San Luis Obispo

San Luis Obispo

San Luis Obispo (SLO to locals) sits halfway between LA and San Francisco on the central coast, with Cal Poly students, gorgeous wine country (Edna Valley and Paso Robles nearby), and a Thursday night farmers market that takes over downtown. It's been called the happiest city in America (multiple studies, Oprah included), and the vibe really does back that up. Bubblegum Alley is exactly what it sounds like. Mellow and beautiful.

Portland

Portland Maine is lobster rolls, lighthouses (Portland Head Light is the brochure), a working waterfront where fishing boats still come in, and a food scene that has the same per-capita acclaim as the much bigger Portland Oregon. The Old Port's brick streets, breweries, and harbor views are walkable in an afternoon. Casco Bay's islands are a ferry ride away. Tiny, dense, and seriously delicious.