When Ian Ross spotted Virginia Ashe sitting outside on a spring day in Boston eating brunch with some friends, he could never have imagined that less than six years later, in beautiful Cartagena, Colombia, she would become his wife. All he cared about in that moment was talking to her\u2014and he did just that. \u201cHe said something like, \u2018You\u2019re the most beautiful girl I\u2019ve ever seen,'\u201d recalls Virginia, who at the time was a sophomore at Boston University. \u201cWe all started talking, and the whole time I was thinking he\u2019d be perfect for one of my friends.\u201d Ian (accidentally) left his phone at the table, and when he came back for it, he asked Virginia for her number. \u201cI wasn\u2019t in the practice of giving it out to complete strangers, but he lived in New York," she explains. "I was planning on interning in the city, so I thought, you never know." In June, they went on one amazing date in downtown New York City at Bacaro , but nothing really came of it and Virginia returned to school. (Though they did discover they share the same birthday\u2014and that she had lied about being 21 when they met.) A second date in Manhattan took place in October, and it went so well that Ian, who works in commercial real estate, convinced her to spend an extra day there. From then on, they were a couple; after three semesters of long distance, Virginia relocated to New York. The couple moved in together two years after that fateful brunch. In October 2016, Ian popped the question\u2014and somehow, he was able to keep it all a secret. \u201cI\u2019m super nosy, so I\u2019m a tough person to surprise,\u201d Virginia says. Ian pulled it off by pretending to go on a two-day work trip, and asking a friend to invite Virginia to a fake event at The Metrograph theater while he was gone. \u201cWhen I got there, there was no sign of anything going on\u2014and I still wasn\u2019t suspicious,\u201d says Virginia, a fashion and lifestyle publicist and the founder of ASHE Agency . An usher led her into the theater, where Ian had arranged to play a video that chronicled their relationship, before getting down on one knee with an Asscher-cut ring from Cory Friedman Fine Jewels in New York. But the surprises didn\u2019t end there; Ian had planned an engagement party at Bacaro\u2014and the next morning whisked Virginia off to Paris for four days. \u201cShe told me about six months ago that she had known about the trip all along,\u201d Ian says. Choosing the destination for the wedding was easy. Virginia\u2019s parents are from Cali, Colombia, and she always envisioned herself getting married in Cartagena, a quintessential tropical escape. \u201cIan and I vacationed there a few years prior, when he came to meet my family, and we had this magical time,\u201d she says. \u201cNot only did we want a place with a personal connection, we wanted to bring our friends there to experience the vibrant culture.\u201d She turned to Instagram for inspiration, and happened upon a reposted image of an outdoor dinner on the island of Baru, just off the coast of Cartagena. \u201cI began stalking who originally posted the picture, and found that it was the New York-based wedding planner Matthew Robbins Design .\u201d After discovering that one of the owners, Luis Otoya, is Colombian and that they have an office in Cartagena, RobbinsOtoya , Virginia knew she had found her dream team. The festivities took place over a holiday weekend, beginning with Cuban-inspired welcome cocktails at Casa Pombo , inspired by the decor of the bride's favorite restaurant, La Vitrola \u2014complete with a cigar roller and a salsa band. For Saturday\u2019s rehearsal dinner\u2014which Virginia describes as \u201cvibrant, tropical, and sexy\u201d\u2014the couple invited everyone to a beautifully rustic and bohemian home on Baru. \u201cIt was meant to be casual and relaxed,\u201d says Ian. \u201cThe meal was actually on the beach, and people were even barefoot.