The warmth and sun of Florida is a major attraction any time of year. Lounging in the sun or splashing around in the water of the Gulf of Mexico is a fun and relaxing way to while away the time on a Florida getaway, but you’ll want to make sure to experience some of the Siesta Key Halloween fun and excitement when you plan a fall break around one of the spookiest days of the year.

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Siesta Key Safe Treats

Trick or Treat on Siesta Key is safe and fun, thanks to the Siesta Key Chamber of Commerce. The 37th annual Safe Treats for Kids is an event where merchants across the island will be handing out sweets and treats to costumed children. The afternoon event is a fun, relaxed event and the free Siesta Key Breeze Trolley can help you get between Siesta Key Village and Turtle Beach so you can maximize the fun. The free event is Saturday, October 30 from 1-4 p.m. at participating businesses across the island.

Sarasota Dog-O-Ween Costume Contest

If your furry friend made the trip with you, grab the leash and your fur baby’s costume and head to the Sarasota Annual Dog-O-Ween costume contest. Humans bring their canine companions to Paul Thorpe Park for some Siesta Key Halloween fun at the Sarasota Farmers Market Halloween Festival. Canines dress in their howl-o-ween best to compete for prizes including a complimentary exam donated by the Animal Medical Clinic at Rosemary, a gift basket full of toys donated by New Barker Magazine, and a $50 cash prize donated by the Sarasota Downtown Enrichment Association. The contest is Saturday, October 30. Registration is from 9-9:45 a.m. and the costume contest starts at 10 a.m. The cost is $5, and proceeds benefit the Donte’s Den Foundation. Keep in mind contestants must be leashed at all times and no retractable leashes are allowed. Make sure your dog visits the potty before the contest starts!

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Ghost Stories & Tours at The Point

You’ll have to take a short trip to the mainland for this ghostly fun. Marie Selby Botanical Gardens historic Spanish Point campus in Osprey is leading spooky stories and ghost tours at Spanish Point. Take a tour led by storytellers as they reveal the spookier history of the Spanish Point campus. Tours take place from 7:30-9 p.m. October 28-30. Admission is $15 for all Selby Gardens members and $20 for non-members. Guests must be 8 years old or older to participate.

The Monsters Cruise

An adults-only party, the Monsters Cruise invites all witches, ghouls, zombies, monsters, and other scary spirits aboard the LeBarge. There will be a full bar and snacks available throughout the night for purchase aboard the vessel. Come in your Halloween best. There will be plenty of adults-only Halloween fun on board, including a drag show. The cruise sets sail Saturday, October 30 and sails from 9-11 p.m. This event is for guests 21 years old and up. If you don’t want the fun to end, look for other events at local restaurants and bars that take place before or after the cruise.

Choose Your Own Adventure

Don’t forget you came to Siesta Key to rest and relax in the Florida sun as well as to have some Halloween fun. There are plenty of indoor and outdoor activities that don’t necessarily have a spooky theme. Gather your group and head to the beach for swimming, stand-up paddleboarding, sandcastle building, and more. Get out to some of the indoor attractions like escape rooms, museums, galleries, restaurants, shopping and an endless number of other activities. You can also choose to decorate your rental with removable, non-damaging decorations or create a Halloween-themed scavenger hunt or other activity that keeps you closer to home and away from the larger crowds of official events.

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Siesta Key Halloween

When you book your spooktacular Halloween getaway to Siesta Key, you won’t be hard pressed to find something to fill every minute of every day of your trip. Fuel up for the day or bring the group together with a delicious home-cooked meal prepared in your unit’s fully equipped kitchen. When the spooky fun is done for the day, relax in a private bedroom, or spread out in the open living area for a game, movie, or TV show. When you’re not at the beach or soaking up the Halloween fun, enjoy some outdoor time on a private patio or balcony. Choose a premium unit for stainless steel appliances, double ovens, flat screen TVs, and more. Rent Siesta Key has a rental to fit your needs, from one-bedroom units for your small family or spookily romantic getaway all the way up to six bedrooms for a Halloween reunion with friends or family.

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