Thanksgiving is all about good food, great company, and being grateful — and this year, Caddy’s is making it easier than ever to enjoy it all without the stress of cooking! Join us for a warm, coastal Thanksgiving celebration at Caddy’s Indian Shores and Caddy’s...
It’s been a year of rebuilding, resilience, and reunion — and to clear any confusion we would like to officially reintroduce Caddy’s to our amazing community. Like so many along the Gulf Coast, our Caddy’s family was deeply impacted by Hurricanes Milton and Helene....
Make your holiday celebration one to remember this season with a waterfront event at Caddy’s! Whether you’re planning a cheerful company party, a festive gathering with friends, or a family get-together by the water, Caddy’s is the perfect spot to eat, drink, and be...
Get ready for a weekend of fresh flavors, lively entertainment, and coastal charm at the 44th Annual John’s Pass Seafood Festival in John’s Pass Village, Florida! From October 24–26, 2025, experience the sights, sounds, and tastes that make Madeira Beach a beloved...
Great news, music lovers! Caddy’s Indian Shores is bringing back live music to make your weekends even more unforgettable. Starting this month, enjoy the sounds of talented local artists while soaking in the perfect dockside views. Live Music Schedule: Friday &...
Get ready to be spellbound! Join us at Caddy’s Madeira Beach on Friday, October 18th from 10 AM – 12 PM for a Wicked Breakfast you won’t forget — just in time to celebrate the upcoming release of part 2 Wicked: For Good this November! Meet the enchanting Elphaba and...
Ready to take your beach day to the next level? Let us do all the work while you sit back, relax, and enjoy a private beachside experience in our brand-new Cabanas at Caddy’s Madeira Beach! Whether you’re soaking up the sun, celebrating with friends, or simply craving...
We’re making it easier (and more rewarding) than ever to enjoy your favorite Caddy’s moments. Our brand-new Caddy’s App is officially live in the Apple App Store and Google Play Store—your all-in-one hub for rewards, food, and exclusive perks. Already a Rewards...
Saturday, October 4 • Starting at 12 PM It’s time to grab your furry friends and head to the beach—Caddy’s Indian Shores is hosting its first ever Barktoberfest and you won’t want to miss it! This dog-friendly celebration is the paw-fect way to spend your Saturday,...
Swifties, get ready to sparkle! 🌟 Join us at Caddy’s Madeira Beach for the ultimate celebration of Taylor Swift’s brand-new album, Life of a Showgirl. We’re throwing a listening party filled with music, cocktails, and friendship (bracelets, of course)! What’s...
We’re excited to introduce a brand-new way to stay connected with our fans, guests, and community—welcome to the official Caddy’s blog! This space will be where we share stories about life on the beach, updates about our menu and events, and behind-the-scenes looks at...
We’re bringing back the pink for a cause! 🌴☀️ The Second Annual Flamingo Float is here, and Caddy’s is proud to team up with our parent company Sunpubs and the Children’s Dream Fund to turn good vibes into dreams come true. Sip for a Cause with Flamingo-Themed...
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