Bookings – Newby to Expert Traveler

We Booked A Trip to Costa Rica on American Airlines Miles

Posted on December 15, 2023December 15, 2023 by David Cox in Bookings, Trips

Booking our spring break trip this year was a different for us. This was essentially the first time that we’ve had an opportunity to book a family trip with both the experience of doing so, and the points to be flexible. When we booked our trip to Europe last summer, we didn’t have a bunch of points in various programs, and we basically had to book what we needed with the available points, and for us that meant that we had to work around United Airlines since that was where we had points.

This time it was much different, since we had significant amounts of points in Chase Ultimate Rewards and a decent amount of Capital One Venture miles. Ultimate Rewards transfers to 11 different airline programs and Capital One Venture miles transfer to 15 different airline programs (many of them overlap with Ultimate Rewards). On top of that, we also had a couple of American Airlines cards that we were working toward signup bonuses on, with no plans to use those AAdvantage miles.

What this meant was that we had a lot of different choices of ways to book flights. But we needed a destination. I was looking pretty hard at Madrid, Europe is off-peak in March and a flight from Chicago to Madrid is 34,000 Avios (transferable from Chase Ultimate Rewards) round trip and around $225 in taxes and fuel surcharges, through Iberia. That seemed like a steal to me, but there is that pesky problem of jetlag and Jenn wasn’t too thrilled about having to pay $900 for four flights (I know it honestly sounds silly, but this is apparently who we are now).

I wasn’t too excited about staying in the US, because in March you basically have Florida if you want to be warm, and that’s so overrun by drunken college students it’s hard to really enjoy it. A lot of the other places we thought about like Cancun, Punta Cana, Aruba, etc seemed to be both not really what we wanted and probably would’ve also been full of drunken college students. We wanted something different.

What About Costa Rica?

Jenn and I were having a beer at our favorite taphouse talking about spring break and I said “What about Costa Rica?” She looked at me a little strange, and said “Why Costa Rica, what’s there?” I replied “beaches, mountains, jungles, great food, it’s pretty much a tropical paradise.” Within a few minutes she was on Airbnb and somehow managed to find an absolutely gorgeous 3 bedroom Airbnb in the middle of a coffee growing region near San Jose for just $75 per night. Since Airbnb allows free cancellations, she booked it right there.

This kitchen is nicer than what we have at home

Now that the rental was booked it was up to me to make the airfare work.

Beating my Head Against a Wall

The Airbnb Jenn booked was only a 40 minute Uber from San Jose Airport, so that’s fantastic. I started to look at flights coming to and from San Jose from our home airport in Moline, and it was pretty clear right away that we were going to want to fly American Airlines if we wanted to leave out of Moline. They were running a special that cost around 8,000 points to San Jose and about 20,000 points coming back, and I thought, that’s pretty good, I just need to wait until we earn our signup bonuses and the points show up in our accounts.

The problem was, Jenn got her bonus from a Barclay’s card and they very specifically mention that they could take 4-6 weeks for the bonus to hit her account. I knew what I wanted but the clock was ticking and availability is never guaranteed.

When they finally hit her account the miles for those flights had increased to 11,500 miles out, and 32,000 miles back and we didn’t have enough points in our accounts for the more than 160,000 miles needed. I started shopping around and found a flight itinerary that would cost 17,500 miles through Avianca Lifemiles for the way home and keep the 11,500 mile AA flight down to San Jose.

What The Hell Am I doing?

I set Jenn up with a Lifemiles account with the intention of moving 70,000 Capital One Venture miles to Lifemiles to book the flight. The flights would have to be out of Peoria (an hour and a half drive away), since that’s where the Lifemiles flight itinerary took us.

I almost pulled the trigger and then I looked at the itinerary once again. On the way out, Moline to Charlotte to Miami, with a 7 hour overnight stay in the Miami airport before taking off to San Jose. I wasn’t thrilled about sleeping in the airport, that’s not ideal. Then on the way back, we would leave San Jose in the afternoon, stop in Guatemala for an hour then fly to Washington Dulles airport, land at 1 AM, go through customs, catch an uber to Reagan National Airport, go back through security (probably at 3 AM) and wait for a 6 AM flight to Chicago and then another flight back to Peoria, where we would have to drive an hour and a half home.

