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- Quick stats about this trip:
- ✈️: 5,200 miles
- 💳 : 100,550 points
- Chase: 77,464
- Amex: 23,806
- 💰: $108.82 per person per day (double occupancy)
After weeks of hard work with no travel, my husband and I were itching to get away for a short trip that would entail just two days away from work. We decided on an extended weekend trip in Puerto Rico, as that would give us the perfect number of days to explore, plus Chabad in Puerto Rico is a great place to spend Shabbos. An additional factor in deciding on this destination was the cheap JetBlue mileage flights available for our dates.
Thursday right after work we loaded our backpacks into the car and headed to JFK airport for our flight to SJU. As is our usual, we packed with the intent of checking no bags- this was an easy feat for such a short trip! Other than our backpacks we had just a small cooler bag the size of a personal item, which was stuffed with our mini-betty crocker, frozen shelf-stable CY milks (even though these bottles are 8oz, they can be taken past TSA as long as it’s solid frozen), and CY cheeses- we purchased the rest of our foodstuffs in Puerto Rico. We parked in an area with no ASP (in this neighborhood) and walked to the nearby Howard Beach AirTrain station for a free train ride to Terminal 5. TSA Precheck in Terminal 5 was a breeze, and within minutes we were at the gate. Since we had booked Blue Basic fare for 11,200 JetBlue points + $5.60 per person, we were not assigned seats at check-in, and headed to the gate agent for seat assignment- luckily for us they assigned us the exit row with extra legroom! The flight was uneventful, and after 4 hours we landed in SJU. I had previously checked Uber prices, and saw that prices ranged $7-$8 to get to Isla Verde, the residential area located just outside the airport. Unfortunately that was not the case when we got there, as several flights landed at the same time, and Uber instituted a price-surge, which raised the price to $35. The local taxi guys wanted $25 for the trip, which still seemed overpriced to me. After waiting for several minutes to see if Uber prices would come down, we started walking around the airport area, and noticed a parking garage nearby with a taxi stand. The prices there were slightly more reasonable at $16, and 6 minutes later we were checking into the Residence Inn by Marriott San Juan Isla Verde.
We had booked the Residence Inn due to its proximity to Chabad and the pricing for that week, which set us back 41.7k Chase Sapphire Reserve points (1.75cpp) + $147 in resort fees for our Thursday- Sunday stay. The resort benefits include $5/day in their snack shop and $17/day in their bar. We made sure to max out on those daily purchasing water bottles… The service at the hotel was great, as they are familiar with Shabbos needs, but the property itself was less than stellar. The rooms are all suites with kitchens, fairly large, and there’s a nice pool, as well as a kids wading pool with slides. On the downside, the entire building, excepting the lobby, has a strong mold smell (at least by my feminine standards- my husband wasn’t sure he smelled anything). On Thursday night I decided to give it a few hours to see if I could get used to the smell, but on Friday morning it was still bothering me, so we asked to change rooms. They readily agreed and while the second room might have been a degree or two better, overall I was still bothered by it.
After a lazy Friday morning, we walked to the nearby Pueblo supermarket and loaded up on buns, wraps, eggs, pizza sauce, smoked salmon, snacks, pareve cookies, ices, pareve ice cream, and potatoes of course, to make some delicious betty crocker potato kugel. Even though our cooking on the road doesn’t require a kitchen or an oven, having the counter space, sink, glasses, and the peace of mind that cooking is allowed in the space was a huge help.
At the zman on Friday we walked 5 minutes to the Chabad center for candlelighting and davening, followed by a beautiful and lively meal. See the eiruv map here. After the meal we walked around Isla Verde for a bit, a lively area, and then headed back to our hotel for a good night’s sleep. Shabbos morning the crowd was once again animated, buoyed by the fact that the Rebbetzin had given birth to a ? that morning- mazel tov! After the meal various board games were set up, and we had fun watching a team play an intense game of backgammon. We then headed to the beach, walked around Isla Verde some more, and walked along the airport perimeter to watch planes land and takeoff.
After the zman Motzei we took an Uber to Payless Car Rental at SJU airport, to retrieve a car for the remainder of our stay. The Uber to the airport this time was just $3.99, and was covered by my United rideshare credits. We had reserved a small vehicle with Payless in advance for $54.15 for 2 days, but upon arrival they notified us that they’re an offline location and don’t have a record of online reservations, and charged us $89.88 instead. Payless has since refunded us the $54.15 of the original reservation, and we disputed the remaining amount with Chase so that we’re only out $54.15 for this rental. We also paid for a toll transponder, since we were planning on driving out of the city and did not want to stop at toll booths. Once the car was in our possession we drove back to the Residence Inn and dropped it at a nearby lot for $8 for the night. Street parking is possible in some areas, but the likelihood of finding a spot is low.
Sunday morning we were up bright and early and headed to Old San Juan for our free walking tour. We dropped the car in a nearby lot for $5, and then proceeded into the Old City. The tour was good, and we especially appreciated how our guide explained local politics to us- it’s less about right and left and more about full independence vs US statehood. It was brutally hot and humid throughout, which put a damper on things (literally).






