Ever thought about taking a trip to Puerto Rico? Here are some personal recommendations from guest writer Reggie (a.k.a. ContentiousBenjamin). A couple of months ago Reggie was able to take advantage of a unique airfare opportunity to Puerto Rico that he found through Fly.com. Reggie is currently traveling the world with no particular destination in mind but hopes to one day work for the United Nations.

I was recently approached by Fly.com to write about my adventures in Puerto Rico. Hopefully this post comes in time to help someone with their decision to go to Puerto Rico for the first time, a return trip, or just to travel!

How I got to Puerto Rico

Knowing that the Memorial Holiday was fast approaching and ticket prices would once again inflate, I was in a good position with work and life to take an inexpensive trip (budget of $600) to somewhere I had never been before. I live in St. Louis, Missouri, and I know from experience that if I am able to travel to a major airline hub like Chicago via bus, train, or lucky enough to find a friend road tripping, I can fly out at a cheaper rate than in my hometown. This typically saves me somewhere between $50-$100+, depending on date, time of departure, and distance.

I did a simple Internet search “price calendar flying out of Chicago” and was patient enough to excuse the two sites that I wasted my time on, before coming to the third site which was Fly.com. I knew that I wanted to find a destination that I could brag about to my friends, but I just didn’t know where to go. With their site breaking down domestic and international flights in a list and showing daily pricing on a calendar format, I knew immediately that I was not only going to bookmark their site for future use, but also purchase a ticket before the end of that day.

Fly.com’s Low Fare Calendar convinced me that Puerto Rico was the place for me. An international flight for as cheap as $296 (taxes included); it’s hard to go cross-country for those prices, let alone cross international waters! This fact allowed me to stay true to myself and be cheap as hell, yet feel unique in my decisions.

After catching a really cheap bus ticket with Megabus (that was equal to a meal for two at Applebees), I was in Chicago. Staying overnight with a friend saved me money and I caught the early 9:15 am flight the next morning. It was my first time riding on AirTran and I had no problems whatsoever. After a 40-minute layover in Atlanta, I landed in San Juan on time at 4:10 pm just as the sky was clearing from a brief rain storm.

Before I left Missouri I got a Lonely Planet travel guide from my local library, but I didn’t really need it as much as I thought because most signs were in English and every single person I met spoke English as well as Spanish. Puerto Ricans are so used to English speaking tourists and, with their relations with the United States, they grow up bilingual. Plus, when you’re a black guy from the Midwest, most responses are naturally in English. This was slightly disappointing because I had wanted to practice my Spanish while I was there.

Because I was traveling alone and I am super cheap, I downloaded an app called hostelworld on my iPhone and found a reasonable ($24/night mixed room) hostel in the Condado neighborhood called The Palace. The staff were very friendly, the hostel itself quaint, and it was the perfect place for an adventurer to stay. And, because of the time of year, I didn’t have any problems finding a room. However if you are traveling during the high season, you may want to check availability in advance. Getting to The Palace, from the airport, cost $20 including tip and any taxi ride from the airport to an Old San Juan neighborhood shouldn’t cost more than that.

I enjoyed my time at the hostel. The first night I was there they had a toga party. They also offered bike rentals and, on one of the nights, we all had a picnic on the beach for dinner. The added advantage of staying at a hostel is that it is easier to find people to go out to the bars with. Mainly I met people from the United States ( New York, Illinois, Wisconsin, and Texas) but there were also two groups of Dutch staying there. For me this was a good omen because I’ve always found the Dutch to give great travel advice.

Places to Visit

El Yunque National Forest

I was fortunate enough to share a room with a group that had rented a car. So we all took a road trip to the eastern side of the island to visit the El Yunque National Rainforest. This is at least a half a day trip, and I would recommend dressing in layers, wearing comfortable waterproof hiking shoes, and taking plenty of food and water to snack on because there are so many trails and traffic can be crazy.

(Note: If you are interested in going to the rainforest, the Bio Luminescent Bay, or even the island Culebra just rent a car. It is totally worth it – especially going to Culebra).

Culebra

Culebra was by far the number one spot that all the locals told me to go to and they were right. This socially under-developed island is a godsend for the classical traveler who wants to escape from everything and everyone. The island gives you the feeling of being in the middle of nowhere. Nature is at its best and it has the best beach that I have ever been to in my life. It just requires a brief and cheap ferry ride (check times/ask a local).

Historic Sites

Other interesting places to go to include historic sites like old military fortresses. You can generally get a day pass that is good enough for all of them in San Juan. The Bacardi distillery and Nuyorican Café, for salsa dancing, are also exceptionally fun – although you may have a tough time finding the latter because it’s just an unassuming hole in the wall. It is, however, one of the liveliest places in Old San Juan and very much catered to all dance abilities. I feel like I am decent at salsa but there were definitely some moves that I learned from couples and individuals who you would never have thought were so good on their feet.

Restaurants

Walking around local shops and restaurants in Puerto Rico can also give you an adventurous experience. If you are meat eater, I swear the Puerto Ricans cook some of the best pork and beef dishes that you will ever have in your life (on the street too). And because Puerto Rico is an island, it also offers some fantastic fresh seafood options as well.

Special Events

It just so happened that the weekend I was in Puerto Rico, there was a lot of national pride in the air. A boxing match with Floyd Mayweather and local Miguel Cotto was televised one night and, in every bar/restaurant people were glued to the TV and drinks specials were abundant. There was also a week long Caribbean and Americas art festival in Old San Juan, so creativity and unique crafts were everywhere. And when things started to die down, cruise ships came to port just in time to liven everything back up again.

Total Cost of My Trip:

During the 6 days I spent in Puerto Rico, I spent $350. Although it would have been a $100 less if I hadn’t gone crazy at the bars and clubs. Ultimately Puerto Rico can be very inexpensive trip (especially if you are hanging out at the beach for the majority of the day).

Last Piece of Advice:

Don’t be afraid to ask the locals for advice and directions. The Puerto Ricans are very prideful people who want to show off their country and make sure you have a good time. It seemed instinctual for them to go out of their way to put a smile on your face and food in your stomach – not to mention give you incredible experiences that you can tell everyone about back home.

To keep up with Reggie on his travels, be sure to check out his blog: Contentious Benjamin

Featured Image: Ancient Fort in San Juan (Shutterstock.com)

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Fly.com regularly posts guest contributions from travel experts around the world. These articles are written by journalists, bloggers, travel enthusiasts, and specialists from within various segments of the travel industry. Each has an undeniable passion for travel that enables them to share a unique and valuable point of view. We hope you enjoy their stories and advice!
  • Simpsonpenny

    very nice, lots of valuable information. makes me want ot just travel more after reading your expereinces

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