Burton "Spruce" Balkind
Work crews, including Phil Osley (second from left), finish reshingling at the Sunken Ship this week, a reminder that even one of downtown Nantucket’s longest-standing holdouts continues to be maintained, repaired, and carried forward as the streets around it change
Against the Current
As Nantucket changes, The Sunken Ship holds its ground
Carlos Mendoza • April 23, 2026
On the corner of Broad and South Water Streets, just steps from the harbor, there's a store that doesn’t quite conform to what downtown Nantucket has become. It spills outward instead of inward, with racks, flags, buckets, toys, shirts, beach gear, and dive equipment layered together in a way that feels accumulated rather than arranged. It’s not minimal, not curated, and not especially concerned with presentation. It's practical, dense and slightly chaotic, the kind of place where you can find what you need even if you didn’t know you needed it when you walked in.
The Sunken Ship has been there since 1975, and that longevity alone sets it apart, but what makes it different is not just how long it has lasted, it's what it still represents. The store comes from a version of Nantucket that is harder to find downtown now, one where retail was not yet separated from function, where a business could serve both locals and visitors without reshaping itself entirely for either, and where the harbor still had a more direct presence in the rhythm of everyday life.
Before It Was a Store, It Was the Water
The Sunken Ship didn’t begin as a lifestyle shop, and it did not begin with a brand. It started as a small dive and sporting goods operation, built around the needs of people working in and around the water. Fishing poles, scuba gear, tank fills, and the basic tools required to move between land and harbor formed the core of the business, and over time, the store expanded by adding what people asked for and what made sense to carry.
What exists now is not the result of a single idea, but of decades of incremental change layered on top of a working foundation.
At the center of it is Phil Osley, who founded the store and whose life has always been tied to the water in ways that go beyond retail. In the early 1970s, before The Sunken Ship opened, Osley was involved in a project that still stands out in Nantucket’s recent history, helping build a three-man yellow submarine from salvaged materials found around the island. (see related archived news article)
He later wrote about the experience in Yankee Magazine under the title “If We Can Build a Submarine,” a piece that captured a moment when Nantucket still operated with a kind of improvisational energy, where people worked with what they had and figured out how to make it function. Although Below Deck has been unable to locate it, there is, apparently, video documentation of that endeavor: The Yellow Submarine, filmed by Marcel Duranleau, and with a cast of characters including Osley, Stuart Staehle, Norman Moore Sr., Mike Todd, and James Bartsch.
That same sensibility carried into the store. Osley wasn't approaching the business as a retail exercise, he was building something that extended from the life he was already living, one that included diving, marine repair, salvage work, and time spent in the harbor rather than behind a counter. Even today, The Sunken Ship continues to offer scuba instruction, tank fills and dive-related services, maintaining a connection to the water that is increasingly rare downtown.
A Local Figure, Not Just a Shop Owner
Over time, Osley became more than just the owner of a store. He became one of those figures who exist slightly outside formal description, known as much through reputation and memory as through any defined role. People who have spent time on Nantucket tend to recognize his name, or at least the presence of the shop, and for some, the two are inseparable.
Actor Ben Stiller, who worked at The Sunken Ship as a teenager, later described Osley as a “legendary old salt,” adding that the stories surrounding him “would definitely make for a great movie.” It's the kind of comment that only surfaces around certain people, those who accumulate stories over time simply by remaining in place and continuing to do what they do.
That presence extends beyond the walls of the store. For decades, a small red boat associated with Osley has appeared in Nantucket Harbor, tied up near Easy Street or drifting slightly with the tide. Recovered years ago near Great Point and repainted, it has been renamed more than once, sometimes “Sunken Ship,” sometimes something else, but always recognizable. For some, it's just another dinghy among many, but for others, it has become a recurring marker of the harbor itself, something that signals continuity in a place that changes more than it appears to.
Burton "Spruce" Balkind
Phil Osley, outside The Sunken Ship
Downtown Moves, Some Things Stay
Nantucket’s downtown has not stood still. In recent years, storefronts have turned over with increasing frequency, as long-standing businesses close, relocate, or give way to new concepts shaped by a different economic reality. Retail has become more specialized and more polished, with a greater emphasis on presentation and a narrower definition of what a store is expected to be.
That shift is not unique to Nantucket, but it's more visible here because of the scale of the island and the concentration of activity in a relatively small area. As property values have increased and seasonal demand has intensified, the pressure to refine, simplify, and align with a certain aesthetic has followed. The result is a downtown that feels more consistent than it once did, but also more controlled.
Against that backdrop, The Sunken Ship stands out, not because it resists change outright, but because it never fully reorganized itself to match it. The store still operates with a broader definition of purpose, selling beach supplies, clothing, toys, flags, and equipment in a way that feels driven by usefulness rather than identity. It's a place where you go to get something done, not just to browse.
What It Means to Still Be There
There are other long-standing businesses on Nantucket, and not everything old has disappeared, but fewer places occupy the same ground that The Sunken Ship does. It sits between categories, between eras, and between expectations, functioning at once as a retail shop, a supply stop, and a reminder of how the island once operated when the lines between those things were less clearly drawn.
The store hasn’t been preserved in the formal sense, and it's not been reintroduced as a piece of nostalgia. It has simply continued, adapting where necessary but holding onto enough of its original structure to remain recognizable to those who have known it for decades.
That kind of continuity is harder to maintain than it looks. It requires not just longevity, but a willingness to remain slightly out of step with the direction everything else is moving, a business that is not entirely dependent on fitting into a single category, and a person behind it who is comfortable letting it evolve without losing its core.
A Different Kind of Survival
The Sunken Ship doesn't announce itself as a holdout, and it doesn’t present itself as a statement about what Nantucket has become. It's simply there, operating much as it always has, serving the same overlapping needs that defined it from the beginning.
But in a downtown where change has become constant, that kind of presence begins to take on meaning of its own. It becomes less about what the store sells and more about what it represents, a link to a version of Nantucket where businesses were built around function first, where the harbor was not a backdrop but a workplace, and where a shop could grow over time without needing to reinvent itself to stay relevant.
The Sunken Ship remains part of that older logic. Not separate from the present, but not fully absorbed by it either, existing in the narrow space where something can continue without entirely changing, and where that continuity, over time, becomes the story itself.