This last Christmas-eve (like two weeks ago), my friend, Bobby, and I went on an adventure to Puerto RIco for Christmas and the New Years. We’ve been friends for a long time, but this was our first time traveling together outside of work, and though I wasn’t sure about how the trip would go, we quickly found it was quite an awesome trip.
Sometimes You Pick A Bad Egg
After a long day of flying (Portland-Denver-Orlando-San Juan, PR), we touched down into the San Juan Airport around 9pm or so. Our flights were all successful without much of a delay anywhere. Quite nice for three legs of flying. We grabbed our bags (50L backpacks each with a small satchel or backpack), and headed to the taxi zone as bus transportation wasn’t very well known at the time.
We gave the man our hostel (The Palace Hostel) location, got into his van, and made our way to the hostel. Thankfully it was a flat rate for the ride as he gave us quite a little drive of the places around our hostel to go check out for late night eats and drinks. We arrived our hostel and paid the guy $20 for the lift.
The hostel wasn’t very inviting, but I’ve been to enough of them that this is sometimes the case…especially on Christmas eve at 10pm at night when most of the locals are at home having dinner with their families.
Once getting checked in and locating our room, we quickly realized that this place was quite a dive. Now, I understand that I’m staying in budget accommodations, however, I’ve stayed at enough hostels to know a good one from a bad one, and this was on the spectrum of the latter. The room was small with a creaky bunk bed. Thankfully at least it had AC. The bathroom we were supposed to be using didn’t have toilet paper and the light didn’t work…just great. After asking to get a roll of TP and being told that it isn’t a common hostel amenity (maybe in PR – later found out that isn’t true), I was helped out by one of the workers and handed a half roll. It’s better than nothing, I thought. Bathroom use consisted of turning on my cell phone for light which is always a sign of good things to come.
Though the conditions of the hostel weren’t to my liking, we made the best of it and hit the streets around 10:30pm around the hostel to find a drink and some food.
Avoid The Touristy Spots
This is something you must learn, and after almost 3 good years of traveling, I’ve found that you get the best experiences and save the most money avoiding the places all the tourists go.
We talked to the hostel and they didn’t have many recommendations except the tourist spot for drinks, so we just started wandering the streets and soon after, found a place with music and drinks. It was full of locals, and that’s what we wanted. We didn’t speak much Spanish at all, but we were able to get a couple beers however.
The local beer, Medalla, is a lot like any American domestic beer, kinda crappy, however, we were hot, thirsty, and willing to drop the $1.50 a can. I was pretty excited when I found prices like these for a beer as I wasn’t sure what to expect for the prices. Soon after leaving this spot and going to some of the recommended locations (touristy spots), I soon found that we needed to come back to this spot. The recommended spots had the same beer for around $5 a 10oz can. That’s not cool!
This was quite the pricing theme of the trip. If you were willing to walk away from the spots the tourists go to and find spots the locals go, prices went down a lot. One of our favorite spots was near the $1.50 beer spot and they had 200ml bottles of rum for just $3.00 and a bunch of pool tables which Bobby and I enjoyed quite a few nights.
After walking all over the part of San Juan we were in, we finally made it back to the hostel where we stayed up with some of the other guys talking about the plans for the night and drinking lots of rum before Bobby and I decided to call it a night.
Christmas In Old San Juan
After sleeping in a bit, we decided to figure out what Christmas was going to be for us. We kept hearing about Old San Juan and decided to venture out that way.
One of the things I kept reading about were The Forts of Old San Juan. We decided to not worry about the buses and just walk the 45 minutes to Old San Juan. It was hot, but we figured we could manage. The walk was pretty great and gave us a good look at the area on the way to Old San Juan. Lots of friendly faces about the streets and the park we walked through which brightened our moods.
We arrived the San Juan National Historic Site and found out it was closed for the holiday. Damn! Well, what now?! That wasn’t going to stop us. Old San Juan isn’t just about the forts, it’s also a lovely area with colorful buildings and cobblestone streets. Quite a charming place and gave us quite a good time of continuing our walking.
After a couple hours of site seeing around the streets, we stumbled upon a brewery (Old Harbor Brewery) that had some local cervezas (Spanish for beers) – even a tasty seasonal. We went in, realized it was of course more for the tourists, but stayed anyways because we wanted some tasty brews. We learned about the history of the brewery and that they’re pretty much one of the only ones around. After the history lesson, the brews, and our hummus plate, we ventured back out to the streets. We ended up in the direction of the ports and soon were blown away by the size of the cruise liners that were docked. These things were ginormous. I’ve been on my share of ferries, but never a cruise, so I was quite surprised by these massive ships.
