It is hard for Caroline Simpson and Withers Poellnitz to remember a time when they didn’t know each other. The two met when she was just an eighth grader at Tuscaloosa Academy in Alabama and Withers was in ninth grade at the same school. “I’ll never forget,” remembers Caroline, “He was a football player and I was a cheerleader. I was on top of this pyramid, holding one side of a sign that the players were about to run through and Withers looked up and winked at me.” Caroline’s heart melted; Withers, however, claims no recollection. Instead, his first memory of Caroline was when she asked to borrow his T-shirt after swimming in a lake with a bunch of friends. “She ended up stealing it. She never gave it back,” he says, laughing.

Withers, who now works for a private equity firm in Nashville, Tennessee, proposed in June of 2010. He got down on one knee in a yurt atop a North Carolina mountain during a vacation. That night at dinner, Caroline was shocked to see both of their families at the restaurant for a surprise engagement party that Withers had arranged.

Caroline had dreamt about her wedding since she was a little girl. She knew she wanted a destination wedding in Newport, R.I., and Withers agreed, even though he’d never been there before. So, Caroline searched the internet for an event planner and found one she liked: Raina Dawn Filippelli of Raina Dawn Events. “The first time I talked to her I could tell she would be wonderful,” says Caroline, a designer herself at Digs Interiors in Nashville, where the couple now lives.

It wasn’t long before she and her mom traveled to Newport to meet Raina. There, the seeds of an entire wedding weekend started to grow. “We really wanted everyone to feel like they were on vacation when they got to Newport,” explains Caroline.

Raina believed that a quintessential Newport experience should somehow involve water, and she suggested that the groom’s family invite the couple’s 280 guests out for the weekend. Caroline, her mom and Withers’ parents all agreed, and Raina got to work. “She knew all the best people to call to put the weekend together,” says Caroline.

The weekend began on Thursday, when their bridal party of 30 assembled. “People in Newport thought we were nuts to have such a large wedding party, but we’re from the South, where that’s a tradition,” Caroline says. Caroline’s father booked a block of rooms at Hotel Viking and that night the girls gathered for a bridesmaid’s dinner at the Clarke Cooke House. Everyone enjoyed the restaurant’s signature dessert: Snowball in Hell (a chocolate-coated goblet filled with chocolate roulade and vanilla ice cream and topped with callebault chocolate sauce and toasted coconut).

Guests received bronze Euro Totes filled with tourist brochures and goodies like chocolate lobsters made by Newport Chocolates. There were also pink and taupe “Welcome to Newport” itineraries designed by Dallas-based Paradise Design Co.—a Raina favorite.

On Friday, the bridal party spent the early afternoon sailing aboard the Schooner Aurora where custom beer koozies and napkins were added for a personal touch. That evening, after rehearsal at Trinity Episcopal Church, the bridal party joined guests at The Chanler at Cliff Walk for a decadent dinner.

“We used long Tuscan tables with accents of driftwood and stones,” Raina says. “There was a cigar roller, jazz band and lots of orchids.” Caroline surprised Withers with a groom’s cake that emulated a golf course and even featured a tiny golf cart with a tag on the back that said “Withers.”

On Saturday, guests explored Newport until the 6 p.m. ceremony. Afterwards, trolleys brought them to Rosecliff mansion where each table was decorated with different flowers in sleek white vases. “Caroline has a fresh and contemporary style,” describes Raina, who added a few surprise elements including a sculpture of Venus and Neptune and a pearlescent five-tiered wedding cake covered in confectioned flowers. To get the party going, the couple brought in their favorite band 
from Alabama.

Because Rosecliff is an historic mansion, there can be no firework sendoff so Raina came up with an alternative: “Maracas at Midnight.” Each guest shook white maracas as the couple departed for Boston before flying to Antigua where they honeymooned at the Hermitage Bay Resort.

It was truly the wedding weekend of Caroline’s dreams. And she says, the journey to get there couldn’t have been more enjoyable thanks to the creative and collaborative planning of Raina Dawn Filippelli.