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.
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.
Newby to Expert Traveler 