After being blown away by the vastness of the ships, we kept walking and found this Christmas themed park dubbed “Navi Town”. We didn’t stick around long here, but we did enjoy some free canned tea. We saw a large statue of a sea horse so we left Navi Town to go check it out. While there, we saw this little dog and didn’t think much of it. Well, after a bit more time of wandering, we started walking towards the direction out of Old San Juan. On the way out, that same dog we saw earlier was going with the flow of traffic and keeping pace (probably 5-10 miles an hour)…in the middle of the road itself. It was awesome. Such a cool little pup.
After catching our bus, we left Old San Juan, got back to our hostel, and went to the pool hall where we grabbed some rum and played a lot of pool. We ventured back to the hostel where we met some of the others and found out they were going out to Old San Juan to go to some of the bars over there. We didn’t have any plans, and hanging out with people for Christmas sounded good, so we went with them. A couple I saw before in the hostel happened to also be at that bar and after some time of chatting, I got a number of a taxi, and gave them a call to make plans way too early in the morning (5:30am) to go to Vieques Island. The four of us got a taxi to the hostel and quickly passed out.
Couples In Vieques
I woke at 5:30am realizing that my alarm didn’t wake me up and after waking Bobby up, we quickly packed, and barely made our taxi to the ferry. The rush to the ferry was a bit overwhelming, but we made it the hour drive and then got in line to get our ferry tickets to Vieques. Well, we quickly found we got there way earlier than we needed. Got our tickets around 7am, and then waited around for another two hours for the ferry. Oh well, the joy of traveling, right?
The ferry took a couple hours and we quickly got to know our travel companions. A couple with killer dreads from Minnesota who were escaping the normal existence of life back home. Bobby and I had no plans for accommodations that night, and after chatting with these two, finding out they were doing some camping, we went the same direction. We walked into a place to ask about tent rentals and found a price of $40 a night which we turned down. We hopped into a cab and got to the site location on a BEAUTIFUL beach called Sun Bay. Problem was, no tent rental places in site.
I didn’t want to have to take a taxi back into town, so I ended up chatting up the security guard there about the lack of a tent and looking for a place to rent one. He laughed a bit, and once he realized I was serious, he called up a friend and I was told to wait. After about 5 minutes, one of the workers showed up, and he let me and Bobby borrow his tent for $10 a night – SWEET!
The bay was amazingly beautiful, the drinks weren’t too expensive at the tent location, and there were lots of wild horses in the area. Pretty happy with the location. I started chatting up some other campers and learned about an area nearby that had more restaurants and hotels. We all ended up walking along the beach before finding the location mentioned and ate some expensive food and had some poorly made drinks, but we were happy looking over the bay.
After having a pretty uncomfortable night in the tent, Bobby and I decided we needed to figure out if we were staying here or moving on. We made friends with another tent couple from New York, Avery and Nolan, and walked back to the restaurant area to get breakfast with them. The day was filled with beach time and getting to know each other. It was excellent. I’m really hoping to bump into those two again. In the afternoon, we also bumped into a couple that I saw the day before briefly and found out they were wanting to go to Culebra as were we. It’s another popular island around Puerto Rico with supposedly the 3rd best beach in the world, Flamenco Beach. The original plan was to just take a flight over to Culebra, but we were quickly disappointed to find out they were booked. Instead, we found a great deal on chartering a sail boat, so we booked it for the following morning! The couple we were going with, Jake and Maria, invited us to just stay on their extra bed in there hotel. That sounded great for us and gave us a chance to not sleep on the ground.
Culebra Is Rad
We woke up early the next morning, took a taxi, then a dingy over to our sail boat taking us to Culebra. If the winds were favorable, it would take us two hours. Well, they weren’t, so it ended up taking us around 4 hours to get there, but we made the best of it and had some great bonding moments along the way. The owners of the boat, a couple from Denver, made us snacks, provided us drinks, and even let us use their snorkel gear and kayak when we got to Culebra to see the sea turtles. It was quite the amazing sailing trip. I’m also pleased to say that I’ve now sailed in part of the Caribbean.
After seeing some lovely sea turtles and taking a dingy to the island of Culebra, we made our way to our accommodations for the night, a tent, this time with pads and room for four with gear. They even provided us some toilet paper, bug repellent, sun block, and flash lights. The tent was under the trees next to Flamenco beach. We dropped off our gear, and went with Jake and Maria to explore the “3th best beach in the world” under the moon light. The beach was quite nice, however the majority of it was covered in kelp which takes it out of my list for worlds best beaches completely. Not sure what people were smoking when they said it was the “3th best beach.” We enjoyed some great conversations at the beach before heading to our grand hotel (tent) to go to sleep for the day to come.
