Mom Bloggers on Their Top Family Travel Memories in the Caribbean

Mom Bloggers on Their Top Family Travel Memories in the Caribbean

Top Travel Memories

Traveling as a family may seem like a daunting task, but the memories you’ll make on your adventures around the world are more than worth the effort.

Take it from these top mom bloggers who brought the kids along for family vacations near and far. The experiences you share on a trip to a new place are irreplaceable and bond you as a family forever.

Read on for the top family memories and travel tips from bloggers who have explored the Caribbean and Mexico with the whole clan in tow!


Courtesy of Luxury Travel Mom

Connecting With Locals

“When we were visiting Curtain Bluff in Antigua recently, all of the kids on the property started playing soccer together every night, just a random pick up game in the scrubby grass.

After watching this for a few nights, the resort bartender asked them if they would want to play against a local team, all the kids were thrilled with that idea. So the game was set up, just across the street at a local field. Dozens of locals came to watch. The other team arrived with shin guards and cleats, our kids were in swimsuits, a few were barefoot.

Sensing the imbalance, the other team gave us a goalie and loaned some kids shoes. From the sounds of the crowd, you would think they were watching the World Cupso much joyful hooting and hollering!

Not surprisingly, we lost, but not by much. The game was both fair and fun; everyone just wanted to have a good time, and afterward, they all took photos together. I’m not sure we have ever been on a vacation before or since where we felt so included in the local culture.”

Kim-Marie Evans of Luxury Travel Mom


Photo by Sage & Sea Co.

Me-Time for Mom and Dad

“A family vacation is often just a getaway for the kids, leaving mom and dad to run through the daily grind, merely from a different (albeit beautiful) location. It’s so important that parents have downtime, too, so I suggest looking for resorts with reputable kids’ programs.

Be aware that not all resorts take babies and toddlers, so if you have kids under the age of four, do your homework to ensure there’s a kids’ club that’s appropriate.

Two excellent examples of Caribbean and Mexican resorts that are guaranteed to give parents time to play on their own are Beaches Turks & Caicos and Club Med Punta Cana, both of which have expert caregivers and interactive programming geared toward specific age groups.

What will do you with all that free time? Take advantage of included scuba diving at Beaches Resorts or trapeze lessons just for grownups at Club Med—or simply do nothing at all.”

—Andrea Traynor, editor-in-chief of


Courtesy of Elaine Taylor-Klaus

Dolphin Experience in Jamaica

“When we travel, we make friends with everyone. Usually, it keeps things interesting for my ADHD family of five. This time, it gave us the memory of a lifetime.

Our package with Moon Palace in Jamaica offered points that we were able to use to swim with the dolphins. It turns out their facility is also a small training ground. We arrived for our adventure playful and friendly; we followed instructions, joked around with the trainers, and had a terrific experience.

If it had ended there, it would have been wonderful. But our playful banter turned into an invitation to return, and we found ourselves in the water during training sessions for the next three days, assisting the trainers as they taught four baby dolphins how to interact with tourists. We all fell in love with Aria, Circe and the others.

We could never have scripted such an extraordinary experience—and among the many lessons learned, most of all we realized that it pays to be a friendly family!”

—Elaine Taylor-Klaus of and


Courtesy of Modern Boca Mom

Castaway Cay a Hit Among Florida Moms

“It was pretty much a dream for my family to visit Castaway Cay in the Bahamas while on a Disney cruise. You can book excursions for an additional fee, but honestly, we were there the whole day and were completely entertained by all of the complimentary amenities. It was heavenly!

The beauty of this island is that there is something for everyone to do at any age. My favorite memory was watching my husband and daughter rock out on the in-water water-slide. It was a big undertaking for a little 3-year-old! Definitely bring your camera or phone because there are photo opps everywhere and special appearances by Disney characters!”

—Michelle of Modern Boca Mom


Courtesy of The Modern Savvy

“We live in Florida near the water; however, Disney’s private island provided our family the most gorgeous, unparalleled experience with all of the beautiful amenities of beach life at our disposal during a recent Disney cruise.

Our daughter and a new friend had hours of fun playing in the waves, enjoying the super soft sand and splashing into the ocean (thanks to the coolest water slide!), while our younger son loved the calm waters.

We, of course, loved the convenience of complimentary lounge chairs and umbrellas, a nearby cabana for frozen cocktails, and the fro-yo machine!”

Alyson Seligman of The Modern Savvy


Courtesy of Sheri McDonald

The Delight of the Unexpected in Turks & Caicos

“Flight delays, lost luggage and a mix-up at the car rental booth made for a rough start to our vacation in Turks and Caicos.

With three kids in tow, we made our way to the Wheeland Settlement and our Airbnb home. Seeing our fatigue, our hosts graciously offered to take me to get necessities and dinner, since our car would not be ready that day. She and I picked up what I needed in local shops and were headed back to the house when she stopped at a run-down looking shack on the side of the road, appropriately named The Chicken Shack.

She explained that this was a local hot spot for food. She placed an order and told me to pay. I was confused, but it was only $7, so I went along with it. Soon, we were presented with a large brown bag of food and we went on our way.

