#1 HOLIDAY LIGHTED BOAT PARADES
There’s nothing quite like the glow of holiday lights reflecting off the water on a cool December night. In true coastal fashion, Pinellas County celebrates the season with festive lighted boat parades—an annual tradition loved by locals, visitors, and snowbirds alike. Gulfport, Madeira Beach, South Pasadena and Tarpon Springs parades set sail this weekend. Find where to catch the most magical Florida tradition on the water at https://www.paradisenewsfl.com/2025-boat-parades/.
#2 43rd Annual Jingle Bell Run for Boley Centers
Head out to downtown St. Pete this Saturday for Boley Centers’ ultra festive Jingle Bell Run. The fun run starts at 7:30pm and begins/ends at North Straub Park near The Pier. The route is decorated with carolers along the way to bring you joy. Local food trucks will be on hand. No bibs or timers – just fun and holiday cheer! The race supports housing and services for at-risk adults, veterans, youth, and families in our community. $40. Registration deadline is Dec 12th.
Sign up at https://runsignup.com/Race/FL/StPetersburg/BoleyCentersJingleBellRun.
#3 Merry Beach Market
Head out to Madeira Beach’s ROC Park this Friday 5-9pm and Saturday 2-8pm for their annual Merry Beach Market. Over 150 local vendors with a diverse array of handmade crafts, unique gifts and one-of-a-kind seasonal decorations. Food and beverage stands will be on site. Fireworks on Friday evening; watch the Lighted Boat Parade on Saturday. No outside food or drink, no pets. Park at Crabby’s on the Pass, take shuttle to event. Free.
Learn more at https://madeirabeachfl.gov/event/merry-beach-market-holiday-festival-3/
#4 Mistletoe Market
St. Pete Beach is bringing the holiday magic on December 13th! Start your morning with Brunch with Santa from 9–11 AM at 7701 Boca Ciega Drive. Enjoy a delicious brunch, kids’ crafts, and a special visit with Santa himself! Tickets are just $10. To register call 727-363-9219. Then stroll over to Horan Park for the Annual Mistletoe Market from 10 AM–3 PM! Shop local makers, find festive gifts, and enjoy seasonal treats. A festive Saturday for families, locals & visitors!
#5 Gulfport Seafood Crab Boil
Head out to Gulfport this Saturday 12-6pm for their Trolley Square (4900 Tangerine Ave. S) Seafood Carb Boil. This seafood crab boil is packed with all types and styles of seafood, music and good vibes, family fun & a pet-friendly space. Hosted by Saturday Shoppes. Free.
Learn more at https://www.saturdayshoppes.com/event/12-13-25-2/.