The following morning, I got up, and went for a swim (after traversing through the sea kelp). Afterwards, I met up with the other three and we decided getting a golf cart was much desired to explore other parts of this island. Golf carts were the most affordable modes of transportation on the island, so we got one and started our exploration.
We picked up some snorkel gear, made a number of stops, got food for later, and ended up at another beach opposite on the island from Flamenco called Zoni beach. The waves were awesome here, so we spent a good couple hours just body surfing. It was such a good time and what we all needed.
The beach time was followed by more exploration of the island. It wasn’t a huge island, but I wouldn’t have wanted to explore the place just by walking or biking as there were a number of hills and it was quite warm out. The cart was surprisingly powerful being able to take the four of us up some steep hills I wasn’t expecting it to make.
After a day of traveling around the island on our golf cart, booking a flight the following day to the main land, we finished up the evening enjoying some good food and going to the resort nearby Flamenco beach which was actually a really cool place I’d probably stay at if I ever came back to Puerto Rico.
The night came, and so did the sunrise. We got up early, did a little swimming, then carted to drop off our snorkel gear, and drop off our cart. We got a lift over to the airport, made some PB&J sandwiches and checked into our flight. The airport was small, so real security was a joke, but it was a beautiful way to get to the mainland without dealing with the slow ferries.
Our mates had a rental car at the airport from when the came to the smaller islands, so we got on with them and went to the El Yunque Rainforest. After a large number of windy roads, we made it to the gate with a big sign saying it was closed for vehicles. No big, we got out, and started on foot on the main road until we found the picnic area. This area was pretty nice looking with a number of signs warning us to avoid mongooses. I only saw one the entire trip (earlier that day), but that was it. There was a decent trail in the area, but it was rain washed out, so we went up the road. As we got to the only direction cars could end up going, we realized that this place looked like it hasn’t been cleaned up in years. So much overgrowth which took the road of around twelve feet or so, to barely fitting a single person. After a ways in, and getting our shoes covered in mud, we realized that we couldn’t go any further. Well, that’s just great.
We headed out to find a couple other people who we ended up talking to for a while. The guys who was leading the duo has been living in the area for a while and said that we were at the South entrance which most people don’t end up going to and that we wanted the North to see all the waterfalls. That’s just our luck. We ended up finding another trail and made it to what could be considered one before making our way out and heading North to a city called Luquillo. This was a decent beach town I heard about that didn’t really meet up to expectations, but we stayed a little while anyways. Attempted to grab some food at the local “mall” of small restaurants that for being expensive and not very busy, was extremely slow. So we cancelled our orders to beat traffic and took off back towards San Juan as our traveling companions had an 8 am flight they had to catch.
We all went to Old San Juan together and wandered around some of the parts we were last time before we decided to head up North. I’m glad we did cause we stumbled upon the top of the second fort which was a lovely site. While out there we caught the sunset and found a fantastic restaurant called St. Germaine. The atmosphere, the workers, the food, and the fantastic drinks were so good that Bobby and I came back a couple more times the next few days. With one final dinner with Jake and Maria, they gave us a lift to our new hostel (Island Time Hostel) and departed ways.
Always Enjoy Island Time
The first hostel we got was off a site called hostelbookers.com which I use most all the time when booking hostels. Well, this time I found this one on hostelworld.com and I’m glad we did. It was WAAAAAYYYY better than the last one. If I were to ever come back to San Juan, PR, I would be staying here again. The people were friendly, the grounds were clean, and our room was pretty good for being small. Bigger than the last hostel for sure, and it came with a private bathroom. They also provided pancake mix and fruit for breakfast. I wish we could have stayed here longer, but we had places to be and sites to see. So we checked out, and took the bus to get to the Sheraton near the convention center I scored a couple rooms at for New Years.
New Years Eve At The Sheraton
I got a killer deal at the Sheraton using some points I had. Regular rate for the room was $225 a night, and for NYE it was $800 a night. Thanks to my spg points I had, it worked out to around $100 a night. I’ve heard great things about the parties in Puerto Rico, and though I didn’t actually attend the main party at the Sheraton, there were tons of people showing up for the one there and the convention center next door. The cost was $135 for the party, but after Bobby and I scouted the scene to realize most everyone there were couples, we decided to just do our own drinking and soon after, we found the casino.
Earlier that day, Bobby and I bought some cigars from one of the shops in Old San Juan and enjoyed them while also the “free” casino drinks and the games. Games of choice were Craps (though it wasn’t working for me this time), Blackjack, and Roulette. Blackjack was the winner this time and I ended up $20 over the $100 I started with for the six hours we were on the floor.