There is no way that I don’t fall asleep at the wheel coming home after that mess of a flight itinerary. That doesn’t even take into account the number of things that would have to go right just to make sure that we made it back to Peoria. It was time to call an audible, this isn’t going to work.

Let’s Try Guanacaste Airport

When I started looking at LIR airport in the north of Costa Rica, it became so much easier. The flights were more direct, less stops and prices were good. Jenn and I looked through a few choices and while we could get a slightly cheaper flight, we could find good prices for flights with just 1 stop each, and given the fact that there could be snow in March, fewer stops mean a better chance of actually getting to our destination. Each flight had long layovers, but they were long enough to get hotels so they looked great.

The outbound flight is Moline to Chicago to Guanacaste with a 17 hour overnight layover in Chicago and the return flight is Guanacaste to Dallas to Moline with a 18 hour layover in Dallas. We will be able to sleep well, staying in hotels for each and we should be able to be rested and relaxed rather than stressed and tired. Much better, but unfortunately we now have a 3 hour drive from Guanacaste airport to the Airbnb as opposed to a 40 minute drive from San Jose Airport. Oh well, we were going to rent a car anyway.

The flights cost us 120,000 AAdvantage miles and $336.24 in taxes. The cash price total for the same exact flights would have cost us $2,888.48 which means that we saved around $2,550. That means that those miles were redeemed at 2.1 cents per point which is well above the normal 1.5 cents per point for AAdvantage Miles, so I’m happy with the value we got from the points.

Land in Costa Rica as Early as Possible

Here is a little side note that I’ve learned from my research – if you are going to fly to the Guanacaste Airport, you probably want to land early if possible. At first, I was a little annoyed that I couldn’t get to Costa Rica with a 1 day flight itinerary but the more I read I’m okay with it. The reason is that Guanacaste Airport is a regional airport and while it is the best airport to go to for a variety of places in the north of Costa Rica, it’s not really close to anything.

So, what’s the big deal, right? I can drive at night. Yeah, but you probably shouldn’t. It is generally not recommended to drive in Costa Rica at night. The reason for this is that the roads are rural, curvy, unlit, and not always in great shape. It’s never a great idea to drive in an unfamiliar country at night, but with Costa Rica being so rural, it’s really not recommended. Add in the possibility of mountainous terrain with no guardrails and it could get deadly. It’s especially not recommended in the rainy season, where it can get even more treacherous.

It is also of note that it gets dark early in Costa Rica. Since it’s fairly close to the equator, the times don’t change too much from season to season but basically you can expect sunrise to be around 5:30 AM and sunset to be around 5:30 PM. That means that we will be probably cutting it a little close with the 12:30 landing and a 3 hour drive (once you figure in customs, car rental counter and probably some lunch).

Booking the Hotels

Since both the flight to Costa Rica and the flight back have overnight layovers, we needed to book a couple of hotels. We’re not that picky about where we stay, but I definitely like things to be easy and Jenn likes free breakfast if available. On the way there, in Chicago Jenn booked the Springhill Suites because it had a free airport shuttle and free breakfast, for 17,500 Marriott Bonvoy points. It would have cost $129 with cash so it comes out to .7 cents per point which is less than the .8 cents per point that Bonvoy points are typically valued at.

I booked the Hyatt Regency DFW for one reason only. It was actually at the airport. We don’t even need a shuttle, just walk from the terminal to the hotel and vice versa. We burned my 1-4 category Hyatt certificate on it and it’s only a category 2 hotel, so I definitely could have done better. It would have cost $218 for that night, so I think the fact that I get that certificate by paying a $95 annual fee for the World of Hyatt credit card makes it decent.

