My partner’s and my anniversary is in December, just a few days before Christmas. This is not an optimal time to celebrate. It’s cold here in North Carolina at that time, and we’re always too busy with holiday events to do much. 

This year, we decided to take advantage of an existing winter break trip to visit family in Florida, and turn it into a tropical mini-getaway. 

Flights

We booked tickets for our whole family of four from our home airport of RDU to Fort Lauderdale, where my partner’s parents live. This will give us an opportunity to spend some of our winter break in the warmer weather and in the company of family. As we do not have a companion pass for this year, we initially booked our outbound flight on Southwest for 10,029 Rapid Rewards points per person, times four. Our return flights, also on Southwest, were booked at 11,572 points per person. 

I transferred these points from Chase Ultimate Rewards, and I must admit, transferring over 80,000 points for flights that are only two hours each way made me a little bit ill. However, I knew that we were traveling at peak times, and the dates and times were especially convenient for us, a family traveling with two young children. 

I monitored the prices of our flights, checking daily to see if the cost came down below what we originally paid. The outbound flight did eventually come down, and I was able to rebook it during a sale for 5,859 points per person, recouping almost half of my original points outlay for these flights. The return flight only came down to 11,032 points per person. 

This is why it pays to keep an eye on the price of your Southwest flights! Now that Southwest is on Google flights, you can automate this process. Whenever I book an award flight on Southwest, I look up that flight in Google Flights and toggle on “track price.” This enables email notifications whenever the cash price changes. This works for Southwest and JetBlue, two programs our family uses frequently, because the cost of their award flights is directly correlated to cash prices. 

Hotel

My in-laws generously agreed to watch our kids for a night so that my partner and I could have a little getaway. We booked the Hyatt Centric Olas Fort Lauderdale, a category four Hyatt, for 15,000 points, at a cash value of $340. 

We made dinner reservations at a plant-based restaurant just a few blocks away from the hotel. This dinner will be subsidized by the $50 semiannual Resy credit on my American Express Gold card.

A note about these cash prices: I log the cash prices of flights at the time that I initially book them, because if I was booking with cash, this is the outlay of cash I would have to make in order to secure these flights. You can use the same technique I’ve outlined here to rebook flights booked with cash when the price drops, and receive a Southwest flight credit. However, because you can only use a maximum of three flight credits to pay for a new Southwest flight, it is unwise to collect many flight credits in small denominations.

In my mind, the flexibility of booking with points is part of the value proposition, so when calculating the value of my redemptions, I always use the cash price that I would have paid at the time of booking, since this is the price I would have been locked into. 

In previous years, we wouldn’t have spent the money to travel during peak season like this, but this year, my partner and kids are actually going down to Florida three times in the span of three months. Having the cost of our flights, hotel, and even our dinner offset by credit card benefits make our anniversary celebration even sweeter.