Rum and whiskey come from different worlds—the former is rooted in sugarcane, the latter in grain. But both spirits are usually matured in barrels—whiskey virtually always is, and aged rum touches some type of wood—meaning they have more in common than you might initially think. Oak, climate, and time shape both spirits in ways that whiskey drinkers will recognize immediately, even if the raw materials and traditions are different. Some rums pick up the dried‑fruit depth of sherry casks, others lean into bourbon‑barrel notes of vanilla and spice, and a few carry just enough funk or smoke to feel familiar. The bottles here aren’t meant to replace anyone’s favorite scotch or bourbon; they’re simply great entry points for whiskey drinkers who want to see how those same levers—barrel, proof, yeast strains, and maturation environment—play out in rum, and maybe discover a new favorite along the way.

Brugal 1888 Doblemente Añejado (Dominican Republic, 40% ABV, $45) Brugal 1888 Doblemente Añejado is a logical match for scotch drinkers who enjoy sherry‑influenced malts, but don’t mind a touch more sweetness. It is double-aged in bourbon and sherry casks, which creates a flavor profile in which vanilla, toffee, and red‑fruit richness sit alongside a clear oak presence. The rum is undeniably sweet, yet the tannins and toasted‑spice notes keep it from feeling heavy—and make it a bit reminiscent of Speyside and Highland whiskies.

Mister Fogg Navy Rum Sail N°2 (Caribbean & France, 55.7% ABV, $38) Mister Fogg Sail N°2 is a bold, high‑proof, Navy‑style rum that will resonate with bourbon drinkers who enjoy the intensity of barrel‑strength releases. Aged in ex‑bourbon barrels, matured at sea, and finished in Cognac casks in France, it delivers dense notes of molasses, dark chocolate, dried fruit, and warming spice. There’s a noticeable fruity funk here—not unlike the ferment‑forward character you sometimes find in Wilderness Trail’s whiskeys—adding dimension without overwhelming the sweetness. Big and warm, it’s a natural pick for bourbon fans who like heat and depth.

Mount Gay Single Estate 25_04 (Barbados, 55% ABV, $350) Mount Gay’s Single Estate Series is designed to express terroir in rum, in the same way that whiskeys like Bruichladdich explore the impact of using barley only grown on Islay, or Maker’s Mark's experiment with locally-grown wheat for their Star Hill Farm Whiskey. Each release is made from estate‑grown sugar cane, distilled on site, and shaped by the character of St. Lucy’s (the Mount Gay estate) soils, climate, and a proprietary yeast strain. The 25_04 edition, distilled from the 2019 harvest and double pot distilled, matures five years in ex‑bourbon barrels and is bottled at 55% ABV. Its earthy funk edge, salty smokiness, red‑fruit notes, and intense oak make it an appealing crossover for peated‑scotch drinkers who appreciate layered structure and a sense of place.

Zacapa Edición Negra (Guatemala, 43% ABV, $70) Zacapa Edición Negra is a strong match for whiskey drinkers who enjoy the smoky‑sweet balance of High West Campfire. Aged in double‑charred American oak, it carries a darker, wood‑driven smokiness rather than peat, wrapped in Zacapa’s signature sweetness. Notes of caramelized sugar, vanilla, and a subtle root‑beer–like spice sit alongside gentle smoke and dried fruit, creating a profile that feels both familiar and new. It’s richer and sweeter than Campfire, but the interplay of smoke, oak, and warmth makes it a fit for drinkers who like their whiskey with a touch of char.

Dos Maderas Origen Thailand (Thailand & Spain, 47% ABC $83) Dos Maderas Origen Thailand is an easy match for whiskey drinkers who love the oloroso‑driven richness of Redbreast 21. After 12 years aging in bourbon casks in Thailand, followed by a rare finish in 80‑year‑old oloroso barrels in Spain, it shows a deep mix of cocoa, toasted coconut, roasted nuts, and dried fruit, with a subtle aged‑spirit note that almost reads as smoke. The sherry influence is refined rather than heavy, giving the rum a mature, oxidative depth that is like the warmth of long‑aged Irish pot still whiskey.

Ron del Barrilito Autobiografía Selection III (Puerto Rico, 43.6% ABV, $1,500) Aged 31 years in a single oloroso sherry cask, Selection III offers the kind of depth whiskey drinkers associate with Glendronach 21 or the richest batches of Aberlour A’Bunadh. The cask yielded just 186 bottles, with concentrated notes of dried fruit, roasted nuts, cocoa, and a refined oxidative warmth. Because the rum enters the barrel just above bottling proof, the cask’s sherry character integrates slowly and evenly over decades, creating a profile that mirrors top sherried whiskies while still reflecting the long, tropical aging that defines Barrilito’s style.