Back in August 2014, our family got in on an amazing mistake fare between our home airport of Cleveland and Grand Cayman for under $200 per person. While we had to work quick to secure the flights, it made out summer 2015 travel plans an easy and quick decision.

As the months got closer, we secured some amazing deals on hotels, as well as rental vehicle, which we will get more into later.

Flights

Perhaps the most unnerving aspect of travel for any parent is the process of flying. Between waking kids up earlier than normal, and dealing with an onslaught of people at all points of the airport adventure, flying can surely be a major trial for parents.

It is amazing how when your kid starts to throw a little cry, people immediately say things like “I hope I’m not sitting next to that kid” or when you try and walk your child around to get them to stop crying, and get told to “shut up.”

Traveling with kids is always an adventure, and it is quite amazing the amount of people that feel compelled to not have any compassion for parents that are working it and trying to alleviate any situations that arise.

Travel is not always pretty, and certainly not with kids in small, cramped spaces. However, our 6, 4, and 2 year old did an amazing job on both flights coming down with minimal instances. As a parent, we certainly could not have asked for a better travel day.

Upon our arrival to the island, it is always amazing to see a one runway airport where guests depart via rollaway stairs into a small little airport. Though truth be told, this is our families first international travel experience, and first time experiencing small airports outside of the U.S.

Rental Car

We had secured a reservation for a mini SUV with Budget rental car months in advance of the trip. The original reservation was in the $450 range for 9 days of rental. After inputting the data into AutoSlash, our reservation had been rebooked several times, bringing the cost down to $266.

However, after realizing we forgot our travel booster seats at home, adding two boosters and a car seat quickly shot the booking up to over $500, plus guests are required to get a $25 permit license to drive.

The sticker shock only starts there, as you quickly realize that driving in Grand Cayman is nothing like in the U.S., since you drive on the opposite side of the road. Seeing as we had never done so before, it was quite the surreal experience and takes some getting used to for sure.

Hotels

We really tossed around a lot of ideas where to stay when in Grand Cayman. First, we had some US Bank points we had been sitting on for several years, and needed to use them. So we booked two nights at one of the better rated hotels on the island, the Comfort Suites, which we will be staying at later in the trip.

For the rest of the trip, we decided to book the Holiday Inn, as we were able to secure a great rate of around $100 per night. We also had hopes, which really worked out well, that our Platinum status would get us an upgrade.

Upon arrival, we were given the option of an upgraded suite, with not that good of a view. However, when we got into the room, we were REALLY impressed, as the room had a large kitchen, dining room, seating area with sleeper sofa, king bedroom, double sink large bathroom, and a balcony overlooking the ocean.

Really, the Holiday Inn Grand Cayman is probably one of the nicer hotels we have stayed in, and a true bargain at only around $100 per night by Grand Cayman standards.

Following checking into the hotel, we elected to drive down to the Georgetown area and visit Margaritaville. We had heard they had a pool and slide, so we went well prepared with bathing suits and towels.

What an experience! We had the whole place practically to ourselves, the food was fantastic, though service was rather terrible, and we all spent several hours using the pool and slide.

After a short stop at the grocery store to stock our fridge, we were back at the hotel discussing what an amazing time we had already on Grand Cayman.