I always envisioned wanting to go somewhere warm in the winter. So this year I decided I would take a trip by myself to somewhere that I have never been.  Let me tell you this…traveling solo was a phenomenal experience.  I don’t even know where to start.

I flew Delta out of RDU connected in ATL and then finally ended up at SJU.  I have been flying for a long time, so the flight for me was a breeze.I booked a room at the Hyatt House San Juan and it was beautiful.( Pictures are below) I will describe the highlights from my trip.

When I arrived in SJU I had a driver that showed up in the airport with a sign with my name on it.  That was cool, until I realized my name was misspelled.   I told them, and we laughed about it and kept it moving.  The driver took me in an SUV to my hotel.   As we rode around town she mentioned different places I needed to go and what to do and eat.  She was very friendly and nice. She then mentioned that she had to pick someone up in Old San Juan so she could take me over there after I took my bags to my hotel.   So of course I said yes, so that I could get a brief glimpse of Old San Juan.

She dropped me off and told me that when it was time for me to come back that I needed to go to the section where they have cabs, and a cab could take me back to the hotel. This was great, so I am here in another country and I am able to just explore without any planned schedule. So I walked around for a bit and looked at some bars.  I got a little thirsty, so I tried some fresh coconut water.  Yes, they cut the coconut in front of me and put a straw in it.  It was delicious.   I also got a little bowl of chicken mofongo (Puerto Rican dish that is made with plantains) At this point I realized I was a little tired and wanted to sit down to eat.  As I looked around, there were no free tables anywhere.  This young guy and his girlfriend asked me to come sit with them.  He then explained how his dad owned the food place and a couple of restaurants, they asked if I was alone and then proceeded to tell me all of the cool things to try while I am here.  Oh yeah, and lets not forget, he let me know that they had uber in Puerto Rico and it would be super cheap to travel, but be mindful of the rules to using uber in PR.

So apparently the taxis are regulated by a gov’t body, so uber is infringing on some peoples job.  This can mean hostility as serious as a fist fight between a cab driver and an uber driver.  So there are certain places that uber drivers are allowed to pick up and drop off and I found this out  quickly as my first uber driver told me I was in the wrong spot and near some cabs and had to move so that he could pick me up.   For me this was interesting. So I got in and my uber driver is talking to me about how uber just got there last year and he enjoys driving.  He also told me some places I needed to check out, one important place was Casa Cortes, where he described he had the best chocolate french toast ever.  He dropped me off at the hotel and I thanked him for my trip.  So I made a point to tell myself I need to go to that place for brunch.

Saturday night was uneventful as I was tired, so I decided to order in and veg out.  Which is really one of my favorite things to do when I travel. So I ordered some delicious pizza and wings from Mike’s Pizza, watched lifetime movies (which I never do), and relaxed.

I woke up Sunday morning ready to get out.  So this day I woke up got dressed and decided I would go through all of Old San Juan today and get this delicious french toast I heard about. So I used my uber app and got transportation to  Casa Cortes. So, I get there and there is a line that looks like I am about to go to a nightclub.  The hostess has a clipboard and is recording all the names of the parties waiting, as she walks closer to me, I said, “it’s just me, I need a table for 1”. She smiles and then comes someone with some “hot chocolate to taste” as you look around you realize that this place is definitely a house of chocolate. There was even a tree in the front that was made out of chocolate. (Pictured below) An older gentleman behind me, looks at me and says, if  it is just one of you, maybe they will make a place for you at the bar.  Me “it doesn’t hurt to try to see”.  So I walked up to the bar and saw all of the seats were full.  Then I looked closer and realized there was a backpack in one of the seats.  I asked the person sitting next to the bag if I could sit there.  He said, “yes”. So that was great I had a seat in what looked like a very busy brunch place. I looked back at the line and the gentleman that told me to walk up was near the end of the line with his wife and that line was not moving.   This made me want to thank the guy sitting next to me again.  I noticed a bit of an accent, and found out that they were from California.  So we talked about what they did while they were here, and of course the question came up again, “Are you here by yourself”, “Really?’.   Me: “Yes” . It actually felt liberating to say it.  Meanwhile, the bartender comes over and describes what sounds like an amazing watermelon drink, then she says oh the rim is covered in chocolate. Me: “Wait, chocolate and watermelon?” She says, “Yes”.  Me: “Ok, I’ll try it”.  This turned out to be a great decision.  I also ordered the chocolate french toast that I heard about the day before.  So I am expecting to get some french toast with a chocolate sauce or something.  When  they brought it out, I realized the bread was actually chocolate.  Man, this was great. I ordered another drink and decided I didn’t want to drink to much and was going to be doing some walking around, so I also ordered some water.

