November 2009

The Reilley Family: Nature or Nurture?

Author: Ann DeMart

The Reilleys have “restaurant running” in their blood

When so many members of a family are in the same business or field, you tend to wonder if they inherited the tendency or if they’ve simply learned from their environment. Whatever the cause, the effect of the Reilley family’s proclivity for the restaurant business has been satisfying success.

Tom and David Reilley have been dishing up gastronomic pleasure, friendly ambiance and special events on Hilton Head Island for more than 30 years, from their early work at the Hofbrauhaus and local country clubs to ownership and operation of some of the most popular restaurants on the island. Today, Reilley’s North, Reilley’s South and Aunt Chilada’s are dining destinations and favorite haunts for visitors and islanders alike. In addition to Tom and David, partners and participants in the family business include Tom’s wife Diane, David’s wife Laura, Tom’s daughter Erin and her husband James Booth, Tom’s son Brendan and daughter-in-law Jill, and many other Reilleys and spouses. At one time or another, siblings Mary, Michaela, Mike and Dennis contributed to the family’s success. Tom and David’s father, Tom, even did the books.

The brothers grew up in the business in Rhode Island, where their father owned a bar when they were very young. Both boys worked in bingo parlors, washed dishes and waited tables from the time they were kids. Tom worked for Hyatt and for a food purveyor in Atlanta. David Reilley, the seventh of eight siblings, fell in love with Hilton Head when he visited his sister, Mary, in 1973. He moved to the island in 1974, Tom and Diane joined them in 1977, and their parents and many siblings soon followed. Eventually, almost all members of the family became Hilton Head Island residents.

So, do the Reilley’s think their proclivity for running restaurants is due to nature of nurture? “You have the mindset, and then you just do it,” said Tom. He and Diane opened the first Reilley’s restaurant in 1982 on the south end of the island at the Gallery of Shops. After a fire, they moved it across the street to its current location at Hilton Head Plaza on Greenwood Circle in 1995. The Irish pub proved so successful that the family opened a second Reilley’s on the north end of the island in 1988 at Port Royal Plaza. In 1993, they even opened a Reilley’s on Maui in Hawaii.

In 1989, Tom opened Aunt Chilada’s, which offers Mexican, Tex-Mex, American and authentic Italian dishes—truly something for everyone—and later sold the restaurant to brother David and son Brendan. James Booth got involved in the restaurant business when he married Erin, Tom and Diane’s daughter. Today Erin and James are the general managers of Reilley’s South and North, respectively. David Reilley met his wife, Laura, when she was a waitress at one of the restaurants. Another of Tom and Diane’s children, Brendan, the only Reilley with any formal culinary training, met his wife Jill when they both attended the Culinary Institute of Arts in New York.

The Reilleys believe that there are definite advantages for a locally run, family operation. “It creates a friendly environment for our customers,” said Erin. “We have a huge, varied clientele—families, singles, groups and golfers—and all feel welcome here. Visitors look forward to seeing us, and locals enjoy the familiar faces and comfortable atmosphere.”

David agrees, “People are more inclined to talk with you and get to know you when they know you own the business. You meet people from all over the world. I’ve made friends from Scotland, England and Canada. Visitors come back year after year to see us, he said.”

There are also challenges in working so closely with family. The Reilley’s have weekly meetings where many decisions are made. Menus are changed several times a year, operations are reviewed and new ideas are discussed. The question, “If you could compare your decision-making process to a country’s government, which one would it be?” drew a couple of interesting responses. Tom said, “America. It’s a democracy. Everyone gets to have an opinion.” Erin said, “Well, there are a lot of chiefs…everyone has an opinion.” And Jamie laughed and asked,
“What did Tom say?”

Opinions on the best cook in the family might create some interesting discussions. Tom said, “Diane.” James agreed, but added, “Although Brendan is excellent.” David said, “Brendan is the best chef. And I’m the best cook,” he chuckled, and quickly added, “But Diane, Jill and Laura are pretty darned good.”
It was no surprise that opinions also differed on favorite items on the restaurants’ menus. Tom named Chicken Milanese and the prime rib. James likes the sashimi. Erin listed the Buffalo Chicken Wrap, Bacon-wrapped Shrimp and the Black and Blue Wedge Salad. David said, “rib eye, pastas, ribs and the DR Burrito, which is named for my son.”

Children in the family, some now pursuing other careers, started working in the restaurants as teenagers. Many who are currently attending college still work there during summers. Do the more senior Reilleys want the third generation of Reilleys to follow in their culinary footsteps? It depends on whom you ask. Tom said, “I’d like to see the next generation follow in our footsteps, so there will always be a Reilley’s.” Other family members aren’t quite sure; they know how tough the restaurant business is, especially these days. “I’d like to see my children pursue other careers,” said Erin. “This is a challenging business. And, there’s a certain irony in our being a family-run, family-friendly restaurant. We almost never get to sit down to dinner together.”



The Reilleys are also responsible for some of the island’s longest standing traditions. Hilton Head’s first St Patrick’s Day Parade and The Reilley’s Invitational Golf Tournament were conceived at Reilley’s South. Both continue to this day, 27 years later. This year, the Reilley’s Mortgage Network Golf Tournament will take place November 18-21 at Oyster Reef and Old South with participants from 25 states and four countries, including Canada, Ireland and Scotland.

Reilley’s South is located in Hilton Head Plaza at 7D Greenwood Drive.
(843) 842-4414.

Reilley’s North is located in Port Royal Plaza at 95 Matthews Drive.
(843) 681-4153.

Aunt Chilada’s is located at 69 Pope Avenue.
(843) 785-7700.

Easy Street Catering
(843) 785-7700.

All are on Hilton Head Island, S.C. Websites: and

  1. What a handsome looking family! Great article CH2! The Reilleys are great people…get to know them :~)

    — Becca Ross    Oct 29, 10:10 am   

  2. Tom’s approach to anything is , “The answer is Yes, what’s the question?” Great family that continues to do a lot for the Island.
    Well deserved article.

    — Don Calhoon    Oct 30, 10:49 am   

  3. It has been many years- and I am glad that I am on your list- someday I plan to play the golf outing- in the meantime I will be down your way for a visit – we have a 2nd home at Pawleys Island so it is not far- maybe drive our boat down for a visit! Say hello to my friend Gary Duren ! Best wishes to you Tom & David Reilley and your families- glad that all is going well for you and your businesses !

    — Paul T Furth    Nov 19, 12:31 pm   

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