There is a real difference here between a restaurant with a water view and a restaurant on the water. The second kind is what people fly in for.
Broadly: the Gulf side gives you sunset and sand, the Intracoastal side gives you boats, dolphins and calmer water. Both are worth doing.
Feet in the sand, Gulf side
Paradise Grille at Pass-a-Grille is about as simple as it gets, and its position at the southern tip means the sunset view is the best on the beach.
Caddy's puts tables straight onto the sand. Bongo's and Coconut Charlie's sit on the beach behind their respective resorts and are easy walk-ups.
Waterfront Dining · 5250 Gulf Blvd
grandplazaflorida.com
Waterfront Dining · 6100 Gulf Blvd
coconutcharliesstpete.com
On the Intracoastal, boat side
The bay side is where you watch pelicans work the dock while you eat. Crabby's On The Pass and the John's Pass restaurants put you right on the channel, which at Madeira Beach means a constant stream of boats coming through the pass.
For a proper dinner
When you want white tablecloths rather than flip flops, the Don CeSar's restaurants are the classic choice, and the hotel itself is worth seeing even if you only go for a drink.
Last updated August 8, 2026. Something changed? Tell us.
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