Booking a Cheap, Refundable, Family Trip to Puerto Rico

We are about to take a four day “test” trip with the baby! It looks like everything is going to work out, but if something comes up at the last minute we can walk away, no strings attached. That’s right, this budget Caribbean trip is entirely refundable family vacation. 

We started planning our baby’s first vacation months before she was even born. As first time parents, we had no idea what to expect in the coming months, so flexibility was key. We booked well in advance in order to lock in good prices, but we were also strategic in setting up an adventure which is free to cancel. It made for a fun logistical exercise.

The view from Castillo San Felipe del Morro in Old San Juan.

Timing the Trip

Our goal is to get our daughter on a plane ASAP, but we want to be responsible parents. For us, that means waiting until her first round of vaccines kick in before loading her into a flying germ tube. Pediatricians won’t administer the first round of vaccinations until a child is at least 6 weeks old, and it takes two additional weeks before the vaccines become effective. So that brings us to a minimum of 8 weeks from the child’s birth.

We planned on a natural birth so we only had a vague idea of when she would make her appearance. It seemed foolish to book a flight exactly 8 weeks after the due date because those are almost always wrong. In the end, we gave ourselves a 10 week buffer and thank goodness for that. Baby E decided to stay hidden until 10 days past her due date!

Of course, while my wife is still on maternity leave, I burned through my three days of paternity leave with the birth. So I have to factor in work. At my job, April is a BUSY time so I wanted to get the trip in before work kicked up. That meant zeroing in on the last week of March. Still a busy time but I figured I could get my kind coworkers into covering for me for a few days. 

Picking a Destination

We love visiting new destinations, particularly new international destinations. Unfortunately, even infants need a passport to leave the country and it takes time to acquire one. In fact, Tennessee takes between 30 and 45 days to issue the long form birth certificate. You need that before you can even begin the passport application process. We didn’t want to wait that long so we were limited to destinations within the United States. 

Esperanza, Vieques.

We also wanted to book a (cheap) fully refundable trip. Many airlines will allow free cancellations for their top tier customers, but because neither my wife nor I travel much for work, we don’t have elite status with any airline. Thankfully, Southwest Airlines has an awesome cancellation policy. In effect, you can cancel your flight up to ten minutes before the doors close. If you pay cash for one of their cheapest “Wanna Get Away” fares then, when you cancel, you get an airline credit that must be used within 12 months of your original purchase. If you pay with points then you get a full reimbursement with no strings attached. I love points.

Flying Southwest has other benefits, as well. Families get early boarding, we have a stockpile of Rapid Reward Points, and we are currently enjoying our fourth straight year of BOGO tickets, thanks to the Southwest Companion Pass. That means that we only need to use points to buy my wife an award ticket. She can then add me for free as her companion AND baby E for free as a lap infant. 

In the end, we decided that, given the time of year, our best domestic option is Puerto Rico. We have spent time in Old San Juan and Vieques in the past, but there are plenty of new places to visit on the island. That includes the area around Luquillo, a beach town located an easy 45 minute drive from Luis Munoz Marin International Airport. While there are not direct flights from Nashville, Southwest does offer multiple one-stop options. Given the constraints, it seems like an ideal place to test the waters of traveling with a child.

Finalizing the Logistics

With the flight booked, all we needed to do in order to finalize the logistics was reserve a rental car and accommodation. The rental car was easy. I just booked the cheapest mid-sized option that I could find using the Southwest Rapid Rewards portal (for the extra points.) 

Boarding a small plane to Vieques.

Finding accommodation was a bit trickier. We often use AirBnB when we travel, but AirBnB charges a non-refundable service charge for each booking. That means that even if you cancel a “flexible” booking you will still loose the service fee. For this trip, I just couldn’t accept that on principle. Luckily, Booking.com offers a number of inexpensive accommodation options with no down payment and no booking fee. Done.

Conclusion

It is possible to book a fully refundable Caribbean adventure on a budget. I will report back after it is all said and done, but so far so good. Our family of three will be spending a total of $385 for the airline taxes, rental car, and three nights of accommodation beside the beach. The price tag will go up once gas, food, diapers, and a ride share to the Nashville airport are factored in, but we would need to spend money on food and diapers even if we stayed here.