that’s also the point. If it was so easy for everyone in the world to use, it wouldn’t exist. For those who want to put in a little bit of work, I think there’s still a really high reward.

Some examples: I’ve been to the Maldives, Paris and Japan on rewards points.

Airline technology can sometimes mess up in your favor. When US Airways was getting acquired by American back in 2013 or so, I had redeemed 130,000 points for a first-class, round-trip flight to Australia. I was flying during the tech transition, and they ended up refunding all of my points. I flew to Australia for absolutely free.

The technology makes it really interesting these days.

Before, you had to be an expert and know how to use 10 different airline websites. There are tools now, like seats.aero and Thrifty Traveler, that are a little wonky but not that hard to use. Award redemption is shifting, but with these technologies, it’s easier today to find those sweet spots than before.

Certain airlines and partnerships still have really great value. Mostly the foreign programs, like Air Canada’s Aeroplan or Air France. You can fly business class to Japan on Japan Airlines with 60,000 American Airlines miles.

The foreign airlines are eventually going to catch on. I just think they are several years behind. The prices will rise. Use points now and maximize the sweet spots.

It’s important for everyone to understand credit.

Start with one card — it’s about getting credit cards with the big sign-up bonuses. But really the key is making sure you’re strategic about where you’re charging your dining, groceries and rent. You want to have a credit card portfolio, even if it’s just three cards. Start small, engage in the programs and then expand from there and put together a strategy that’s points and perks like trip disruption coverage.

I pay every bill in full every month.

I still fly economy! Preferably for flights under an hour.

Some O.T.A.s are better than others, but a lot of their customer service is abysmal. Be careful which ones you choose.

I’ve talked to hotel front desk agents: For hotel bookings, your O.T.A.s are generally looked upon as sort of the last priority. So don’t treat yourself poorly on purpose. If the price is the same, book direct.

When we’re chasing elite status, we’re often spending more than we have to, or inconveniencing ourselves because we feel we have to keep up on the hamster wheel. I love being a free agent. I will fly the best flight for me and my family to get us there the most comfortably. I pretty much use points for all of my airfare.

People mistakenly assume all planes are the same, but different planes can be the dramatically much better or worse experiences: legroom, noise, amenities. Cheap is expensive, too, when you account for fees and a bad experience.

My older son is 2 years old and has been to 16 countries. My second son was born in December. We’re heading to Thailand for a month in April, flying with points on the Etihad Residence, where you get your own bedroom on the plane. It’ll be my second son’s first international flight. Later this year, we’re going on a cruise in Antarctica. (The cruise itself is not on points, but all of the flights and hotels before and after will be.)

I think the younger you start, the better they are about traveling. When they’re young, it’s easy. It’s about preparation; snacks, activities and timing flights to sleep schedules has worked for me.

I plan on giving them this character-building experience when I don’t have to be there with them!

There are so many credit cards and ways to earn points. It’s constantly evolving. It’s pivoting toward a more stable valuation for miles and points as more and more people get in. This might mean that points and miles will kind of land at a lower overall value. Potentially less sweet spots overall, but more easy to attain value. Because if airlines don’t become more clear about how consumers can get their value, I think they do face regulation from the government, which they obviously want to avoid.

It’s not just airlines that have these new pricing technologies; consumers do too. There’s all sorts of new tools and tricks. It goes both ways.

  • Amex Centurion or Chase Sapphire lounge? Sapphire.

  • Oneworld, SkyTeam or Star Alliance? Oneworld.

  • TSA PreCheck, Global Entry or Clear? Global Entry.

  • Favorite city to travel to? Cape Town.

  • Favorite airport? Hamad International Airport in Doha.

  • Best first class? Air France.

  • Best airline loyalty program? Alaska Airlines.

  • Hotel loyalty program? World of Hyatt.

  • Carry on or check? Carry on, when possible.

  • Babies in first and business class? Hell to the yes!

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