Planning our Puerto Rico dream vacation; 7 nights, 4 guests, Kayaking, El Conquistador resort, points and miles, $2000

The Finance Patriot’s family is happy to announce our plans for a dream vacation, to Puerto Rico, in May.  This will take place just prior to our kids’ elementary school lets out. The four of us will spend a week relaxing, sunning, swimming, eating, celebrating my wonderful wife’s 19th anniversary of her 21st birthday, and Kayaking to see the world’s most stunning Bio-luminescence display.  After our week in paradise, it’s going to be hard to go back to the day job.

We chose Puerto Rico, in part, because of the ease of travel with children.  As a US territory, Puerto Rico doesn’t require passports or onerous customs questioning for US Citizens.  In addition, our kids don’t yet have passports.  For now, we will save the expense, of an additional $220, to obtain two more passports.  Plus, our family will still get to enjoy our beloved Caribbean in a land where the primary language is Spanish, which is foreign to us.  An added bonus is Puerto Rico is steeped in history.  Who doesn’t love old Forts, narrow streets, and really cool bad shit that went on a long time ago?

Before we dive into the details as to how we planned this trip, let’s listen to this oldie but goodie from Madonna, “La Isla Bonita,” or in English, “The Beautiful Island.”

How we did it?

 Near the end of the last year, and the start of this year, both my wife and I signed up for a special bonus offer for the Chase Sapphire Reserve credit card.  To sum up the offer, if you spent $4000 on the card in the first 3 months, you would get a phenomenal 100,000 Chase points.
Below is a screen shot of all my reward activity in my Chase Sapphire Reserve account.
 On the lower right hand corner, you see “Other Rewards activity.”  These were the 100,000 bonus points I received for this offer.  These points are great because they are transferable to 7 different airlines and 4 different hotel chains.

Booking the flights

From a combination of work travel, along with points from a prior Chase Southwest credit card offer, I already had about 39,800 points in my Southwest Rapid Rewards account.  Therefore, to fly four people down to San Juan, I knew we would likely need more points transferred to Southwest.  Since Southwest is one of Chase’s “transfer partners,” I knew we could transfer our Chase points into our Southwest Rapid Rewards accounts, and then book the flights.

After researching the best flights, we found a combination in May that would allow for flights at a point value, round-trip from Nashville to San Juan and back, for 27,000 points per person.  One advantage of flying Southwest is they allow up to two checked bags per passenger, at no extra charge.

In order to find reasonably priced Southwest flights, we logged into our Southwest Rapid Reward account and viewed their “low fare calendar.”  This calendar shows you how many points you would need to fly each day.  Below is a picture of their low fare calendar, for April.

Tip: Use the Southwest Low Fare calendar to find the best value for points redemption

We found flights, in May, and needed a total of 108,072 Southwest points, but we only had 39,672 in our account.  We had a shortfall of about 68,400 Southwest points needed to book these flights.  Ouch.

Chase to the rescue, thank you JP Morgan

Luckily for us, the benevolent folks at Chase credit cards have got our back!  We were able to transfer, 1:1, 69,000 points from our Chase Sapphire Reserve account, into our Southwest Rapid Rewards account.  This transfer happens instantly.  Below is a picture of what a Chase transfer of points looks like.

A sample screen shot of a Chase transfer of points to Southwest. First enter your Southwest Rapid Rewards information into Chase, before you make this transfer.

Once we transferred our points to Southwest Rapid rewards, we booked four tickets, round trip, from Nashville to San Juan and back, for 108,000 points total.  The only fees we paid for these flights were the $5.60, per person, fee for the TSA.  The total of all fees, round trip, came out to $44.80.  Had we booked these four flights with cash instead, they would have cost us a total of ~$1,700 round trip.  Luckily for us, we travel hacked our way there instead.

Booking the Hotel

For our lodging, we had 114,718 Marriott reward points available (from a Chase credit card sign up last fall) that we could have used towards free nights.  We did consider Marriott properties in Puerto Rico, but at the end of the day, experience trumps our frugality.  We had a reference, from a family that has traveled there many times, to stay at the El Conquistador resort.  This resort is a Hilton property.

Palamino Island, El Conquistador Resort, Puerto Rico

One of the draws to stay at this resort was its private Island, Palamino, along with a free 8 minute ferry ride each way.  Here is a blurb, from the El Conquistador website, about Palamino:

El Conquistador Resort offers invigorating activity and serene relaxation. Spend the day on Palomino Island with the family to enjoy horseback riding, snorkeling or just soaking up the sun while lounging in a chair on a white-sand beach. Unwind with a restorative massage at the spa.

For an extra charge (about $20 per person, for a full day, lower charges for a half day), the resort offers a Water Park.  I imagine we will spend at least one day at the water park, given how desirable and fun this experience will be for the kids.  Here is a blurb about the water park at El Conquistador resort:

Create family vacation memories on a visit to Coqui Water Park. Compete to see which family member speeds down a waterslide the fastest. Children will enjoy Camp Coqui, where they can make new friends, go kayaking and swimming, or learn about nature. Watch children play in the pools or build a sand castle on the beach. Arrange a babysitter to have a peaceful and pleasant night out.

