A Hilton Head Island staple since 1999, The Smokehouse serves award-winning barbecue in a spacious setting with a retractable window wall and a generous outdoor deck. The Chimney Bar, a rooftop addition, offers handcrafted drinks and a relaxed atmosphere. With 15 TVs, it's a prime spot for sports enthusiasts.

Located on Hilton Head Island's south end, Local Legend Brewing Company is a family-friendly brewery and restaurant that honors the island's 1970s and 1980s roots. The spacious interior features a 35-foot bar adorned with local memorabilia and vintage photos, creating a nostalgic yet modern atmosphere. The expansive beer garden, shaded by live oaks, offers a relaxed outdoor space for guests to enjoy. The menu, crafted by Executive Chef Alan Ford, includes shareable plates, vegetarian and vegan options, and creative takes on Lowcountry classics. Entertainment options abound with games like shuffleboard, giant Jenga, arcade games, and wall-to-wall TVs for sports viewing. The brewery also hosts live music events and game night tournaments, making it a vibrant community hub.

Hinchey's Chicago Bar & Grill has been a Hilton Head Island favorite since 1996, offering a slice of Chicago in a relaxed setting. The menu features classic bar fare, including deep-dish pizzas and Chicago-style sandwiches. With 25 satellite TVs, it's a go-to spot for sports enthusiasts. The welcoming atmosphere makes it a popular choice for both locals and visitors.

Located within Palmetto Dunes Oceanfront Resort, Alexander's has been a Hilton Head Island staple since 1977. This upscale seafood restaurant offers seasonally inspired dishes crafted from locally caught seafood and ingredients. Signature items like Shrimp and Grits and Wiener Schnitzel are complemented by an extensive wine list. The lagoon-front setting provides a serene dining experience. Reservations are recommended.

A father-son venture from Vermont, Lincoln & South Brewing Company brings New England-style IPAs to Hilton Head Island. Their taproom offers a mix of indoor and outdoor seating, often featuring live music and games like cornhole and billiards. The menu includes house-made charcuterie boards, burgers, sandwiches, and tacos, with a kid’s menu available. Open daily at noon, they don't take reservations, so arrive early to snag a spot.

Tucked away in a small shopping center on Palmetto Bay Road, Cool Cats Lounge is a local dive bar that feels like a hidden gem. The space is cozy, with a jukebox spinning tunes and a few dartboards for entertainment. The friendly staff and regulars create a welcoming atmosphere, making it a favorite spot for both locals and visitors. Happy hour runs from 3 to 7 PM, offering reasonably priced drinks. It's a great place to unwind, play some trivia, or just enjoy a quiet drink.

Located within Shipyard Golf Club, Brickyard Pub offers a relaxed atmosphere with views of the 18th hole. The menu features pub favorites like fish tacos, burgers, and pretzels with cheese dip. Happy hour runs daily from 4:00 to 7:00 p.m., offering specials like Yard of Wings, Guinness, and Beer Towers. The covered patio provides a pleasant setting for outdoor dining.

Established in 1987, Callahan's is Hilton Head Island's only Irish-owned bar, offering a classic pub experience with a modern twist. The spacious interior features multiple big-screen TVs broadcasting a variety of sports, and six Diamond pool tables for friendly competition. The menu boasts traditional Irish dishes like Fish & Chips and Bangers & Mash, alongside American favorites such as wings and burgers. An extensive selection of premium bourbons, ryes, whiskeys, and tequilas complements the offerings. The lively atmosphere is enhanced by live music events and a well-stocked jukebox, making it a popular spot for both locals and visitors.

Rollers Wine & Spirits, a family-owned establishment since 1960, offers an extensive selection of fine wines, spirits, craft beers, and cigars. Their Palmetto Bay Road location features a wine bar where you can enjoy wines by the glass or bottle, wine flights, and a variety of cheese plates and small bites. The garden patio provides a pleasant setting to savor a glass of wine or beer, accompanied by a cigar from their walk-in humidor. They also host weekly wine tastings every Tuesday and Thursday from 5:00-7:00pm, accompanied by live music.

Located in a repurposed bank building, Side Hustle Brewing Company offers a unique setting with a spacious beer garden and indoor seating. Their rotating selection of craft beers includes IPAs, stouts, and seasonal brews, catering to a variety of tastes. The venue also features a merchandise shop and hosts food trucks like Taco Bills and Bank Burgers, providing a diverse dining experience. With live entertainment and a family-friendly atmosphere, it's a popular spot for both locals and visitors.