Helping a Relative Plan a Getaway to Puerto Rico in Exchange for Babysitting and a Trip Report

Few months ago I wrote a post on how later this year my husband and I will be flying to Chicago for a quick getaway.  My cousin-in-law who is an avid reader of this blog saw the post and mentioned that she really wanted to do something similar with her spouse.

At the time, they did have 50,000 AAdvantage miles, but  we couldn’t come up with a good plan. I suggested going to Canada or Alaska to maximize value.  Unfortunately, all flights required a connection and came with grueling schedule. Since they could only leave for three nights, she wanted something super easy. They weren’t interested in big cities in US, and mostly just wanted a place to relax.

Yes, you can have my Spirit miles

I had some extra Spirit miles with no plans to use them, so I offered them to her. Their trip happened to fall within off-peak pricing period, which meant for 5,000 miles roundtrip they could fly to a Caribbean island. How cool is that?  Since they don’t have passports, it only left Puerto Rico and St. Thomas as two possible candidates. I checked  and  while there weren’t too many options, we did put together a flight to San Juan. And they are leaving today. She told me she would take my kids for the weekend as a thank you for using Spirit miles. Winning!

Total cost for two? Just 10,000 miles and $48 in taxes. It’s not the best option for those who have kids in school, but in this case, her retired parents will be taking care of them. Spirit  was by far the cheapest choice out of Fort Lauderdale. I checked, and the same tickets were $175 each on Spirit and $240 on Southwest. Instead, I used 5,000 miles per person. Yes, you do have to pay for checked bags and buy your own water. And?

Is Spirit really that bad?

Sure, the company was just voted as the worst in customer satisfaction. Sorry, Jen. If you are reading this, it’s too late to back out now! I’m certain many complaints are perfectly legitimate. Still, for people who can’t afford to drop $480 on Southwest alternative, it’s worth the risk. That’s why I asked her to write a fair trip report to let readers know if Spirit truly is as bad as many say it is. According to the survey, its ranking has improved compared to last year, so I choose to look at it as “glass half full” kind of thing.

I certainly don’t plan to cancel my Spirit flight to Chicago. Out of curiosity, I checked, and fares on Southwest run at 17,500 points roundtrip for our dates. That would be  35,000 points total for my husband and I. I could redeem that amount for a $350 Amazon gift card, which to me is almost as good as cash (this redemption  option is available via Southwest credit card).

So, I’ll take my chances with Spirit. Sometimes I wish my brain wasn’t wired to always calculate opportunity cost, but that’s just how I think. Flights via Rapid Rewards points are not free, but they are pretty darn close when you use Spirit miles from a sign-up bonus.

I have a feeling that many hate Spirit for all the extra charges. Nothing is free with that airline. Guess what? It’s not free with other airlines either. They just bundle it into your fare. Bag fees are charged on most airlines, so it’s a wash in that respect.

Besides, you may be able to get by with a carry-on. Check the bags you already have because you might have one that would work. Spirit requires that your free personal item does not exceed these dimensions: 16″x14″x12″  Believe it or not,  some companies actually make bags and market them specifically for Spirit flights. My reader Audrey mentioned it to me.

You can find this type of bag on Amazon (affiliate link) for $48 by looking up item B0161MIZ3O.

spirit amazon carry-on

You could stuff a lot of junk into that duffel and avoid paying $70 in bag fees (on roundtrip flight) each and every time. I recommend you also check on Ebay by typing “Spirit personal item” and all kinds of options will usually pop up. Of course, first, I recommend you take a look at what you already have, so you don’t spend money needlessly.

My cousin-in-law actually ended up buying one for her Spirit flight and said I could borrow it for my trip to Chicago. I’ll take it! I think we can get by for two days and spend $70 on a restaurant meal instead.

Tip: Roll your clothes tightly to avoid wrinkles and fit in more stuff.

What about lodging?

So, the flights were all set and my cousin-in-law started researching hotel options. They are going in May (off-season), so prices on lodging aren’t too bad.  However, since they are on a tight budget, she asked me for advice on hotel card bonuses. The problem is, she is only comfortable with very low minimum spending requirements.

