Colorado One of the world's most beautiful train routes, the Durango & Silverton Narrow Gauge Railroad runs between the Colorado towns of Durango and Silverton, along the Animas River. The tracks were laid in 1882, and the locomotives date from the 1920s (and are still coal-fired). The train was historically accurate enough to star in Butch Cassidy and the Sundance Kid. The round-trip Silverton Summer Excursion is available May 7 to October 29, and takes 31D2 hours to go 45 miles. $62, kids $31; 888/872-4607, durangotrain.com.
Massachusetts The Elegant Dinner Train, offered by the Cape Cod Central Railroad, is a three-hour scenic excursion from Hyannis to the Cape Cod Canal and back, during which a five-course dinner is served. Proper dress is required. The best time to go: Friday evenings, when the train crosses the canal on the vertical-lift railroad bridge at Buzzards Bay. $60, cocktails and gratuity not included; 888/797-7245, capetrain.com.
Mexico On the Tequila Express, which is run by the Mexican government, mariachis provide a festive soundtrack for the 90-minute ride from Guadalajara through the blue-agave-studded landscape of Jalisco, Mexico's largest tequila-producing state, to the Herradura distillery. Contrary to what the name suggests, it's not a cheesy booze cruise--though there is an open tequila bar for sampling the local specialty. You get a firsthand look at the tequila-making process past and present, from wheel presses once pulled by mule to the steam ovens where the agave is cooked today. Tours are followed by an authentic buffet, and you're back in town by 8 p.m. $69, kids 6 to 12 $36; 011-52/33-3880-9099, tequilaexpress.com.mx.
Hot tickets, cool shows
Boston Catch the Red Sox from the newest seats in Fenway Park--atop the 37-foot-tall Green Monster in left field. Tickets go on sale via preseason online lottery. Standing room from $25, seats from $80, 617/226-6000, redsox.com.
Cancún Celebrate Mexican culture at Xcaret Spectacular Nights--a folklore show at the Xcaret Eco Park in Playa Del Carmen. Kids will love the lacrosse-like game, which is based on a Mayan ritual and played with a flaming ball. Included with $49 park admission, kids $25, 011-52/998-883-3144, xcaret.com.
Chicago With alumni named Belushi and Murray, The Second City changed the face of comedy. It all began 45 years ago on its Chicago Mainstage--now one of five companies in the U.S. and Canada. From $18, 312/337-3992, secondcity.com.
Las Vegas Kà, at the MGM Grand, is Cirque du Soleil's most ambitious show (and each seat has speakers). Two shows nightly, Friday through Tuesday. From $99, 877/880-0880, cirquedusoleil.com.
New York City The cabaret at Feinstein's at the Regency is world-class, with such past performers as Patti LuPone and Chita Rivera. $100, 212/339-4095, feinsteinsattheregency.com, mid-September to mid-June. Did someone say send in the clowns? None of the seats at the Big Apple Circus is more than 50 feet from the action. After its signature engagement every winter in Manhattan, the show tours the East Coast. From $15, 800/899-2775, bigapplecircus.org.
San Francisco Steve Silver's Beach Blanket Babylon has wowed crowds for more than 30 years. Recent spoofs include Arnold Schwarzenegger in leather gear. From $25, 415/421-4222, beachblanketbabylon.com; 21 and over for evening performances.
What does it feel like to live in the Coolest Small Town in America? Ask the folks in Grand Marais, Minnesota, who earned the top spot in our 10th annual contest. Their town showed us the perfect blend of edgy, sweet, beautiful, and travel-worthy that adds up to “cool” in our book. Read on to stoke your wanderlust.