Grand Cayman 2019 | Part One

Earlier this month, we headed out on our first vacation as a family of four! We wanted something beautiful and relaxing, so our favorite island was just the ticket.

Were we a little ambitious to book international travel with a high-maintenance, generally fussy baby? Yes. However, in between booking said travel and actually doing the traveling, Finn calmed down quite a bit, actually started napping, and became a much more amenable baby in general. He did great on our two-leg journey through Charlotte to Grand Cayman. Parker, as always, was our star traveler.

This was Parker's second time to Grand Cayman, my third, and Max's fourth. On the immigration form, there are special boxes for the number of previous visits: none, one, and 2+. I was stoked to move up to the 2+ and Parker got bumped up as well. (Side note, there is also a special box for marking your travel as a "dive vacation" which is what we did back in 2011 - we are so missing diving these days, but nothing compares to having excited kiddos in tow.) Upon landing, we walked over to pick up our mid-sized car and Max got settled in the right-hand drive seat. On our first visit together, we relied on taxis and the (somewhat sketchy, sporadic) bus system, however on our last trip we tried renting a vehicle and it was a total game changer for us. We loved the ability to go wherever, whenever. You just need a driver brave enough to tackle a right-sided vehicle, driving on the left, and more traffic circles than you can imagine (five minutes into last year's trip I changed my "maybe" attitude to "most definitely not" for getting behind the wheel there).

It was a quick ten minutes to get to our hotel on Seven Mile Beach. On our previous trips, we stayed at The Westin, but switched it up this year and tried The Kimpton Seafire. Spoiler alert: I'll never stay anywhere else! From literally the moment we pulled up, the service was over-the-top spectacular. The only thing I can compare it to was our honeymoon in Bora Bora. The Seafire is branded as a "luxury" resort and they really go all-out to get that feel. Check-in included complimentary bottled water and rosé, and greeting our kids with stingray stuffed animals. Over our time there, the helpful staff offered to set up pack-and-plays at the beach, gave restaurant recommendations, handed out complimentary popsicles at the pool, and greeted us by name. Not to mention that the actual resort was new, modern, and gorgeous. When we compared them later on in the week, the only area that The Westin won out in was their ground-level beachfront room that offered direct beach access (the Kimpton is more of a high rise set-up with the pool in between the hotel and beach). But as far as the actual room went, Kimpton still won that comparison hands-down (especially since we were upgraded to a suite, thank you business travel hotel points!).

This was the pull-out bed in the main "living area" or, what we referred to as Parker's room for the rest of the trip. Little Man was stoked to get his own room. Also, we were totally spoiled by all the space (our walk-in closet could have been a room of its own!).

We arrived in the afternoon, so after changing and freshening up we headed out to explore the property. It was a bit of a windy/rainy day, but still so beautiful!

Since we started our day in the wee morning hours (we had a 6AM flight out of Huntsville), we decided on an early dinner at the hotel's casual beach-front restaurant.

Our waiter promised us that they served the island's best ceviche and Piña Coladas, and he was so right. I literally ended up having some sort of ceviche every. single. day.

We all felt like this by early evening so we called it a night after dinner.

The next morning (our first full day!) we had the beach on our itinerary! But first up, hitting the complimentary coffee bar with my best helper.

We brought back up coffee for mama, tea for dada, and cereal from the hotel pantry for Parker. We started out each morning here on our balcony, and it was just the perfect way to greet each day.


On this day, the water was a bit choppy for Seven Mile Beach (you can see the seaweed all stirred up)  - however, choppy for Seven Mile Beach is pretty much calm and still for anywhere else.

After our morning at the beach, we drove over to our favorite restaurant, Macabuca at The Cracked Conch. It's a casual, outdoor restaurant right on the water. Max always orders the cracked conch sandwich here - I switched it up and got the island lobster sandwich this time which was equally as yummy, and Parker chose the local Fish and Chips.

Next up was the grocery store! We wanted some snack items to bring on the boat the next day, and some breakfast items to keep in the hotel room for Parker. We picked up a passionfruit as well as some local lychee to try, plus some drinks and snacks that aren't widely found in the U.S. Oh, and milk. Always milk for Parker!

When we returned to the hotel, we let Finn get a good nap in his crib, and Parker and I went on search for the life-size chess set on the property. Unfortunately, we found out that it was damaged and being repaired, and we were instead given a regular set to take with us (I told you the customer service was impeccable!). Parker and I took it back to Coccoloba and played while enjoying blended drinks (a Mudslide for me, some sort of coconut, banana, cream, and chocolate concoction for him).

Finn was still sleeping when we got back to our room, so we took the opportunity to dig into some of our grocery store finds.

Dinner that night was The Brasserie in Georgetown (a ten minute drive from the hotel). Our waiter from the night before recommended it to us. It was the only restaurant on our list that wasn't on the water, so since it was a rainy night, we decided it was the perfect time to try it. Max got the local swordfish (fantastic), and I ordered the local snapper (also delicious). Max proclaimed this the best restaurant of the trip. The staff was also super friendly, especially to Parker. The hostess literally took him around the restaurant at one point and he also got in a game of chess with one of the busboys.

Finn was still getting up twice a night to nurse, and I snapped this photo of Parker after one of the sessions.

The next morning, he was up bright and early and super excited because it was Stingray City day!

But first, breakfast.

And, a morning at the pool. Parker practiced his snorkeling in preparation for our boat trip.

After a poolside lunch, we headed out to catch our boat! We did Red Sail's Ecotour which had stops at Stingray City, the Rum Point Reef, and Starfish Point.

That night, Coccoloba (Seafire's casual beachfront restaurant) had Taco Tuesday Night which we were told was not to be missed! We enjoyed live music, plus specialty margaritas (mine was watermelon) and the best tacos. 

Just looking at the photos has me feeling so happy and relaxed! More to come in Part 2...

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