Our Flight

I used Southwest Airlines frequent flyer points in 2015 because I worked a Southwest credit card in 2014. In June, while checking sale fares to Las Vegas (because I’m constantly checking air fare to Vegas) I noticed a really good fare from Philadelphia to Fort Lauderdale. We had driven the Overseas Highway from mainland Florida to Key West for the first time in February, but I immediately booked this fare, so we could give the trip to each other for Christmas. (The Florida Keys are worth more than one trip!) The beauty of no change fees on Southwest is that I could book a December trip in June, and if circumstances changed, the points would be re-deposited with no penalty! It was 10,146 points per person, but two weeks later I re-booked for 9,754 per person—a small savings but worth keeping on top of fares.

The flight times were a bit hard on the body but great for maximizing time. We left at 5:30am on a Thursday and were supposed to return 9:45pm on a Monday night, so we only needed four hotel nights for almost five days of fun! I didn’t spring the vacation idea on my boyfriend until October and reasonably priced hotels in Key West book up quickly and sometimes a year in advance, but I was able to get Sugarloaf Lodge for the first night (in Sugarloaf Key, seventeen miles outside of Key West) then three nights at the Blue Parrot Inn in Key West.

Car Rental

On our February trip, we took an evening flight and arrived in Miami at about 11pm. (Southwest Airlines does not fly to Miami but Fort Lauderdale is only 29 miles away). It took at least 45 minutes for us to walk, take the MIA Mover and the moving walkways, elevators and escalators to the Rental Car Center (RCC). We had no idea how big MIA is. We were wiped out when we arrived, only to find that Payless Car Rental was out of cars, even though I had specifically prepaid for the car to avoid this situation. A whole group of us were directed over to Budget, where we were able to get a car for only $33.53 more than I had prepaid for the Payless car. (I was told by the Payless manager that Payless owns Budget. I feel PAYLESS should have handled getting the cars from Budget rather than stressing out weary travelers at midnight!)

Once home from the trip, getting my prepaid amount back from Payless was not a problem, but getting the $33.53 difference that I was promised, took multiple phone calls. It seems that rental car companies in Florida run out of cars all the time! When researching car rentals, I read horror stories about people not being able to get a car, even though they had a confirmed reservation. That is why I prepaid for the car and chose Payless. (There are other rental companies rated even lower than them.) Now I know that prepaying means nothing and the likelihood of any car rental company running out of cars, if you arrive late at night, is high. If you need a car in the evening, make multiple reservations.

The rental car companies and the horrible reviews are the same in Fort Lauderdale as they are in Miami, so researching a car to pick up in Fort Lauderdale was time consuming. I finally decided on a decent rate through Alamo, prepaid (for a slightly lower rate) on a credit card if I had to argue over the charges. I also signed up for Alamo Insiders so I could check in online, but when I went to check in online, there was error message after error message. It was only at 2am, after multiple phone calls, that an Alamo agent explained that because I prepaid, I could only use online check in 24 hours ahead of time. Had I not had so much trouble with the car reservation in February, I wouldn’t have been so worried about it and would have been asleep by 2am!

Luckily, Southwest flies into Terminal 1, which is right at the Rental Car Center. The agent tried to upsell a larger car, which we got anyway, because they were out of economy cars. Sugarloaf Key, here we come!

Keep reading! Here’s part 2 on our trip to Florida Keys