Nothing says summer on Florida’s Gulf Coast quite like live music, ocean breezes, cold drinks, and unforgettable sunsets. This season, Caddy’s is bringing the energy all weekend long with Sunset Sessions at all three beachfront locations: Treasure Island, Madeira Beach, and Indian Shores.
🎸 Caddy’s Treasure Island
Make the most of your weekend at Caddy’s Treasure Island with beachfront views, refreshing drink specials, and live entertainment all weekend long. Relax in our complimentary beach chairs and umbrellas while taking in a breathtaking Gulf Coast sunset. Enjoy live music every Friday and Saturday from 7PM–10PM and Sundays from 6PM–9PM, with live DJs spinning your favorite tunes on Saturdays and Sundays from 12PM–4PM. Whether you’re stopping by for the beach, the food, the drinks, or the music, Caddy’s is your go-to spot for the perfect weekend by the water.
Drink Specials
Available Friday, Saturday, Sunday from 7PM until close
● $4 Domestic Beers
● $6 House Margaritas
● $6 House Rum Runners
🍷 Caddy’s Madeira Beach
Enjoy stunning waterfront sunsets, live entertainment, and exclusive evening specials at Caddy’s Madeira Beach. Kick back with your favorite drink and take in the view while enjoying live music every Friday and Saturday from 7PM–10PM and Sundays from 2PM–6PM. Whether you’re gathering with friends, enjoying a date night, or simply soaking up the beachside atmosphere, there’s no better place to spend your weekend.
Drink Specials
Available Friday, Saturday, Sunday from 7PM until close
● BOGO House Wine
● $4 Domestic Beers
● $6 House Margaritas
● $6 House Rum Runners
🌴 Caddy’s Indian Shores
Soak up the waterfront vibes at Caddy’s Indian Shores with a full weekend lineup of live entertainment, great food, free parking and refreshing drinks just steps from the sand. Enjoy live music every Friday and Saturday from 5PM–9PM and Sundays from 2PM–6PM while taking in the beautiful Gulf views. Whether you’re winding down after a day at the beach or gathering with friends for a sunset cocktail, Caddy’s Indian Shores is the perfect place to spend your weekend.
Drink Specials
Available Friday, Saturday, Sunday from 7PM until close
● BOGO House Wine
● $4 Domestic Beers
● $6 House Margaritas
● $6 House Rum Runners
🌅 Your New Summer Tradition
From acoustic beach tunes and energetic bands to sunset cocktails and oceanfront views, Sunset Sessions are the perfect excuse to gather your friends, kick back in the sand, and make the most of summer.
Join us every weekend at Caddy’s Treasure Island, Madeira Beach, or Indian Shores and experience the best sunsets on the Gulf paired with live entertainment, refreshing drinks, and unbeatable beach vibes.
Drink specials may not be available during holidays and special events. Live music is weather permitting.