Plotting Puerto Rico — And Tips for Planning a Family Vacation

Since the beginning of September, Kavya’s had the whole house practicing Spanish as she does her dual-language Pre-K program. She’s picked up a remarkable amount in a short month — and she’s definitely faster at it than her mama, who took Spanish for five years in school and still can barely get by. So we decided it was time for some immersion.

We had a few specific criteria: not too far away (read: cheap tickets!), not too expensive (read: cheap tickets), yummy food, warm weather, and a Spanish-speaking culture that’s fun to explore. A beach and old school architecture? Bonus! With that wish list in place, it quickly became clear that we had one really solid option: Puerto Rico. And we wouldn’t even need our passports!

But here’s the thing with having family far away: as fun as it is to go visit, it usually means your holidays are not really vacations, but cozy, solid chunks of family time, spent baking cookies at home or doing crafts with the little ones, snuggling on the sofa while watching an old Bollywood film, or sharing stories.

That’s what happens twice a year — once in the summer and once in the winter, for three weeks to a month each time — when we go to visit Dadu and Dadi and Navreet and the little ones in California. It’s a critical time for Kavya — and now for Shaiyar — because it means they really get to bond with their grandparents and cousins, to feel at home with them as they do with Masi and Nanima and all here on the East Coast.

But it also means that we don’t get to take an adventure-y vacation anywhere else. We’ve been plotting Greece since before Kavya was born, and while we’ve snuck off to New Orleans (just Navdeep and I) and made a quick jaunt to San Diego (with Kavya, sans car!), the longest distance we’ve traveled of late has been to the dearly departed Revel in Atlantic City or Rockaway Beach in New York. Those are fun trips, certainly, but plotting a grander adventure takes strategy, time, and effort.

We’ve definitely done it before. Hawaii was a big, fat, fun-filled family trip — with eight adults and a little Kavya (then under two, so a free ticket!) hitting three islands in two weeks. It was an amazing experience, and also an exhausting once. We also planned a Thanksgiving weekend getaway to Disneyland over last Thanksgiving — when I was seven months pregnant. The Puerto Rico adventure will be a smaller trip — just about 10 days or so — and we’ve asked Dadu and Dadi to join us, so it will be a smaller party as well.

But as I’ve started working on booking it, there have been a few things we learned from the other trips that I’m keeping front of mind.

• -In Hawaii, we booked houses on two of the islands — with that many people, a kitchen is key, plus there were multiple bedrooms, which made for comfy sleeping arrangements while still presenting a cozy, family vibe. Definitely doing apartment rentals for this one, too. It’s cheaper, it’s more relaxed, there’s a kitchen. We want the comforts of home, even while we’re far, far away.
• Know your audience: not everyone wants the same experience out of any trip. On the Hawaii adventure, we had folks who wanted to sight-see, those who wanted to laze on the beach, and those who wanted to jump out of planes or take boats to see hot lava. Luckily, we were able to stagger things so everyone got to do a bit of what they wanted, but some sense of consensus is helpful! This time around, we’ve sort of managed that. Our aim: to chill. We want the beach, some sight-seeing, and lots of cozy family time.
• Know where you’re going! Research, read up, and narrow things down. Make a wishlist of places you hope to check out, but don’t get too attached. For a trip like this, where we’ll only have ten days, we decided to pick two places to stay in, and make one a base for exploring other areas. We’ve pinned down Old San Juan for the old school city adventure, and Rio Grande for a beachy keen time, with easy access to El Yunque rainforest and the biolumescent bays.
• Designate responsibilities. On our Hawaii trip, I booked pretty much everything, from coordinating flights, house rentals, car rentals, and even little day trips like the underwater scooter trip in Oahu. This was a) a lot of work b) difficult when something went wrong, because they all looked at me as the culprit. But as much as I say this: I tend to want to do everything myself. Then I have no one but myself to blame!
• Figure out the food. Again, a kitchen is key. But even if you don’t have one, stash some snacks and stock up on a few easy breakfast items, like fruit, bread and, if required caffeine (required). Set a schedule for mealtimes — whether you’re eating out, or cooking at home. Eat frequently! And if someone won’t function without a.m. coffee or chai (read: me), make sure they know how to get it without needing everyone else to tag along. For me, this means knowing where the nearest coffee shop is, but also bringing along chai-ka-saman so that I can make myself a cup whenever I need to. After all, we’re going to have those handy-dandy kitchens!
• Decide on downtime. It’s so easy to overpack a trip activity-wise, which can be rough on older adults, little kids, pregnant women, and just humans in general. You’re on vacation. If you don’t get to see Minnie Mouse or the open fire lava flows, it won’t be the end of the world. Take it easy. Sleep in. Enjoy!
• There will be some drama. It’s close quarters, you’re frequently hangry, it’s family. Expect a flare-up or two. But lots of fun moments, too.

I’m sure I’ll remember plenty of other goodies as I go about booking our latest adventure. What are your best tips for family trips? And have you been to Puerto Rico yet?