“Life is a series of choices of what hurts and what hurts worse.” I heard this phrase from Nicole Sachs, who hosts an amazing podcast called The Cure for Chronic Pain, which I highly recommend! When I first heard this statement, my initial thought was, “Well, that’s depressing.” But after sitting with it for a while, I realized that it’s not depressing at all. It’s actually an honest, practical, and empowering decision-making tool.
Over the past year, making any decision has felt as complex as needing a calculus degree. Weighing every option is exhausting, and the second-guessing can drive you crazy! I’ve found that using the simple equation of what hurts versus what hurts worse really helps clarify things.
This was exactly the tool I used when my husband and I decided to take a family trip during COVID. Trust me, I second-guessed that decision about a million times, but every time I asked myself, “What hurts versus what hurts worse?” I always landed on the same answer.
At the start of winter break, we were coming off many weeks of the kids being home due to school closures. It was hard, to say the least. Every time I thought about winter break and all the kids being home again for weeks on end, with not much to keep us busy, I panicked. So, without going into every detail, staying home would have hurt worse for our family—full stop! Yes, traveling under these circumstances also hurt and came with a lot of complicated and sticky situations, but it was the better choice for us.
I am so grateful we were able to make this choice, and I’m fully aware that many others are not in the same position.
That was an exceptionally long introduction to sharing our family trip to Puerto Rico!
We chose Puerto Rico for a few reasons:
1. We desperately needed sun, sand, and water.
2. My husband had applied to renew his passport, but there was no telling when it would arrive, so we needed to stay within the United States.
3. After researching the COVID rules, it seemed doable (more on that later, as there were a few surprises).
4. We could order kosher food. I was not in a place to travel somewhere where I’d have to worry about food. Just prepping and coordinating Zeesy’s meals is hard enough (check out the post Glut-1 for Zeesy’s story).
5. Considering places for family vacations, the cost of flights and Airbnbs were on the lower end.
We also needed to make a quick stop in New York, as it was my mother-in-law’s 10th yahrzeit (anniversary of her passing), and all of my husband’s siblings were gathering to visit her resting place.
We landed in New York late Sunday night. We spent a day and a half enjoying some good kosher food—ice cream, sushi, you know, all the important stuff. We managed to get in some much-needed praying at the Ohel (the Rebbe’s resting place), visited my maternal Bubby (grandmother) from a distance for her safety, and then we were off to Puerto Rico on Tuesday.



I’m going to give you a brief summary of what we did each day, along with my thoughts and recommendations. If this doesn’t interest you, feel free to stop reading! I always love and appreciate reading about people’s travel adventures, so I thought maybe you would too.
Wednesday - We arrived at our Airbnb at 2:00 AM. By the time we got all the kids settled, it was around 3:00 AM, so we had a late start on Wednesday morning. We were just half a block from the beach, so we headed down there for the afternoon. We got some boogie boards and sand toys, and that was all we needed for the day. I’m telling you, there’s something about the ocean that is so healing! But oh my gosh, the sand. It was quite the feat getting everyone showered and “de-beached.” Yes I made that word up, but come on—it’s a good one.








After everyone was showered, we went to Old San Juan to do a little exploring. We walked around and enjoyed the gorgeous views.


Thursday – We went horseback riding in the El Yunque Rain Forest, and this might have been the highlight of the trip for me. Besides the stunning views and my love for horses, the guides, Patrick and Oscar, were amazing. They managed to help my 3-year-old, Chana Laya, who had never been on a horse before, ride the trail on her own for over an hour! They put her on an old, slow horse and had a guide right next to her. At first, she was crying and upset, and I was thinking, “What am I doing?” I considered taking her off and waiting for the rest of the family. But Patrick reassured me: “Don’t worry; give it 10 minutes, and you’ll see she’ll be fine.” I took a deep breath and decided to trust him. Sure enough, at the 10-minute mark, she calmed down. Not only did she calm down, but she also rocked it, loved it, and you could see how proud she felt! It doesn’t get much better than that for a mom.
It was also eye-opening to see Menny connect with his horse on a deep level. He loved the experience so much that he kept asking if we could do it again. Seeing how calming it was for him is definitely motivating me to find a way to incorporate horseback riding into his life back in Bozeman.



Next on the agenda was zip-lining, which was just a few minutes away in the rainforest. We got all of our gear on, and then it started to rain cats and dogs. We were in the rainforest, after all... We waited for a bit to see if the rain would calm down, but it showed no signs of stopping, so zip-lining was scrapped.
I secretly appreciate when things don’t go as planned because it’s an opportunity to model flexibility and hope that, one day, the kids will be able to incorporate some of the tools we try to teach them.
Friday/Shabbat – We were fortunate to book a snorkeling experience even though it was Xmas. It was fantastic, and Zeesy really excelled at it. I loved seeing each of the kids connect with different activities and discovering new things about them. Before Shabbat, we took a beautiful walk with more gorgeous views near El Morro Palace.
We had a cozy family Shabbat meal in our Airbnb, with delicious food catered by the local Chabad Center. On Shabbat morning, we spent time praying and enjoyed Shabbat lunch at Chabad, where the rabbi, Rebbetzin, and their children welcomed us warmly. They, of course, followed all the COVID protocols, but even masks and social distancing couldn’t take away from the feeling of having a “home away from home.”





Sunday – This is where we got a little caught off guard. We found out that, since the pandemic began, Puerto Rico goes into lockdown every Sunday. This means you can’t be outside unless you’re going to the pharmacy or grocery store. No walks, no beaches, nothing. Being stuck inside an Airbnb in a foreign place was not what I had envisioned…
Thank G-d for my super creative husband! We discovered that if you’re staying at a hotel, you’re allowed to use any facilities on the hotel property, including the pool. So, we quickly booked a hotel room at a place down the block and spent the day at the pool. It turned out to be an awesome day, for which I’m especially grateful, as it could have been super challenging otherwise.




Monday – It was our last day on the island, and we packed in as much as we could. We started off with surf lessons and ended the day parasailing. The kids did an amazing job surfing; the water was quite rough, but they handled it like pros! Shoshana surfed for two hours straight and really mastered some impressive techniques. Chaya initially refused to participate, but eventually felt comfortable enough to give it a try. On her first attempt, the surfboard slammed into her face, giving her a bloody nose. I thought for sure she’d be done and wouldn’t want to surf again, but she surprised me by getting right back into the water. I’m so glad she did because she turned out to be a real natural.
After a quick shower and lunch break, we headed out for our final adventure: parasailing. It’s not as scary as it looks, and it was pretty spectacular to sit up there, taking in the vast view of the ocean.









All good things come to an end, and we had to pack up and get ready for our 12-hour trip home the next morning.


For my family, trips are a vital part of creating a cohesive family environment and making unforgettable memories. Some may view them as frivolous, luxurious, or even a big shlep, but I’ve realized that for us, this is a priority—something I will advocate for strongly. I wish I could say we came home and everyone is getting along beautifully and that it’s all good, ha! But that’s not the case. It’s more like making investments in the bank; with time, you see slow gains.
Adios until next time!