Clear As Mud

Puerto Rico

“Life is a series of choices of what hurts and what hurts worse”. I heard this phrase from Nicole Sachs who has an amazing podcast called “the cure for chronic pain” which I highly recommend! Anyway, 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 rather honest, practical, empowering and an amazing decision-making tool. 

For the last year, making any decision feels like you need a calculus degree, weighing every option is exhausting, the second guessing can make you crazy! I found that when I use the simple equation of what hurts vs what hurts worse, it really helps clarify things. 

This is the exact tool I used when my husband and I made the decision to take a family trip during COVID. Trust me, I second guessed it about a million times, but every time I asked myself the question “what hurts vs. what hurts worse” I always landed on the same answer. 

At the start of winter break we were just 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 literally panicked. So, without going into every detail, for our family what hurt worse was staying home full stop! Yes, traveling in these circumstances also hurts and comes with a lot of complicated and sticky situations but it was the better choice for our family. 

I am so grateful to have been able to do this and that it was even a choice for us, as I’m so aware that many aren’t in the position to do so!

That was an exceptionally long intro to me sharing about our family trip to Puerto Rico. 

We decided on Puerto Rico for a few reasons. 1. We needed sun, sand, and water desperately. 2. My husband had applied to renew his passport but there was no telling when it would arrive, so we needed to stay in America. 3. After Researching the COVID rules it seemed doable (more on that later as there were a few surprises). 4. The ability to order kosher food. I really was not in a place to go somewhere and have to worry about food. Just prepping and coordinating Zeesy’s food is hard enough (check out the post Glut-1 for Zeesy’s story). 5. Considering places for family vacations, the cost of flights/AirBNB were on the lower end. 

We also needed to make a quick stop on New York as it was my mother-in-law’s 10th Yartzait (anniversary of death) and all his 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. Got in some much needed praying at the Ohel (the Rebbes resting place ), visited my maternal Bubby (grandmother) from a distance for her safety, and we were off to Puerto Rico on Tuesday.

I’m going to give you a brief summary of what we did every day and my thoughts and recommendations. If this doesn’t interest you stop reading 🙂 

I always love and appreciate reading about people’s travel adventures, so I thought maybe you will too! 

Wednesday – We arrived at our AirBNB at 2:00 AM, till we got all the kids settled, it was about 3:00 AM so we had a late start later Wednesday morning. We were just a half a block from the beach, so we headed down for the afternoon. Got some boogie boards and sand toys and the day was made. I’m telling you there is something about the ocean that is so healing! But omg the sand 🤦‍♀️ quite the feet 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 mostly walked around and enjoyed the gorgeous views.

Thursday – We went horseback riding in the El Yunque Rain Forest. This might have been the highlight for me. Besides for the stunning views and my love for horses, the guides, Patrick and Oscar, were so amazing that they facilitated my 3-year-old Chana Laya (who’s never been on a horse before) to ride the trail on a horse by herself for over an hour! They put her on an old slow horse and had a guide right next to her. She was crying and upset in the beginning, and I was like “what am I doing?” I should just take her off and we’ll wait for the rest of the family. But Patrick said “don’t worry give it 10 min and you’ll see she will be fine”. I took a deep breath and decided to trust him. Literally at the 10 min mark, she calmed down. Not only was she calm, she rocked it and loved it and you can tell how proud she felt! Doesn’t get much better the that for a mom! It was also eye opening to see Menny connect to his horse on a deep level. He loved it so much he kept asking if we can do it again. Seeing how calming it was for him is definitely motivating me to find a way to incorporate some horse riding for him in Bozeman.

Next on the agenda was to go zip-lining which was only a few min away in the rainforest. We got all our gear on and it started to rain cats and dogs. We were in the rainforest after all…. we waited for a little while to see if it would calm down, but it showed no signs of doing so, so zip-lining was scrapped. 

