Welcome to the third edition of the artist formerly known as the Cool Kid’s Guide to Orlando. This year we’ve changed the name and age cohort to teens, but consulted once again with our favorite rock photographer and rock dad, Jim Leatherman. With his son and daughter both well into their teenage years, we were curious what this impeccably hip family do for quality bonding time — when kids aren’t quite “kids” anymore. Read on …
Semoran Skateway
This place is a big teen hangout still — lots of kids from Winter Park High go there on a Friday night. Surreally, this place was very popular as a teen hangout back when I was in high school …
2670 Cassel Creek Blvd., Casselberry, semoranskateway.com
Oviedo Bowling Center
It’s worth the longer car drive to head over to this bowling alley in Oviedo. The big draw is the Pinball Lounge, a vast collection of current and some vintage pinball machines.
376 E. Broadway St., Oviedo, oviedobowlingcenter.com
Dutch Bros. Coffee
With apologies to Easy Luck and Drunken Monkey, my daughter loves this place. Their Golden Eagle is a favorite. Also the strawberry lemonade is a hit.
Le Macaron French Pastries
This Winter Park desert shop, tucked away on Park Avenue, is a favorite of my daughter, who loves their mille-feuille Napoleon pastry.
216 N. Park Ave., Winter Park, lemacaron-us.com
Boba tea
My kids still love boba tea. We often go to Möge Tea and Bin Bông, both at Mills and Colonial, and Frosty Fox on New Broad Street.
Sporting life
My son loves Orlando City Lions, so we’ll go to matches at Inter&Co/Orlando City Stadium. Just as fun — but a little more under the radar — is catching a Tars baseball game at Alfond Stadium at Rollins College.
Bibliomania
Both my son and daughter still love going to the downtown Orlando Public Library, especially the Melrose technology center. My daughter also loves the Winter Park Library for their used book shop, New Leaf Bookstore.
101 E. Central Blvd., ocls.org
1052 W. Morse Blvd., Winter Park, winterparklibrary.org
The great outdoors
To get out of the house and spend some quality time outdoors, we enjoy walking around Park Avenue in Winter Park, trekking around Lake Eola and going to Menchie’s Frozen Yogurt, strolling through Dickson Azalea Park or Blue Jacket Park and taking the dog to Lake Baldwin Dog Park. To cool down in the water, we’ll head to Wekiva Island and rent a canoe to drift down the river.
Staying in the neighborhood
Right in our neighborhood of Audubon Park, we go shopping for records and CDs at Park Ave CDs. A lot of my daughter’s friends are in love with the vintage photo booth at Stardust Video and Coffee. We enjoy shopping at Owl’s Attic, East End Market, grabbing a treat at Kelly’s Homemade Ice Cream or browsing the Lovely Boutique Market and Hellcats USA.
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This article appears in City Guide 2025 and City Guide (2025).