Sanibel Mayor, Chamber Award January Facemask Challenge Winners

provided to The Santiva Chronicle

A mask appliqued with a smile in the shape of Sanibel Island and another featuring a lottery ticket won the second round of the Mayor’s Mask Challenge for January entries. In partnership with the Sanibel & Captiva Islands Chamber of Commerce, Sanibel Mayor Mick Denham has been awarding cash prizes every month, December through February, for the most fashionable, flamboyant, or ostentatious masks entered into the challenge.

Each month, typically one prize-winner from Sanibel and one from Captiva receive a $200 award. Since there were no Captiva entries in January, both awards went to winners on Sanibel Island.

Part-time Sanibel resident Lauren Schneider emailed the chamber a photo of her wearing a mask with a copy of a lottery ticket attached in Bailey’s General Store. Photo entries must be taken indoors at an island place of business.

“Once I found out that Mayor Denham had actually donated half of my winnings out of his own pocket, my husband and I decided that we are going to donate half of my winnings to FISH,” she said.

Eleven-year-old Neven Connor, who is living temporarily with her family on Sanibel, where her grandfather resides, entered three masks, which won as a set.

“The Sanibel Smile was meant to signify a smile because you cannot see someone’s smile through a mask,” she wrote when she submitted her photo entries by email. “During times of Covid-19 a smile has to replicate a hug, kiss and high five. The smile on the Sanibel smile mask is the shape of the Sanibel and Captiva islands!”

Her other two entries she titled “The Junonia Jumble” and “The Abstract Art.” The fifth-grader said she would be using the $200 in award money to put toward her college fund.

“We had 17 entries in January, a jump from the 12 we received previously for the partial month of December when we started the challenge,” said John Lai, chamber president and chief executive officer. “Exactly as we were hoping, people are having fun with the challenge, which is meant to lighten the dire pandemic mood.”

The mayor will award more cash prizes, matched by the chamber, after the end of February. Entries can be made by the end of the month to the chamber’s Instagram or Facebook page using #mayorsmaskchallenge or via email to Once Mayor Denham and the chamber’s executive board choose the month’s two winners, they will award the cash prizes at the beginning of the following month.

“We all know wearing a mask helps keep the pandemic numbers down, so we’re trying to ease the tension while facing a very serious problem,” said Denham. “It still has the same objective to keep the islands safe.”

Entrants can submit as many photos as they wish, but cannot submit the same mask for more than one month. Business owners and city or chamber employees are ineligible to enter.

“The Mayor’s Mask Challenge celebrates those doing their part to comply with the chamber’s SanCap Safe initiative,” said Lai. “We know that wearing a facemask is so important and will ultimately be a symbol of this time, so we might as well have some fun and work together to slow the spread and fight COVID-19.”

The Sanibel & Captiva Islands Chamber of Commerce is dedicated to promoting the prosperity of its members and preserving the quality of life of our community. With over 560 active Chamber members from both islands including businesses from Lee and Collier counties, the Chamber plays a key role in facilitating communication and cooperation between business, residents and government to enhance the economic health of the islands. The Francis P. Bailey, Jr. Chamber Visitor Center is located at the entrance to Sanibel Island and welcomes over 160,000 visitors each year. VISIT FLORIDA named the Visitor Center one of thirteen official Florida Certified Tourism Information Centers. The Visitor Center is open 365 days a year and provides visitors with comprehensive information about things to do, places to visit, where to stay, shop and dine. The Chamber website receives over 1.3 million website visits per year.

For more information about the chamber, visit or contact John Lai, president and CEO, at 239-472-2348 or

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