How Do I Feel About the Bookings

I feel pretty good about these bookings. I tend not to worry too much about maximizing hotel certificates, because I’m really not a hotel snob. I’m not sure I could tell the difference between a category 2 and a category 5 Hyatt. Jenn used a few more of her Marriott points to book another night, it almost seems like she always has Bonvoy points when we need them.

I’m pretty happy about the flight booking. We get to leave from our small home airport and still only have one stop. The stops are all long enough to relax at a hotel instead of being uncomfortable at the airport. On top of that, we got good value for our American Airline miles. I had been slow to look at American Airlines because they don’t have any transfer partners except Bilt, but I’m going to have to work a little harder to keep some AAdvantage miles around because that was a good deal.

It always feels great to get a trip booked, because now I can concentrate on what we are going to do when we are there, where we are going to eat and what we want to explore. I have read that Costa Rica is not a place to “wing it” since destinations are typically far away and roads can be unpredictable. That’s okay with me though, I like planning out the fun stuff.

Girls’ Trip booked to Playa Del Carmen (I Guess I’ll Stay Home With The Kids)

Posted on August 26, 2023December 15, 2023 by David Cox in Bookings, Travel Hacking, Trips

Sometime this last winter, Jenn was talking about wanting to take a Girls’ trip (with her Mom and her Sister) to celebrate a milestone birthday for her Sister. We had basically just completed booking our European vacation just a couple of months earlier and we had learned a valuable lesson from that booking that we didn’t want to repeat – don’t be dependent on one way to book.

What I mean by that is that when we booked our flights to Europe, all we had was United miles, and that was our only option. If the flights weren’t cheap enough on United, we weren’t going or we were paying cash. So the solution to this issue was to find multiple ways of booking flights on points and make sure that we stockpile points in multiple areas.

The Power of Stockpiling Points

Jenn had already begun to accumulate Ultimate Reward points by taking advantage of two 90k bonuses for Chase Ink cards as well as a 60k Chase Sapphire bonus. Since they were thinking Mexico or the Caribbean, Chase Ultimate Reward points, having the ability to transfer to Southwest Airlines or United Airlines, might make sense.

We also added over 80k points by meeting the the minimum spend on a Capital One Venture card. That’s intriguing because Capital One miles transfers to the Turkish Airlines Miles & Smiles program where booking round trip United Airlines saver flights to Mexico and the Caribbean often costs only 20k points .

Jenn also jumped on a 75k point bonus offer on the Delta Business Gold Card. When she did it, I scoffed a little because a lot of people joke about Delta Skymiles as being “Sky Pesos”. It’s a bit of a joke because Delta is notoriously expensive to fly to Europe or in business class on points. That being said, I think people might find that Skymiles could be particularly valuable for domestic and North American international economy award tickets and Jenn found that out.

In this case, Jenn received an email from Delta about a flash sale, and went on to Delta’s website, where she was surprised to find a round trip flight out of Moline Airport to Cancun in January for 26k Skymiles each. Because of the 15% award discount afforded to Delta Gold Card holders, she was able to book it for 22k Skymiles and $116 in taxes each for a total of 66K and $348. Those flights were priced at that time at $631 each, which means that this redemption was more than 2.3 cents per point which is a really good value for airline miles and definitely not worthy of being derided as “Sky Pesos”. This is particularly great, because good award rates out of the Moline Airport are usually hard to find, and typically we fly out of Chicago because of it, which usually means booking a hotel and paying for pretty expensive parking.

Because of the fact that we had significant amounts of Chase Ultimate Rewards points, Capital One Venture miles and Delta Skymiles, we were able to keep our eyes open for special rates with Delta, United, and Southwest Airlines, as well as being able to book Sky Alliance flights through Turkish Miles and Smiles or Avianca Lifemiles. I’m sure that we could get more creative than that, but honestly, it wasn’t needed in this case. Having flexibility in multiple programs allowed Jenn to be patient and wait for a great deal, and then jump on it when she had the opportunity.

The nice thing about a vacation rental is having a working kitchen, and this one looks pretty nice.