Not a picture of my family, but a picture of a really cool water slide, at Coqui water park, at the El Conquistador resort

In order to get the best deal on this property, we searched the Hilton website for their best rates.  We had to open up a Hilton Honors account in order to obtain their best rates for our mid May trip.  I was able to find a promotion for our dates, “another day in Paradise.”  This promotion would give us a 4th night free, for booking 3 at full price.  This was a non refundable booking.  Let’s hope nothing goes wrong before this trip.  We used this special rate to book 5 of the 7 nights.  Below is a screen shot of what this cost us.

Booking a 5-night stay at the El Conquistador in Puerto Rico, using “Anthr Day In Paradse” rate special on the Hilton Honors website.

Our out-of-pocket expense for these five nights, as seen above, was $1,152.76, which includes both taxes and the resort charges.  At the time we booked these nights, my wife hadn’t yet achieved her 100,000 point sign up bonus, on her Sapphire Reserve card, yet.  So we were able to use her card to book these nights, and it helped us achieve the spend requirement on the second Reserve card, for a second helping of 100,000 MORE Chase bonus points.

Booking two free nights with Chase Rewards

If you have been trying to follow along so far, you will have noted that we will be staying 7 nights total at El Conquistador, but have so far only booked 5 nights.  The reason we only paid for 5 nights is, drumroll please, we had enough Chase points leftover to book two free nights through Chase Ultimate Rewards. We had to pick the same room type, which for us is a Garden View, in hopes of being able to stay in the same room for the entire 7 nights.  If we are unable to stay in the same room, we will happily move to another one during our stay.

For the two free nights we booked using Chase, we spent 34,161 points.  Please see details below, from our Chase Sapphire Reserve ultimate rewards account.

Although the room rate was higher for the two nights, due to the nights not being part of the “another day in paradise” special, I still thought using our remaining points was a good value.  Points don’t increase in value as they sit in your account idle, so we went ahead and used ours.

Kayaking and Fajardo’s Bio-luminescent Lagoon

Before we get into the details of our excursion, let me first define what bioluminescence is.  According to the internet, bioluminescence is:

the biochemical emission of light by living organisms such as fireflies and deep-sea fishes.

Doesn’t that just sound cool?  We thought so too.  Puerto Rico is world-famous for having some of the best bioluminescence displays anywhere.  Since our resort is close to the City of Fajardo, we decided to book a Kayaking trip.  Total cost of this excursion, for 2 adults, and 2 kids is $225.  Here is where we booked our trip. 

We had two options of when we could go.

February – May

Early Evening Check In: 5:45pm
Mid Evening Check In: 8:15pm

We contemplated the late tour, to get the full darkness of the experience.  However, the good people at Bio Bay tours suggested we take the earlier trip, as kids get scared in full darkness at the later trip.  Given our kids are going to be 6 and almost 8 at the time of this epic trip, we really appreciated this advice and booked the earlier trip.  By the end of the trip, it will be full darkness and everyone should get to enjoy the show.

Booking our car rental

At the time we booked the flights, we did not have any Chase points left.  We decided, instead, to wait for our second Sapphire Reserve bonus in order to book the rental car.  Chase is known to have good rates for rental cars in its ultimate rewards travel portal.  For our 7 night stay, we decided to rent a mid sized car with our new chase points, at Alamo.  Here is what our rental booking looks like, via Chase travel portal:

Alamo car rental via Chase ultimate rewards travel portal

For 7 days, I thought $176 was a darn good rate.  We only used 11,730 Chase points for this rental booking.   The hotel is approximately one hour away from the airport in San Juan.  Once we arrive at the resort, we also want some flexibility to drive into Fajardo, which is nearby.  The price of a car rental might actually be cheaper than booking a private driver, round trip, to this resort.

Food & eating on the cheap

We plan on shopping at Wal-Mart, on our way to the resort, to get some low-cost food, breakfast and snacks for our trip, and bring them to the resort with us.  Depending on the day, we may go into Fajardo and eat at one of their fantastic and reasonably priced outdoor food trucks/vendors.  We do not plan on eating at a lot of restaurants, but we may hit up a few depending on our mood and what’s recommended.  There is also a grocery store, nearby, in Fajardo that we can shop at during the week.  I imagine we may hit that place up as well.  Food is a bit more expensive in Puerto Rico, but certainly groceries are less expensive than eating at the resort restaurants.  I can’t wait to try a Mofongo.

For those of you who have no idea of what a Mo-what is, here is the internet definition:

[moˈfoŋɡo]) is an Afro-Puerto Rican dish [1] with fried plantains as its main ingredient. Plantains are picked green and fried then mashed with salt, garlic and oil in a wooden pilón, a kitchen device also known as mortar and pestle.[2][3] The object is to produce a tight ball of mashed plantains that would absorb the attending condiments and have either pork cracklings (Chicharrón) or bits of bacon inside. Most dressings and mixtures include broth, garlic, and olive oil. It is traditionally served with fried meat and chicken broth soup.[4] Particular flavors result from variations that include vegetables, chicken, shrimp, beef, or octopus packed inside or around the plantain orb.

