The pleasure of changing or cancelling a flight with Southwest Airlines

I’ve written before about how much we’ve traveled on Southwest recently and even how we haven’t paid for a flight on Southwest Airlines since 2015.  Well, the time eventually came when I had to book a ticket on Southwest with cash instead of miles. I just didn’t have enough Southwest miles left to cover the cost of the flight for both of us on this trip.

Photo By Brian from Toronto, Canada – Southwest 737, CC BY-SA 2.0,

17761038_1121957987914685_4477871181367452954_oWe are flying to Chicago for a weekend to see Hamilton  (Again. Don’t hate us.) and I know I cleared these dates with Sharon before I booked the airline tickets. But sometimes life happens and plans change. This time we needed to change our travel dates because Sharon was cast in the choir of Encore!  for their upcoming production of Hairspray at the Dr. Phillips Center in Orlando (shameless plug – tickets are on sale here).  This did cause a bit of a dilemma as Sharon now has a rehearsal scheduled for the day we were going to be flying to Chicago, and that just wasn’t going to work.

When we realized this, I immediately was relieved because I knew I had booked the Continue reading “The pleasure of changing or cancelling a flight with Southwest Airlines”

This is why you need to sign up for hotel programs before booking your room.

l’ve already posted about how you can sign up for hotel programs. Not surprisingly, I’ve certainly signed up for quite a few. When I look at AwardWallet, I see that I have accounts with these hotel programs:

  • Starwood Preferred Guest
  • Marriott Rewards
  • Hilton Honors
  • World of Hyatt
  • IHG Rewards Club
  • Le Club Accorhotels
  • Wyndham Rewards
  • Choice Privileges
  • La Quinta Rewards
  • M Life (MGM Resorts)
  • Kimpton Karma Rewards

I’ll freely admit that I wasn’t enrolled in the last two programs on this list until this week. I signed up for them because I was staying, or thinking about staying, in hotels belonging Continue reading “This is why you need to sign up for hotel programs before booking your room.”

The joy of being disloyal

When it comes to making travel reservations, I’m disloyal. There, I said it and truth be told I get a bit of a thrill in making that statement. You see, I am an Eagle Scout. Therefore, loyalty is part of the deal. Right here, second on the list behind being trustworthy.

00000460 - Version 2A Scout is:

  • Trustworthy,
  • Loyal,
  • Helpful,
  • Friendly,
  • Courteous,
  • Kind,
  • Obedient,
  • Cheerful,
  • Thrifty,
  • Brave,
  • Clean,
  • and Reverent.

So why am I not loyal when it comes to my travel? Simply stated, I don’t travel enough to Continue reading “The joy of being disloyal”

Hotel Review: Hyatt Centric Key West Resort and Spa

Spoiler alert – I had a really hard time deciding how I felt about this hotel. I mean, my reviews are normally my thoughts about a hotel based on my stay. But after visiting the Hyatt Centric Key West for a few days, I discovered my thoughts about a hotel can be changed by what I expect going in (and how much the hotel costs).


Right after getting home from our stay, I wrote about how I spent 75,000 Hyatt points to stay at this hotel. I would normally think that many points for a 3 night stay would be expensive. That was until I looked up a cash price of a room and saw it would have cost us $1876.84. That means this hotel, after taxes and fees, would have cost $650 a night. Turned out this was “season” for Key West and as our favorite bartender told us, “Those Continue reading “Hotel Review: Hyatt Centric Key West Resort and Spa”

Staying at Disneyland – Backup Plans (DVC Points, Hotel Points or Citi Prestige 4th night free)

I’ve already documented the difficulties I came across when trying to book a room at Disneyland with my DVC points in a previous article and now it was time to start looking at Plan B, Plan C and Plan D. Now, I don’t have much experience with booking hotels in and around Disneyland. We’ve stayed in the Grand Californian and Disneyland Hotel several times. Going back many years ago, we stayed at the Sheraton Anaheim Hotel (now renamed the Anaheim Majestic Garden Hotel) with a group discount from a theme park message board we helped moderate. On our most recent trip, we stayed at the Sheraton Park Hotel at the Anaheim Resort (that’s a mouthful). It wasn’t my original choice, but I was lucky enough to win a free night during a online contest that had to be Continue reading “Staying at Disneyland – Backup Plans (DVC Points, Hotel Points or Citi Prestige 4th night free)”

We are flying to Charlotte for $25!!!!

Forgive the clickbait headline. But truth be told, we really are flying for an out-of-pocket expense of less than $25. How? Thanks for asking!


