May 2015

Welcome to The Boardroom

Author: Kent Thune | Photographer: Mark Staff Photography

The Boardroom Team (from left to right): Brendan Reilley, Caitlyn Overstreet, Anthony Triceri, Thomas Reilley, Alana Allison and Scott Gruber

The best things in life are not planned—they happen. This universal truth sums up the evolving story of the Hilton Head Island hot spot, The Boardroom, which is located in Reilley’s Plaza, affectionately known by locals as “The Barmuda Triangle.”

The Boardroom, as people may know today, is a four-year-old bar and lounge that kind of popped up out of nowhere; but in reality, The Boardroom has served private members since 1984. It was back in the ’80s when Tom Reilley and a group of buddies decided they wanted a personal retreat, a hangout and a hideout—a cigar smoking, dart throwing, pool shooting place to pow-wow—that The Boardroom was born.

For the next 26 years, Tom and his friends would welcome in hundreds of members. “Everything about the Boardroom is countless,” Tom said. “The holes in the wall from darts, the games of pool played, the laughs, rounds of golf watched, scorecards compared, and the memories are countless.”

“Some might also say the secrets are countless,” said his son, Thomas Reilley, “but that might be just a feeling you get when you hear about a hidden bar in the triangle with no windows and private membership, a self-stocked bar, and cigar smoking going on. Imagine a modern day prohibition bar; that is the feeling you got in those last days as a private club.”

The Will Snyder band featuring Haley Davis entertains the crowd onstage at The Boardroom.

In 2010, with membership dwindling, and the location booming, Brendan Riley urged his father to lease the space to him and his younger brother, Thomas. The Boardroom was opened to the public.

Thomas reflected on the early days: “We were open to anyone, but we didn’t want to diminish the feel my dad had set for the place. We wanted to be a secret still, a hideout, and we wanted to treat every guest like they were a member of something special. Basically tell your good friends, but not all of them, if you know what I mean.”

But when spring came, an incredible and fateful transformation began to take place. “Brendan decided we should do some music on the outside bar,” Thomas said. “We had solo acoustic shows on the weekends and people loved it. Live music in the triangle was new and innovative. Solo acts on Fridays and Saturdays turned into duos and then trios, and as the crowds grew over the years so did our reputation as a live music venue.”

It didn’t hurt that two of The Boardroom’s best bar customers at the time were Phil Sirmans and John Cranford, of Cranford Hollow. “They really opened my eyes to what we could do as a venue, and they helped legitimize our small stage when other musicians at the time might have turned their noses up to it,” Thomas said. “They believed in The Boardroom since day one, and they are still a phone call away when I need advice or anything in general. I hope they see me the same way—a phone call away.”

Today the legitimacy of their small stage has been confirmed by artists both locally, up and down the East Coast and throughout the Midwest. This year, the musical excitement and diversity continues at The Boardroom. “We have bands coming this summer from Louisville, Nashville, Tuscaloosa, Washington DC, Ohio, North Carolina, Florida, Myrtle Beach, Atlanta, and I haven’t even filled my schedule,” Thomas said.

The musical acts range from solo artists to bands with varying styles including rock, funk, jazz, and reggae. You can also catch local acts, such as Hannah Wicklund from the Steppin Stones (Mondays); Peter Buonaiuto (Tuesdays); occasional appearances by the fun and popular Cranford Hollow; indescribably energetic and talented Groove Town Assault; and smooth, laid back nights by Will Snyder and Nick Poulin. See the full calendar at

When asked which atmosphere he prefers, Brendan Reilley said, “I can’t tell you. Obviously the music is something we put a lot of time and effort into, and we support and love all the musicians who play the outside bar. But there is something about that inside bar that brings us all back to the original Boardroom. We grew up in there as kids; we would bug my dad for his key, and he would let us go over there so long as there wasn’t any other member in there smoking cigars.

“As far as hidden forts, or treehouses that our friends all had, the Boardroom was by far the most envied hideout. It’s not just me that has those memories; previous members must walk in and have similar feelings, like ‘wow if these walls could talk!’ I just know this place was jam packed with memories for my dad and his friends, so it is very special to keep the name and the location alive.”

One thing The Boardroom was then and is now is unsuspected. “I remember how unique it was that absolutely no one who walked past the Boardroom had any idea what was behind the door. There were no windows; there was no signage; it was just a door. Behind that door was a different story,” Thomas said. “Today, ‘unsuspected’ is still exactly what the Boardroom is. Walk past the small patio with a tiny stage at any point when the sun is up, and you might question if this is the same Boardroom you have been hearing about. Wait until 11 p.m., and you will know that you are in the right place. I am so surprised, even today, that they continue to show up. But when the stage lights start flashing and the drumsticks start clapping, an incredible migration of energy and bodies flood our patio, night after night, in such a rapid way that you don’t even see it coming.”

When asked what he loves most about The Boardroom, Thomas says without hesitation, “The staff, the staff, the staff! I have Alana, who was supposed to work for three months, and now she is my bar manager, my right hand lady, and keeps everyone in check. Scott, Anthony, Caitlyn, Ace, Lauren, and Jeff…it’s just funny to think of them as working for me; they work with me. They are my friends; they are my family, and in two cases, they live with me. They literally are a part of every day of my life, and they make The Boardroom. I don’t know if it is the music, the money, or the Kool-Aid that keeps them here, but for some reason, I have a staff that believes in this place as much as I do.”

If you would like to know the complete history of The Boardroom, good luck getting someone to tell you all those secrets. But if you would like to be a part of the ongoing and unexpected great nights, stop by any night after five. 

The Boardroom is located in the Reilley’s Plaza at 4 Greenwood Drive, Hilton Head Island. Hours of operation are 5 p.m. to 2 a.m., seven days a week. For more information, call (843) 363-6636, or visit

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