BOSTON TO LENOX, MASSACHUSETTS
Distance: 130 miles
Time: 2 hours 15 minutes
THE TRIP: If you love the classics, you'll love Lenox. This quaint New England town is the summer home of the Boston Symphony Orchestra's Tanglewood Music Festival, and Shakespeare & Company offers year-round performances at the intimate Elayne P. Bernstein Theatre. Be sure to visit The Mount Estate & Gardens—better known as The Mount—designed by author Edith Wharton. The stately mansion and its elaborate, European-style gardens were recently restored, and you can stroll through Wharton's bedroom suite, where she wrote some of her best-known novels, includingThe House of Mirth.
A WORTHWHILE DETOUR: Cambridge, Massachusetts
Just ten minutes from Boston, Cambridge has more than 30 bookstores within a six-mile radius, giving it more bookstores per capita than any other U.S. city. Buy a book, then enjoy a rich Middle Eastern-style coffee at Café Algiers (617-492-1557) on Brattle Street.
ORLANDO TO FLORIDA'S SPACE COAST
Distance: 47 miles
Time: 1 hour 10 minutes
THE TRIP: Yes, it's touristy. But the Space Coast—a 72-mile stretch of beaches that includes the Kennedy Space Center and Cape Canaveral—offers a unique blend of relaxation and rockets. An astronaut talks with guests each day at the Space Center (if you're lucky, you might even see a shuttle launch), and you can take your own wild space journey on the Shuttle Launch Experience (tip: don't eat first). The coast is also a popular outdoorsy spot, with bird watching and flat hikes at the Canaveral National Seashore and the Merritt Island National Wildlife Refuge.
A WORTHWHILE DETOUR: Christmas, Florida
Despite the name, the main attraction here is gator watching: several airboat companies can whisk you through the Everglades.
CHICAGO, ILLINOIS, TO MILWAUKEE, WISCONSIN
Distance: 92 miles
Time: 1 hour 40 minutes
THE TRIP: Unless you're a big Laverne & Shirley fan, Milwaukee probably doesn't top your list of must-see places. But Chicago's overlooked neighbor has plenty of attractions. The Harley-Davidson Museum is a must (see the bike that Elvis bought just days before releasing "Heartbreak Hotel"). The city also boasts such sights as the 15th-century St. Joan of Arc Chapel, which was shipped to the United States from France in 1927 (and donated to Marquette University in '64), and the Tripoli Shrine (headquarters for the Milwaukee Shriners), which looks like a mini Taj Mahal.
A WORTHWHILE DETOUR: Galena, Illinois
Okay, Galena is over 160 miles from Chicago, but it's packed with pubs, cafés, galleries-and well-preserved historic buildings.
PHOENIX TO JEROME, ARIZONA
Distance: 110 miles
Time: 2 hours
THE TRIP: Phoenix is a great jumping-off point for day trips. Low-cost air service from Southwest and Mesa Air is one reason, and Phoenix's central-Arizona location is the other, putting the city within driving distance of several one-tank destinations. You know about Sedona, but don't overlook the mile-high town of Jerome. This former copper-mining locale is a haven for painters, potters, furniture makers, and jewelers. On the first Saturday of every month, the town sponsors an evening Art Walk that takes you to 30 galleries and studios (or, you can grab an Art Walk map and take a stroll on your own). A good starting point is the Jerome Artists Cooperative Gallery, which showcases the works of more than 30 local artists.
A WORTHWHILE DETOUR: Prescott , Arizona
Prescott is an unusual mix of Old West and Victorian architecture. Don't miss Whiskey Row, once the local red-light district. You can still experience its old-time flavor at Matt's Saloon or Jersey Lilly Saloon.
LOS ANGELES TO LOS OLIVOS, CALIFORNIA
Distance: 129 miles
Time: 2 hours 25 minutes
THE TRIP: A tiny town packed with tasting rooms, boutiques, and restaurants, Los Olivos is in the heart of Santa Barbara's wine region. The Los Olivos Grocery is one of the few places selling Sea Smoke pinot noirs, one of the area's top wines, as well as artisanal cheeses and olive oil. Mattei's Tavern has been serving customers since it was built as a stagecoach stop in 1886.
A WORTHWHILE DETOUR: Ojai, California
The Ojai-Ventura International Film Festival attracts major celebs—without the chaos of Sundance.
Peter Greenberg is AARP's Travel Expert and the author of Tough Times, Great Travels (Rodale, 2009).