Resort Happenings

TradeWinds offers the perfect setting for a holiday weekend getaway or special event. Check back as the holidays approach for event details.


A Group Of People Walking On A Beach

Christmas Weekend Activities

Stay at TradeWinds over Christmas weekend and enjoy all the Holiday Happenings that we are offering our guests!

  • Ugly Sweater Contest and poolside bash with games, trivia and more!
  • Letters to Santa and Cookie Decorating
  • Campfire Stories and S'mores with Mrs. Clause
  • Sea-sonal Poolside Holiday Crafts
  • Santa Photo Opp and more!
  • Don't forget to pre-order your stocking full of treats by 5pm on the 23rd.

Christmas Activities Christmas Activity Schedule

Christmas Day Brunch & Dinner

Join us in the elegant Island Ballroom for some light jazz and Christmas Day Brunch. Location: Island Grand Beach Resort. Dec. 25, 2023 from 11:00 a.m. - 3:00 p.m.

Brunch Details & Purchase Tickets Brunch Details & Purchase Tickets

A traditional plated Christmas dinner will be available at RumFish Grill from 4:00 p.m. - 10:00 p.m., and Palm Court Italian Grill from 4:00 p.m. - 9:00 p.m. on Christmas day. Call 727.363.2290 to reserve your table.

Palm Court Christmas Dinner Palm Court Christmas Dinner       RumFish Grill Christmas Dinner RumFish Grill Christmas Dinner

A Person Wearing A Mask

Toast by the Coast - New Year's Eve Party

Grab your loved ones and wear your best mask at our "Toast by the Coast" New Year’s Eve Masquerade Party which offers hors d'oeuvres and stations, chef’s carvery, pasta bar, a decadent dessert table and unlimited wine and beer. Groove the night away with dance hits, and celebrate with a champagne toast at midnight. Also offering a Glitter & Glow New Year's Eve Kids celebration for an additional fee, which includes dinner, crafts, games, a glow party and more!

Party Details & Purchase Tickets Party Details & Purchase Tickets

A special New Year's Eve dinner will be available at RumFish Grill and Palm Court Italian Grill on New Year's Eve. Check back soon for menu details.

View New Year's Activity Schedule View New Year's Activity Schedule

A Person Holding A Child On A Beach

Valentine's Day Escape

Spice things up this Valentine's and enjoy a romantic dinner for two with a special Valentine's Day menu being offered in two incredible locations: Palm Court Italian Grill and RumFish Grill.  Also be sure to check out our Romance Package.

A Little Girl Standing Next To A Beach

Easter Weekend Eggstravaganza!

Stay at TradeWinds over Easter weekend and enjoy all the Holiday Weekend Happenings that we are offering our guests!

  • Build-A-Bunny - fluff and stuff your buddy to bring it to life! 
  • Easter Baskets deliveries - make sure the Easter Bunny knows where you're sleeping so your little ones won't be disappointed on Easter morning.
  • Easter egg hunt in the Garden Courtyard. The Easter Bunny hides thousands of treat filled eggs for your little ones to find.
  • Easter Sunrise Service - Join us for an unforgettable way to begin Easter with a beachfront sunrise service.
  • Pictures with the Easter Bunny and a holiday dive-in movie.
A Person Sitting On A Table

Mother's Day Specials

Show how much you care by treating your mom to Mother's Day brunch or dinner. We offer special menus in Palm Court Italian Grill and RumFish Grill, plus a Mother's Day brunch buffet. Enjoy a week in paradise, spa treatments and our complimentary sip-and-savor reception.

Fireworks In The Sand On A Beach

Seas the Summer Memorial Day Weekend

Stay at TradeWinds over Memorial Day weekend and kick off the summer with all the Holiday Weekend Happenings that we offer our guests!

  • Live music, food and drink specials all weekend!
  • Beachfront cookout featuring seasonal favorites.
  • Holiday Poolside Party with games, contests, poolside crafts and entertainment!
  • Glow Beach Bash featuring Glow Volleyball and Glow Corn Hole - all set to a DJ playing your favorite hits!
  • Fantastic Fireworks display on the beach.
A Blue Umbrella Sitting On Top Of A Sandy Beach

Red, White & Views 4th of July Weekend

Celebrate this spark-tacular weekend with sand between your toes and a cocktail in your hand, not to mention activities and entertainment throughout the holiday weekend!

  • Live music, food and drink specials all weekend!
  • Fireworks display on the beach.
  • Beachfront cookout featuring seasonal favorites.
  • Be A Star: Make a giant American Flag on the beach out of beach towels.
  • Patriotic Costume Contest: Wear your best Red, White and Blue and strut down the pool deck.
  • Holiday Poolside Party with games, contests, poolside crafts and entertainment.
  • Additional Fun includes: Red, White and Blue Tie Dye, Family Magic Show, Pirate Party, Sea Glass Wall Art and Jewelry Making, and more!
A Little Girl That Is Playing In The Water

Labor Day Weekend Activities

Close the chapter on summer with a spark-tacular weekend Gulf front at TradeWinds Island Resorts with sand between your toes and a cocktail in your hand, as well as activities galore. End summer with a BANG and enjoy fireworks on the beach on Sunday!

  • Salty's Floribbean Fiesta: Caribbean BBQ, Jerk Chicken, Pulled Pork, and more!
  • Live music all weekend and fireworks on the beach.
  • Dive Into The Vibe Pool Party: featuring a DJ spinning beachy jams, plus games of skill, and prizes.
  • Watermelon eating contest, Red, White & Blue tie dye, beach volleyball contest, kid's crafts and more!
A Person Playing Frisbee On The Beach

Bucs Beach Bash

Get ready for a weekend of sun, fun, and football at the annual Bucs Beach Bash. Stay at the official partner of the Tampa Bay Buccaneers where you can party like a pirate and enjoy live music on the beach, the Buccaneers season opener and more! 

A Group Of People Wearing Clothing

Halloween Weekend Activities

Carve into your calendars to plan a gathering with your best witches and wizards, for we will brew up some spooky activities on Halloween weekend!

  • Pool Parties: RumFish Spooky Splash Bash and Dive into the Vibe: Fright Fest
  • Potion Commotion supervised kids camp
  • Spooky Story Time around the campfire
  • Trick-Or-Treat around the property
  • Costume Contest for a chance to win big!
  • Poolside activities including Mummy Wrap and Spooky Slime, and more!
A Table Full Of Food

Thanksgiving Weekend

Spend Thanksgiving on the beach and enjoy family-friendly activities over the holiday! Join us for a timeless tradition in the elegant Island Grand Ballroom for a traditional Thanksgiving brunch to tantalize your taste buds and provide an unforgettable experience. Thanksgiving dinner specials are also served in two incredible locations: Palm Court Italian Grill and RumFish Grill.

  • Morning Turkey Trot 1 mile fun run or 5k on the beach
  • Watch a live stream of the Thanksgiving Day parade, poolside on the big screen
  • Apple Bobbing and Pie Eating Contests
  • Beaker's Poolside Bash and Poolside Crafts
  • Pictures with Santa