The night ended around six or so before having one final cigar, a couple drinks, and passing out to some Puerto Rican soap opera on the TV.
We slept until around noon the following day before getting up and figuring out what our day was going to be like. The only thing either of us had scheduled was to watch the Ducks play Florida State in the first round of the playoffs at 6pm. That gave us enough time to relax, get some grub, and enjoy the game.
Leaving the room around 2pm or so, we went on a hunt for lunch and were surprised to find out that there wasn’t much open in the hotel outside of the Brazilian joint charging $40 a plate. So at around 3pm, we got the bus, and took it to Old San Juan. We heard about a good pizza joint (Pirilo Pizza Rustica) where we ordered two large pizzas. While the pizzas were being made we went to Walgreens (all over PR), and got two twelve packs of Medalla. Leaving there, we left just in time to get our pizzas, and make it back to the bus depot before they had their shift change (added 30 minutes to the trip) and made our way back to the hotel around 5:30. Just in time to eat, and get prepped for the game.
We decided that it would be a smart idea to make the game into a drinking game. Each point or first down Oregon got would be a sip of our beer. Each turnover would be to finish the drink we had. Well if you watched the game, you’ll know that our beer didn’t last too long as we scored 59 points and there were six turnovers in the game! Suffice to say, we finished both our twelve packs and didn’t feel amazing afterwards. Only thing left to do then, get up and go hit the table games in our casino where we watched the next match where Ohio State defeated Alabama.
We only were at the casino a couple hours before the effects of the pizza and beer caught up to us and we hit the beds for our final night in the Sheraton.
The Forts of Old San Juan: Guardians of the Caribbean
The majority of our final full day in San Juan was spent exploring the forts of Old San Juan. It’s only $5 to enter the fort and it covers the other fort as well. We started with the larger fort called San Cristóbal. This place has a lot of history and is quite a cool place to explore. Bobby and I made it into a game of sorts where we tried to explore as much of the place as we could. I’d say our ventures were quite a success.
Following this we walked along the road towards the fort that protected the entrance to the port called El Morro. Another awesome fort to explore and has a lot more stairs and goes much lower than the first. A couple days before when we were in this area we saw a road that went around the parameter of the fort we wanted to get to and though they said the only way to get to it was from the port entrance, we were able to hop a couple fences and scramble over some rocks to get down to the trail. Glad we did, cause it was a hot day and we didn’t want to have to walk the same path twice.
The road/trail was around a mile long and gave some pretty views of the water with the walls that make up the fort. Along the path we stumbled up a grassy area where we saw dozens of large iguanas. They were fast and wouldn’t let anyone get to close to take some pictures. Jerks!
We finished up the trail and made it back into Old San Juan where we stopped in a Hawaiian coffee shop and had a late afternoon meal and some tasty iced coffee.
Finished In The Atlantic
We left Old San Juan by bus, grabbed our stored items from the Sheraton and made it to our final night in San Juan staying at The Atlantic Beach hotel. This place was the cheapest in the area (still $99 a night) and was pretty central to the north side beaches of San Juan. The guy who greeted us was a nice man and gave us some good info for the area. We checked out the drink prices at the hotel and didn’t give into the expensive cheap beer, and instead made our way out onto the streets where we found more hotels, casinos, and good food for not that expensive of a price.
Bobby and I went to three casinos that night, one of which payed me quite well off of $12 at roulette. I kept hitting the numbers and when I left, I was up to $210. Which I quickly cut in half as I played a few other games. All in all, I was successful at the table games and left PR a winner. I also had the best Pina Colada while playing Blackjack which was surprising as the other places in PR just made them terrible.
After some tasty food, gambling, and another of the local beers (Magna, still crappy), we hit the hay and had one final bit of sleep (around 3 hours) before getting up for our taxi to get to the airport for a day of travel.
Bye Puerto Rico
We got up around 3am, and our travel day didn’t end until we arive Portland at 2pm (PST), so around 13 hours of travel. The flights were thankfully all on time and we each made it home in one piece.
Though the prices of Puerto Rico were more than I was expecting, the experience I was able to get from traveling with my friend Bobby for the first time made it all worthwhile. You never know who you are able to travel with and I’m glad to say that we can travel together. Outside of a couple rough spots, it was smooth sailing.
I recommend Puerto Rico if you want something different than Hawaii or Mexico with amazing beaches, a place you don’t need a passport, and gives you a taste of the Caribbean.
Here’s to the next adventure!