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A Real Wedding · Raffles Boston & Kaia
Gabi & Jimmy: A Thursday Wedding at Raffles Boston
June 18, 2026
Over 200 weddings · 15 years behind the camera · 116 five-star reviews · Limited to 20 weddings per year
Gabi and Jimmy got married on a Thursday. It was a quiet nod to tradition on Gabi’s side of the family, who call Bermuda home, and it set the tone for everything that followed: a day built their way, on their own clock, in two of the most interesting rooms in Boston.
The shape of it: a morning ceremony nineteen floors above Back Bay at Raffles Boston, a three hour brunch under the ballroom chandeliers, a deliberate pause in the middle of the afternoon, and then a full takeover of Kaia, the Aegean restaurant in the South End, until the plates ran out. I photograph a lot of wedding timelines. This one might be the smartest I have seen all year.
The morning at Raffles
Getting ready
Bridesmaids in shades of lilac, a satin Jaxon James Couture gown that needed its own room key, and morning light doing half my job for me. Jimmy answered with a white dinner jacket over burnt orange trousers, which tells you most of what you need to know about this couple.
A ceremony in the round, nineteen floors up
No straight rows. No arch. The ballroom was set in the round: gold chairs, velvet ottomans, low lounge seating, and wildflower clusters growing from the floor, so every guest sat within a few feet of the vows and the whole city stood in as the backdrop.
The Raffles Ballroom
Floor to ceiling glass means a morning ceremony here is lit by the sky, not by fixtures. It is the reason I call this one of the best lit wedding rooms in the city in my Raffles Boston venue guide.
Brunch, not a banquet
After the vows, nobody left for six hours of limbo. First came an hour of cocktails right there at Raffles, with live watercolor painters catching guests mid laugh and a magician working the room. Then everyone sat down to a three hour brunch: pastry towers under garden florals, cake before noon, toasts in full daylight. Guests actually talk at eleven in the morning. It photographs like a garden party that happens to float above the city.
The pause, and Blind Duck
Then the day did something almost no wedding day does: it stopped. Two hours of nothing on the schedule. Guests went up to their rooms. We went down to Blind Duck, the speakeasy tucked below the ballroom floors, and made the kind of portraits you cannot make at golden hour in a garden.
Blind Duck
Leather, brass, a mural like a dark Dutch still life, and two people with nowhere to be. This is what the pause bought them.
Kaia after dark
At six the day changed neighborhoods. Across town in the South End, Gabi and Jimmy had rented out all of Kaia, the Aegean restaurant on Harrison Avenue, and met it in second looks: Gabi in a beaded scalloped mini dress, Jimmy in an olive suit embroidered with gold florals. DJ Dukes took the night from there.
The Raffles house car carried them across town, and gave us one more frame on the way: a kiss beside the Range Rover with the veil doing exactly what veils are supposed to do.
Kaia
A Greek island restaurant for a bride with island roots of her own. Wine velvet banquettes and amber candlelight mean the evening gallery looks nothing like the morning one, which is exactly the point of a two venue day.
Opa
A Greek restaurant rented to the studs deserves a Greek sendoff. The plates came out and did not survive the night.
The last frame
The last shot of the night: the two of them under the Kaia sign, the South End sky burning out behind them, still holding hands.
Why this timeline worked: a photographer’s note
A morning ceremony in a glass ballroom means real light at the altar. A brunch reception means guests with energy and no sunset panic. A midday pause means editorial portraits that cost the couple nothing socially. And a second venue means the day gets two complete visual identities, sky and candlelight, in one gallery. If you are planning something like this, my guide to weddings at Raffles Boston covers the ballroom, the staircase and honest cost context, and Raffles sits alongside the classics in my best Boston wedding venues guide. Gabi and Jimmy’s story also starts earlier on this site: their Back Bay engagement session ran from Krasi to a rooftop at sunset.
The team
Event production: Eventsavy · Event design: TP Hancock · Ceremony and brunch venue: Raffles Boston · Reception venue: Kaia · Florals: Rafael Floral Event Design · Photography: Perla Images · Makeup: Christina G · Hair: Hair by NMG · Dress: Jaxon James Couture · DJ: DJ Dukes · Rentals: Form Creative Services and Peak Event Services · Live watercolor sketches: Art Experienced
This wedding is featured on PartySlate, alongside the best events in Boston.