Pop. 5,454
GPS: 59°36'N 151°25'W

Big mountains, big glaciers, and even bigger tracts of undeveloped land will always be Alaska’s main draws—but that doesn’t mean you can’t find a little art and culture there, too. Homer, a funky enclave at the southern tip of the Kenai Peninsula, is living proof. The town began as a fishing and mining outpost, but more recently, creative types have staked claims here as well. Homer’s streets are packed with studios and galleries; its Pratt Museum showcases locally made wares and a rotating roster of marquee-name exhibits; and Pier One Theater shows community plays.

Your first introduction should be by sea kayak—there’s no better way to take in the sandy beaches, sparkling glaciers, and snowcapped Kenai Mountains looming out of the Pacific. Launch from the Spit, a wisp of a shore where commercial fisherman rub elbows with transient hipsters. Rent a boat with True North Kayak Adventures, and keep an eye out for porpoises and whales ($45 a day; truenorthkayak.com).

Homestead Restaurant spices its fresh-caught halibut with chipotle or cilantro (homesteadrestaurant.net).

Overnight in one of the cozy suites above Two Sisters Bakery, then roll out the next a.m. to fresh-made cinnamon-raisin bread (doubles from $105; twosistersbakery.net).