Anchorage is a pedestrian- and bike-friendly city. Downtown Anchorage's flower-lined streets are easily explored on foot, and several businesses rent bicycles. The grid plan was laid out by the Army Corps of Engineers, and streets and avenues run exactly east–west and north–south, with numbers in the first direction and letters of the alphabet or Alaska place-names (Barrow, Cordova, Denali, etc.) in the other. The only aberration is the absence of a J Street—a concession, some say, to the city's early Swedish settlers, who had difficulty pronouncing the letter. You'll need a car for longer stays, expeditions, and to reach some of the city's better restaurants without relying on taxis.
Outside Downtown, Anchorage is composed of widely scattered neighborhoods and large shopping malls clustered along busy thoroughfares. And although there's no shortage of excellent restaurants Downtown, many of the town's best places are found in cheesy strip malls. Also, you're never more than a block or two from a good espresso stand or shop.
Once you're done wandering the shops Downtown, consider heading south to Midtown. The neighborhood has some of Anchorage's best restaurants. It's also a good neighborhood to stay in if you would rather be slightly outside the main tourist fray.
The next neighborhood heading away from Downtown is South Anchorage. Until recently South Anchorage was more of a local spot, but with several new restaurants opening there's been a growing tourist presence in the area. South Anchorage also has a large mall.
Another neighborhood worth exploring is Spenard, just west of Midtown (Spenard Road is considered the dividing line). The neighborhood, which celebrates its annual Spenardi Gras every March, has an artsy, hip vibe and is home to some of the city's best casual restaurants, a good farmers' market, and Anchorage's largest independent bookstore.
You'll find plenty to do year-round in Anchorage, though most visitors (particularly first-timers) might be happiest in June, July, or August, when the days are longer—up to 19 hours, 21 minutes during the summer solstice—and the temperatures warmer. If you must choose one of the shoulder seasons, choose fall. There's less chance of rain, the snow has not yet arrived on trails except in the highest mountain passes, and there's an excellent chance for warm, sunny days, cool nights, and dazzling color changes in the trees and tundra. But if you choose fall, pack a few extra layers as a just-in-case for early snow (or be prepared to visit one of Anchorage's many gear shops): the city's earliest measurable dose of snow fell on September 20, 1947.