Before I left the restaurant a lady came over and said that there was an art exhibit upstairs featuring Afro-inspired art and masks.  So I definitely wanted to take a look.  After looking at the art I went for a walk.  I literally walked all over Old San Juan, tried some local food from food trucks, stopped and got a water.  Then after a couple of hours of walking and a few thousand steps I decided it was time  to go home.  As I am waiting on my uber driver, I see some people in my sight that asked me if I was waiting on the trolley.  I mentioned that I heard about the trolley at brunch but hadn’t seen it.  This group was 3 generations of women that lived in Georgia. So I said I will ride the trolley with you guys, so I canceled my uber. This was great, all of the walking that I did all day, I was able to see riding on the trolley.  I rode the trolley all around until it returned back to where I was going to get my uber.  I booked another uber and actually went home this time.

Now in this uber the driver told me about a place called “La Placita” and said you need to go there. Me: “ok”.  My Manager from work had some friends that lived not that far from my hotel so I they picked me up and took me to La Placita.(Pictures from that night below) It was like a street festival that happens almost every night of the weekend, which was so much fun.  We had some amazing mojitos and danced in the street.  This was a good time.    I definitely recommend this for anyone wanting to travel to PR. Got dropped off at my hotel and was thinking about what I may want to do the next day.

I woke up Monday morning and asked the staff where I could go eat breakfast on the water.  The front desk person recommended going to La Playita in Isle Verde. (Only the view and food are pictured below)  So I used my uber app as usual and when I saw the building that I was getting dropped off at, I thought I was being punked.  So I walked through and asked someone where the restaurant was.  The view was breathtaking and the water literally came up to the edge of the restaurant.  The food was pretty good too.  Of course I ordered a drink.  They had something called a coco loco, it was 4 or 5 rums and in a coconut.  Once I finished that and my meal it was time to go.  I hit the uber app and walked outside.  I saw the easiest access to a beach, there was someone sitting there having a drink and just looking at the water.  So I looked too until my uber arrived.

This uber experience was different than the others.  My uber driver didn’t speak English.  I don’t speak spanish, but I do know how modern technology works. So I used google translator to tell her that I didn’t understand what she was saying but I would listen just in case I knew some words that sounded familiar.  Now is when it became interesting because she talked to me from the time I got in the car until we got back to the hotel which was about a 15 minute drive.  Can you imagine listening to someone talk to you and you have no idea what they are saying.  It made me think it must be incredibly frustrating for people that don’t know any English and people still try to talk to them, because it basically sounds like Charlie Brown’s teacher.

For the evening I decided that I would like to go sailing.  So I went online and picked Sail San Juan Bay, and it turned out to be a great choice.  The Captain, Captain Ivan, was great he mentioned that no matter what his boat has never tipped over, so if we are leaning a little bit, don’t worry.  So I took that information and was prepared for the ride. (Pics below)  The other people that were going on the boat with me were US Military veterans that were on an excursion from a cruise ship, 2 from Desert Storm and 2 from Vietnam. I told them my Dad was a vet and they started talking to me.  Well you know what the number one question was, “Are you here by yourself?”, Me: “Yes”.  Them: “Really”. Me: “Yes”.  After we went back and forth about it they finally accepted it.   Out comes the first mate and he says, “Do you want a drink”, (by the way, this sailing trip has unlimited drinks) Me: “Of course” . So he pours me a drink and we set sail.  This was probably the best part of my trip.  As he is sailing the boat he starts discussing the history of old san juan as we are sailing around the bay.  The scenery is beautiful.  I just relaxed and took it all in.  The captain says, “You seem so comfortable, are you enjoying this?” Me: “Of course”. We sailed around the bay for over an hour and it was great.  I would definitely recommend Sail San Juan Bay to everyone.  Once we docked, I hopped off the boat and walked back to my hotel.

These were some of the highlights from my trip.

I even have a list of things to try when I return to Puerto Rico.  So if you are traveling there add these to your list if you want:

1. Bio Bay: Best if the moon is full, so that the light from the sea creatures is seen
2. La Factoria: One of the best bars in the world
3. Pinones: Has some really good street food; a good place to go in the daytime
4. Take a Catamaran and go snorkeling or do a jungle hike: There are plenty of these tours.
5. Casa Bacardi: If you like rum, check it out. They have different packages.
6. La Placita: I went, but would definitely go again.  Fun festival type atmosphere
7. La Respuerta: They have hip hop/R&B night on mondays so I would definitely check it out
8. La Concha lobby: In this hotel they have a world famous lobby bar.
9. Club Brava: Nightclub
10. Club Kronos: Nightclub

Oh yeah, by the way.  My airport experience on my way home was phenomenal. I took an uber to the airport. He dropped me off, they ran my bag through a machine, and I went through TSA in all of 10 minutes. So it was quick and they were efficient.

So all in all, solo traveling can be fun.  However if you feel uncomfortable answering the questions about why you are alone, take someone with you.