Select Your Location

The Jilted Lover’s Guide to Summer Vacation

By The Second City | May 15, 2013

Hello there, Savvy Travelers! It’s me, Ben Whitaker, The Second City Network’s Savvy Travel Guide. Wouldn’t you know it? Summer is comin’ round the bend! If you’ve been squirreling away your pennies like I advised you to back in my January article, “Don’t BRRRRRReak the Bank,” then you’re sitting on a tidy little pile of ducats and ready to spend them on a warm-weather getaway! Maybe some of you are like your own Savvy Travel Guide and have amassed a particularly large vacation nest egg because all of a sudden…WHOOPS!…your romantic rendezvous for two just became a solo adventure. I guess you can say I’m on a “permanent vacation” from my relationship of four years, as well as from my own apartment!

Oh, Boise!

Sorry for the TMI, gang! Guess I was writing to you from the penthouse suite at the Heartbreak Hotel, but that’s nothing a little globe-trotting and sunshine can’t cure. Especially when the money you were going to use to buy an engagement ring is now BURNIN’ A HOLE IN YOUR POCKET! YEOWCH! That’s a scorcher!

Cozumel, Mexico

Water as salty as my buckets of tears!

Speaking of scorcher… there’s no señor or señorita on God’s green earth that can have a bad time down south of the border. The weather is caliente, the resorts are all-inclusive, and the good times are mucho plentiful. You’ll be partying ‘til you siesta! And don’t forget the food! Like the carnitas that Leighanne loved so much, or the burritos you brought home the night she told you she met someone else… OH THAT’S ME AGAIN WEEEOOOOWWWEEEOOOO SADSACK ALERT.

Grand Cayman

Stroll along the pier, holding your own hand.

Beaches as far as the eye can see! Water so clear you’ll think you’re swimmin’ in glass! Ideal for young people whose souls haven’t been crushed by betrayal or families like the one I should have by now, you’d be hard-pressed to find a better locale to kick back and chillax. People still say chillax, right? It doesn’t come off like I’m trying too hard? Like I’m trying to be someone I’m not? Like certain people whose name rhymes with “Leighanne” might throw at you when you’re not totally not expecting it? Oh boy, somebody left the back gate open and my entire future got out!

Rio de Janeiro, Brazil

Come see a statue of someone who clearly doesn't exist!

CARNAVAL!!! Might be during the summer time. I have no idea, but what an escape it would be to one of the grand cities of South America. Did you know they speak Portuguese in Brazil? And so does the pilates instructor Leighanne walked out on me for? WHAT MAN DOES PILATES…?

Rome, Italy

Has anyone ever drowned themselves in the Fountain of Love?

Ancient history so rich you’ll forget the recent history of your girlfriend recounting your sexual shortcomings loudly in front of the neighbors. NEXT SPOT…

Paris, France

It's a 1,063 jump to the bottom.


Ibiza, Spain

Tapas. Architecture. Who cares.


Portland, Oregon or Maine

Great and everything and DEAR GOD LEIGHANNE TAKE ME BACK.

Chicago, Illinois

Why have you forsaken me?

You know what? Why not stay-cation in the hometown? Where EVERYTHING REMINDS YOU OF HER I CAN’T FEEL MY HANDS.

Milwaukee, Wisconsin

Look at what I've become. Happy now?

Jewel of the Midwest, where a dark room at my brother’s house will greet me along with a case of Schlitz and a Brewers games or 4. No one does pilates in Wisconsin! It’s against the law! AHAHAHAOWMYSPIRIT.



Kevin Sciretta is a writer and improviser living in Chicago. In addition to working for The Second City, he is also a contributing writer for The Onion News Network and a regular performer at iO Chicago.

Hilarious Right? Follow the Second City For More