I’m getting hungry already.

Conclusion and Cost

If you have been following along so far, you will note that we have spent the following, to date:

Hotel stay:  $1,153                                                                                                                                       Kayaking Excursion for 4:  $225                                                                                                                         TSA fees for SW flights:  $45

Total, out-of-pocket, so far:  $1,423

There will be additional expenses for our trip, that we have yet to spend such as airport parking in Nashville ($72), gasoline for the car rental, ($100), one day at the water park ($80).  Total preliminary budget is $1,672.  There will also be additional expense for food.  For food, I don’t typically count normal grocery spending we would have done at home.  However, let’s estimate total “above and beyond” eating expense at $328, to get to a nice even number of $2,000.

I sincerely hope you enjoyed all the details behind the travel planning, and hacking, we used for this dream vacation to Puerto Rico.  I plan on doing at least one Facebook live video during our trip.  If you would like to watch this as it happens, please like the Finance Patriot facebook page.  While $2,000, or so, is far from free, using points and miles really helped us book a much more exotic trip than we normally would have taken, for a family of four.  If you would like to learn more about how you, too, can travel hack your way to places, check out the Frequent Miler for some great tips.

Are you planning any trips soon?  Any suggestions on visiting Puerto Rico?  If you’ve been to any of these places, what is number one must see on your list?


  1. That is AWESOME! To tell the truth, you had me at “Bioluminescence.” I am a sucker for natural phenomena and am ashamed to report two different weeklong camping trips to deepest darkest Alaska resulted in 0 viewings of the northern lights. *sigh*

    At least I saw a black wallaby once. Kinda cute once you ignored the huge teeth.

    1. Thanks, I agree and can’t wait to go and it’s a double bonus going with young kids. I have always heard Hawaii is great, but when you live East of the Mississippi, the Caribbean is the place to go for ease of travel. And heck, we also get to go to Mexico from here too, just the Gulf side which is stunningly beautiful!

      1. I’m going to Hawaii next week, on points of course 🙂

        Is it difficult because of cost or distance with the little ones? You can get a ticket for 25k points so if you have any points left on that second Chase Reserve card you could totally lock it down.

        1. Congrats, that sounds awesome. We live in TN, I’ve yet to see flights as low as 25k from here. Award flights are harder if you’re trying to find 4 seats. Plus, we adore the Caribbean.

          We have about 180,000 chase points left between the two of us 🙂

  2. I’ve been to PR once a long time ago. I’d love to go back but have been touring the different islands 🙂 That’s awesome about the travel hacking that you’ve done. I definitely need to get into that when we start traveling again. My little one isn’t ready to quite travel that far yet but I’m looking forward to the day that he is 🙂

  3. I went to PR one time for work over a decade ago. From what I remember it was beautiful. I do have one bit of advise. Be sure your comfortable driving there. It’s not like driving at home. I’ve personally done it, but I also remember sometimes it was a bit harried..

    1. Thanks, I have heard the same. Luckily for us, booking the car through the Chase travel rewards portal actually provides primary car insurance for this rental, which is cool. Most of our driving will be outside of San Juan, so I am hopeful this makes a difference.

  4. So . . . you spent $8000 (2 cards) to save how much for a nice vacation? My wife and I don’t spend 8k in normal expenses in 3 months for a family of 5.
    It does sound like a cool trip by the way.

    1. We saved over $2,000 by using points. I agree that others are far more efficient than we are. If you take out “work spending,” that is travel and other items that work reimburses me for, the personal spend isn’t nearly as bad.

      It’s important to note we did not spend “extra” to obtain these miles and points. We did our ordinary spend (which arguably is too high).

  5. Love this! And I am completely jealous, it looks stunning there. I’m sure that you will have the best time. I love how you’ve broken down how you managed the financial side of it too.

  6. 2K for 7 days is pretty expensive. We are spending 2 weeks at the seaside with less than this, but we stay in a studio apartment and do some of our cooking. The reason, most hotel food is lousy and overpriced.

    But, if you are looking just to have fun and really enjoy those days, you did get a pretty decent deal. What matters the most is that you feel great.

    1. Thanks Ramona, for a family of four this isn’t bad, given we are flying everyone down. We are super excited to go, and even more excited that Spanish is the primary language.

  7. We don’t have credit cards, but your points make me wonder if we should put some stuff on one and pay it right off?

    And how smart to choose Puerto Rico and save on passports!

    1. Hi Lacey, if you are disciplined and pay off your credit cards in full each month, I highly recommend travel hacking. Basically, you and or your husband sign up for a credit card with a large sign up bonus, meet the minimum spend, and move on to the next one. Simultaneously, you take free or reduced cost vacations with those points. There is actually a cottage industry around this. I list the best travel hacking website, in my opinion, on my recommendations page on this blog.

      I am more than willing to help you out if you have any questions. You are one of my early readers and you’ll be taken care of appropriately.

      1. Awesome! Thank you, we will look into it. We have been good about paying them down in the past, but when we got to be debt free (besides our house) we just quit using them. The travel points sound worth it though. Thank you!!

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