We opted not to visit the Bacardi rum factory for $40/pp, as my husband and I are not particular rum fans, and we didn’t feel it was worth the time or the money.
After our tour we walked around the Old City some more, before heading back to our car for what should have been a one hour drive to Ceiba, where we had a 3PM flight booked to Vieques. This flight was not bookable via Chase, so we paid $86.80/pp round-trip. Being Sunday, the roads were understandably fuller, but the fun started when we came across a group bicycling on the highway. They were not pros by any means, and the cops kept closing the road every 5 minutes to give them room. At 2:30PM we were still 15 minutes away from the airport, and with our ETA climbing I attempted to call Vieques AirLink to see what our options were to rebook, but there was no response. At 2:48PM we rolled into the ‘airport’- more of a parking lot with a small building- parked in the spot closest to the terminal door, and ran to the Vieques AirLink desk. The staff was a bit confused at our haste, and informed us that we still had 10 minutes before our flight boarded, so why the rush? The flight from Ceiba to Vieques took all of 10 minutes, and we landed at 3:10PM.



A word about Vieques: when planning our trip to Puerto Rico, we decided that experiencing a biobay was high on our list. The three best biobays worldwide are all located in Puerto Rico- #1 in Vieques, #2 in La Parguera, and #3 in Fajardo. Fajardo is the easiest to access from San Juan, but being the 3rd best we decided to aim for #1 or #2. Vieques is an island off the coast of Puerto Rico, so driving is not an option. The two ways to access the island are via ferry or via airplane. The ferry is bumpy and sells out fast, especially on Sunday. An additional downside is that the last ferry back barely allows for time to explore the earliest possible biobay tour after dark, so that wasn’t an option for us either. We spent some time exploring the possibility of driving to La Parguera, but decided that in lieu of the extra driving time we’d rather spend more $, and stay for a night in Vieques.
Keep in mind that biobays are best visited when there’s little to no moon, as the brightness of the moon reduces the brightness of the biobay. Being frum we didn’t have to think twice about the stages of the moon, and as Rosh Chodesh was a day prior to us leaving for this trip, we knew we would have dark skies.
Vieques is a small laid-back island, and many tourists get around by renting a UTV, which is about $60/day. Avis on the island has just one vehicle type available- a Jeep Wrangler, and with a $50 Avis coupon I’d previously earned bringing our total rental to just $40, we opted for that over a UTV. Prior to booking the vehicle I noticed that Avis closes early in the day, and since we were landing after 3PM, I inquired if pickup would be possible (they have a Whatsapp number and are highly responsive- my best Avis experience to date). They informed me that they’ll drop off the car at the airport parking lot for us and leave the keys with airline staff- what a breeze!


As soon as we exited the airport parking lot we noticed something interesting- multitudes of wild horses just roaming around. Turns out they’d been left by the Spanish, and have been multiplying ever since- today there are some 3,000 horses on the island.



