Cruising the Southern Caribbean: Pre-Cruise Fun in San Juan

If you have read around on my blog at all, you may already know about my crazy love for Puerto Rico.  No matter how many times we have visited, it has yet to get old to me. And this time around we were even more enthusiastic to be there because we had some first time visitors with us on this trip, and we would get to show off our favorite places.

Our travel group consisted of eight adults.  Four of us chose the redeye route, arriving at about 11:15am, and the other four left in the morning, arriving at about 11:45pm.  Since the second group that arrived at night were the ones who had yet to visit Puerto Rico, we decided to spend the first afternoon enjoying a relaxing day at the Caribe Hilton, saving a tour of Old San Juan for the next day.

Thursday: Relaxing at the Caribe

Our resort day at the Caribe was great.  We were way too early to get into our rooms, but we went ahead and stowed our luggage and checked in for resort access.  From there, we headed straight out to the pool area to enjoy the beautiful weather and some snacks.  Of course, being the Caribbean, the weather is ready to change in an instant and so, after sitting down and ordering some food, the clouds moved in and it started to rain.  Our waitress was quick to find us some sheltered seats from which we could enjoy the pool area without getting drenched.  And then of course the rain stopped and the sun peeked back out.  Oh that silly Caribbean weather!  In case you are wondering what kinds of health food we enjoyed, here you go.

After stuffing ourselves with fried goodness, we headed out to swim.  The Caribe has plenty of areas to park yourself by both the pool and the beach: loungers, hammocks, and private cabanas. But our favorite place is the round deck that juts out into the ocean.  I could seriously just lay there forever, occasionally rolling into the ocean when I overheat.  Bliss.

Once we were all beached out (if there even is such a thing?) we got our room keys and headed up to our rooms.  I won’t do any kind of room review since I have already reviewed the Caribe in this previous post, but I will give you a quick look at the view from our balcony.  It’s terrible.  You would hate it.

caribe hilton room view

After dumping our stuff and getting cleaned up (from a lovely combination of overnight travel, sunscreen, and salt water) we headed out to Old San Juan to have dinner.  Normally when we head to OSJ during the day, we like to take the local bus, but since it was evening, we decided to take an Uber instead.

Once we were dropped off downtown, we headed to one of our favorite restaurants, El Patio de Sam.  We’ve eaten here almost every time we have come to San Juan, and I am pretty sure we will gladly keep the tradition alive on our next return.  They have great burgers as well as local dishes, and service is good.


el patio 2

After dinner, the day of travel finally caught up with us and we called it quits.  We wandered the streets of Old San Juan for a bit and then got an Uber back to the hotel for some well-deserved sleep.

Friday: Exploring Old San Juan

We were up bright and early on Friday morning.  Since we were 3 hours ahead, I would have thought that we would have trouble dragging ourselves out of bed, but sure enough we were up and at ’em by about 7am.

Being that it was our friends’ first time in San Juan, we wanted them to experience as much as possible, including the local bus.  So we got some quarters and headed out to the bus stop that was right around the corner from the Caribe.  Or rather the bus stop that used to be around the corner from the Caribe.  Where did it go???  Apparently since our last trip in 2015, they have added a really nice bike path which seems to have necessitated moving the bus stop.  Oops.  So we started walking toward our destination, hoping that maybe we would find the bus stop along the way.  Which we did not, of course.  But on the bright side, it was a lovely walk.  And after a few blocks of enjoying the sweltering heat, we went ahead and hit up Uber again.

old bus stop
The park where the bus stop used to live
lovely stroll to old san juan
Enjoying a nice walk toward OSJ

When we got into Old San Juan, we made a beeline for La Bombonera.  I have mentioned this gem of restaurant before in Old San Juan: My Top Five.  It was a favorite of ours until it closed down, but has since reopened and we were so excited!  Our group of eight was seated pretty quickly and we enjoyed good service and wonderful food.  If you ever find yourself at this restaurant, be sure to order a cafe con leche and a mallorca sandwich.  Delicious.

la bombonera

After breakfast, we meandered around the beautiful streets of Old San Juan and enjoyed the sights.  Our first stop was the Castillo San Felipe Del Morro.  We did not go into the fort this time around, but we spent some time walking around the outside and enjoying the views.

el morro 7
Castillo San Felipe Del Morro
el morro cemetery
Santa Maria Magdalena de Pazzis Cemetery

After El Morro, we headed over to the Hotel El Convento for refreshments in their lovely courtyard–no pictures, sorry–and then across the street to the Cathedral de San Juan Bautista.  The cathedral has free entry, but donations are appreciated.

From there we headed toward the Puerta de San Juan and then down the Paseo de la Princesa.  I love this area, as you are walking along the old walls and the water.

old san juan gate
Puerta de San Juan

old san juan walls 2

old san juan walls view
view from the Paseo de la Princesa

At this point, we realized that we had officially burned through our breakfast and it was time for a late lunch.  We headed to El Jibarito, a popular restaurant with local fare.  The decor and atmosphere capture the colorful flare of San Juan, and the mofongo is tasty.

el jibarito

After filling up on the delicious criolla comida at El Jibarito, we decided to head down to the CVS Pharmacy to buy waters to bring with us on the cruise the next day.  When we got outside, we realized that the clouds had rolled in while we were in the restaurant.  And as we were walking down toward the CVS, the rain started pouring on us.  Gotta love the crazy weather!  Taking shelter in the store, we managed to avoid most of the shower and even dry off a bit while we got our shopping done.  Then, feeling pretty exhausted and already having covered a lot of our OSJ favorites, we headed back to the Caribe to unwind and get repacked for the next day’s cruise.

Tips and Lessons Learned:

  1. When planning for a day or two traveling before your cruise, it is smart to plan out what you will need for the first few days and pack it where it is easily accessible.  We were very thankful to have our beach clothes in our carry-ons for the day we arrived–it would have been a nuisance to have to dig through our suitcases in the hotel lobby.
  2. Things may be different than you expect when you travel.  Even though we have been to San Juan many times and thought we knew where everything was, we were completely at a loss when we could not find our usual bus stop.  So be sure to confirm that your travel plans are still current.
  3. Weather can change quickly in the Caribbean.  If you don’t mind a little rain, it’s no big deal.  But if you would rather stay dry, be sure to pack a small umbrella or rain jacket.
  4. Eat local!  The local dishes like mofongo and totstones were some of our favorite things we ate in Puerto Rico.
  5. Water on a cruise ship is perfectly fine to drink, but if you prefer bottled water, it is a good idea to stop and pick some up beforehand at a grocery store or pharmacy.  It will be MUCH cheaper than buying water onboard or at the ports of call.

Next Up:

Cruising the Southern Caribbean: Pre-Cruise Fun in San Juan (the way-too-many-pictures edition)




8 thoughts on “Cruising the Southern Caribbean: Pre-Cruise Fun in San Juan

  1. Old San Juan looks so charming. The weathered walls of the castle add to the atmosphere. La Bombonera’s mallorca looks tempting with the cafe con leche. I want to sit in a cafe in a foreign town Right Now. Boo hoo hoo!

    Liked by 1 person

    1. I wish the same. My gladness to be home was rather short lived. Now I am ready to take off again. I’ll meet you at La Bombonera, okay? I can be there in approximately 12 hours 😬 (that would be an expensive trip for coffee 😜)

      Liked by 1 person

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