Toddlers Jagger and Henley Schomp are fulfilling a dream many work a lifetime for: the opportunity to retire on the Caribbean’s white sand beaches.

In a “Benjamin Button” case of sorts, this 2- and 4-year-old reversed the timeline and skipped straight to retirement years. The two have been on the road for a year and a half and counting, traveling the world with their parents, Jake and Michelle, who run the website

The couple from Tampa, Florida, sold their home last summer and decided to take an extended break from traditional life. What began as a long summer vacation has transformed into an indefinite trip from country to country.

The family is now winding down the Caribbean leg of its journey with a month in Grand Cayman’s Rum Point.

“They love it,” Michelle Schomp said about her children’s experience in North Side.

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“They’re having a blast. Our place is right on the sand in an inlet. So our backyard is sand. They literally just run out and play in the sand and water. There are not many places that they don’t love. They’re kids but they’re adaptable, which is really nice.”

At least for the time being, the family has swapped days in day care with kayaking, snorkeling and other water sports.

Henley excitedly recounted her experience in North Side’s bioluminescent bay, her favorite experience so far in Grand Cayman.

The trip, which has already taken the Schomps across much of Asia and Europe, has been an experiment for the family in defying social norms.

“We had to let go of what we felt like our peers or society puts on you, that you should get a bigger house and get two cars and put your kids in school. So we had to let go of those societal expectations. That took a little bit of adjusting for us to be OK with it ourselves to take this trip,” Jake Schomp said.

“I think since we’ve made that decision and gone on this trip, everywhere we go, it reinforces our decision more and more that we’ve made [the right choice]. We are very thankful we took the opportunity when we had it, and feel like it’s absolutely been the right choice for our family.”

Facing hurricane season

From trying lionfish at East End’s Tukka to climbing temple steps in Cambodia, the family has taken in a world of experiences in a short amount of time.

Not all of the days have been easy, however. The Schomps arrived in the Caribbean ahead of what would be a devastating hurricane season. As Hurricane Irma struck island after island, the family found itself stuck in St. Thomas, U.S. Virgin Islands.

“We buckled down for the storm. It was terrifying, really terrifying. It ended up being an off-the-charts Category 5 [hurricane] …. It just sounded like a freight train about to blow down our windows,” Mrs. Schomp said.

“The pressure was just so intense. So we put the kids in the bathtub, gave them a bathtub party with some treats and endless movies, which to them is heaven, and they were super excited about. So it didn’t even really bother them.”

After the storm, the Schomps discovered a Caribbean sense of community, coming together with neighbors for support and to pool resources.

“We couldn’t even get to the grocery stores, the roads were so badly damaged,” Mrs. Schomp said.

“Eventually the National Guard came in and had some food rations. We tried to evacuate a couple of times. We were told FEMA was bringing us a jet, so we all packed our bags, got up there at 8 o’clock. Nobody came. No plane came. Nothing came.”

Her husband chimed in, “We were disconnected from information. It was a lot of uncertainty over security and food and what would happen next, a lot of hearsay about what’s happening in the next town over. We decided it would be best for our family to get off the island, however we could. We didn’t want to take resources away from the people who were trying to rebuild there.”

Eventually, the family made it on a ship to Puerto Rico, where they would later be forced to evacuate the day before Hurricane Maria hit.

“[The kids] were troopers. In the aftermath, they brought so many smiles to people’s faces. It was a huge benefit to everybody around us. Also, everyone was so kind to them,” Mr. Schomp said.

Despite the intensity of their Caribbean welcome, the Schomps were not deterred in their travels. After a couple of weeks back home in Florida, the family returned to the Caribbean, deciding to spend the last leg of hurricane season in Grand Cayman.

“I’ve really enjoyed Grand Cayman as a whole. It has a different feel to it than some of the other islands do. In some ways it’s more developed. In other ways, it’s more rustic. Being out at Rum Point feels so much like we’re in the middle of nature every day,” Mr. Schomp said.

The highlight for the couple has been the quality time the family has spent together.

In two weeks, the four will return to the United States to spend the holiday season with relatives.

After that the Schomps plan to hit the road again, this time to Mexico and then Guatemala.

When asked how long their travels will last, Mrs. Schomp laughs. She is not sure. While the kids are young, the couple sees no rush to return to their old life.

“I hope they remember how much quality time we got to spend together as a family. That’s why we’re doing this,” Mr. Schomp said.

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  1. If one can afford it why not! Enjoy! I would advise to take the sunglasses off, for you are messing with circadian rhythm. Especially children’s! The only places one should wear sunglasses are snow skiing high up in the mountains and water sports. Our eyes are not cameras but clocks.
    But don’t take my word for it.