Three carved pumpkins with various facial expressions are placed side by side on a wooden surface, likely for Halloween.

Celebrate Halloween with Tropical Style at The Islands of Islamorada

Published on September 28, 2021

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Ready for a new take on Halloween? The perfect place to experience a spooky tropical celebration is at The Islands of Islamorada! Here are some of the ways we can help you can bring the holiday to life:

Carve A Pineapple

Instead of pumpkins, carve pineapples, watermelons, honeydew melons and other tropical fruits. Bonus: you can eat what you scoop out! Another fun idea is to paint coconuts to look like jack-o’-lanterns. The ground-floor waterfront loggia of your villa is the perfect place for this family activity. Afterward, jump in the ocean to rinse off!

A pineapple is carved with a face, resembling a jack-o'-lantern, and lit from within, placed on a white surface.

Create a Costume

Challenge each member of your group to create a costume that starts with your swimsuit. Participants have to get creative with whatever they can find in your villa or around the resort to build their looks. Give prizes for different categories and then be sure to take a group photo!

Two kids in Halloween costumes hold pumpkin props on a decorated sofa with balloons, cobwebs, and hanging decorations.

Cook up a scare

Have fun wowing the kids with these Halloween-themed dishes! From Eyeball Pasta and Mummy Hot Dogs to Graveyard Chicken Enchilada Dip and Jack-'O-Lantern Quesadillas, these fun foods can be put together easily in the kitchen in your villa so everyone can eat a meal before you break out the candy and other treats. You’ll find the recipes at Delish.com and we can do the grocery shopping for you.

Two carved pumpkins on a table with chips and guacamole arranged creatively, one looks like it's vomiting, creating a fun Halloween theme.

Trick-or-Treat

With a three-story villa, there are plenty of places to make candy stations for your little ones. And they’re already in costume!

The image shows white villas surrounded by palm trees at sunset, creating a tropical and serene atmosphere.

Spooky Movie Night

Pick your favorite scary movie for the whole family to gather and watch in the dark while lounging together in your Halloween pajamas. Autumn-themed snacks, such as caramel corn, candy apples and warm apple cider, are sure to be a hit with everyone.

People are gathered around a fire pit by the sea, roasting marshmallows on sticks while sitting on Adirondack chairs.

If you are up for a little exploring of The Florida Keys, there are several events in October that make for a fun family outing or a date night:

Sixth Annual Oktoberfest

Islamorada’s Sixth Annual Oktoberfest brings a taste of Germany to The Keys on Oct. 9 and 10. Sample German beers on draft and locally brewed German-style beers on draft, food trucks, and traditional German food. Plus, enjoy live music, art vendors, face painting, games and a traditional Das Boot competition.

Key West Fantasy Fest

The signature event in The Keys during October is Key West Fantasy Fest, an outrageous 10-day costuming and masking celebration featuring flamboyant masquerade competitions and more than 30 cleverly themed parties and performances, including Togas, Tutu’s, Body Paint and Burlesque, Halo’s and Homemade Bikinis. The 2021 theme is ‘All a Daze for a Holiday!’ Fantasy Fest is a mostly adult event that takes place Oct. 22 to 31.

A person in festive Day of the Dead attire with face paint and a large red hat decorated with candles and skulls, posing with a smile.

Scarecrows in the Forest Art Exhibit and Contest

The Key West Tropical Forest & Botanical Garden showcases local artists’, community members’ and local students’ unique versions of the fall season’s ‘Scarecrows in the Tropical Forest.’ Made from natural and recycled materials, the exhibit, open 10 a.m. to 4 p.m. daily during October, will be a lesson in recycling, art talent and a contest with cash prizes for the entries. The Garden is located at 5210 College Road.

Happy Halloween!