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Calendar of Fun

There's Always Something Going on Here

Ready for endless fun in the sun? At TradeWinds Island Resorts, you can stay at one, and play at two! Our calendar is always full of unbeatable events to build your stay around, so take a look at the upcoming events, activities, and celebrations we have planned, and get ready for your own island adventure!

Spring activities April 1 - 16 and May 4 - 24, 2024: Spring Activities 2024 Spring Activities 2024

Spring activities April 17 - May 3, 2024: Spring Activities 2024 Spring Activities 2024

Upcoming Events & Activities

Pirate Show

Pirate Show

Pirate Show

From Monday, March 21, 2022 March 21, 2022 TradeWinds Island Resorts Every Wednesday, Saturday ...

Join Captain RedBeard’s crew for family fun, dancing and giggles. Captain RedBeard’s Pirate Show is an action-packed show highlighting one of RedBeard’s Adventures. Why did the pirate go on vacation? For arrrgh and arrrgh!
Meet at Pirate Island at Island Grand. FREE
Every Wednesday and Saturday at 7:30 p.m.

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A Beach With A Pool And Umbrellas

5500 Gulf Blvd, St Pete Beach, FL 33706

As the largest beachfront resort on a top-ranked U.S. beach, Island Grand is the perfect place to just let go and enjoy all of the sun and fun Florida has to offer. Even better, you’re invited to stay at one, play at two! Our adjacent property, RumFish Beach Resort, is just next door and offers even more fun for you to enjoy during your stay. Relax alongside the soft white sands and warm gulf waters of St. Pete Beach and take advantage of our endless array of restaurants, bars, and activities. From intimate escapes to family fun, let this waterfront paradise be the setting for your island escape.

  • 28 Beachfront Acres
  • 5 Pools, 450 Cabanas
  • 3 Story Waterslide
  • 12 Waterway Paddleboats
  • 545 Rooms + Villas
  • Floating Water Park
  • 10 Restaurants + Bars
A Person Swimming In A Body Of Water

6000 Gulf Blvd, St Pete Beach, FL 33706

RumFish Beach Resort is the ultimate aquatic oasis, with a premiere location on a top-ranked U.S. beach. It’s also just 60 flip-flops away from our connecting resort — Island Grand — meaning you’ll stay at one, play at two! Relax on the soft white sand, savor fresh local seafood at RumFish Grill, discover local marine life at the touch tank, and enjoy your own adventures on the gulf waters. Whether you’re planning a romantic escape or a family getaway, this is the perfect place to just let go.

  • 12 Beachfront Acres
  • Touch Tank Experience
  • 5 Restaurants & Lounges
  • 33,500 gallon Aquarium
  • 352 Rooms + Villas
  • 4 Pools, 192 Beach Cabanas
  • 1 Fire Pit, 5 Open Fire Tables