Top 10 Must-Do & Must-See in Treasure Island in 2026
- December 20, 2025
- Chloe Ketterer
Top 10 Must-Do & Must-See in Treasure Island in 2026
Treasure Island, Florida, is one of the Gulf Coast’s most relaxed and charming beach towns with an easygoing blend of soft white sand, warm sunsets, great food, and friendly coastal vibes. Whether you’re visiting for a family vacation, a relaxing retreat, or a romantic getaway, 2026 is shaping up to be a perfect year to explore everything TI has to offer. From waterfront dining and beachside cocktails to local hotspots and natural beauty, this list highlights the best of the best. Here are the Top 10 Must-Do & Must-See Experiences in Treasure Island to make your trip unforgettable.
1. Have a Waterfront Dinner at Caddy’s Treasure Island
Caddy’s is a TI classic, with its casual, colorful atmosphere and location right on the sand, making it one of the best places for toes-in-the-sand dining. Visit at sunset and enjoy dishes like their Grouper Reuben, Mahi Taco Trio, or a fresh Blackened Shrimp Salad. The ocean breeze and live music give every meal a quintessential Florida feel. Order a frozen piña colada or a fresh mojito to pair perfectly with the beachfront atmosphere. It’s the kind of dinner you’ll remember long after you’ve left.
2. Grab Craft Cocktails at Sloppy Joe’s on the Beach
Sloppy Joe’s offers a lively, beachfront bar scene with panoramic Gulf views that never disappoint. Their cocktail menu is surprisingly creative. Try the Joe’s Hurricane, Key Lime Martini, or the refreshing Beach Breeze Cooler. It’s a great spot to sip, relax, and watch the waves roll in. Whether you sit inside or out on the deck, you’ll feel the laid-back energy that defines Treasure Island. Happy hour here hits the spot after a long day in the sun.
3. Walk the Treasure Island Beach Trail
The TI Beach Trail runs along the coastline and offers one of the easiest, breeziest ways to enjoy the shore. You’ll pass sand dunes, beach cottages, cafés, and beautiful Gulf overlooks. It’s ideal for morning walks, afternoon exploration, or sunset strolls with your favorite drink in hand. Several benches line the trail for scenic breaks and photo opportunities. It’s simple, beautiful, and authentically Treasure Island.
4. Explore John’s Pass Village & Boardwalk
Just over the bridge, John’s Pass is a bustling waterfront destination full of shops, restaurants, and fun activities. The boardwalk stretches along the Intracoastal Waterway, where you can watch dolphins, check out boats, or simply browse the local boutiques. Grab an ice cream from Kilwin’s, pick up souvenirs, or enjoy a fresh seafood lunch with a view. There’s always something happening, from street performers and live music to seasonal festivals. It’s one of the liveliest spots near Treasure Island.
5. Join a Dolphin-Watching or Sunset Cruise
Boat tours leaving from John’s Pass offer magical experiences on the water, especially in the early evening. Dolphins frequently swim alongside boats, playing in the wake and delighting everyone onboard. A sunset cruise is equally stunning as the sky explodes with color, and the Gulf feels calm and expansive. Many tours include narration about the area’s wildlife and history, adding depth to the journey. It’s one of the most memorable activities you can do in TI.
6. Enjoy a Beach Day at Sunset Beach Park
Sunset Beach is a local favorite, offering quieter, more peaceful surroundings and boasting some of the clearest water on the island. It’s perfect for families, couples, and anyone seeking a relaxed slice of shoreline. Bring a cooler, beach chairs, and sunscreen for a full day of swimming and sunbathing. The vibe is laid-back and friendly, making it feel like a small, seaside retreat away from busier beaches. And yes, the sunsets here are legendary.
7. Treat Yourself to Breakfast at Britt’s Pizza & Grill
Don’t let the name fool you! Britt’s serves a surprisingly great breakfast before shifting into pizza mode later in the day. Their Breakfast Burrito, Banana Pancakes, and Fried Egg Sandwich are local favorites. Portions are hearty, prices are reasonable, and the staff is always friendly. Sit outside if the weather is nice to enjoy Florida’s morning breeze. It’s a comfort-food start to a perfect beach day.
8. Go Parasailing Over the Gulf
If you’re craving a little adventure, parasailing gives you a breathtaking bird’s-eye view of Treasure Island’s coastline. The takeoff is smooth, the ride is surprisingly peaceful, and the views from the air are unforgettable. You can spot marine life, admire the curve of the shoreline, and enjoy the quiet beauty of hovering above the Gulf. Most parasail operators accommodate pairs, making it a fun shared experience. It’s thrilling without being intimidating, ideal for first-timers.
9. Catch an Iconic Treasure Island Sunset
No matter how many times you see it, a TI sunset always feels magical. The sky transforms into layers of tangerine, lavender, rose, and deep gold reflecting off the water in a glowing mirror. Couples gather, families snap photos, and locals simply sit and soak in the view. Bring a blanket or grab a drink from a beachfront bar to enjoy the show. It’s the simplest must-see on this list and arguably the most beautiful.
10. Stay at Crystal Palms Beach Resort
Make your 2026 Treasure Island getaway complete by staying at Crystal Palms Beach Resort, a boutique-style property known for its spacious condo-style suites and serene atmosphere. Guests will love the private balconies with sweeping views of the Gulf or Intracoastal Waterway—perfect for enjoying morning coffee or unwinding at sunset. Guests also love the beautiful pool area, peaceful surroundings, and the convenience of a full kitchen in their suite. With the beach just across the street and TI’s best attractions nearby, it’s the perfect blend of comfort and location. Book your stay at Crystal Palms and experience Treasure Island the way it was meant to be enjoyed—relaxed, scenic, and unforgettable.