Best Beach Bars

Our favorite US and Caribbean watering holes.
By: K.C. Summers

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What makes a great beach bar? Cold drinks and warm breezes, at the very minimum, with bonus points for thatched roofs, sunset views and flaming tiki torches. But the best places go beyond all that to achieve true legendary status. Whether quirky or classy, here are a few of our favorite watering holes on US and Caribbean shores.
Negril, Jamaica, is known for its super laid-back vibe, yet the cliff divers who perform daily at Rick's Cafe are anything but -- which they emphasize by crossing themselves dramatically before making the 60-foot plunge. Be generous with your donation (you don't think they're just diving for their health, do you?) and then prepare to be dazzled when the sun sets. Nature's nightly spectacle is the other big attraction here, and this one will just cost you the price of a drink.
In the immortal words of musicians Alan Jackson and Jimmy Buffett, it's 5 o'clock somewhere, and there's no better place to celebrate that sentiment than this friendly bar on Florida's Jupiter Inlet. That's because the singers’ 2003 "Five O'Clock" music video was filmed here, making the place a national as well as a local landmark. There's live music 6 days a week, and postcard views of the Jupiter Lighthouse and adjacent marina. "Square Groupers," by the way, refers to the bales of marijuana thrown overboard, or out of airplanes, that have been known to up wash along the inlet.
If you've been to San Pedro Town on Belize's Ambergris Caye, you know about the chicken drop at the Spindrift Hotel's Pier Lounge. It's what counts as high drama on this supremely laid-back island. Simply place your bet with the bartender, wait for the bar's pet chicken to have its dinner, then gather around a giant bingo card on the beach. If the bird poops on your card, you win some cash -- after you clean up the mess. Ah, good times. Even if you're not into excretory-themed gambling, the oceanside bar is a comfortable place to kick back with a Belikin (the local brew) and chat up some of the island's colorful characters.
Ocean City, MD, is not known for its Caribbean vibe, so one inspired bar owner set out to remedy that by importing fully grown palm trees, tiki huts and tons of sand to its mid-Atlantic location. Seacrets is huge, with 14 sandy-floored bars, a restaurant serving Jamaican-inspired food, a nightclub, a dance hall and, during daylight hours, outdoor rafts with waitress service. Be forewarned, the crowd can get raucous. But when you settle in at a floating table and admire the sunset on the Chesapeake Bay, you just might think you're in the islands.
Rusty's is a shrine to surfing and the '60s, which is only fitting, given its location on California's iconic Santa Monica Pier. The pier dates from 1909, and families still come to take a spin on its historic carousel. You can prolong the day with dinner and drinks at Rusty's, where live music (both local and national bands) attracts a good crowd. There's dancing, karaoke, pool and other games, too. For a quieter evening, settle in for cocktails and conversation on one of the outdoor patios overlooking the Pacific.
If you've ever enjoyed a Painkiller or 3, you've come to the right place: The legendary rum drink was invented at the Soggy Dollar, a charming bar on the British Virgin Island of Jost Van Dyke. The bar is attached to the equally charming Sandcastle Hotel, a favorite of the many sailors who visit here. Tradition has it that you swim over from your sailboat or yacht, ending up with a pocketful of sodden cash, hence the bar's name. But you can get there by road or dinghy, too. However you arrive, there's no prettier setting in which to feel no pain.

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