Dirtbag Travel: Southwest Love and Snowbirding in Jax

Anybody that lives in New England or any other cold weather climate knows the importance of getting away during the winter months. Born and raised in the Boston area, the winter months wore me so thin that after graduating college in Boston I moved out west to San Diego to escape the cold weather. Family, friends, and work drew me back to Boston but I cannot stand the winter months here.

Thankfully, a couple years ago I discovered the wonderful world of frequent flyer mile collecting. In about a year and a half, I have collected about a million points and miles from various airlines and hotel chains. Personally, I prefer airline miles as I can and will stay basically anywhere. From couches to campsites, my number one goal is to travel and experience the world on a budget.

In October of last year I read a blog discussion from Million Mile Secrets about the Chase Southwest credit card promos and the Southwest Companion Pass. Chase was offering 50k Rapid Reward points for their Southwest Premier Personal and Business card in exchange for a $69 annual fee. 100k RR points definitely sparked my interest although like most I prefer cards with no annual fee. Another concern was that I had made what I would later come to find was a rookie mistake: I had applied and been approved for the Chase Sapphire Preferred card in September. I checked my Experian request history on Annualcreditreport.com and seemed to be in good enough shape to be approved for both, but I was reading reports that Chase was being tough on approving both cards especially for those who had applied for a Chase card in the past month.

My solution was that I would wait until the end of October so that the previous Chase application would be over a month old before I applied in the same day for both the personal and business cards. Much to my delight, I applied and was approved instantly for the personal card but I was told more information was needed for my business application. I called into the Chase decision line and explained that I own a multi-family property and wanted to use the card for home improvements and maintenance. I don't actually own a business of my own with a tax ID but there was some great info on the Million Mile Secrets blog on how to apply for business cards as a sole proprietor. After about a five minute discussion I was approved for the business card and I verified with the agent that I was confirmed to receive the 50k bonus with each.

As I mentioned before the 100k RR points were definitely very appealing, but I now had my eyes set on the Southwest Companion Pass. The Companion Pass allows a friend or companion of the member to fly anywhere with the member for the minimal $10 fee in taxes for the remainder of the calendar year as well as the following year in its entirety. In order to obtain the Companion Pass a member must either fly 100 Southwest flights or earn 110k RR points from flights or credit card promotions. Purchased miles through Southwest do not count towards the Companion Pass.

I received both cards in the mail by the second week in November. Part of me wanted to instantly activate the cards and collect the miles to earn my CP as quickly as possible, but after reading the fine print I decided that it would be more beneficial to wait for January before activating so that I could have my CP for all of 2012 and 2013 instead of the remainder of 2011 and 2012. That month and a half of waiting was a test in and of itself as I kept reading that Southwest was going to change their policy at the beginning of 2012 and I may be out of luck to receive the CP at all. Ultimately, I decided the risk was worth the reward of having a friend fly with me anywhere I go with my 110k RR points basically for free.

So I waited for the new year and activated both cards and completed my first spend by 1/3/12. The 100k points posted to my account by 1/10/12. I was thrilled that the points posted by more importantly counted towards the CP qualification. My job was not done yet as I still had 10k more points to earn. Since I travel like a dirtbag I don't exactly have 10 grand to spend on a card right away to get the rest of the 10k points I needed for the pass. After doing some more research, I discovered that I could transfer some of my Ultimate Rewards points that I had earned through the my initial Chase Sapphire Preferred card that I had applied for in September. It took a little finagling as UR points transferred directly as RR do not count towards the pass. I decided that my best rate of return would be to transfer UR to Hyatt Gold miles and from Hyatt GP miles to RR for the final 10k. I completed the complex transfer by 1/11/12 and now could only wait patiently for the HGP miles to show up as RR to complete the CP.

On 1/20/12, I received an email from Southwest that I had achieved CP status and asking who I wanted to administer as my companion. I was stoked and instantly set my girlfriend Allie as my companion and booked a trip for the next weekend to escape the cold. After a couple hours of online searching on Southwest.com, we booked a flight down to Jacksonville, FL and a campsite at Kathryn Abbey Hanna Park right on the beach.

It was a great trip with great weather. We got some much needed flip flop time and were able to explore the cool beach towns of Neptune and Jacksonville Beach. I even lucked into a fun little waist to chest high swell at Jacksonville Beach pier. We had some great coffee and acai bowls at the Delicomb in Jacksonville Beach and some great craft beer and pizza at the Mellow Mushroom. Jacksonville Beach is a great young town with clean beaches and fun nightlife. The Abbey-Hanna campground was also fantastic as it was right on the beach a little north of town but also offered bike trails and a little fishing pond. Allie and I also decided to make a day trip down to the old town of St. Augustine. It was about a 45 minute drive down scenic A1A. Personally, I loved St Auggie as it was my kind of town. The combination of pirate outpost and classic architecture instantly drew me in. We found ourselves exploring every alley and nook that we came across. Each building and street was bursting with cultural flavor that rivaled New Orleans, Charleston SC, or even Boston. A day trip definitely did not do that town justice and I can't wait to go back and explore for a longer period of time. I've attached a few of the many pics we took over the weekend to give you a feel of what Jacksonville and all of North Florida has to offer. Thanks for reading!

Until next time
Dirtbag Traveler