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Important Fundraisers in the Florida Keys

There are several major fundraisers in the Florida Keys every year. Check out our list of the top fundraisers and get ready to donate to a good cause.

The Key West Headdress Ball

Part of the Fantasy Fest celebration, the Key West Headdress Ball is a fundraiser that collects money for LGBT charities. It often takes place in the Key West Amphitheater, which is located in the Truman Waterfront Park. 

This fundraiser is an annual gala that attracts people from all over. At the event, individuals compete for the best headdress costumes. With at least 25 contestants, the competition is quite the show. The winner receives $3,000 and bragging rights for years to come.

Key West has had a strong LGBT presence for years, with the nation’s oldest LGBT Chamber of Commerce having been found in Key West more than 30 years ago. Not long after its inception, the organization put together this ball as a way of raising money. In addition to enjoying the ball, you can also participate in some of the other exciting Fantasy Fest events.

Annual Mayors’ Ball For The Children

For over 17 years, the Annual Mayors’ Ball has been raising money for the Florida Keys Children’s Shelter. Every year, the fundraiser has a different theme. And every year, the event brings joy to the Florida Keys. In 2020, the fundraiser’s theme was the Mad Hatter. Even the food stations stuck with the theme.

For the first 17 years, this festival took place in Florida Keys. However, the event was moved to a more central location in Marathon. The move was done to make the event more accessible to others in the state and to remind everyone that the Children’s Shelter helps families and kids throughout all of Monroe County.

One of the highlights of the fundraiser is the live auction. In 2020, renowned painter Adam S. Rote donated his “Alice in Wonderland Drink Me” painting for the auction. You never know what you’ll find and who you’ll see at this fundraiser.

What you can be certain of is the fact that the money will go towards a great cause. The Florida Keys Children’s Shelter offers several services to children and families throughout the Keys. They have counselors that visit homes and also offer services via the Monroe County School system.

Annual Spring Social

There are many stray cats and dogs in the Florida Keys, and they all deserve a better life. Thanks to the Florida Keys SPCA, those animals are on their way to finding homes. The Annual Spring Social is one of the most important fundraisers in the Florida Keys because it raises money for the non-profit organization.

For over 12 years, the social has been a popular event in Key West. In 2019, the event took place on the Key West Golf Course. Individuals who bought VIP tickets were greeted with a champagne reception, appetizers, and early access to a silent auction.

By far, the highlight of this event is the silent auction. It’s one of the largest silent auctions in the Keys and always features a variety of items. When you participate in the auction, your money goes towards a good cause.

It’s worth mentioning that there are other annual fundraisers for the Keys SPCA. However, this is one of the most popular and interesting fundraisers for the organization.

The ReMARCable Mattheessen’s Ice Cream & Fresh Fruit Social

You can’t go wrong with an ice cream sundae. But that sundae tastes even sweeter when you know you’re helping a great organization. All of the proceeds from the ReMARCable Ice Cream Social go towards the Monroe Association for ReMARCable Citizens.

The non-profit organization helps adult individuals with developmental disabilities. Working throughout Monroe County, the organization gives much-needed support to those who have cerebral palsy, traumatic brain injuries, and spina bifida. 

This fundraiser allows participants to make their own Mattheessen sundaes. If you’re not in the mood for a frozen treat, you can also buy cupcakes, crepes, and strawberry shortcakes. 

Island Fest

For over two decades, the Islamorada Annual Island Fest has been bringing joy to the Florida Keys. The event is a fundraiser that usually takes place in Founders Park. Money from the fundraiser goes to the Islamorada Chamber of Commerce. 

Every year, the fundraiser features several events. In the past, events have included a juried art show, classic car show, and craft show. There’s always live music and delicious food. If you want a souvenir, you’re sure to find something at the arts and crafts show. Past fundraisers have featured more than 100 artists, with works ranging from paintings to jewelry. 

Another fun event is the Who Floats Your Boat race. Prior to the event, participants build their own boat with unusual materials. An award is given to the winner of the race, the craziest crew, and the thriftiest boat. 

Foodies can also enjoy the fundraiser with the Taste of Islamorada. During this event, the best restaurants in the area showcase their talent. You can try the food and vote for your favorite dish. 

Whether you’re an Islamorada local or someone who’s never stepped foot in the island town, you’ll enjoy this event. Learn more about this unique place and give back to the community.

Enjoying Important Fundraisers in the Florida Keys

Everything is more fun in the Florida Keys, and that includes fundraisers. Attend one of the fundraisers above and give back to a worthy cause while you enjoy yourself.


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