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With an October calendar full of festivals, charity events, house tours, and other enticing activities occurring throughout the area, we asked TSG Hilton Head Island, Beaufort & Bluffton editor Cindy Owens to walk us through a long weekend in her city. Here’s her guide to enjoying Hilton Head, Beaufort, and Bluffton like an insider:

Beaufort County is located on the southern-most tip of the South Carolina coast, less than a thirty minute drive from Savannah, GA. Those lucky enough to live there—or visit regularly—share a love of the countless golf courses, wide, welcoming beaches, meandering rivers, and timeless tidal marshes that sprawl beneath cerulean blue skies. The county is comprised of some 25 islands across 925 square miles, 350 of which are water. From Historic Beaufort to Old Town Bluffton to the beaches of Hilton Head Island and Daufuskie, the vastness of Beaufort County affords each of us a look at what ties these islands and estuaries together and what makes each unique, and makes a getaway to the South Carolina Lowcounty an experience that is second to none.

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DAY 1, 12:00 noon: Regardless of how you get there, be sure to arrive in Old Town Bluffton mid-day in order to dine at one of the locals’ favorite spots: Bluffton BBQ. Owners Ted and Donna Huffman are icons in the community and serve the best BBQ in town at their self-described “BBQ joint.” Go early, because they shut down at 3 p.m. and occasionally sell out before closing time.

1:00 p.m.:
 After lunch, take a stroll around Old Town Bluffton, where you’ll find several art galleries and small, eclectic, specialty shops. If it’s Thursday, you’ll also be able to enjoy the Bluffton Farmers Market—voted number 1 in the state.

5:00 p.m.:
 Happy Hour at Vineyard 55 is the perfect place to relax and enjoy a glass of wine or craft beer after a day of sightseeing. The front porch at Vineyard also happens to be a great place to take in the sights and sounds of Calhoun Street, a great vantage point from which to people watch.

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7:30 p.m.:
 For dinner, both locals and visitors alike flock to Old Town, which offers a variety of wonderful options. At The Bluffton Family Seafood House, which is owned by the Toomer family—also proprietors of The Bluffton Oyster Company, the last working oyster factory in the state of South Carolina—they specialize in fresh, local seafood harvested right from the May River. If your preference is turf over the local surf, head to the Old Town Dispensary, which features live entertainment and a variety of spectacular dishes, including burgers that have made Garden & Gun’s list of the South’s best. If you’re craving Italian fare, Moon Mi Pizza at River Town Tavern is the place to go.

10:00 p.m.: 
After a day of traveling and touring the town, you’ll probably be ready for some R&R, so head down the moss-draped, oak-lined drive to the Inn at Palmetto Bluff (featured above) and experience a night of sleep in the lap of five-star luxury.

tsg-local-long-weekend-hhibb-5DAY 2, 10:00 a.m.: 
After sleeping in or enjoying a walk along the trails, head to The Corner Perk for the best coffee and breakfast menu around. Owners Josh and Kali Cooke will take great care of you in their beautiful new location in the heart of Bluffton.

11:30 a.m.: Set your GPS for Hilton Head Island and get on the road. Before crossing the bridge, pick up a to-go order at Pino Gelato Gourmet Cafe. Hungarian-born Krisztian and Attila make the best sandwiches around, and will stock your cooler with plenty of drinks and decadent desserts to enjoy throughout the day.

12:00 noon:
 You’ve finally arrived on the island! The beach is just minutes away for sun worshipers, and for those seeking an adventure, Captain Michael Perry of Papa Bear Charters will be happy to accommodate all on a fishing or skeet-shoot charter. Other choice island activities include golfing, parasailing, catamaran and dolphin watch charters, jet ski, kayak, paddle board and bicycle rentals, as well as horseback riding.

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7:00 p.m.:
 After freshening up, head to Hudson’s on the Docks. Operated by the Carmines family, Hudson’s is a casual, local institution well known for the spectacular views overlooking Skull Creek and, of course, its fresh, locally caught seafood.

9:00 p.m.:
 On your way back to the Inn, stop in at HogsHead Kitchen and Wine Bar for a nightcap and sample the selection of delectable desserts prepared by multiple James Beard Award nominee Chef John Pashak. Even if you don’t have room for dessert, take one to go—it’ll make a wonderful breakfast treat in the morning.

DAY 3, 10:00 a.m.:
 Bid Bluffton farewell and head north to Beaufort, which is known as the crown jewel of the sea islands. Check in to a bed and breakfast—The Beaufort Inn, The Cuthbert House Inn, The North Street Inn, Two Suns Inn, The Rhett House Inn, or the Beaulieu House on Cat Island are all lovely, and each has its own ambiance and charm—and get ready for a fun afternoon.

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12:00 Noon: 
The first order of business in Beaufort: lunch (or brunch, depending on the day of the week) at Plums on Bay Street. Known for their seasonal Lowcountry fare, everything on the menu is spectacular, but be sure to order the sweet potato fries—they’re to die for.

1:00 p.m.:
 Bay Street is just a block off the river and the centerpiece of the Beaufort shopping district. Comprised of quaint shops, galleries, and restaurants, it’s unique to anything you’ll ever experience. After you’ve had a chance to explore all the artisans and merchants have to offer, treat yourself to a historical Southurn Rose Buggy Tour of downtown Beaufort, the second oldest city in the state.

5:00 p.m.: 
Once back on Bay, head across the street to Wined It Up for a snack and your choice of libation before getting refreshed for your dinner reservation. Cheers!

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7:00 p.m.:
 Put on your best resort-casual attire and indulge yourself the last night in town by dining at Emily’s Restaurant and Tapas Bar, a Beaufort favorite for over twenty-five years. They’ve got an extensive selection of tapas and entrees to ensure there’s something for everyone.

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Look Like A Local: Casual is key throughout the Carolina Lowcountry, and in Beaufort County, there are plenty of local boutiques for residents to frequent, including Gigi’s, The Bleu Companies, Luciana and Knickers. Colorful geometric prints with matching jewelry are everywhere this year, as well as nautical prints, which are a timeless staple in our area. Golf and tennis attire is also common, as Hilton Head is a popular destination for fans of both sports. Footwear favorites include sandals and chic flip flops – perfect for showing off bright nail colors—as well as cowboy boots to accompany anything from shorts to long dresses. Finally, locals like to finish off their look with bags and accessories from Daufuskie Island based Spartina 449. {TSG’s picks for getting the local book featured above: 1. Jada Dress from Monkee’s of Charlotte 2. Stewardess tote from Satchel 3. Sophia studs in coral from Bishop Boutique 4. Dorado buckle riding boot from Monkee’s of the Pines; images below collage: left: CJ Lang‘s signature ikat coats; right: stripe poncho from Periwinkle}

{Beaufort photos courtesy of EatSleepPlayBeaufort
* (Closing shot caption/photo credit) Henry C. Chambers Waterfront Park photo courtesy of Phil Heim}