Fortunately, I had just the offer in mind: Wyndham Visa Signature. As of right now, direct link for 45,000 points’ bonus is still working. You have to spend $1,000 in 3 months. The annual fee of $69 is not waived, but hey, you get 3 nights at any Wyndham property, including Wyndham Grand Rio Mar Beach Resort She got approved and quickly met minimum spending requirements on the card. The points posted promptly, and check out what she was able to book with her bonus:

wyndham family suite san juan

Yes, she got a 1274 square feet suite for only 15,000 points per night. Is it wrong that I’m a little bit resentful? But I’m 99% happy for them. Ok, it’s more like 90% happy, 10% resentful. We were actually supposed to vacation here with my parents, but I decided to stay in Florida.

Wyndham program is quirky and aggravating, so I recommend you read my post before applying for this card. Availability in this and many other properties vanishes without rhyme or reason. Still, this is a pretty good deal, no question. Most rooms here fit 4, so even if you don’t snag a family suite, you should be fine. Puerto Rico has another Wyndham resort property, though not quite as fancy. Worst case scenario: use your points at one of Wyndham beachfront properties in Florida.

My cousin-in-law said that if she likes this hotel, they will get a Spirit credit card and another Wyndham Visa Signature. Fort Lauderdale is 2.5 hours from their house, and they can potentially take kids over MLK weekend, which qualifies for off-peak pricing.

You can do it too!

Obviously, off-peak Spirit award flights to Caribbean are mostly of use to those who live in Florida. You also need a lot of flexibility because  availability can be hard to come by, especially when booking only few months in advance. For most families, Southwest is probably the way to go. Aside from few airports in Florida, they fly non-stop to San Juan from Houston and Baltimore and you can find a connecting flight from many other places in US. I checked Chicago-San Juan route, and it looks like prices start at 10,000 points each way, which isn’t too bad.

I have  a personal referral link for Chase Southwest Premier card ($99 annual fee, not waived). It gives me 5,000 points for each approval and you get 50,000 points after spending $2,000 in 3 months. You can also use this direct link for Plus version that comes with $69 annual fee.

The sign-up bonus is otherwise identical, but there are  a few differences between the cards. For example, Premier version doesn’t have Forex fees. Assuming each spouse gets either offer, you should easily have enough points to cover airfare for 4 people. Look at this page to read more on this card and make sure to check out an article on Companion Pass.

What’s nice about Puerto Rico is that you don’t need a passport, yet the island still feels exotic. El Yunque national park is very impressive and has many hiking trails, some leading to waterfalls. We took our daughter there when she was only 18 months old.


Wyndham Grand Rio Mar beachfront resort I’ve mentioned earlier is located right next to the park, which would make it easy to explore. Just one credit card bonus could potentially give you 3 nights at this property. Get another one for your spouse, and you’ll have 6 nights in Puerto Rico for around $158 (annual fees). Rental car prices are fairly reasonable, and roads are well-maintained, a rarity in Caribbean. Check out this page on Trip Advisor that highlights various activities in Puerto Rico.

All in all, with some planning, you can have an affordable family getaway to a real Caribbean island, no passport required.

P.S. Speaking of Wyndham program, you may want to read this post on why their latest promotion could be mattress run worthy. If your summer travel plans will take you places where this chain has decent presence, I recommend you at least consider it. Not sure if Wyndham properties will let you check in over the phone, but that’s another strategy to look into.


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6 thoughts on “Helping a Relative Plan a Getaway to Puerto Rico in Exchange for Babysitting and a Trip Report

  1. I’ve been trying to figure out how Spirit can be any good. I have 16k miles (from hating me hem, remember?). The thing is that when I look domestic flights, the fees are $ 89. Is there a way to know about their fee structure?


    • @Leticia Spirit miles can definitely be useful, but you do need their credit card in order to take advantage of 2,500 mile one-way pricing. I think maybe the reason you are seeing high fees is because you are looking at departures within a week or so. I know they do charge close-in fees, but the further away you book, the lower they are. I paid $5 per person for Chicago flights. Maybe you are seeing luggage fees too? You have to be careful with Spirit. They sometimes add fees automatically, and you have to manually remove them.
      When you look at award availability, check flights that depart 3 months in the future (or more). Also, you can just get a one-way flight for 10K miles without credit card if that’s your preference.
      My cousin-in-law said her Spirit flight was great, no problem whatsoever.


  2. Pingback: Why You May Want to Consider Renewing Chase Southwest Airlines Premier Rewards Card | Miles For Family

  3. Pingback: A Kid-Free Getaway to Puerto Rico with the Help of Miles and Points | Miles For Family

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