I secretly can appreciate when things don’t go as planned, because it’s an opportunity to model flexibility, and hope that one day the kids are able to incorporate some of the tools we try to teach them 🤪

Friday/Shabbat – We were fortunate to be able to book a snorkeling experience even though it was Xmas. It was great, Zeesy really excelled at it, I loved seeing each kid connect to different activities. I really discovered new things about them. Before Shabbos we took a beautiful walk with more gorgeous views near the El Morro Palace. We had a cozy family Shabbos meal in our AirBNB, with the delicious food catered by the local Chabad Center. Shabbat morning, we spent praying and enjoying Shabbat lunch at Chabad where the rabbi and Rebbetzin (and their children) welcomed us warmly. They of course follow all the COVID protocols, but even masks and social distancing can’t take away the atmosphere of having a “home away from home”. 

Sunday – This is where we got a little caught off guard. We were informed that every Sunday since the pandemic, Puerto Rico goes into lockdown, meaning you can’t be outside unless you are going to the pharmacy or the grocery. No walks outside, no beaches, nothing. Being stuck inside in an AirBNB in a foreign place was not what I had envisioned… Thank G-d for my super creative husband, we found out that if you are staying at a hotel, anything on the hotel property is allowed including the pool. So, we booked a hotel room at a hotel down the block and we were able to spend the day at the pool. It turned out to be an awesome day, which I am extra grateful for, as it could’ve been super challenging…

Monday – it was our last day on the Island and we packed it in. We started off with surf lessons and ended the day parasailing. The kids did so awesome surfing; the water was quite rough, but they rocked it! Shoshana surfed for 2 hours straight and really mastered some great techniques. Chaya refused to participate in the beginning, but eventually felt comfortable to try. The first time out, the surfboard slammed her in the face, and she got quite the bloody nose. I thought that for sure she was done and would never surf again, but she surprised me by getting right back into the water, and I’m so glad she did, because she’s a real natural. After a quick shower and lunch break, we headed back out to end off our trip with parasailing. It’s not as scary as it looks, and it was pretty spectacular sitting up there with a 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 very important part of creating a cohesive family environment, and unforgettable memories. Some may view them as frivolous or luxurious or even a big Shlepp, but I have figured out, that for us this is a priority and something I will advocate for strongly. I wish I can say that we came home, and everyone is getting along beautifully and it’s all good, ha! That’s not the case. But it’s like putting investments in the bank and with time you make slow gains.

Adios till next time 😉



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Noah has cooked in a variety of kitchens and has studied many different cuisines, but his favorite meals to prepare are the ones that make his guests smile. Be it Thai, Italian, Caribbean or Latin, there is always a fun surprise waiting for you at meal time. Noah welcomes special requests and guests in his kitchen! Just stop by and say hi.

Yocheved Sidof is a social entrepreneur, psycho-mystical depth work facilitator, writer, educator, speaker, and activist. After a decade as a filmmaker and photographer, she founded Lamplighters Yeshivah, a grassroots, internationally acclaimed, progressive Chassidic Montessori school. Yocheved builds communities with healing at the center. Most recently, she founded Ohm’ek, an intentional collective focusing on meditation, embodied mysticism, and micro-retreats.

A lifelong learner, she’s completed extensive training in adaptive leadership, therapeutic coaching, and systemic change. She is currently in a two-year intensive training with Thomas Hubl, studying psycho-somatic-mystical models of healing personal, collective, and ancestral trauma. She also writes, consults, works 1:1 with clients, facilitates group transformational work, and regularly teaches Jewish spiritual studies.

Yocheved sits on boards supporting innovations in mental health awareness and self-transformation. She has studied Jewish mysticism and meditation extensively, including with Rav Katz since 2018, completing Elevation Teacher Training and sitting on his advisory board for over a year.

Yocheved, her husband, and five children live in Crown Heights, Brooklyn. Come say “Hi!” if you’re in the neighborhood.