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The Perfect Winter Weekend Getaway to Hilton Head Island

There’s a chill in the air now. Leaves are falling, the days are getting shorter and golfers are starting to see their breath during morning rounds. That can only mean one thing: winter is coming (cue Game of Thrones music).

Thankfully, winter is one of the best times to visit Hilton Head Island. The weather is beyond pleasant and conditions on its world-famous golf courses are wonderful. Even better, with non-stop service from more than 20 major cities including New York, Boston, Cincinnati and Chicago, getting to “Golf Island” is quick and convenient. In fact, the hardest part of the vacation is picking which courses to play.

To make the decision a bit easier here’s a sample itinerary of the perfect weekend getaway to the island recently ranked among the top three in the U.S. by Conde Nast Traveler.

Day 1 – It was smooth sailing from Boston to Savannah/Hilton Head International Airport; the non-stop flight was less than three hours and even arrived a few minutes early. Grab the clubs and the rental car (the Mustang is tempting but stick with the SUV, it has more trunk space for your precious cargo), and make the quick, 40-minute drive to Old South Golf Links in Bluffton just before the bridge. Designed by Clyde Johnston, the 6,772-yard, par-72 course deliver a warm welcome as its layout perfectly captures the beauty of the legendary Lowcountry. Named a “Top 10 New Public Course” by Golf Digest when it opened in 1992, it winds through towering oaks and over rolling terrain; the closing three holes on both nines are among the most picturesque in all of Hilton Head.

Day 2 – It’s an early wakeup call in the two-bedroom villa at Palmetto Dunes Oceanfront Resort, today’s plan calls for 36 holes. Standing on the first tee of the famed Robert Trent Jones oceanfront course, the sun finally creeps above the tree line revealing one of the island’s most picturesque layouts. When the group reaches the signature par-5 10th hole, sleepy golfers are rewarded with breathtaking views of the Atlantic Ocean (helpful hint: don’t forget your camera). A quick lunch at Big Jim’s then it’s back to the golf course. The afternoon will be spent on the Heritage Golf Collection’s championship course, Robber’s Row, just 10 minutes up the road. Tipping out at 6,657 yards, the par-72 layout was redesigned by Dye in 1994, so creativity and shot-making are a must to play well here. Golfers will also take a walk through history as its holes are set atop former Civil War grounds, so prepare to live, laugh and learn.

Day 3 – No trip to Hilton Head Island is complete without taking a selfie with the iconic red-and-white striped Harbour Town Lighthouse. So snap a quick pic then head to the newest course on the island – Atlantic Dunes by Davis Love III. The Ryder Cup captain and his design firm completely reconstructed and recreated Sea Pines Resort’s historic Ocean Course, the first built on Hilton Head Island. The end result is nothing short of stunning; the course has a pronounced seaside ambiance and Lowcountry feel. Restored sand dunes and tens of thousands of newly installed indigenous plants treats golfers to an unmatched experience, and the view from the signature par-3 15th is postcard material. It’s the perfect complement to Sea Pines’ famed Harbour Town Golf Links and Heron Point by Pete Dye.

Finally, all that’s left is the quick trip back to the airport to catch a 4:30 p.m. non-stop flight back home. Traffic is minimal so there’s enough time to grab a quick drink at the bar, which is the perfect opportunity to start planning a return trip. After all, there’s still so much more great golf to play.

And for golfers looking to stay an extra day (calling in to work sick is acceptable in this case), a quick trip over to Fripp Island is a must. Named one of the “100 Best Golf Resorts in North America” by LINKS Magazine, its Ocean Point Golf Links was designed by George Cobb and is a true oceanside gem. With views of the Atlantic or inlet on 10 of the 18 holes, the 6,556-yard, par-72, links-style layout is a wonderful end to any Hilton Head Island visit.

By Andy Dekeuster

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Find Your Island Time

Hilton Head is America’s favorite island, offering 12 miles of pristine beaches and everything you need for the ultimate retreat. Enjoy easy days relaxing in the sun, sand and surf on some of the best beaches in the country.
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