Flexibility on Booking Lodging

We had some flexibility built into our points for lodging as well. We had accumulated a decent amount of Wyndham points, and a respectable but not huge amount of Marriott Bonvoy points. However, with Jenn having a nice stockpile of Chase Ultimate Reward points, which transfers 1:1 to World of Hyatt points, that also made Hyatt a good possibility as well. Because of a status match made possible by Jenn’s Wyndham Business Earner card to Ceasars Rewards (visit Upgraded Points for more details), we also had a 4 night “free” stay available at Atlantis in Nassau in the Bahamas. The Atlantis stay would have had a bunch of extra resort fees that would have added up to over $200 a night and was quickly eliminated. Chase and Marriott were definitely possibilities, but the Wyndham-Vacasa partnership is just too good to pass up. We booked a Vacasa with Wyndham points before and got great value for that redemption.

The rental is in a complex with a pool on the beach.

Jenn decided to book a 1 bedroom Vacasa in Playa Del Carmen for 54,000 Wyndham points total for a 4 night stay. That particular Vacasa typically would rent for $1,325 for a 4 night stay in January meaning that those points were redeemed at 2.4 cents per point. This is another ridiculous value considering Wyndham points are generally valued at 1.1 cents per point. Booking a Vacasa rental with Wyndham points is a little weird because you have to call a special line to do it, but the rules are simple. Vacasa rentals cost $15k points per night per bedroom and is bookable with points as long as the cash price is under $500 per night per bedroom. For example, a one bedroom is bookable for 15K points per night as long as it costs under $500 and a 2 bedroom is bookable for 30k points per night as long as the cash rate is under $1000. Having a Wyndham Business Earner card gives you a 10% point discount on those rates. (Update – the program has recently changed and now the ceiling on cash price is $350 per bedroom per night, this changed in October 2023)

Obviously we’ll have to wait until they get there to find out if the Vacasa rental is as nice as the photos, but it looks gorgeous. It looks like Jenn did a great job booking this trip and I really hope they all have a great time (I’m sure she’ll feel sorry for me shoveling mounds of snow out of our driveway while she’s sipping a Bohemia Oscura cerveza on the beach). In the end, this was made possible because Jenn had the ability to be flexible with dates, locations and points programs. It allowed them to book what looks like a great vacation for not a lot of points and cash.

I may Have Created a Monster

When we got started with points and miles, it was pretty much me doing all of the research, listening to podcasts, reading blogs, and doing as much internet research as I could. As we started to have some success, with booking trips to Cabo San Lucas as well as our trip to Europe this summer, Jenn really started to not only get interested in points and miles, but she actually really gets it now. I expected to have to guide her on planning this trip, but for the most part, other than a couple of suggestions, she did this on her own and it was undoubtedly the best trip in terms of redemption value that we’ve made. Going forward, I think with both of us having a solid understanding of points and miles, we should have some great trips ahead, as long as she decides to come back from Mexico, of course.

Should we keep Vacasa a secret?

Posted on April 12, 2023December 15, 2023 by David Cox in Bookings, Hotel Programs, Travel Hacking

Jenn booked 3 days in a Vacasa in Nashville for September this week and it’s a crazy good deal. I mean, it’s the kind of deal that you’re afraid if you start talking about it, the company might start to realize how much money they’re losing on it and shut it down. I’d like to think we could keep this quiet but I think this cat is getting out of the bag about this so you might as well get it while it’s still available.

What’s Vacasa?

Like Airbnb, VRBO and Marriott Homes and Villas, Vacasa is a short term vacation rental booking company. They team up with individual owners to list properties for rent and they take a portion of that rent payment for processing, advertising and managing the booking process. Like Marriott Homes and Villas, Vacasas are bookable with points, in this case Wyndham points. Unlike Marriott Homes and Villas, Vacasas have a set point chart which allows you to get ridiculously good value for those points if you choose well.

