"I talk about the situation where he didn't even realize where he was," Kolowith said. "And we talked about how he was very, very mean, very bossy."
Columbus' stature in U.S. classrooms has declined somewhat through the years, and many districts will not observe his namesake holiday on Monday. Although lessons vary, many teachers are trying to present a more balanced perspective of what happened after Columbus reached the Caribbean and the suffering of indigenous populations.
"The whole terminology has changed," said James Kracht, executive associate dean for academic affairs in the Texas A&M College of Education and Human Development. "You don't hear people using the world 'discovery' anymore like they used to. 'Columbus discovers America.' Because how could he discover America if there were already people living here?"
In Texas, students start learning in the fifth grade about the "Columbian Exchange" - which consisted not only of gold, crops and goods shipped back and forth across the Atlantic Ocean, but diseases carried by settlers that decimated native populations.
In McDonald, Pa., 30 miles southwest of Pittsburgh, fourth-grade students at Fort Cherry Elementary put Columbus on trial this year - charging him with misrepresenting the Spanish crown and thievery. They found him guilty and sentenced him to life in prison.
"In their own verbiage, he was a bad guy," teacher Laurie Crawford said.
Of course, the perspective given varies across classrooms and grades. Donna Sabis-Burns, a team leader with the U.S. Department of Education's School Support and Technology Program, surveyed teachers nationwide about the Columbus reading materials they used in class for her University of Florida dissertation. She examined 62 picture books, and found the majority were outdated and contained inaccurate - and sometimes outright demeaning - depictions of the native Taino population.
The federal holiday itself also is not universally recognized. Schools in Miami, Dallas, Los Angeles and Seattle will be open; New York City, Washington and Chicago schools will be closed.
The day is an especially sensitive issue in places with larger native American populations.
"We have a very large Alaska native population, so just the whole Columbus being the founder of the United States, doesn't sit well with a lot of people, myself included," said Paul Prussing, deputy director of Alaska's Division of Teaching and Learning Support.
Many recall decades ago when there was scant mention of indigenous groups in discussions about Columbus. Kracht remembers a picture in one of his fifth-grade textbooks that showed Columbus wading to shore with a huge flag and cross.
"The indigenous population was kind of waiting expectantly, almost with smiles on their faces," Kracht said. "'I wonder what this guy is bringing us?' Well, he's bringing us smallpox, for one thing, and none of us are going to live very long."
Kracht said an emerging multiculturalism led more people to investigate the cruelties suffered by the Taino population in the 1960s and '70s, along with the 500th anniversary in 1992.
However, there are people who believe the discussion has shifted too far. Patrick Korten, vice president of communications for the Catholic fraternal service organization the Knights of Columbus, recalled a note from a member who saw a lesson at a New Jersey school.
The students were forced to stand in a cafeteria and not allowed to eat while other students teased and intimidated them - apparently so they could better understand the suffering indigenous populations endured because of Columbus, Korten said.
"My impression is that in some classrooms, it's anything but a balanced presentation," Korten, said. "That it's deliberately very negative, which is a matter of great concern because that is not accurate."
Korten said he doesn't believe such activities are widespread - though the lessons will certainly vary.
In Kolowith's Tampa class, students gathered around a white carpet, where they examined a pile of bright plastic fruits and vegetables, baby dolls, construction paper and other items as they decided what would be best for their voyage.
"Do you think it would be good to take babies on a long and dangerous boat ride?" he asked the class. "No!" they replied.
Fifteen miles away, in Seffner, Fla., Colson Elementary assistant principal Jack Keller visited students in a colonial outfit and gray wig, pretending to be Columbus and discussing his voyages. The suffering of natives was not mentioned.
"Our thing was to show exploration," he said.
Meanwhile, Crawford's Pennsylvania class dressed up as characters from the era, assigned roles for a mock trial and put Columbus on the stand. Out of a jury of 12 students, nine found him guilty of the charges.
"Every hero is somebody else's villain," said Felipe Fernandez-Armesto, a scholar and author of several books related to Columbus, including "1492: The Year the World Began."
"Heroism and villainy are just two sides of the same coin."