Lindsay and Andy's Destination Wedding in Florence

Lindsay Docherty, a photographer, found Andy Rachlin on the dating website OkCupid. She initially browsed his profile from her pretend account—one she created for vetting potential matches. If a man looked suitable, she would then contact him from her genuine account. However, during this particular quest for Mr. Right, Lindsay slipped up and messaged Andy from her empty profile. Despite her blunder, Andy bravely proposed a meeting. The two got together for a first date of dinner, drinks, and live jazz that concluded with a romantic kiss. 

One year later, Andy popped the question. The Philadelphia residents flew to Florence with 25 of their nearest and dearest for a three-day wedding celebration that included a walking tour of the historic city and a festive send-off brunch. The pair tied the knot at Castello di Vincigliata, a restored castle nestled in the city's foothills, on July 14, 2014. A second, local bash, aptly titled "Party in the USA," followed one month later with their own home as the venue. 

The bride-to-be designed the vellum-printed invitations with a watercolor painting of the wedding venue by Carole Poole in the background.

Lindsay paired her custom champagne dress with a friend's long mantilla veil, Calvin Klein shoes, and a jade Anzie necklace for a pop of color. 

Andy wore a tan linen suit, blue French cuff Thomas Pink shirt, polka-dot tie, and pair of bold Bugatchi socks. 

Tanti Lina, owner of Papertini Floral and Event Design and friend of the bride, created a loose and textural bouquet. Large dahlias stole the show, accompanied by sweet peas, freesia, jasmine, ferns, astilbe, and assorted greenery picked from the gardens around the Residenza del Palmerino, the 15th-century villa where the bridal party prepped the morning of the celebration. 

A piece of tartan from the kilt of Lindsay's late Scottish father and two photograph charms thoughtfully adorned the stems. Floor-length strips of lace and ribbon added a touch of color.

Small clusters of astilbe, eucalyptus, and olives wrapped in crocheted lace brightened the groom's neutral lapel.

Because Lindsay and her best friend live in different cities, the bride-to-be opted for a cheeky way of asking Liz to be her maid of honor. "I sent a singing telegram to her with a little jingle about us and a handkerchief tucked into a passport, asking if she would do me the honor in Italy," says Lindsay. Liz, who accepted, wore a neutral Adrianna Papell sheath dress and clutched a smaller version of the bride's bouquet. 

Lindsay and Andy exchanged thoughtful keepsakes on their wedding day. Lindsay gifted Andy with a first edition of Innocents Abroad by Mark Twain, Andy's favorite hometown author. 

Andy gave Lindsay a Victorian-era locket to carry memories of her late father and stepfather. "It wasn't until after I picked it out and brought it home that I noticed it had our initials inscribed on the back," says Andy. 

Shortly before tying the knot, Lindsay and Andy met on the steps of Santa Maria Novella, a grand 15th-century basilica in Florence.

After their first look, the couple roamed the streets of Florence, enjoying gelato together on the warm summer day. "I had to talk Andy out of getting the chocolate lest he get it on his suit before the day really began!" says Lindsay.

The couple wed at 5:30 p.m. in the inner courtyard of the Castello di Vincigliata, a medieval Tuscan castle on a vast hill overlooking the city of Florence. 

Predicting sweltering summer heat and an emotional ceremony, the couple considerately gifted guests with handkerchiefs before the nuptials. Lindsay collected the vintage hankies and personalized them with a delicate decal.

Witty and detailed programs that hung from each seat entertained and informed guests. The bride and groom penned the humorous plan of events and printed them on a wash of blue-green watercolor paper.

Sandalwood fans and a vine of ivy hung from the cushioned bistro chair backs alongside the programs. The seating was arranged in a circle around the happy couple, who stood under an ivy-wrapped arch draped with swags of fabric.

Photographer Alison Conklin captured a precious exchange between Andy and his mother just as she dropped him off at the front of the aisle.

Nodding to the bride's parents' Scottish heritage, Nick MacVicar, better known as "Nick the Piper," led Lindsay and her mother down the aisle. 

Andy met Lindsay halfway down the aisle, per Italian tradition.

For the ceremony, the couple turned to their favorite customs and traditions. The result? A Quaker-inspired, self-uniting ritual, in which the duo invited guests to give mini-sermons and share readings on marriage, including advice on longevity, change, loss, and family.

The almost-newlyweds signed a "Quakubah," combining the Jewish ketubah and the Quaker marriage certificate, before their first kiss as husband and wife. With the document, Lindsay and Andy promised their love to one another. They also asked guests to sign it as witnesses of the exchange. Kate Farley calligraphed the couples' vows on a watercolor background, painted by the bride. 

Lindsay and Andy snuck inside the medieval castle to enjoy the first moments of marriage alone, savoring a time of seclusion known in Jewish custom as a yichud.

Nick, the bagpiper, exchanged his pipes for an accordion during cocktail hour and led guests in Scottish country dances and a traditional hora. Lindsay's bustle broke early in the revelry, but according to her, it was well worth it.

Small bottles filled with olive oil and rosemary sprigs from Residenza del Palmerino, a local villa, doubled as both the escort cards and favors.

Guests took their seats at the single wooden farmhouse table, decorated with a sheer white runner and topped with a garland of eucalyptus, dahlias, astilbe, ferns, sweet peas, freesia, and jasmine. Soft candlelight and quintessential Tuscan string lights cast a warm glow on the medieval room in Castello di Vincigliata.  

Long tapered candles and sprigs of rosemary filled glass olive-oil bottles, illuminating the long table with a warm glow.

Strings of lace and ribbon distinguished the newlyweds' bistro chairs from the pack. 

"As a little joke, the favors told guests their table number, although there was only one table," says Lindsay. "I brought the 'one' and a small easel, while Tanti and Andy created a beautiful table number display out of moss," Lindsay recalls.

Lindsay designed the long menu cards with breezy fonts and a blue-green watercolor background. Once seated, guests enjoyed a four-course Italian meal beginning with an antipasti salad of buffalo mozzarella with green tomatoes, basil, oregano, and arugula. Dishes of homemade ravioli with cherry tomatoes, asparagus, and Pecorino marked the primi course. Guests were then offered fillet of wild boar with bacon and prune, topped with a Brunello sauce, and accompanied by potatoes. Tiramisu served as the dolci, and the wedding cake, a mille-feuille with French cream and fresh strawberries, was the meal's grand finale. 

Lindsay and Andy, lovers of humor and prose, encouraged guests to sign their guestbook, a 1914 Webster's dictionary. The couple dubbed the term "Racherty," a combination of their last names, and used it throughout the day, including as their celebration hashtag.

Friends and family signed the century-old dictionary with colored pencils and flagged encouraging words with rainbow-hued tags, creating a meaningful, long-lasting memento for the happy couple.

Location: Castello di Vincigliata

Event Planning: Weddings in Italy    

Catering and Cake: Preludio Catering

Flowers: Papertini 

Photography: Alison Conklin Photography 

Calligraphy: Kate Farley Designs 

Reception Music and Lighting: The Alma Project 

Bagpiper: Nick the Piper 

Makeup: Pretty Owl Makeup 

Watercolor Art: Carole Poole Gallery