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Beacon Hill’s new cocktail bar 89 Charles is the sort of place that arrives with a striking sense of identity, from the moody interior to the theatrically constructed drinks. The room leans into a kind of modern nostalgia: low, retro-style, curved booths that still feel unmistakably upscale, a bar that glows under welcoming dim lighting, and candles that flicker on every table. It is the aesthetic equivalent of a well-tailored evening: Polished, a little theatrical, and clearly designed to spotlight what the bar cares about most — the drinks.

When 89 Charles follows through on that drink-forward mission, its cocktails are among the most thoughtful in the neighborhood. They’re structured, deliberate, often built to unfold over the course of the glass. In fact, at their best, they tell a story.

The Charles St. Espresso is the clearest and most frequently-ordered example of the bar’s ambitions. On paper, it’s an espresso martini. In the glass, it’s closer to a three-act performance. The opening is all coffee, carried mostly by the whipped coconut cream that caps the glass in lovely meringue dollops. It’s lush and frothy, with a texture and flavor profile that immediately evokes a coffee frappuccino: sweet, creamy, and disarmingly familiar. The coconut appears for a very brief moment but doesn’t linger; those tropical notes are quickly swallowed by the espresso’s acidity, making that introduction feel fleeting rather than indulgent. Then, just as quickly, the sip shifts into the middle act. Just as the drink threatens to reside purely in coffee-shop comfort, the spirits leap forward in a sudden grand entrance. The rum’s molasses depth and the cacao’s dark, almost roasted chocolate notes bloom together, adding weight and heat that cut cleanly through the whipped dairy top. The alcohol does, in fact, shout a little here, arriving with such vigor as to jolt the palate back into cocktail territory. And, by the time the glass is nearly empty, the structure has turned. What began bright, creamy, and latte-like now ends darker and more insistent. Those final sips concentrate the bitterness of the espresso and liqueur, pushing the alcohol further to the forefront until it feels like a John Hancock signature written with a bold, unmissable, and almost confrontational finish. For some, that late-stage intensity may feel abrupt and overwhelming with the swing from coffee-forward to spirit-heavy. But as an example of layered, narrative-driven cocktail design, it’s impressive.

As a bar establishment, 89 Charles’ food offerings typically would not be the main characters. However, an order of the Charles St. Espresso should be paired with the Warm Chocolate Chip Cookies, a recommendation delivered with particular conviction by the server. The duo is framed as a must-order combination, and the suggestion is quickly proven superb. The cookies are an instant hit of nostalgia — thick, soft-centered, and faintly crisped at the edges like a toasted marshmallow. Studded generously with chocolate and cooked to a just-underbaked goo, they call forth the fantasy of cookies pulled from the oven minutes too soon and feel like a quietly central part of the whole experience. The dessert is accompanied by the so-called Mudslide, served in a tiny pitcher and advertised on the menu as a “boozy milkshake.” It plays a supporting role: a richer, more concentrated cousin to the espresso martini, built on espresso liqueur, sorbet, and Braulio that echo and deepen the coffee-and-chocolate notes already on the table. Alternating sips of espresso martini or mudslide with bites of cookie — and occasionally dipping the cookies straight into the cocktails — creates a rhythm of sweetness, bitterness, and warmth that feels deliberately well-composed. It becomes an unexpectedly sophisticated way of turning a childhood comfort into a grown-up bar moment.

Where these first two orders lean into richness, the Melon Baller cocktail aims for something brighter and almost deceptively innocent. Built on an avocado-washed tequila and Midori alcoholic base, it arrives as a vivid, slightly-neon green drink in a tall, ridged glass that has a spiral of chili-togarashi blend climbing the outside like a lit fuse. The first sip is strikingly refreshing, with the cool melon sweetness from the Midori lifted by lime and elderflower to transform into something bright, floral, and smooth. But there’s a twist. Threaded through that fruity, flowery profile is togarashi itself, a Japanese spice blend that incorporates ingredients like chili pepper, ginger, orange peel, and sesame seeds to produce a citrusy heat. That spiciness announces itself boldly, accessed by placing one’s lips deliberately along the portion of the rim dusted with the spice or, in a less elegant but equally effective move, by brushing the tongue against the spiral on the outside. After the first swallow, the cocktail ignites around the edges of the mouth in little fireworks of spice that slowly build and leave the lips tingling.

In contrast with the Charles St. Espresso, the alcohol in the Melon Baller is notably harder to detect under this interplay of melon, citrus, florals, and heat — and that is both its charm and its weakness. On one hand, it showcases technical skill, a fully integrated spirit that contributes thoroughly to structure without sticking out sorely. On the other hand, the drink can feel almost too easygoing, with perhaps not enough potency for those seeking an alcohol-forward experience. Still, it stands out from the rest of the menu as a riskier, more inventive option that backs up its theatrics with real flavor balance.

As a whole, 89 Charles is staged as an intimate, retro-luxe lounge. Its space gestures towards a romanticized past — somewhere between an upscale hotel piano bar and a polished saloon — without slipping into a pretentious costume. It is, in theory, the ideal backdrop for slow, attentive drinking and long, low conversations. In practice, though, the bar’s success complicates that vision. A late-evening arrival can mean a wait of around half an hour, with bar seats snapped up on a first-come basis and the compact room quickly filling to capacity. Once inside, the volume rises to a steady din of overlapping conversations, occasionally punctured by a faint drift of cigarette smoke from a neighboring table that nudges the experience out of its carefully constructed fantasy. The staff keep the operation grounded, though, moving through the menu with easy fluency, breaking down ingredients, explaining flavor profiles, and guiding guests toward choices fitting personalities. The overall effect is a stylish hybrid: a swanky, cinematic setting that aspires to be a refined hideaway but currently operates as one of Beacon Hill’s buzziest and most in-demand cocktail destinations.

—Staff writer Audrey Zhang can be reached at audrey.zhang@thecrimson.com.