Not all trips on points and miles are glamourous. Some are rather plain, yet important. Like when you and your wife want to fly to Charlotte for a friend’s wedding in little over than a month from now.

When I first started looking at flights, I was like “That’s like less than 500 miles. It can’t be that expensive of a flight.” Continue reading “We are flying to Charlotte for $25!!!!”

Don’t be fooled by false point valuations

If you follow travel blogs, like I do, you’re bound to read headlines about how someone just got 12 cents per point on their most recent booking. I guarantee you, there was something iffy in their calculations.


When looking at how good of a deal you are getting for your points, there are two things you always have to consider. How many points are your using and how much would the same reservation cost you in cash? The first answer is usually a constant, as the number of points needed for a reservation, if you are not dealing with a fixed-value program, do not change. The problem when making these calculations comes with the cost of the reservation in cash.

Take, for example, the 75,000 points we just used to stay at the Hyatt Centric Key West Resort and Spa.  When I booked the hotel, I wrote this post.

So, was this redemption really worth almost $1,900 for a 3 night stay? If it was, my redemption was worth 2.50 cents per point. That’s a good value even before including the $30 a day resort fee that I wouldn’t have to pay (because Hyatt excludes the resort fee on all points stays).

Unfortunately, that valuation isn’t even close to my actual value. I could never see myself paying $650 a night for a hotel room in Key West. We’ve stayed at several hotels there and not paid anything close to that. However, this trip was different from our usual trips in 2 important ways.

  1. We had never gone to Key West “in-season” before
  2. We were booking only a month in advance of our trip

This trip was a spur of the moment idea. I had the long weekend off of work and we had no plans. It had been a long time, for us, to be away from Key West (which is one of our favorite places for a quick escape). The lack of knowledge of when the busy season is and the close in booking time meant the prices of hotels I’ve stayed at before were costing $300 to over $400. That’s a little more than I was willing to pay for a last-minute getaway.

So I went to Plan B, which was looking for hotels with points. One of the things we like about Key West is the lack of corporate influence. This has been changing over the years, but it does mean there is also a lack of points hotels in the Old Town section. Since the Westin was recently sold and rebranded as the Margaritaville Resort, there is no other Starwood property in the area. The only Marriott hotels are on the far side of the island and Sharon wasn’t willing to stay that far from the action. The LaConcha Hotel and Spa, which is right on Duval St., is an IHG Crowne Plaza property that costs 50,000 points a night, but was unavailable to book with points for our stay.

That meant the only other option we had was the Hyatt. Luckily, they showed availability for 25,000 points a night. I didn’t have enough Hyatt points, so I would have to transfer points from my Chase Ultimate Rewards account. Being able to transfer points like this is the advantage of earning flexible points. I can wait until I need them before transferring them to other programs. I know that Chase points transfer almost immediately to Hyatt.

Is staying here worth 25,000 points a night? My vacation depended on that answer.

I needed to decide if the Hyatt was worth the 25,000 points a night. For reference, if I redeemed my points as a statement credit, they would be worth $250. If I used the points to book travel through the Chase Travel Portal, I could get $312.50 in value (points are worth 1.25 cents toward travel bookings if you have a Sapphire Preferred card).

The more I thought about it, the more I realized that I was comparing the prices I was used to (usually during the fall) with the prices for rooms during high season. While I would never pay $600 for a room at the Hyatt, a room at the Eden House (where we have stayed before) was going for more than $300 for our dates. I then realized that my points for a room at the Hyatt would be worth about $350 a night. That’s the lowest price I could find at a hotel I wanted to stay at. I also had to take into consideration that I had enough Chase Ultimate Rewards points and didn’t have a current use for them. I might as well use them to pay for our trip. At that point, if I had to pay those prices out pocket for a room, we probably would not have went on the trip.

Decision made. I transferred the points, made the reservation and we had a wonderful time on our trip. We had absolutely perfect weather and I can see why this is considered high season for the Florida Keys. While I still stand by my decision that I would NEVER spend $600+ for a room at this hotel, it was worth the points we redeemed for it and that’s the only measure that means anything.

I’ve found that, for me, collecting points is the easy part. Eventually, you need to learn to let go of them. Spend the points and miles on trips that make you happy. While I might not have scored the “perfect” redemption, I’m happy with it. In the end, that’s all you can hope for. Your Mileage May Vary.

Photo Apr 08, 7 44 41 PM
This sunset was totally worth the 25,000 Hyatt points.