A Modern, Orange-and-Blue Wedding in Italy

"It was the most romantic date I've ever been on," says Dennis Whitehead of his first time out with Bryan Darling—and that's saying a lot, since it took place in the decidedly prosaic ambience of a bustling airport. The two had met online and hit it off through texts and phone calls, but Dennis was living in Memphis, where he works professionally and academically in the performing arts, while Bryan, a neonatologist, was 100 miles away in Tupelo, Mississippi. They finally connected over a quick drink when Bryan was flying out of Memphis, and the in-person attraction was mutual. "Bryan went to board his plane, and months later we found out we'd both felt as if we were saying goodbye to our boyfriend at that moment," says Dennis.

It wasn't long before they were indeed a couple—and three years later almost to the day, at their annual New Year's Eve party, their status changed from boyfriends to fiancés. Each year, Dennis would sit down at the piano at midnight and sing "Auld Lang Syne," but this time Bryan had slipped a new piece of sheet music onto the stand: Train's "Marry Me," with lyrics he'd reworked to fit their relationship. "Dennis didn't see the title at first, so I pointed it out to him, then got down on one knee and proposed as a friend placed a crystal ice bucket of Champagne on the piano," says Bryan. "We were in tears, and so were many of our guests."

The twosome, who now live in Memphis, agreed on a destination wedding (befitting the setting of their first date), and chose Italy after finding Castello delle Serre, a castle and boutique hotel in Serre di Rapolano, near Siena. "Bryan said, 'Wouldn't it be cool to get married in a castle?'" recalls Dennis. "I replied, 'Two princes getting married in a castle? Perfect!'" A stylish celebration was hatched in shades of blue, orange, and gray.

To set the tone for the event, their welcome dinner at the castello had an Italian-chic theme, stealing a note from La Dolce Vita. The result, says Dennis, "looked like a movie set of a fashionable cocktail party." The pair began the next day, July 20, 2015, with a drive around the countryside and a private lunch. Then, at 6:30 p.m., they walked down the aisle of the grand hall together to an a cappella jazz rendition of "I Will Be Here" by Steven Curtis Chapman, with Dennis singing the end to his groom as they reached the front. After the Christian vows, the party of 38 went outside to celebrate, beginning with a cocktail hour around the pool, followed by a multicourse meal. Bryan's son toasted the new husbands, and a friend sang an original song called "By Your Side" that was so beautiful, the two didn't even dance—they just stood there and listened as the sun went down in a blaze of red on their glorious Tuscan day.

WATCH DENNIS AND BRYAN'S VIDEO

"We wanted to spoil our guests for coming all this way to celebrate with us," says Dennis of the linen bags filled with goodies such as a candle, amaretti cookies, and sparkling Italian sips. Tarah Catalano designed packaging that would also tie in to the other paper goods at the wedding.

Black-and-white stills from classic movies set in Italy made cool postcards for guests to send home to loved ones.

Savory items were also included, with a pairing of rosemary salt and truffle oil (plus a nice cotton dish towel) rounding out the welcome goodies.

At 8 a.m. on the big day, the couple, their photographer, and a driver with an old Fiat (adorned with a "Just Married" sign in Italian) went from one picturesque Tuscan spot to another, taking prewedding photos. "We felt like models on a photo shoot—it was so much fun!" says Dennis.

At noon, they stopped in a neighboring town, Rapolano Terme, for lunch at a quaint osteria. And then headed back to the hotel to get ready for the wedding.

The grooms donned their bespoke gray suits in the castle's Contessa suite.

Bryan engraved pocket watches with the wedding date and the French phrase Mon amour, mon coeur, pour toujours, which means "my love, my heart, forever."

The tiepins on the grooms' cravats were made from a pair of antique cufflinks.

In the pair's matching Cartier trinity rings, rose gold represents love, yellow gold stands for fidelity, and white gold symbolizes friendship. Not only does each of the three metals in the bands carry its own meaning, but the design also was commissioned in the 1920s by Jean Cocteau, an openly gay French artist.

The castello is located among rolling hills and cypress trees.

Reverend Cheryl Cornish, from the couple's home Congregational church, officiated the vows in the castello's ornate grand hall.

Escort cards in the shape of Italy's famed cypress tree directed guests to their seats.

Guests mingled and noshed on traditional Italian canapés by the castle's pool. Later that evening, after the reception officially ended, many of them (grooms included) returned for a late night swim and more cocktails.

Guests sipped on Campari fizzes during cocktail hour.

The color of the night's specialty beverage fit in with the event's palette, and the cocktails were finished off with customized drink stirrers, too.

Everyone gathered for a group photo at the end of cocktail hour.

Table settings showcased a myriad of blue shades: Hand-cut, heptagon-shaped menus with the couple's monogram had a cobalt marbled backdrop that matched some of the candles, and a light azure linen runner graced the length of the table. Persimmon highlights provided pops of mod color. The grooms opted for candles in place of flower centerpieces.

"Whenever Bryan and I dine with friends, we do so by candlelight. We think it's romantic, peaceful, and beautiful. So my only request was that there be many, many candles," Dennis says of the décor, which included 89 candles total. "Our planner, Brenda Babcock [of Italia Celebrations], listened to me—and how! The table was illuminated with dozens and dozens of candles in our colors." Adds Bryan, "It was visually the most impressive setting. When the sun went down, the candles and the string lights overhead had the dinner area all aglow."

The intimate group dined at one long table in the gardens.

Guests dined on antipasto, pasta, and a choice of osso buco or Tuscan filet mignon during the al fresco meal.

Sugar cookies iced with marbled fondant resembled Italian tiles—only much tastier.

The couple joined all their guests and danced to the sounds of a sextet playing supper-club classics and jazz standards.

The fondant-covered lemon cake with lemon ganache and wild strawberries had a simple adornment of two cypress trees to represent the grooms.

Custom chocolates from Memphis were placed on pillows during turndown service.

Location and catering, Castello delle Serre
Event planning, rentals, and string lighting, Italia Celebrations
Photography and art direction, Corbin Gurkin
Videography, Evergreen Film
Officiant, Rev. Cheryl Cornish
Stationery, Tarah Catalano
Cake and cookies, Rose Cakes
Processional music arrangement, J.D. Frizzell
Special reception song, Brennan Villines
Grooms' custom suits, White Chalk
Grooms' shirts, Eton
Grooms' tiepins, Alice Kwartler
Grooms' cufflinks, Brooks Brothers
Grooms' shoes and Bryan's prewedding shoes, Magnanni
Rings, Cartier
Best men's tuxedos, Vera Wang
Best men's ties, Nordstrom
Transportation and car rental, Slowhills
Welcome bags, 100 Bofora
Hand-painted canvas tapestry for escort cards, Natalie Taylor Humphrey
Chocolates, Phillip Ashley Chocolates
Dennis's prewedding suit, Caporiccio
Groom's prewedding shirts and Bryan's prewedding suit, Express
Dennis's prewedding shoes, Casuccio & Scalera, 39-06-4821907
Bryan's prewedding tie, A. Testoni
Bryan's prewedding pocket square, Men's Wearhouse