Perfect for walkers, bikers, and joggers, this trail offers scenic views of Boca Ciega Bay. It’s a local favorite for early mornings or late afternoons when the light hits the water just right, giving you an incredible backdrop for your workout or leisure stroll.

If you’re looking for seafood with a side of toes-in-the-sand dining, Caddy’s is a must. Located right on the beach, this lively spot serves up everything from blackened mahi-mahi tacos to peel-and-eat shrimp, all while you soak up the sea breeze and live music.

Taste of The Beaches

October 4–12, 2025 / Various Locations

Savor the flavors of the Gulf Beaches during this weeklong culinary celebration. With participating restaurants in Treasure Island—including Caddy’s Treasure Island, Sloppy Joe’s, Taco Bus, Curious Soul Bakery & Coffee Shop, and Sea Dog Brewing Co.—and many more nearby, guests can sample signature “Tastes” from a variety of local spots. Simply select the dishes you’d like to try, purchase tickets, and redeem them at participating restaurants from October 4-12. Proceeds benefit Big Brothers Big Sisters of Tampa Bay, making each bite a way to give back.

Jazz Holiday Festival

October 16-19, 2025 / Coashman Park

This annual festival celebrates 46 years and blends traditional jazz with modern twists under the Florida sky, making it a beloved tradition. New for 2025, two side stages add 14 more performances for a pre-party vibe before headliners hit the main stage. Expect a diverse bill with smooth jazz, funk, soul, blues, and more for a different feel each day.

Halloween Trick or Treat Trail

October 24, 2025 / 6 – 8 PM / Treasure Bay Golf, Tennis & Recreation Center

Treasure Island is hosting a Trick-or-Treat Trail for little ghouls and goblins on Oct. 24 from 6 to 8 p.m. at the Treasure Bay Golf, Tennis & Recreation Center. Kids can enjoy trick-or-treating, interactive entertainers, inflatables, food, drinks, and more, with prizes for costumes. A costume contest kicks off at 7 p.m. – bring a pail and have a howling good time!

Halloween On Central

October 25, 2025 / Central Ave between Dr M.L.K. Jr St and 31st St

Halloween On Central is back with costume contests, trick-or-treating, and more at a huge street festival. Central Avenue transforms into a car-free, family-friendly celebration with lots of fun activities. You can bring your dressed-up pup for the dog costume contest. This event is free for everyone!

Sueños de Dalí

October 25, 2025 / 1 Dali Blvd.

Sueños de Dalí promises an enchanting escape into a realm where art and fantasy collide at the Museum’s most anticipated event. Revel in themed bars, bites, and entertainment that dance on the edge of reality and imagination within the iconic building and gardens. This unforgettable soirée supports the Museum’s vital nonprofit mission in culture and education. Admission grants access to galleries plus the special exhibition.

Morning:
Start your day with coffee and breakfast at the on-site café, perfect for a quick bite before heading out. Then it’s off to explore Treasure Island by bike or paddleboard—rentals are easily accessible nearby.

Midday:
Treat yourself to a local lunch at Ricky T’s Bar & Grille. Try the Ding Dang Shrimp and catch some live music if you’re lucky. After lunch, stroll along the Treasure Island Beach Trail, dotted with quaint shops and beachy vibes.

Afternoon:
Cool off back at Sunset Vistas with some downtime by the pool or enjoy a cocktail at the poolside bar.

Evening:
Have a sunset dinner at Middle Grounds Grill, a local favorite known for its fresh seafood and elevated cuisine. Don’t miss the Honey Ginger Glazed Salmon.

A local favorite, Ricky T’s Bar & Grille combines a lively atmosphere with a diverse menu. With live entertainment seven nights a week, it’s a great spot to enjoy good food and music.​

Must-Try Dishes:

Ding Dang Shrimp: Crispy shrimp tossed in a flavorful sauce, offering a perfect balance of spice and sweetness.​

Jumbo Chicken Wings: Served with a variety of sauces, these wings are a crowd-pleaser.​