Sasha Hennessy and TJ Hennessy first met in 2016 after being introduced by Sasha’s stepbrother on her 21st birthday. “It took a bit for us to start hanging out,” Sasha shares, “but once we did, we were inseparable.” Eight years later, on July 26, 2024, that same connection led them to Sintra, Portugal, where they celebrated their wedding surrounded by family, friends, and intentional design.
Five years into their relationship, TJ proposed during what Sasha believed was a family photoshoot in Austin, Texas. Everyone wore soft whites and blues, and even when Sasha was asked to wear white, she didn’t suspect a thing. As the sun set and they stayed behind for the final couple of portraits, TJ proposed. Unbeknownst to her, he had secretly flown both her parents in from Los Angeles, along with his own, who watched quietly nearby. “It was so special to have our immediate family there,” Sasha says. “His sister was the only one who knew the plan.”
When the couple toured Quinta de Bella Vista in Sintra, the decision felt immediate. Working with planner and designer Sofia Nascimento Studios, they envisioned a weekend where each event felt distinct. The welcome night leaned bright and colorful, while the wedding day embraced deep purples and dark greens, creating a moodier, more romantic atmosphere. Prettie Weddings created the paper goods heavily featured throughout the weekend, with custom illustrations by Carolina Branco adding a personal layer to the design.
To the welcome dinner at Queluz National Palace, Sasha wore a bright yellow Valentino dress styled by Kristin Fernandez, paired with an Anya Hindmarch bag. TJ wore a cream silk corduroy Tom Ford double-breasted suit. Guests were seated at playful, colorful tablescapes, each featuring a different Ginori 1735 plate. Name cards were designed to appear engraved, with menus printed on the back. “Guests swore the names were actually engraved,” Sasha says. “We color-matched the menus almost too well.”
On the morning of the wedding, Sasha got ready wearing a vintage La Perla set and Natori silk robe, while Tom Perdigao handled hair and makeup. She slipped into her vintage Reem Acra dress from Happy Isles, paired with a veil embroidered with her late father’s signature. Their first look was emotional and unfiltered. “We both sobbed,” Sasha recalls. “TJ couldn’t stop crying—he just kept saying, ‘Wow.’”
Captured by The Edges, the wedding day unfolded beneath towering trees, with soft baby’s breath and natural light setting the tone. The ceremony was designed to feel light and airy with white baby’s breath throughout. Fresh grass was laid the morning of the wedding to seamlessly blend the space with the venue. TJ’s father officiated, while Sasha’s stepdad and mother walked her down the aisle. Getting married on her stepdad’s birthday added another layer of meaning. “It really felt like it was all meant to be,” she says. As they read their vows aloud, Sasha felt a sense of calm she hadn’t anticipated. “I felt peaceful and completely present. We were locked into each other.””
Guests moved into cocktail hour with spritzes flowing and canapés by The Mad Kitchen, before entering a reception transformed, dramatic florals by Sofia Nascimento Studios, and chandeliers imported in from Spain by Rental Co. Deep colors played off the venue as fog continued to roll in. Dinner featured fresh brioche, crab tartar, coffee-crusted filet, and Portuguese seabass, followed by a dessert bar guests could enjoy throughout the night. Music by Papaaz, the resident DJ at Les Caves in St. Tropez, kept the dance floor full, while a MirMir photo booth added a playful touch.
The couple entered the reception to Fred again..’s “I Adore You” before sharing their first dance to “Treat You Better” by Rüfüs Du Sol. “After a few moments, we invited everyone to join us,” Sasha says. “Seeing the joy on everyone’s faces made it unforgettable.” She also surprised her mother with a mother-daughter dance to their favorite song.
Sasha later changed into a Berta Privée dress as the night transitioned into the after-party, which the couple dubbed Club do Tiago. TJ surprised guests by taking over the DJ booth, launching the party he had secretly prepared for months. Espresso martinis flowed, pizza was served, and the celebration continued until 3:30 a.m. Sasha finished the night in a custom pink mini dress by Undone By Kate, calling it “perfect for dancing.”
The weekend concluded with an all-white farewell beach party at Praia Princesa. Sasha wore a vintage two-piece set from Happy Isles, styled with Dior pearl earrings and her Olympia Le-Tan “Mermaid Song” bag. “Our family had the best time reminiscing about the weekend,” she says.
Sasha and TJ began their honeymoon with a mini-moon in the Douro Valley, followed by what they lovingly call a “homie-moon” in Ibiza and Mallorca—an effortless extension of a celebration that felt as thoughtful as it was joyful.
