Puerto Rico Winter Escape – Paid for with Points

Puerto Rico Trip for Two

We chose to visit Puerto Rico in March to escape the seemingly incessant Cleveland Winter.  Originally, the 51st state wouldnt even be on my radar… but thanks to the SouthWest Companion Pass and their dozen ‘Caribbean area’ destinations, we thought we’d explore a new Rainforest / Tropical area, since we liked Costa Rica so much.

To ‘Finance‘ this trip, we finally started utilizing Hotel Cards as well as Airline Points:


Cards Utilized:

Chase SouthWest Personal:  Came with 50,000 points and Previously attained Companion Pass

Cost to Fly TWO from Cleveland to San Juan:  27,510 SW Points  – Round Trip

IHG Rewards Club:  Earned 80,000 Points at sign up, 60,000 which were utilized for four nights at the Holiday Inn Express near the beach in San Juan.  For more details on getting the most out of IHG Hotels, visit TravelisFree.

AirBnB:  $75 Credit from referring 3 Friends to AirBnb

You get $25 per referral, awarded after that person uses AirBnB for the 1st time on a property

Car Rental:  Could have been done through Chase’s UR Portal, but we found better rates from CostCo, which included free Spouse Driving Privvies. The CSP card gives you Free Supplemental Insurance, saving you hundreds with that benefit some people are not even aware of.


Things to Do and See in Puerto Rico:

My wife and I are the more adventurous type, so we thought nothing of renting a car in a place where everything is in Spanish. (Foreign to us).  This was huge, because some of the coolest things to do/see are far away from each other in Puerto Rico.  I am of the mindset that you gain a lot more by having your own rental car, vs paying shuttle fees or wasting time being frugal with public transportation.  Plus its more fun to drive yourself around anyways.

Like most visitors, we stayed in the San Juan area, the biggest city in PR.   This was the view from our comparatively cheap Holiday Inn Express, which was a 3 minute walk to the beach.

The main ‘Beach on the Strip’ is Condando Beach, which was really nice for the most part.   I was surprised to see a few ‘abandoned’ hotels that were situated right on the beach.  Prime Real Estate just going to waste.  The area felt safe though and had just enough security presence.  The nicer hotels had infinity pools that butted up against the beach…. but probably cost twice as much as where we stayed 300 yards away.

HIE PR View   Condado Beach


You can rent lounge Charis, boogie boards and other things on the beach, and the waves were big enough to have fun with.   Near this same area were a slew of restaurants, hotels, and boutique stores.  The food in Puerto Rico was good overall, but the service was usually the ‘Non-American’ style.  By that I mean slower, less concerned, and places close up whenever they feel like it.  However there were waiters we talked to that were super helpful.  Their signature dish seemed to be Mofongo, which is a  fried plantain-based dish. It is typically filled with seafood, veggies, or other meats and pretty damn tasty.  Another favorite we discovered was Ceviche’, which is any seafood cured (cooked if you will)  in lemon/lime juice, and served with cilantro, red onions and sometimes other veggies mixed in.


Puerto Rico also has a lot to offer Nature Lovers.  The El Yunque Rainforest is a beautiful, vast stretch of land reserved as a National Park.  The panoramic views from Fort Britt give you an amazing 360 vista of the entire forest, and the hike up there is enjoyable as well.  Very easy even for beginners since its all paved… and there are benches and places to rest on the way up.

View from El Yunque

Getting to El Yunque is an hour and a half from San Juan, or you can stay in Fajardo which is closer to the North entrance.  If you stay in Fajardo, you’ll also be near the Bio luminescent Bay in the same area.  We actually stayed in the South Eastern part of the island, at a nice AirBnB in Naguabo.  This is a small little fishing town, where things are done a little slower and you can discover another side of P.R.  If you explore outside the San Juan area, I recommend AirBnB over the hotels… You get a better ‘local’s view’ of the area, and it gives you a chance to meet more ‘real’ people and experience less touristy things.  Plus you can get a room with a nice view of the beach and n empty pool for as much as a regular hotel.

One thing that is probably only enjoyed by tourists, is the Tanamá River Adventures Tour.  Cave Tubing, Rappelling and trail forest adventures – with a local informative guide who can teach you everything you’ve wanted to know about the local Ecosystem and then some.  We really enjoyed going through cave in an inner-tube, eating oranges right off the tree, using the river clay as a facial mask, and to a lesser extent…seeing a cave full of bats above us.


We planned to visit Culebra Island when we were on the East coast.  You have to take a $3 ferry there, which sounds great but it only runs at 3 times during the day, and the 1st run always sells out and gives Locals preference in boarding…  So you could show up at 7 for a 9 PM departure, and someone who shows up at 7:30 can get your ticket.  Kind of unfair, but they say its to help the locals out who live there.   Instead we opted for the 3:00 Ferry Departure to Culebra.

Our plan was to have dinner at the main strip of restaurants near the Culebra Ferry Terminal… But it turns out they’re ALL closed til 5:30 PM.  So we waited around for an hour or so, then had some nice Ceviche’.  Afterwards we tried to catch the Shuttle that supposedly runs every 15 minutes to Flemenco Beach, but there were none in sight… after an hour we figured ‘its getting dark, and we still have to get to the beach campgrounds and setup our hammocks…we gotta get there somehow…’ …So we Hitchhiked.  A nice couple in a pick up truck actually offered us a ride, and even though the floor of their car was covered with beer bottles, we rolled the dice and hopped in.  The lady in the passenger seat, also drinking, was actually really nice.  It was about a mile and a half to the Beach/campsite, and we wouldn’t have been able to get there without automotive assistance.

By the time we got there, it was dark.  And with less light pollution, it was actually beautiful to see the stars – MILLIONS more of them, than we get in the city.  We setup our hammocks in the dark, took a night stroll on the beach, and got a drink at the beach bar-stand which was miraculously still open.  Falling asleep to the waves was really cool, and i loved the vibe of roughing it Ocean style.  However, 62 degrees is pretty cold, and we didnt have blankets… Our bug spray proved to be ineffective against the 7 Trillion mosquitoes,  so we spent the next couple days itching like crack-fiends.  The Morning was really nice, being the 1st ones on this absolutely gorgeous white sandy beach at 5 AM.  We swam with the fishes in the water, and just chilled all afternoon which was really relaxing.  Overall it was an interesting experience, but I wouldnt recommend ‘Hammock only’ camping, even if it was free.


Leave a Reply