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Charlie Sheen-Inspired Vacations: Where to be a Winner

Maybe we’ve all got it wrong. Maybe our vacations shouldn’t be about relaxing and seeing new things and spending special bonding time with loved ones. Maybe our vacations should be about something else entirely: winning. If you’re going by the Charlie Sheen playbook, your every day should be filled with “wins,” which means your vacation days should, too. After all, despite his recent firing, he’s someone who “win[s] so radically in [his] underwear before [his] first cup of coffee, it’s scary.” Well, you can do that too, with one of these winning escapes.

Winning Escape #1: Ferocious Golf Getaways
You don’t need Sheen’s purported “tiger blood” to make like Tiger Woods on the golf green. Head to golf-friendly destinations like Scottsdale in Arizona, St. Andrews in Scotland, or Bermuda where you can sport some really spiffy shorts to add to your winning look. If you want to ensure that you come out a winner, then make sure you play with people who have less experience—or a bigger hangover—than you.

Winning Escape #2: King-of-the-Mountain Moments
There’s nothing that demonstrates a winner’s spirit more than conquering a mountaintop—and nobody has to know that mountaintop is a just few measly feet off the ground. Sure, you could gear up and cross-train for a summit attempt on Denali, Kilimanjaro, or the Matterhorn. Or, you could attempt a softer, more manageable (read: winnable) slope like Mt. Tamalpais in Marin or Sugarloaf Mountain in Maryland.

Winning Escape #3: Teeth-Baring Shark-Diving Adventures
If you want up to rack up one big win on your next vacation, then show all the sharks who’s boss by going on a shark dive in the Bahamas, off the coast of Fiji, or along the ominously named “Shark Alley” at the tip of South Africa. Suit up and stay inside the cage (no wild-eyed mug shot needed), where you can safely shake your champion’s fist at some of the world’s scariest, most ferocious, and most winning sea creatures. Then, show your own winning smile by barring your teeth to the top of the food chain.

Winning Escape #4: Epic Casino Jackpot Weekends
Whether it’s Atlantic City, on a boat off Biloxi, in the luxe surroundings of Monte Carlo, or at your pick of casinos in Las Vegas, a gambling vacation gives you a chance to really come out a big winner. Choose your poison: the slow and simmering roll of playing penny or nickel slots or put it all on red and bet everything. Even if you come out a loser, you can still come out a winner if you lose enough to get yourself a comped room or meal.

Next time you plan your vacation, remember that your every vacation day could be filled with wins if you go on one of the trips listed above. Got any other “winning” vacations to recommend?

Climbing Mt. Kilimanjaro (The Window Seat)

Swim with Sharks at Dubai Mall (

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My name: Rachel Berg.

Favorite way to get around: By Venetian gondola during starlit high tide, gliding past decaying and slightly spooky palaces, with perhaps a bottle of prosecco placed between the gondola seat cushions.

View that took my breath away: Unable to sleep in the mystical city of Sfat in Israel, I wandered outdoors predawn and was treated to a purple-on-purple sunrise below the mountaintop that seemed to emerge feet-first through ground-level clouds.

Greatest travel lesson learned: Sunny weather isn't everything. Some of my best travel memories involve go-karting through a deluge turned mud-fest in Mexico, drinking tea in the cold Denali tundra, and watching electric thunderstorms roll through national parks out West.

Most challenging travel moment: Getting leveled by altitude sickness in Cuzco and realizing that my body was forcing me to slow down and rest despite the fact that there was so much to do and see.

Travel ambition: To see the northern lights.



GREAT article!

Bruce Wayne

The Ma-Sheen rides a tsunami on a mercury surfboard, but do you think any smoking hotties might want to having a winning vacation at the Skee-Ball lanes?


Scottsdale is your 1 day #Winning escape: 1) hike Camelback Mountain in the morn, 2) Golf 18 holes in the afterooon, 3) sink your teeth in a mouth-watering steak, and 4) gamble at the new Talking Stick Resort. #Winning mancation weekend

Eric Graham

Haha. I call taking huge risk for extra excitement on your vacation.

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Sugarloaf Mountain in Maryland sure is an exciting place to getaway.

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