11 Reasons Why We're Booking Our Trip to the Cayman Islands This Winter Break

Raise your hand if you’re already over this cold weather! Okay, now that we’re all in agreement, we can start dreaming of a winter break where we no longer have to squeeze kids into fifteen layers of clothing before heading out the door. While ski cabins and Vermont diners can be fun, I can tell you that a few days of real sunshine will put you in an infinitely better mood.

If you’re looking to swap snowballs for sandcastles this winter, I’d like to introduce you to the heaven that is the Cayman Islands. The second you get off the plane, the warmth hits you instantly. Yes, WARMTH. Remember that? It’s wonderful. Plus, all of the locals are incredibly friendly, shake your hand, and are interesting to talk to, which was a welcomed change of pace for someone like me who comes from NYC, where we all mind our own business and move at super speed.

And once you leave the airport (yes, there’s more!), you’ll be welcomed into an oasis where your only job is to relax (and you know, parent and keep your tiny humans alive, but you get it). From the laidback beachside restaurants to fun water activities, the Cayman Islands make for a truly unforgettable family vacation. And if you don’t believe me, American Express Travel can back me up, as they listed the Cayman Islands as one of the trending destinations for 2020.

Still need more motivating? All of my best recommendations for family-friendly fun in the Caymans are below.

Where to Stay

If you’re traveling as a family, I think it’s 100 percent worth it to grab a place on the beach. Being able to walk out the back door and onto the sand will save you so much stress and packing-of-cars.

AirBnB is an option here, if you’d prefer the privacy and space. But in my opinion, if you’re coming for a relaxing time, it’s nice to take advantage of the perks of being in a hotel…like not making the bed.

There are a ton of oceanside hotels to choose from in the Cayman Islands, including Palm Heights, Grand Cayman Marriot Beach Resort, with a favorite being Kimpton Seafire Resort + Spa. Not only is the Kimpton Seafire Resort + Spa stunning in its modern design and palm tree-lined pathways, it also has a variety of activities and accommodations specifically set up for kids. They even have a kid section of the pool (which has a view of the ocean) that has water sprinklers and kid-sized cabanas.

Camp Seafire is the hotel’s daily program for kids, which includes their own popcorn check-in station, a kids’ corner that serves chocolate milk in the morning, and an itinerary of activities with a new theme each day. And, while the kids are occupied, I’m just gonna throw it out there that there’s a spa right downstairs…

For more family fun at the Kimpston Seafire, the resort also has a “glamping” experience for your hotel room for an additional fee, that decks out your hotel room with a tent, plush toys, books, and more. How fun is that? And bonus, if you’re an American Express Platinum Card Member, you get a bunch of amenities like 4p.m. check-out and complimentary breakfast.

Where to Eat & Drink


Kaibo is located in Rum Point and is literally right on the beach. Grab a picnic table outside, smoosh your toes in the white sand, and enjoy their fresh, simple, and local menu options. Everyone here is wearing jean shorts or beach cover-ups and here for a chill time.


If you decide to stay at the Kimpton Seafire Resort + Spa (or even if you don’t!), you have to try their beachfront restaurant, Coccoloba. This spot features a mashup of Cayman Island and Mexico influences, and is an easy spot to hang out with kids. The food is both adult- and kid-friendly, with my personal faves being the elote corn, ceviche, and fish tacos. And when the kids inevitably get restless waiting for the food to come, you can take two steps down and play on the beach or make a game of spotting their pet cats and rooster.

Cracked Conch

You’ll come for fresh seafood, but stay for the string lights and ocean views. Cracked Conch has both indoor and outdoor seating, but sitting on the back deck is well worth it. They masterfully create an intimate, cozy atmosphere that will make you want to sit there all night (or well, as long as the kids can last before a tantrum hits). We also had a great time watching the night divers swim in from the ocean off the deck.

What to Do

Get Out on the Water

Snorkeling, kayaking, petting stingrays…the Cayman Islands have it all!

Perhaps what they’re best known for is Stingray City, a series of shallow sandbars frequented by stingrays. It’s said that the stingrays gravitated there decades ago when fisherman returned from an excursion and cleaned their fish in the shallow water. Now, it’s a tourist attraction where visitors can get up close and personal with the sea life. Note that it can get crowded out there with multiple tour groups, but kissing a stingray is supposed to give you seven years of good luck…so you decide if it’s worth it!

Along the barrier reef are other spots to scope out sea creatures, too, while snorkeling. If your kiddos are old enough (the recommended age is 6 and up), they will be endlessly fascinated by the beautifully colored fish, stingrays, coral, and maybe even a nurse shark!

I’d recommend Big Lex Charters, a private boat tour that you can customize yourself. The boat comes equipped with most everything you need for the excursion, including a waterproof camera to take cool photos of you and your kids underwater (hello, Instagram likes!). They’ll also make fresh ceviche using locally sourced ingredients right on the boat. And I’d be remiss not to mention that Captain Lex and his crew are so friendly and a blast to spend a day at sea with.

Starfish Point Beach

If you’re in the area, Starfish Point, which is located on the north side of Grand Cayman, makes a great stop for you and your family. The beach has shallow, clear water and is populated with starfish. Your kids will love to scope out and touch real starfish in the ocean (just be sure not to lift them out of the water). It’s like taking an aquarium visit to the next level.

Rum Point Beach

Also located on the north side of the island, Rum Point is a quaint spot with hammocks held up by palm trees, a restaurant with outdoor picnic tables, and the best mudslides you’ll ever have. Seriously, they’re SO delicious.

And after sipping on that refreshing cocktail, you and/or your kids can get their hair braided at one of the vendors, do some shopping, play volleyball on the beach, or relax on the white sand. It’s the perfect low-key spot to spend an afternoon.

Beach Day

Let’s be real, we’re all really here for the beach. When your visiting the Cayman Islands, be sure to schedule in a full beach day for the fam. If you do stay at a beachfront place, I’d recommend parking yourselves right outside that establishment and take in those rays. That way, you can run back up to your room whenever you need and you’ll get more time to actually relax. If you do end up staying at the Kimpton Seafire, you can get your own beach chairs and umbrellas and order food and drinks right from the beach.

Sea Turtles

While I was there, we were lucky enough to catch the Cayman Turtle Centre release sea turtles into the ocean, which was so cool to be a part of. Their annual release happens in November, so if you happen to be taking your trip during that month, check it out!

Local Celebrations and Activities

The Cayman islanders are really into their local events and celebrations. They partake in Barbecue Mondays and happy hours, and also put on the Batabano Carnival, a Christmas boat parade, food and art festivals, and a thing called Pirate Week. If your vacation lands on one of these festivities, join in!

Now if you’ll excuse me, I need to go start drafting my out of office email.

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