Unlike Scotch or American whiskey, Irish whiskey has been embattled in its quest to secure a place on the top shelf of luxury resorts outside of Ireland. Beyond perhaps the token Jameson, you’d be hard-pressed to find a bottle of Irish whiskey in most parts of the Caribbean, at the best of times. Yet in November 2025, a 300-passenger yacht was transformed into a floating embassy for Ireland’s indigenous spirit.
This was the first ever Irish whiskey cruise; a wildly ambitious endeavour that traded typical distillery hopping in the homelands of the water of life for the sun-soaked Caribbean. It sounds like it shouldn’t work. That it should be at odds with whiskey. The Caribbean sun, even in November, possesses a demanding, indiscriminate quality. It is a part of the world where rum gets muddled with herbs and crushed ice. It is not what the mind conjures when you imagine a group cracking open a 100-year-old bottle of Dunville’s from the 1920s. And yet, somehow, it succeeded.
The cruise included custom Glencairn glassware, a cadre of industry luminaries giving formal talks and joining as part of the group after, nightly cabin gift drops, and a bespoke menu of 45 curated and rare Irish whiskeys.
Guests were there to learn about whiskey, sure, but they were actually there, in the Irish parlance, to have what its founder calls a “curated session.”
The art of the session is mystical in Ireland. A session, sometimes spelt sessiún, or referred to in more youthful enclaves of Ireland as The Sesh, is the name given to how the Irish people socialise. Sessions are the lifeblood of centuries-old traditions. They revolve around music, chatting, flirting, dancing, and drinking.
But to understand how we get from centuries-old Irish tradition to a cruise in the Caribbean, we have to go
to Ohio on a charity bike ride with a man named Barry Chandler. An accidental impresario.
Chandler is a native of Cobh, County Cork, and a former food and beverage controller for the Cunard Line. He is the often turtlenecked force behind Stories & Sips — a social media-steered platform that is an engine of communal experience shared through passion for Irish whiskey.
The genesis of Chandler’s empire contains a novelist’s tidy irony. A decade ago, while actively trying to find new ways to raise money for a charity bike race, a friend inadvertently brought him into the world of whiskey. This unnamed friend suggested Chandler host a whiskey tasting. The only problem? He knew absolutely nothing about whiskey.
“I went to a local supermarket, found Irish whiskeys on the shelf and bought five bottles,” Chandler recalls. After picking the bottles based almost entirely on the aesthetic merits of their typography, he got to Googling. Armed with internet facts and notes, his initial tasting was an exercise in strategic deferral. “I’ll pay for the whiskey, you sponsor me for my cycle,” he proposed. It succeeded. He raised the money he needed to get back on his bike.
This asynchronous education proved surprisingly popular. Emails begat YouTube videos; videos attracted the attention of Ohio’s liquor distributors, who found in Chandler an articulate, if initially uninformed, conduit to a burgeoning market. Over time, Irish whiskey became a hobby which in turn metastasised into a vocation.
The true inflexion point, however, arrived with the mandated shutdowns of the 2020 pandemic. Denied the physical infrastructure of the pub, Chandler launched The Lock-in. For 63 consecutive Friday nights, he orchestrated four-hour live broadcasts. It was a staggering commitment, demanding 15 hours of preparation weekly. He hired out-of-work Irish musicians; he coaxed distillers into the living rooms of the isolated via all manner of web chats and apps. This was the crucible where his modern Irish whiskey community was forged.
As global commerce resumed, the whiskey industry predictably reverted to its default mechanism of engagement: the distillery tour. But Chandler, observing his followers, noted a creeping fatigue with the industrial go-to. “If you have a seven-day trip, by day seven, they’re still telling you it’s a mash tun.” When he was organising the next phase of Stories & Sips, he wanted something more community-oriented. “We explicitly say, ‘We don’t want to walk through the distillery. We just want to sit down with you.’”
This birthed a new economic model for Irish whiskey tourism: the experiential retreat.
Chandler, ever the organiser, transported eager groups to all sorts of alternative whiskey events. He led them to the peat bogs of Connemara, the kitchen of Brendan Carty, and the iconoclastic distiller behind Killowen. But the one he remembers most fondly was one where he walked tourists into the woods of Stradbally in County Laois, locating the precise tree stump from which the oak for their whiskey barrel was felled, and poured them a dram atop it.
When these kinds of once-in-a-lifetime sessions started to feel de rigueur for Chandler, he started to dream bigger. With his previous cruise industry experience, Chandler asked a natural, if audacious, question: Could we put a tasting on a ship?
Fast-forward to the Caribbean. Chandler chose the Caribbean for his inaugural cruise because it’s so incongruous. There was also a stroke of good fortune. When it came time to charter a 300-passenger yacht for his grandest ever dream last November, the ship they secured was the exact same vessel Chandler had worked on decades prior.
Partnering with Windstar Cruises, a line known for its small and community-oriented ships, Chandler and his co-founder Anthony Sheehy brought the notion of their whiskey cruise to fruition. The logistics were monumental. They had to organise shipping, insurance, and transit for both the guests and the whiskey personalities. It was a massive financial risk.
When the ship’s doors finally closed, and they set sail, the relief was palpable. “I remember hugging Anthony Sheehy and literally crying,” he admits. The payoff was an unprecedented seven-night, all-inclusive Caribbean voyage. Guests, who were an even gender split, enjoyed an exclusive menu of 45 Irish whiskeys available around the clock. One attendee said they were afraid it was going to be like a festival where things got out of control, but that it never veered that way. Chandler managed to make it feel like a luxury yachting-style cruise and not a booze cruise. It never became about the drinking; it was always about the heart of the dram.
Everything was open to everyone. A simple WhatsApp message might alert guests to a rare 30-year-old Bushmills being opened on deck in 60 minutes.
Chandler knows the art of hosting is as much about making people feel special as it is about the products being platformed. He was always able to curate a vibe to go with the evening — though he had to leave the signature turtlenecks he built his brand on behind.
The Stories & Sips empire, such as it is now, orbits the people. For Chandler, it is people who are at the heart of his network — a network that brings in a cultish following. It’s a following so loyal that 80 per cent of the guests on his inaugural Caribbean cruise had already travelled on a previous land-based experience with him in one of
his buses.
So, what’s next? The community has solidified, and the maritime model has proven its viability. Chandler is already looking toward the horizon, trading the Caribbean for the Mediterranean with a new cruise scheduled from Athens to Rome in August 2027.
As Chandler prepares for the second iteration of his dream, the legacy of that first voyage is clear. Recently crowned Ireland’s Communicator of the Year at the 2026 Icons of Whisky Awards, he proves that a brilliant host can take a spirit and turn it into a living, breathing community.