The food she had ordered was my family’s dinner that night and it was some of the most delicious food we had on the island. Had our luggage arrived and our car been available, we never would have discovered the local stores or The Chicken Shack, which became a regular stop during our stay.”

Sheri McDonald of


Courtesy of MommyTravels

All-Inclusive Adventures in Jamaica

“If you are going to Jamaica, I suggest staying at a resort that offers everything, including water activities. It can be difficult to get around the island, especially with some of the road-widening efforts going on now; your kids will be much happier staying at the resort and playing than riding in a bus for hours to go do something!

I recommend staying at Beaches Negril with kids. It’s all-inclusive, including drinks, food, kids’ clubs, and activities.”

Meagan Wristen of MommyTravels


Courtesy of Thrifty Mommas Tips

Making Special Memories in Cancún

“When my girls were 5 and 7, we took a trip to Cancún and stayed at a beautiful all-inclusive resort as a family. We have a daughter with sensory processing disorder and some other diagnoses too. Parenting her is a challenge sometimes, and school is constant advocacy and an uphill battle daily.

When we travel, there’s a calm sense of respite from systems that are hard to negotiate and unsupportive. But it took a lot of work to get her to a point where she embraces travel and enjoys it; change is hard for kids with her disability.

This one day on the beach, a bunch of kids staying at the resort started playing baseball. My girl has always been super athletic. At 5, she was super tiny and one of the youngest playing, but she joined in the game anyway. I watched nearby as she picked up the bat when it was her turn; she belted the baseball way down the beach and raced across the sandy makeshift bases.

When she returned after getting a home run, she walked over to me for some water and I heard one of the older boys who had started the game say, ‘Man, that little girl can hit!’

I carry that memory with me through long Canadian winters and long days spent advocating at her school. I’m still beaming thinking of it.

To me, that’s what travel is about as a special needs family. Memories like this one are exactly why I strive to take my family away to explore a new destination and a new set of people as often as possible.”

Paula Schuck of Thrifty Mommas Tips


Courtesy of My Family Stuff

Pilgrimage in Puerto Vallarta

“Get out of the resort and experience true Mexican culture.”

“One of our favorite memories was experiencing the pilgrimage to the Cathedral of Our Lady of Guadalupe with our children in Puerto Vallarta. This celebration happens every December and draws crowds of people following the pilgrimage to the town church. There were food stands, balloon stands, and fun everywhere you turned.”

—Ladena of My Family Stuff


Courtesy of Have Baby Will Travel

Family Fun in Cuba

“As a family, we have been to Cuba seven times. We have never returned to the same place twice, but after our last visit, we just might.

We stayed at Memories Holguin Beach Resort and, for us, it was the perfect combination of quiet, lazy beach destination infused with lots of culture and cool things to do. While Varadero is bigger and busier, Holguin was actually Cuba’s first region developed for tourism, so, unlike some of the smaller resort areas on the island, the tourist infrastructure is well in place and suitable for every type of traveler, especially families.

Cuba is safe and clean, and Cubans adore children, so it’s a win/win if you’re lucky enough to visit!

We loved that we were able to snorkel straight from the beach, or we would sign out paddleboats and pedal over to the reef. Definitely sign up for a catamaran ride; on a breezy day it feels like you are flying across the water. If you’ll be doing an excursion, sign up for the trip to Cayo Saetia. It’s a beautiful day on a small, uninhabited island, with a glorious beach and a fun ride in an old Russian military vehicle through the island’s former game reserve.”

Corinne McDermott of Have Baby Will Travel


Courtesy of Kid & Coe

Authentic Connection in Mexico

“We loved our stay at the Palmeras Residence in Mexico. This sunny paradise is located on a beachfront compound of lovely private-owned homes, with a shared pool. There was a lot of privacy and the beach was often ours alone.

Our kids had fun playing in the pool with the other children, and the high point was releasing baby turtles into the sea, which was absolutely amazing and a special memory for the kids. There was no WiFi, which was refreshing, and the kids roamed the beautiful grounds, through the palm trees and down to the beach. We enjoyed the simple connection with nature and each other.”

Zoie Kingsbery Coe, Founder of Kid & Coe

Taking It Easy in Punta Cana

“The best part of our family’s trip to Punta Cana was spending long days at the beach. The all-inclusive property we stayed at had BBQs everyday right on the beach, so we literally never had to leave! Plus, with the calm shoreline the Caribbean is known for, I felt at ease watching my young sons play in the water. My boys were able to climb trees, play in the sand, and swim every day. It was truly a paradise vacation.”

Bethany Braun-Silva of


Courtesy of Henry and Andrew’s Guide

Perfect Place for Parental Leave

“We went to Puerto Vallarta when my son Henry was 2 and my son Andrew was only 7 weeks old. We stayed at an all-inclusive right on the beach. We had the best time! Notably, Henry fell in love with one of the workers there (it was adorable), he conquered his fears of the pool and the ocean every dayby the end of our 11-day trip, he loved playing in the water.”

“Best of all, it was the perfect way to spend our parental leave, bonding as a new family of 4.”

Emily Jenks, Owner and Writer at Henry and Andrew’s Guide

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