Just now getting back to writing after spending almost a month and a half on the go. Where was I? A visual probably works best:

Most of my travel is about the people I see, but I got to visit some fun locations too – Marco Island in Florida has a beautiful white sand beach, and Sedona has striking landscapes even in winter.

Traveling on Points

I fielded a lot of questions on how my sabbatical is going, but I also got some questions about how I plan travel, and specifically using points for free travel, that I thought I’d walk through here. I do always look at the cash options first, to see if there are any deals that it makes more sense to just pay out of pocket for.

Syracuse, NY to Fort Lauderdale, FL

There’s only one direct flight on this route in the winter, on the no-frills low cost carrier Allegiant, and by the time you add simple things like a carry-on (yes, that’s a fee) and advance seat assignment, it was $127 one-way, more expensive than a traditional carrier.

I decided to book with Delta and take a layover in Atlanta, and used 11,000 points to book it.

I want to note something important about points purchases. With the recent advent of “Basic” and “Saver” fares on almost every airline, most of the cheapest tickets you find nowadays are in this category, which strip out basics like seat assignments or carry-on luggage and have the lowest priority for boarding. Going back up to a “Main” ticket can almost double the price on an inexpensive one-way. However, points tickets count as the Main, not Saver, category – which means you’re getting even more value out of them. In the case of Delta, the differences are advance seat assignment and boarding priority, both of which were valuable to me.

Fort Lauderdale, FL to Phoenix, AZ

This leg was an example of where being flexible is an advantage. I could have departed from either Miami or Fort Lauderdale, but I needed to arrive on Friday by lunchtime to meet up with the others from our group. Being a 5+ hour flight, there weren’t many options that arrived in time, and the ones that did were expensive. American had a 10:23 am arrival, but it was blacked out for Avios (points) purchase. Instead, I opted to fly the night before and overnight in Phoenix. The out of pocket cost would have broken even compared to the pricier plane ticket the following morning, plus I’d get down time and a relaxing morning versus rushing all day.

I flew JetBlue for 7,000 points, and upgraded myself to Even More Space for $50 to get 38″ of pitch (legroom) in addition to early boarding. Well worth it for such a long flight! I stayed near the airport at the Hyatt Place for 8,000 points (the cash rate was $179, higher than usual), which had a free hotel shuttle and free breakfast. Also, the shuttle doesn’t just go to the airport, they’ll take you anywhere within a few miles. I had them drop me at our lunch location and it saved me an $8 Lyft ride!

Phoenix, AZ to Sedona, AZ

I rented a midsize car Friday-Monday through Dollar using 8,188 Chase Ultimate Rewards points. The cash rate was $123 or $41/day, which is actually quite reasonable, especially for a holiday weekend. Some of my friends were staying at Enchantment Resort, but there was no way I could pay $550/night for three nights. The Hyatt Residence Club was only 20 minutes away, located downtown in a great location, and I had enough Hyatt points to cover the cost: 45,000. They treated me exceedingly well, and actually gave me an upgrade to a huge one bedroom suite. 

Phoenix, AZ to San Francisco, CA

I thought this short 650 mile flight would be cheap, but I was wrong. Again, coming back on a holiday, prices were inflated. The best option for both price and timing ended up being a United flight, which I got for 16,000 United miles. (I haven’t flown United in a long time, I was astonished I still had any.)

San Francisco, CA to Seattle, WA

These flights are typically cheap in the winter, around $59 one way. I have a lot of Alaska Airlines miles, and used 5,000 miles in each direction. 

Trip Points Summary

Booking Cost
SYR to FLL (flight) 11,000 Delta miles
FLL to PHX (flight) 7,000 JetBlue miles + $50 upgrade
PHX to Sedona, 3 days (car) 8,188 Chase Ultimate Reward points
Hyatt Residence Club Sedona, 3 nights (hotel) 45,000 Hyatt points
PHX to SFO (flight) 16,000 United miles
SFO to SEA (flight) 5,000 Alaska miles (each way)

How to get points?

I got some of my airline miles the hard way, by actually paying for and taking flights in the past. In most cases, it was for work travel, so I wasn’t actually paying out of pocket. In others, regular personal travel. In a few cases, I booked really cheap tickets somewhere myself just because the miles payback was even more than the cost of the flights.

However, the easier answer is credit cards. A lot of the travel blogs heavily push getting every card known to man since they’re getting hefty commissions on your signups, but the truth is the right cards and strategies can produce a ton of value. 

Here’s an example. Years ago, I got an Amex Gold card with a 75,000 point signup bonus and a waived annual fee for the first year. I got it hoping that I’d like the early access to concert tickets, but the value wasn’t what I’d hoped. I decided to cancel before renewal (you need to pull your points out before you cancel a card or you lose them all!), so I waited for a good transfer bonus to a different program, Avios, basically British Airway’s miles program. When it hit 50%, I transferred my 75k points over, getting 112k miles in return.

My out of pocket cost was $0, nothing, since I canceled before the card renewed. What did I do with those miles?

Cathay Pacific First Class, Manila, Philippines to Hong Kong (vacation): 22,500 miles one way. I was the only First Class passenger, and had the entire nose cone of the 747 to myself. Short 1.5 hour flight, but amazing.

Cathay Pacific Business Class, Hong Kong to New Delhi (wedding): 37,500 miles. This is a 6 hour flight, so having an entire lie-flat pod to yourself is great.

The out of pocket cost for those flights is thousands of dollars. I paid about $40 in fees, and I’d only “spent” half of the miles I’d gotten. That’s the potential value of using miles/points.

That sounds complicated.

It can be, for sure – rules and programs change constantly, and if it’s not a passion, it’ll feel like work. There are also a huge number of travel hacks that range from very simple to extremely difficult. But it can be really easy if you take it slow and just do the basics.

Three steps to start

If you travel, step one is just signing up for the hotel, car, and airline frequent traveler programs. They’re free, and there’s no reason not to earn points on what you’re already doing. 

Step two is find a credit card that gives you a good return on the kind of travel that you do. If you like Hyatt, maybe that’s a Hyatt card with its status grant, free night award and low fee. If you fly United, God help you… I mean, seriously, have you looked at other carriers… ok, ok, maybe one of the United cards works for you. If you travel a lot with various carriers (I do), getting a flexible program like Chase’s Ultimate Rewards program often makes sense. The Chase Sapphire Reserve is a premium card that’s been massively successful because it’s so good, but over time the points bonus has gone down and the annual fee has gone up. I’ll point you to this excellent article on the ups and downs of that card, it’s my personal favorite for my situation.

Step three is use your awards. Don’t hoard them! First, it’s an amazing feeling to travel for free. Second, awards devalue over time, so you don’t want to hold on to them for years if you can help it. Spend them and enjoy yourself!

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