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Aspen, Colorado
Aspen began as a 19th-century silver mining boomtown before the industry's collapse left it a near-ghost town for decades, until a group of investors led by Chicago industrialist Walter Paepcke began redeveloping it as a ski destination and cultural retreat in the 1940s, founding the Aspen Music Festival and the Aspen Institute alongside the ski resort itself. The town's four connected ski mountains — Aspen Mountain, Aspen Highlands, Buttermilk, and Snowmass — give it one of the largest and most varied ski terrain offerings of any single resort town in North America, drawing skiers across a wide range of skill levels rather than catering purely to experts or beginners. Aspen has built a reputation as one of the most expensive and celebrity-frequented ski destinations in the country, with its compact, walkable downtown lined with luxury boutiques and restaurants that draw a genuinely different clientele than more budget-oriented ski towns elsewhere in Colorado. Aspen's combination of a genuine mining-town-to-ski-resort reinvention story, four distinct connected mountains, and its enduring luxury reputation has made it one of the most consistently recommended winter vacation destinations in the entire country, even as its summer cultural festivals draw a substantial non-skiing visitor base as well.
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Maui, Hawaii
Maui is the second-largest of the Hawaiian Islands, and its combination of the Road to Hana — a roughly 64-mile winding coastal drive past waterfalls, black-sand beaches, and rainforest lookouts — with the volcanic summit of Haleakalā National Park gives visitors two dramatically different landscapes within the same island. The island's West Maui and South Maui coastlines are lined with resort towns like Lahaina and Wailea, built around calm, reef-protected beaches well suited to snorkeling, while Haleakalā's roughly 10,000-foot summit draws visitors well before dawn specifically to watch sunrise above the cloud line, a bucket-list experience Mark Twain once described as the most sublime spectacle he'd ever witnessed. Lahaina, the island's historic former whaling port and onetime capital of the Hawaiian Kingdom, suffered a devastating wildfire in August 2023 that destroyed much of the town's historic core, and the island's tourism economy and residents have spent the years since navigating a genuinely difficult rebuilding process. Maui's combination of dramatic volcanic terrain, calm resort beaches, and a historic port town now rebuilding after tragedy has kept it one of the most consistently recommended Hawaiian Islands for travelers seeking both relaxation and genuine natural spectacle in a single trip.
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