Weather-wise, late spring and fall are the optimal times for a visit. Aside from mild temperatures, May offers blooming gardens throughout the city and October finds the surrounding countryside ablaze with colorful foliage. At both times, however, expect hordes of visitors.
More than 250,000 students flood into the area each September, then pull out again in May and June. So hotels and restaurants fill up especially fast on move-in, move-out, and graduation weekends.
The good news is that Boston is a four-season destination. Along with the most reliable sunshine, summer brings sailboats to Boston Harbor, concerts to the Esplanade, and café tables to sidewalks. Summer is prime time for a shore vacation, but advance planning is imperative.
Even winter has its pleasures. The cultural season heats up when it’s cold, and Boston gets a holiday glow, thanks to the thousands of lights strung around the Common, Public Garden, and Commonwealth Avenue Mall. During the post-Christmas lull, temperatures fall, but lodging prices do, too. You’re only two to three hours south of quality ski slopes.