School’s out soon for much of America, and that long-looked-forward-to bell begins our traditional high season, here in Swallowtail at Sea Pines. As a family-friendly resort from the start, Hilton Head Island for many years was considered a summer place, because that’s when the kids were available to come along. For nearly 20 years now, more and more island lovers have discovered the pleasures of the spring and fall on America’s favorite vacation island. Our friends from Canada and upstate New York, too, have a particular fondness for long stays in midwinter. Trading a parka for a golf jacket is exotic enough when lake-effect snow is your frame of reference. Offseason here is heaven.

What started as inside information – the advantages of Hilton Head Island’s “shoulder seasons” – is now well known and widespread. Still, some features of our seemingly endless summer stand out. One of those summer standbys is the evening performance of singer-songwriter Gregg Russell, beneath the Liberty Oak, just seven blocks down Lighthouse Road from Swallowtail

The Pied Piper of Harbour Town

This gentle Pied Piper has entertained and enchanted children and adults alike with his music for more than 40 years. The tradition is so well established that the children of the children who joined Greg Russell there for a balmy evening of songs are coming to see him now. It’s a Hilton Head Island tradition that we point to with pride, because Gregg was a personal discovery of Sea Pines Founder Charles Fraser. Gregg credits Charles with giving him a regular job – rare enough for a musician – and in paradise, too, for which Gregg has never stopped showing his gratitude.

The pure entertainment Gregg Russell provides is equaled only by his devotion to local charities and to the audience that grows and changes every year, who gave him this opportunity.

Legacy of a Legend

A few years ago, some proud parents sent Gregg a photo of their grade-school son sitting in Gregg Russell’s chair and holding Gregg’s guitar. The grade school son was country music hero Brad Paisley. We never tire of the story. What could say it better?

Swallowtail at Sea Pines is a vacation residence that people have passed down through the pleasure of generations, too. People who came to rent a week or two sometimes decided that coming back every year would be a good idea. Seeing their kids grow strong and happy in the Forest Preserve and on the playgrounds and beaches with the rhythms of the tidal marshes playing in the background, Swallowtail visitors became Swallowtail owners. Some added another unit or two to their holdings as a gift for the kids. Grown children many times made that choice themselves, too.

Reasons in Abundance

Our six-month summer began here with the RBC Heritage, the PGA tournament that many pros look forward to most of all. The summer wind ushers in days that lengthen to unbelievable measures of beauty. High-season rates and traffic are only three months long, so that leaves a lot of time for the smart vacationer to work with.