Welcome to the first of a multi-part series on Puerto Rico, our lovely neighbor to the south. I had the wonderful opportunity to spend a long weekend in Puerto Rico earlier this month, and I absolutely fell in love with the quaint little island territory. In this section, I’ll detail the best way to get to PR and how I started my weekend down south.

View of San Juan after a 2 hour and 15 minute flight from Tampa, FL.

Getting There

Since I currently reside in the Tampa Bay area of Florida, the cheapest and most comfortable airline to Puerto Rico is JetBlue out of Tampa International Airport. The typical cost for this flight is $79 each way, but if you sign up for the JetBlue eNewsletter you can probably get your tickets for $69 each way. Be on the lookout for their newsletter though, they typically offer discounted prices to their popular destinations once a month,  and you only get about 48 hours to purchase at the discounted rate. It’s a quick 2-3 hour flight, so it’s no longer than flying up to New York. I lucked out and ended up with a free ticket in exchange for cashing in built up JetBlue points.

Upon arrival you have a few options to get to your final destination. The most popular choice is to take a taxi into the more touristy sections of San Juan such as Isla Verde where the Ritz Carlton is located or Old San Juan, which is a tourist Mecca of overpriced shops and restaurants. Your other option is to negotiate the local bus system—something I didn’t even attempt during my quick weekend. The third option, and the one that I ultimately settled for, was to allow a fellow couchsurfer to pick me up from the airport and just jump into exploring the city.

Day 1- Friday

In order to catch my 7am flight out of Tampa, I had to leave my house around 4:30 in the morning, which while being absolute torture had me landing in San Juan a little after 11am. I had previously arranged for my couchsufing host to pick me up in Old San Juan Friday evening, which gave me most of the day to explore on my own. Amazing thing that couchsurfing.org website, a few days before departing, I was messaged by an American, Paul, on an extended vacation in PR who wanted to know if I’d like to be shown around. I gladly accepted, and that’s who picked me up from the airport.

Paul and I hit it off as he chatted about his previous employment in the armed forces and all the travel he has been able to accomplish since retirement. In addition to his military pension he has published a few ebooks on real estate and some technical manuals related to his career in the Army. As we ate lunch he exclaimed, “I’ve probably made a sale or two this morning. In essence, I’ve paid for this lunch. ”

I love that, a person with a little ambition. I don’t know if it’s just a Florida thing, but it’s so rare to meet people who want something enough to actually go out and get it. When I seek friends, I always value someone with intelligence and drive over someone with designer shoes and an arrogant demeanor. Okay, back to PR.

Mmmmmm... Fancy coconut rum drinks...

Mmmmmm… Fancy coconut rum drinks…

We ate at an adorable restaurant called “Made in Puerto Rico,” which has amazing food, and waitresses dressed up in nightgowns and curlers in their hair. I would later find out when talking with a local that a couple decades ago women in PR were expected to spend their days in the house cleaning and cooking. That outfit was considered quintessential PR housewife garb, however the feminist movement is in full swing and that sort of lifestyle has all but vanished for the younger generations. Immediately following lunch, we flopped over to a beachside bar and sipped rum deliciousness out of coconuts before driving down to Old San Juan for a quick tour.

A speedy trip past a historic Spanish fort, the avenue of monuments, some designer shops, casinos, outdoor cafes, and high end storefronts and it was time for Rene to pick me up on his way home from work. Want to know what happened next? Check back soon for Part 2.

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