Drinks with George Clooney? 7 Celebrity Vacation Destinations

I am notoriously bad at spotting celebrities, I have friends who could pick out Snoop Dog in a crowd of 10,000 in Times Square. Not me.

To date my most exciting celeb interaction was a nod of acknowledgment from Bradly Whitford (Josh Lyman on the West Wing for you non-nerds out there) on a side street in Manhattan. I obviously get it from my mother, who once spent a full 45 minutes casually chatting with Dr. J at Disney World with nary a clue as to who he was.

So, like many of my generation who grew up reading People Magazine and spending hours a day on Gawker, I have always wanted to just casually bump into someone famous on vacation.

Unfortunately for me, celebs don’t seem to gather at places like the Marriott Courtyard Inn Denver Tech Center or the Hoboken Ramada, where I generally find myself staying.

What’s a girl to do?

Search top celebrity vacations online and make a blog post about it, obviously. At least now that we know the hot spots we can start hatching our stalking vacation plans.


Let’s start easy, shall we? Once we make our way to Maui, all we have to do is casually snorkel our way to the beaches at the Four Seasons or Fairmont. From there, it’s chilling with Ben Affleck and Jennifer Gardner, Kate Hudson, and Alessandra Ambrosio.

Necker Island

Ok, perhaps a touch harder to sort of casually appear on a privately owned island in the middle of the ocean, but a girl can dream, right? If you ever have more than a couple of grand a night to spend here, you might find yourself sharing a beach with Prince Harry, Steven Spielberg, Harrison Ford, and of course, Oprah.


Allegedly London is the place where celebs are oh so casual and normal, of course Madonna and her track suit collection would live there. Explore the area, and you might run into a few famous folks while having tea and crumpets like Spike Lee, Leo DiCaprio and Angelina Jolie (presumably dragging along Brad and the crew).


Ah South Beach, the place where celebs frolic on the white sand beaches and drink pricey bottles of vodka in some of the hottest clubs around. If you can get into places like LIV or Mokai you might end up doing shots with Cameron Diaz, Lenny Kravitz, and the Kardashian Klan.


Finally, a palace I’ve actually been to, although naturally during the off season and decidedly celebrity free. But, Aspen kicks ass, so don your best fuzzy apres ski boots and cozy up to the fireplace with Mariah Carey and Nick Cannon, Goldie Hawn, Jonah Hill and Heidi Klum.

Cabo San Lucas

For those hanging out on the left coast, Cabo is where it’s at. Less than 2 hours from LA, you will find a ton of celebs heading south for a bit of R&R from their very taxing lifestyles. But, once you spot some Hollywood elite, it can be all worthwhile, so grab your tequila and buddy up with George Clooney, Cindy Crawford, Alex Rodriguez and Jennifer Aniston.

Turtle Island

Yes, Turtle Island is spectacular, yes it has crystal clear water and private butlers and you can pick a mango off a tree, but I will issue this warning: Turtle Island is the place were celebrity marriages go to die! Yup, who has honeymooned on Turtle island? Britney Spears and Kevin Federline, Nick Lachey and Jessica Simpson, nuff said.






You probably read this and was like “uhhh where the hell is the George Clooney picture? Don’t put George Clooney in a blog post about celebrity vacations and then don’t show him!” Don’t worry, boo. I got you. Scroll down for gratuitous George Clooney vacation shot.