\u201d Tables were decorated with foliage and accented with exotic tropical fruits such as corozo, granadillas, watermelons, and pitayas. Evento & Cocina created a menu of Colombian dishes like avocado and green mango salad, pl\u00e1tanos en tentaci\u00f3n (baked sweet plantains), and coconut rice. \u201cI thought of this as a Colombian night under the stars,\u201d says Virginia, who wore a jungle-inspired custom gown by the local designer Maria Elena Villamil and Oscar de la Renta gold floral drop earrings. For her wedding gown, Virginia knew she wanted something by a Latin American designer\u2014and also a style that embodied the wedding destination. The result? A timeless gown by the Dominican Republic-born Oscar de la Renta . \u201cThe front was simple, with a deep V, with a ruffle in the back that felt very fun and tropical, like Cartagena,\u201d she says. She paired the look with funky, gold Saint Laurent heels (a gift from her grandmother), vintage diamond stud earrings from Ian\u2019s mother, and a custom-made Sposabella Lace veil\u2014which she didn\u2019t wear for long. \u201cI had to take it off mid-ceremony because of the wind, which made for a funny moment!\u201d she says. The 10 bridesmaids wore dresses of their choice in shades of red, pink, and ivory; while the 10 groomsmen, like Ian, wore suits with white jackets. After a weekend of events and activities in Cartagena, 160 guests gathered to watch Virginia and Ian exchange vows in the courtyard of the Hotel Charleston Santa Teresa . \u201cIt has these terra cotta walls and it felt really intimate,\u201d says Ian, who donned a custom suit with a white dinner jacket (a.k.a. \u201ctropical black tie\u201d). To honor Ian\u2019s Jewish heritage, the couple flew their rabbi over from Brooklyn to officiate the ceremony, which took place under a chuppah decorated with bougainvillea. \u201cWhen I was standing up there and Virginia was walking down the aisle, it was this really emotional, wild moment,\u201d Ian says. \u201cWe\u2019re both big planners, but I never really stopped to think about how much work we had put into the wedding until right then.\u201d After the ceremony, traditional merengue dancers led everyone on a walk around the block\u2014like a second line in New Orleans\u2014dropping them off back at the hotel for outdoor cocktails while Virginia and Ian stole some time away for themselves before entering the property\u2019s ballroom, which used to be a cathedral. \u201cWhen we were designing the look for the reception, I said to Matthew that I liked the idea of \u2018tropical grunge,\u2019\u201d Virginia says. \u201cWe had a lot of burgundy and aubergine tones and deep tropical greens, which made it a little moody and really enhanced the space.\u201d Guests found their seats around teak wood tables, which were decorated with custom-made woven placemats from Usiacur\u00ed, Colombia, and centerpieces made of green foliage, protea, and orchids. But rather than linger over dinner and speeches, the meal\u2014catered by the property\u2019s chef, the celebrated Harry Sasson\u2014was served relatively early on so that the salsa band could get down to business. So after enjoying pepper-crusted steak, grouper with roasted leeks, and grilled hearts of palm, \u201cEveryone got really into the Latin dancing,\u201d Ian says. \u201cAll these people who had never salsa danced were out there doing it.\u201d At around 11:30, they transitioned to a DJ\u2014specifically DJ Chachi , who is a close friend of Ian\u2019s. Around the same time, Virginia says, \u201cI changed into a red, sequined Stella McCartney dress that made me feel totally glam and ready to party!\u201d And just when everyone thought the evening was winding down, out came two trumpet players at 2 A.M. for what\u2019s known as hora loca , or \u201ccrazy hour.\u201d At 3 A.M., the party continued at one of the colonial homes the couple had rented, where many of their friends were staying. On Monday, the newlyweds hosted a brunch at the house where they were staying. \u201cI\u2019ve never been a fan of formal brunches, and we wanted people to feel as comfortable as possible since they may have had a rough night,\u201d Ian says. Guests came and went as they pleased to eat empanadas and arepas, sip on tropical juices, and relax by the pool or on the rooftop. Virginia and Ross left right from Cartagena for a mini honeymoon in Belize, staying a few days on the private island resort of Cayo Espanto . \u201cIt\u2019s really beautiful, and you do nothing except for relax,\u201d she says. \u201cWe did take a helicopter ride, and I\u2019m scared of flying so that was enough adventure for me.\u201d But the real honeymoon happened in the summer, when they had their own Under the Tuscan Sun experience\u2014complete with a Fiat and a playlist loaded with Italian songs. \u201cWe drove through Tuscany, and stopped at these amazing towns, where we walked around and explored,\u201d Ian says. They spent a few nights at the Rosewood Castiglion del Bosco , and the hotel prepared a private picnic in its vineyard, the most perfect setting for a toast to the future.