Grand Cayman Travel Guide
March 4, 2022

As I am sitting here typing out our Grand Cayman travel guide, I want to go give Matt another high five for successfully completing our first trip with two kiddos. I have learned (thanks to you all) that traveling with kids is now called a trip and when you leave the kids behind, that is a vacation! As wild, fun, exhausting and all the in between as this trip was, I would do it all over again in a heartbeat. We heard such great things about Grand Cayman, especially how kid friendly it was, and it didn’t disappoint.

I will work on a separate blog post about traveling with kids, as I saw lots of questions roll in, so stay tuned for that! We were lucky to catch a direct flight out of Newark, NJ making the flight just around 3.5 hours which was more manageable.

Covid Testing:

I was hesitant to even add this since it is ever changing, so just make sure to do your own research before going! To go to Grand Cayman, Matt and I had to test within 24hr before our flight (certified rapid test is acceptable). We also had to fill out and print off certificate to travel declarations for the Cayman Islands for all FOUR of us. Matt filled these out several weeks before going and was able to print them instantly (meaning if you satisfy the requirements, you will instantly get the declaration, there is no prolonged approval process). You do need to be vaccinated to go (if over 5) and you must upload your vaccination status to the web portal. Overall, everything was very straight forward and easy.

For returning home to the US, Matt, Logan and I all had to test within the same 24hr timeframe. We called a few places and the Marriott ended up offering testing the morning of our flight. It was right next door where we were staying and the most convenient so we did that since we had an afternoon flight. We were in and out with our results all within 15 minutes. Just make sure you book and pay ahead of time!

Where We Stayed:

The burning question you all are waiting for!…

Our friends actually got married in Grand Cayman and since then go back almost every year and now have two kids they bring with them. They started staying at this hidden gem called South Bay Beach Club (we were villa #34), which are a bunch of owned villas/condos in which some owners rent out. Matt and I always say that to make a trip more enjoyable for us, AirBNB is always the best option. This was similar to an AirBNB, but better as it provided a few more amenities (management on property Monday – Friday, your condo was cleaned each day, they could help organize activities and groceries, etc.). Maggie, the property manager, oversees everything, so we chatted with her a bunch and sent our grocery list directly to her. But, keep in mind, the property still doesn’t have the full amenities of a hotel (no restaurants, room service, etc). The amenities it does have though, outweighed those lost via hotel life for us personally. The boys were able to have their own bedroom and they provided us with two cribs. While their rooms had darker curtains, I brought two blackout shades to make it extra dark…one for each room worked perfect. We also had a full size kitchen (we did all breakfasts at home), huge outdoor space and washer and dryer, which allowed to cut down on packing (I brought a travel size laundry detergent in my checked back). I saved a “villa tour” in my Grand Cayman Highlight on Instagram.

South Bay Beach Club also has it’s own pool and was directly on the beach (it is the building in the picture above). It was also situated right next to (maybe 20 steps away) from the Marriott, so it was honestly the best of both worlds. If we wanted a quick bite, a fancy drink (their mudslides are the BEST), etc. we just popped over there. We actually ended up doing a few of our meals over there because it was just easy and Logan could even swim in that pool white we hung out there! I will also say for you Marriott/Bonvoy fans, it is a pretty nice one (I think it is a category 7 for point redeemers and we learned it was once the number one Marriott property for redeeming points). Logan also spent a TON of time searching for turtles and lizards in their back courtyard area. We will 110% stay here again every time we visit, it was just so easy and practical!

What We Did:

Before I jump in, I will say getting around was probably the most expensive part of this trip. Taxis come within 10 seconds of calling them which was amazing, but the cost to go anywhere was a lot. We did not rent a car (you drive on the opposite side of the road, fyi) and after talking to a family that did, I think we ended up spending around the same amount on cabs or maybe a little less. I should also note that the whole Island is generally expensive — it has been awhile since we traveled to other islands, but I think with the exchange rate, Grand Cayman is definitely on the more expensive side compared to other islands (but don’t quote me on that!)

Hands down, my favorite activity was renting a boat through Sail With Friends and heading over to Sting Ray City and Starfish Cove. Pat and Alice own and run the company and are the absolute sweetest Irish couple with the best hospitality! We did the half day charter which was perfect for our little crew. They took a pause/hit during Covid and were so excited to finally be able to get back out on the water again. Not only did they show us around, they helped with Landon, entertained Logan and surprised us with treats while sailing (fresh fruit, pizza ocean side and local beers).

Camana Bay was a quick (and easy) walk from where we were staying. There is a big splash pad for the kids to play in, tree lined area with shade (perfect for feeding Landon) and lots of restaurants/shiopping and yummy gelato! A cute area to walk around and unwind. We ate lunch outside at Auga which was delicious.

Cayman Turtle Center was one of the most suggested activities from you all so we decided to check it out. To be honest, in the beginning I was a bit underwhelmed for the price (although both Logan + Landon were free which was a bonus) as we weren’t seeing any animals and a few of the areas were closed. However, when we got to where Logan could touch the turtles, that was a big hit along with the water slide and swimming area! If we never made it here I wouldn’t feel like I missed out on anything, but it was an overcast morning so ended up being a good activity.

Where We Ate:

Tillies – This restaurant is within the Palm Heights and Matt and I both said if we ever came back without kids (although I truly think I would always bring the kids to Grand Cayman, just perfect for a family) we would stay at this beautiful boutique style hotel…we saw Katie Holmes staying here 🙂 The decor and layout is absolutely stunning and Tillies was a great spot nestled right on the beach to grab lunch for our crew. Logan played in the sand and ocean, while I hung out on the couch with Landon in the shade. Food was incredible and drinks delicious!

The Wharf – We grabbed dinner here one night and the big fish that swim up were the perfect entertainment for Logan. Apparently they feed them every night at 7:30pm, we just always eat early with the kids so missed that. Also, I have to give a big shoutout to the waiters who pushed Landon in the stroller while he was fussing so I could eat my dinner. It was the sweetest gesture. Food was fresh and amazing. This is actually where our friends got married!

Coccoloba – One of the best nights was spent here! Tuesdays are tacos and tequila night ($5 tacos // $8 margs) so clearly we choose wisely and went this night. They had live music which Logan LOVED, a tequila competition and the most beautiful sunset as this bar and grill is located right on the beach. It is within the Kimpton hotel, which is beautiful and a great family-friendly option if you are wanting a hotel when you visit.

Sunshine Grill – So many of you recommended this spot for their fish taco! We stopped here after the turtle center to grab lunch. They had a pool Logan quickly hopped in to swim and Matt and I both got the fish tacos, which were so yummy.

Ms. Piper’s Kitchen + Grill – The CUTEST spot right in the “backyard” of where we were staying. The vibe/decor is spot on, food is incredible, and they typically have live music at night. We came here on our last night for the perfect relaxing end to the trip. They also have a big outdoor bar area if you are just wanting to grab a drink.

Calypso – As we were walking in, one gentleman we were chatting with told us this is his favorite spot on the island. It was his first night back and he wasted no time dining here again. This was the furthest drive we did, but worth it! Highly recommend going off the “chef’s recommendations” board when you order and the watermelon mojito was delish! I forgot to snap a pic, so here is what I wore that night!

Veranda – We clocked in a lot of meals here as it was the Marriotts outdoor casual restaurant. The food did not disappoint and was just simple and easy with staying next door.

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