Our Incredible Grand Cayman Family Vacation Itinerary

Today, my daughter and I leave for our very first Grand Cayman vacation. Our mission is to see first-hand why the Cayman Islands are regarded as the world’s friendliest islands and one of the best destinations for family travel. We’re guests of the Cayman Islands Department of Tourism.

Diving into the planning process revealed much more than crystal clear blue water. Things to do in Grand Cayman include bucket list experiences for us from riding swimming ponies bareback to kayaking bioluminescent bays. And, that’s just the beginning as our itinerary will reveal.

Day 1: Travel and Check-In

We found a great set of flights on American Airlines that departs San Diego in the morning and lands in Grand Cayman in the evening. Yes, it does take a full day to get to the Caribbean from the West Coast but it’s always so worth it.

We’ll check into The Ritz-Carlton, Grand Cayman located right on Seven Mile Beach. Needless to say, it looks like a fantastic luxury hotel with a ton of offerings including a kids’ water park, two pools and an oceanfront jacuzzi, a nine-hole golf course, onsite water sports, five restaurants, a spa with la prairie treatments and two resident cats.

Day 2: Swimming Ponies and Swimming with Turtles

We’ve been swimming with pigs, but now we’re swimming with ponies. Yes, Pampered Ponies actually love to swim! We’ll ride along the white sand and then switch to riding bareback as the horses lead us into the water. You can see how they swim starting at about the 3 minute mark.

After a quick lunch at Macabuca Tiki Bar and Grill, a cool oceanfront tiki bar, we’re off to Cayman Turtle Farm.

Day 3: Stingray City and Bioluminescent Bays

We’ll board a luxury catamaran at The Ritz-Carlton with Red Sail Sports destined for Stingray City. It’s a sandbar with waters about 3-4′ deep where you can stand and snorkel with stingrays. The tour also takes guests to another spot with colorful tropical fish. I’ll document the underwater experience with my GoPro.

After that, a rest at the hotel is in order because we’ll be up late on a bioluminescent bay tour with Cayman Kayaks. Millions of bright little sparkles will light up the ocean with each paddle stroke. To get there, we’ll leave the hotel early to tour the eastern side of the island and sample Caribbean fare at Rum Point Club along the way.

Day 4: Underwater Photography Snorkel

Our morning will be spent exploring the hotel and Seven Mile Beach at leisure.

We can’t wait for the afternoon underwater photography tour, a program that is part of The Ritz-Carlton’s partnership with Jean-Michel Cousteau’s Ambassadors of the Environment. Trained naturalists give guests an opportunity to learn more about the natural and cultural environment surrounding hotels all over the world. I’m a huge fan of edutainment and can’t wait to see what it’s like.

Our final dinner will be at Lobster Pot, a family owned and operated waterfront restaurant specializing in seafood.

Day 5: Beach Time and Grand Cayman Departure

Another relaxed morning at the hotel is followed by an afternoon flight. We land a day before school starts for the year. What a way to end the summer!

I must also lob in a big thank-you-in-advance to Majestic Tours, our drivers on this trip. I suspect they’ll be fantastic for people like me who aren’t totally comfortable driving on the left (despite having lived in Hong Kong and London).

Be sure to follow us on Instagram where I’ll be sharing tons of photos. Also, check out the hashtag #CaymanKind for more crystal clear blue waters and photos that will have you booking a Cayman Islands holiday in no time. You can also read about things to do in Grand Cayman with kids.

Have you been to Grand Cayman?