It's the job of travel sites and agents to point out the best places to eat, drink, shop, and sleep, but rarely do we see the best back roads make it onto the agenda. Accordingly, travel aficionado Tom Hale, bored with typical modes of exploration, founded Backroads, an active travel company devoted to creating rewarding alternatives that include the best possible biking, walking, and multisport trips around the globe.

The 'Fame' actor gives us his NYC itinerary.

The 18 year-old M.I.A. protege shows us around Charm City.

Oh, ye old time tested and treasured art of the Bachelor Party. A rite of passage. It signifies an end of one era, heralds another, and reveals just how brilliant or sleazy your male counterparts may be (as if you didn’t already know). Some celebrate with strippers, steak, and one-night stands. Others keep it classy, opting for a day of golf, steak, and cigars. Whatever your forte, gentlemen, South Beach on the Ocean Drive home stretch has this male bonding event covered. A little bit cheesy, a little bit rock 'n' roll. Let the male bonding commence.

If Los Angeles were a band, Hollywood would be the showy lead singer. And Silver Lake would be the understated, contemplative bassist -- the George Harrison of LA neighborhoods. Here’s how to spend a day in this artsy section of the city.

Friday Stay: Hollywood Roosevelt. It's luxe. It's glam. There's all-night pool parties. It's the perfect setting for a weekend away with the ladies. 3 p.m.: Tropicana at the Roosevelt Hotel. Stretch your legs in the sun and have a cocktail (or three). 4 p.m.: Nothing to wear? Head on down to vintage clothing store Jet Rag. Dig through hipster heaven and you might come away with a pair of 70's Frye boots, or a sweet fur shrug. Either way, it's good times.

Friday Stay: Golden Nugget. Check in. Inside the hotel, there’s a Bond villain-worthy pool complex and newly renovated bars and restaurants. Outside the hotel, historic downtown Las Vegas. 3 p.m.: Brass Lounge. Enjoy a “Hello Vegas!” cocktail with a view. 4 p.m.: Nothing in your luggage glamorous enough? For ladies, try the Bettie Page store. Gentlemen can pick up slick threads from days gone by at Valentino’s Zoot Suit Connection.

Montreal is a city where fashion, food, and culture are on equal display, not to mention the Dionysian after-dusk pursuits. Although female-retail-centric, both BFFs and BFs won't mind on this tour de ville.

Do it up in LA, Hollywood style.

Just one night? Alright then. Here's what you do in the Near North Side