Grand Cayman Family Travel Guide

Looking to travel with kids that actually feels like VACATION instead of just a TRIP? Then I’m going to share my absolute favorite travel destination with you: The Cayman Islands. I remember the first time I visited on a cruise stop back when I was a young girl and even though I only spent the day there, the Cayman magic took me. Fast forward twenty years, and my family and I just had an epic winter getaway in the Caymans that was so great we are already booking a return trip. So if you are looking for some fun in the sun that is PERFECT for Chicagoland families, check out my Grand Cayman Family Travel Guide.

Grand Cayman Family Travel Guide - Pool

First off, let’s get something out of the way. This was NOT a sponsored post. I go on tons of sponsored posts, and many of them are fantastic, but my hubby and I shelled out our hard-earned cash for this Grand Cayman trip and it was worth EVERY PENNY. Here’s why:

Grand Cayman Family Travel Guide - Cabana

The PERFECT Winter Escape

Let’s face it, just about all of us Chicagoans enjoy snow and chilly temperatures until the holidays pass and then we are DONE. Unfortunately Mother Nature doesn’t care what we have to say and keeps Chicago temperatures frigid until AT LEAST April. So treat yourself (and your family) to the perfect winter escape in the Cayman Islands.

Grand Cayman Family Travel Guide - Pool Bar

Not only is the temperature a balmy 80 degrees when it is in the teens in Chicago, but there are also direct flights from O’Hare so you can get to a tropical paradise in just under four hours. Or as you would tell your kids, one Disney movie and a couple of shows.

Grand Cayman Family Travel Guide - Pool Towel

Where to Stay

My husband and I did a ton of research when planning our trip to Grand Cayman, comparing prices and locations of resorts, asking friends and family who had traveled to the area—I even had a great talk with representatives from the Cayman Islands Tourism Board at the Chicago Travel and Adventure Show so I had as much information as possible not just planning our own personal vacation, but also in creating my Grand Cayman Family Travel Guide.

Grand Cayman Family Travel Guide - Hammock

Just about everyone we talked to recommended the Westin Grand Cayman and now that we stayed there for five days and four nights, I can see why. Not only is it a beautiful hotel with helpful staff and relaxing accommodations, but it is also SO incredibly family friendly. There are (complimentary) family friendly activities set up throughout the entire day and night, from crafts to a balloon artist station, a large fire pit set up for s’mores, outdoor movies, pool-side bingo and more!

Grand Cayman Family Travel Guide - Seven Mile Beach

With access to the large and pristine Seven Mile Beach off the pool area, the only problem you may encounter at the Westin Grand Cayman is deciding what to do because there are so many phenomenal choices, including water activities from Red Sail Sports, located on the Westin property.

Grand Cayman Family Travel Guide - Westin Resort

What to Do

Stingray City 

Grand Cayman is home of the world renown Stingray City, a group of 25 sandbars located off the shores of Grand Cayman where you can swim with, feed, and take memorable photos with majestic Southern Atlantic Stingrays. Since it is among the Cayman Islands’ most popular attractions, I highly recommend booking a “Breakfast with the Stingrays” cruise from Red Sail Sports so that you can be the FIRST boat at Stingray City in the morning. It’s absolutely surreal.

Grand Cayman Family Travel Guide - Stingray City

Worried that your kids will be afraid of the sting rays (they are most likely the same size)? No worries! Those who don’t want to get in the water with the stingrays can stay on board and still get an AMAZING view of the majestic creatures, especially since the marine experience is set in only in three feet of water. You can also hold your child while in the water since it is shallow enough for them to stay safe in your arms while stingrays brush up against your legs, not theirs.

Cayman Turtle Center

Both of my boys were brave enough to get in the water with the sting rays, but what my youngest REALLY wanted to do was see a sea turtle. So instead of simply snorkeling off Seven Mile Beach in hopes of coming across a sea turtle, we headed to the Cayman Turtle Center where we learned about and interacted with TONS of different turtles.

Grand Cayman Family Travel Guide - Turtle Center

The first animal encounter at The Green’s Breeding Pond will introduce you to Green Sea Turtles, some of the most ancient animals in the world. I couldn’t believe how large they were compared to the smaller yearlings in the Turtle Touch Tanks. But what really blew us away was the chance to snorkel in the Turtle Lagoon, which is filled with coral, turtles and other fish and birds. Since it was a controlled snorkeling environment with life guards on duty my kids were brave enough to swim independently and spent almost an hour snorkeling, which was one of the highlights of our entire trip.

Grand Cayman Family Travel Guide - Beach

Finally, a trip to the Cayman Turtle Center isn’t complete without enjoying the waterfalls and winding slide into Breaker’s Lagoon—one of the largest freshwater pools on the island—or spending some time at the Predator Reef (from behind glass, of course), Aviary, or Butterfly Garden.

Where to Eat

One of the best things about traveling with kids in Grand Cayman is that there are so many family-friendly dinner options. My only tip is to make early reservations not just because of the time change for us Chicagoans (they are an hour ahead of us), but also because your kids will be absolutely EXHAUSTED by the time dinner rolls around.

Grand Cayman Family Travel Guide - Sunshine Grill

For breakfast, Eats Café is a delicious dinner where you can get typical breakfast staples like pancakes and eggs, and it is conveniently located across the street from the Westin. Another fun outdoor restaurant for breakfast, lunch, or dinner at the Sunshine Grill located at the adjacent Sunshine Suits Resort. 

Grand Cayman Family Travel Guide - The Wharf

As for dinners out of the resort, we had a phenomenal meal at the Wharf Restaurant, an upscale outdoor restaurant where kids (and other diners) can help feed the tarpon that swim past your table at 9 p.m. While expensive and potentially considered to be “fine dining,” it is perfect for foodie families.

Grand Cayman Family Travel Guide - Relax

While this Grand Cayman Family Travel Guide might not have covered EVERYTHING on the island, it covered the information that families need to know when planning their escape to Grand Cayman. But if you think that I need to gather more information (wink, wink), let’s plan a trip down together so we can find out more information. You know—in the spirit of research, of course! 

For more travel-related tips, check out this list of destinations and travel hacks.

Grand Cayman Family Travel Guide - Pool

Happy Planning!


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  1. Tami Qualls says

    I do see my son getting anxious over the sting rays but that won’t stop us from visiting Grand Cayman. I know he’ll enjoy seeing the turtles and everything else there is to do.

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