Our experience of the island was a serene paradise. We checked into our hotel for the night, Club Vieques, booked using 23k Amex points (this hotel was not available on Chase), and then headed to Black Sand Beach. To get to the beach there’s a 10-minute (often muddy) trail, but it was blessedly deserted and beautiful.



After that we headed to Sun Bay Beach, where once again we had miles of beach to ourselves.



We watched crabs digging nests and wild horses attempting to overturn a garbage bin in order to snack on its contents…


After sunset, we headed across the road to meet up with our biobay tour operator, Alikei Adventures. All biobay tours utilize the same bay in Vieques, and while I can’t speak for other operators, this one was phenomenal! The drive to the biobay along the beach takes approximately 10 minutes, and it’s a bumpy ride.
Once at the bay we were assigned a kayak, and while it took my husband and I (mostly me…) a few minutes to get our bearings in the choppyish water, it was a blast. 15 minutes into the ride we were both sopping wet, and were wondering if that was all there was to it. Incredibly, over the next few minutes, as we headed further out, we started seeing little points of blue light, which got stronger and stronger as the minutes went by. Vieques has the brightest biobay in the world, and it’s getting stronger year by year. The experience of watching the water light up under our clear kayaks, and to see the otherworldly blue shine of the water each time we lifted our kayaks out, was extraordinary. The guide explained how and why the bay lights up, and encouraged us to touch the water. My favorite part of the night was dipping my hand in and watching little points of blue light explode across my fingers.
Cameras can’t capture the bioluminescence of the bay, so no photos… if you do attempt this trip I highly recommend wearing water shoes/sandals as everything in the kayak will get soaked.
After about an hour in the water we made our way back to shore, and headed to our hotel for the night. The next morning we headed for the Avis location to drop off our vehicle, and thinking we could arrive 10 minutes before departure again, took our sweet time lazying around. When the clerk asked us when our flight back was, as they were shuttling us back to the airport, and we informed them that it was in a mere 20 minutes, they panicked and rushed us to the airport. Apparently this Vieques Air Link desk is not as laid back as on the mainland, and when we made it to the airport at 10:19AM for our 10:30AM flight (no security check), the gate agent cautioned us that check-in is 15 minutes prior to take off, but since our pilot was running late, he’ll make an exception, and allowed us to proceed.
The flight back to the mainland was smooth, and due to balancing, I got to sit up front with the pilot.


After landing on the mainland we headed to El Yunque National Forest (pronounced El Junkay). We skipped the visitor center ($8/pp entry fee), and headed to the main road that cuts through the popular part of the park. The park was fairly packed, and it was hot and sunny throughout. Many of the trails were washed out in various hurricanes and storms, and are currently closed, although they are working on repairs.

We climbed atop Yokahu Tower for some nice views.



The forest is teeming with interesting and weird plants, if you take a deeper look.



At Juan Diego Falls we climbed up behind the main pool for a view of larger waterfalls. The climb was rather dangerous and slippery, and I would not do that again. We were also lucky enough to receive a $150 parking ticket for having parked in a spot that wasn’t strictly legal. How fun.


The last stop in the park was hiking up to Britton Tower. It was rather brutal in the heat, but the views and the cool crosswinds up top made it worth it.


We wore a bug patch for 24 hours prior to our visit to El Yunque, and did not experience a single bug throughout (we actually didn’t see or feel any mosquitos at all during our trip).
As we were driving back to San Juan, we stopped by a shop for some cold drinks, but interestingly basics like Schweppes & Gatorade were not labeled kosher, and are seemingly produced at a local plant.
Back in San Juan, we headed back to the Old City to walk around some more, and stopped at a juice shop for some cold refreshing freshly squeezed juice. The city was much cooler in the afternoon than it had been the previous day.




After getting our fill of Old San Juan, we headed to OMKRT, the only kosher restaurant in Puerto Rico. The food was delicious and filling, and feeling energized, we headed for the airport for our flight home.



Flying Blue Basic on a full flight, we were once again assigned the extra-legroom exit row seats free of charge.
Looking forward to writing my next trip report!
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Love your articles! Well written and informative. Thanks for sharing your travel expertise!