City: Jupiter, FL

Category: Nightlife

Telephone: (561) 575-0252

Address: 1111 Love St.

Description: Remember the video for Alan Jackson’s, Its’ Five O’clock Somewhere, sung with Jimmy Buffet? Well, it was filmed right here. The bar is just as you remember it from the video—a little bit tiki, a little bit Key West-tacky, a little bit lively, and a whole lotta fun. You can listen to live music six nights a week, from good local bands as well as some well-known artists. And as you listen, you can enjoy this little piece of paradise, with panoramic views of the Jupiter Inlet and the famous lighthouse that’s been its landmark for the past 150 years.Jim Burg is the owner of the bar and adjacent marina. After spending most of his life building high-end custom homes, he bought this property that once housed a bait-and-tackle shop. He transformed it into the Square Grouper Tiki Bar and the Castaways Marina. The property has a colorful history dating back to the 1890s. Near the original roadbed of the Jupiter and Lake Worth Railroad, better known as The Celestial Railroad, a two-story hotel and saloon overlooked the waterway. At that time, well-heeled tourists were venturing south on the Indian River by steamer, or aboard their own yachts. Some spent the night at the hotel near the Jupiter dock, while others—President Grover Cleveland among them—stopped by the saloon for dinner and then went on. But hard times came, and the hotel was eventually abandoned.In 1906, the property was purchased for $2,500. This riverfront swampland, then known as Suni Sands, was later filled in. During Prohibition, the site was used by rum-runners for night-time deliveries into this sleepy fishing village. Years later, a different type of illegal activity would occur here, helping to give Jim Burg’s business its name. “Square Groupers” was Coast Guard slang for bales of marijuana tossed overboard or out of airplanes and later found in the Jupiter Inlet.Today a wide variety of specialty drinks, including Captain Morgan Rum Punch Joes, Cuervo Tequila margaritas, mojitos, and frozen drinks, are poured here. And at the Square Grouper—no need to worry—it’s always five o’clock!