Route 66 vs Seattle and Portland

Route 66 is the great American road trip: roughly 2,400 miles of the Mother Road from downtown Chicago to the Pacific at Santa Monica, crossing eight states and three time zones. This Chicago to Santa Monica itinerary packs it into 10 days, which is fast. Expect about 200 to 330 miles and five to seven hours behind the wheel most days, mixing interstate stretches with the best surviving original alignments; two to three weeks is ideal if you can spare it. Start with a photo at the Begin sign, then roll past Illinois giants, the bent Chain of Rocks Bridge over the Mississippi and Ozark frozen custard stands. Cross the short Kansas corner and Oklahoma's diners before painting your own stripe at Cadillac Ranch outside Amarillo. In New Mexico, sleep under the glowing neon of the Blue Swallow Motel in Tucumcari, then drive through the badlands of Petrified Forest National Park, the only national park that protects a stretch of Route 66. A day off the road from Williams takes you to the Grand Canyon's South Rim. The finale climbs over the Black Mountains to Oatman, crosses the Mojave and ends with a sunset at the Santa Monica Pier. Book classic motels ahead in spring and fall.

Two of the Pacific Northwest's most likable cities sit just three hours apart, framed by volcanoes, evergreen forests and waterfalls, which makes Seattle and Portland a natural pairing. Start in Seattle at Pike Place Market, where fishmongers toss salmon, flower stalls spill onto the cobblestones and the waterfront opens onto Elliott Bay. Ride the 1962 monorail to the Space Needle for views of Puget Sound and, on clear days, the snowy cone of Mount Rainier. Then go see that mountain up close on a day trip to Paradise, where summer wildflower meadows and glaciers line the trails. Board the Amtrak Cascades train or drive about three hours down I-5 to Portland, a city of bridges, bikes and coffee. Lose an hour or three in Powell's City of Books, hike the ferny Wildwood Trail in Forest Park and graze your way through the city's famous food cart pods. Finish in the Columbia River Gorge at Multnomah Falls, which needs a timed permit in summer. Longer trips can add Portland's gardens, the Oregon Coast, Mount Hood and Willamette Valley Pinot Noir. Come July to September for the driest weather, and pack a rain jacket the rest of the year.