Vacasa’s Point Chart

The Vacasa point chart is extremely simple. Vacasa charges 15,000 Wyndham points per night, per bedroom. A 1-bedroom Vacasa is 15,000 per night, 2-bedroom is 30,000 points, etc. People have reported that the cash rate ceiling for a 1-bedroom is $500, meaning that if you attempt to book a 1-bedroom that would rent for $550 per night, the redemption will not go through. I don’t know what the cash rate ceiling is for it a 2-bedroom, I assume its higher, though. Wyndham points are generally regarded as being worth 1.1 cents per point, but a 15,000 point rental worth near $500 per night is over 3 cents a point. That’s a outstanding redemption for Wyndham points. (Update – The maximum redemption as of October 2023 is now $350 per bedroom per night, down from $500)

Nashville is crazy expensive!

Blame it on the bachelorette parties, but Nashville hotel prices are out of control. We saw most hotel rooms (not suites, just rooms) going for $350-$500 per night. We planned to use some hotel points or maybe a certificate or two to book a hotel in Nashville, but daaammmmnnnn, it’s overpriced. We literally couldn’t stomach what a redemption would cost near the downtown area. But Vacasa, we’ll, that’s a different story.

Cash Value of Vacasas in Nashville

Im not saying that the Vacasas in Nashville weren’t expensive, they absolutely were, but because of how the chart works, if we want to use points, a 1-bedroom rental for 3 nights is just 45,000 points, it doesn’t matter which one. The only caveat was that we needed to keep the cash rate for that 3 night rental under $1,500. Jenn found one she liked and we wanted to book it, but we didn’t have the points yet, now what?

Buying Wyndham points

Typically, you can buy Wyndham points for 1.3 cents per point and you can buy up to 60,000 points per year. Wyndham was running a special allowing people to buy up to 120,000 points as well as get a 40% bonus. As tempting as it would be to max that out and buy everything I could to get a whopping 168,000 points, we resisted the urge and bought the 29,000 points with 11,600 bonus points for $377. That gave us the 40,500 points we needed to book 3 nights in the Vacasa. I realize that yes, that’s less than 15,000 per night, and that’s because with Jenn’s Wyndham Business Earner card, she gets a 15% discount, so it’s an even better deal!

So here’s another sneaky thing about the price of these Vacasas – just because it’s a 1-bedroom doesn’t mean it’s one bed. We found this rental with 2 beds because one of the bedrooms can’t qualify as a bedroom. Maybe it’s not big enough, maybe it doesn’t have egress, I don’t know, but it’s basically an unqualified bedroom. That means, I’m basically getting a second bedroom for the price of a one bedroom. Actually, this is extremely common in the vacation rental industry because they want to say they sleep 4 or 6, so they cram in beds to try to make it more appealing to families. This normally raises their prices but with the Vacasa/Wyndham reward chart, it counts as a 1-bedroom. That’s great for me, I’m getting a second bedroom for free!

The kitchen is nice and modern, definitely good enough for a weekend.

What would this have cost, normally?

This was going to be more than $1,350 for 3 nights.

So here is what this rental would have cost normally, had we not paid with points. Keep in mind, we didn’t actually have the points, we had to buy them. In other words, we paid $377 for a vacation rental that was posted for $1,357. Essentially, we paid 28% of the listed price just by going through the steps to buy the points, then call Vacasa about what we wanted to book (points redemptions are can be done through email or phone call with them). That was it, huge discount, nice vacation rental. I can’t wait to stay in downtown Nashville, but knowing we didn’t spend a fortune makes it even better. Oh yeah, and all those taxes and cleaning fees, they are included in the redemption, which is nuts, because the taxes and fees section alone was $526!

I’m honestly not sure how or why Vacasa is doing this. It’s possible they know that they will take a loss, but maybe they’re just happy to get their name out there, since compared to Airbnb and VRBO they’re pretty small. My guess is that eventually, they will change the point chart to allow redemptions up to, say $300 per night for 15,000 points then maybe 30,000 points up to $500. This just seems unsustainable to me and I suspect a change is inevitable. That being said, there’s no harm in taking advantage of it now, but maybe we can just keep it between us, right?