South Orlando and Conway 

Between urban and suburban

Hovering among the midcentury houses and educational facilities comprising South Orlando’s mature, canopied escape from downtown’s vertical sprawl – often for the sake of raising a family in relative peace – is a growing sense of pride and adventure. It’s not a unifying identity per se, but the area stretching roughly from South Orange Avenue over to Conway Road, south of the East-West Expressway, has come a long way in a short time to include everything from hip neighborhood eateries to well-manicured parks to little slices of old Florida served on the half-shell. Sure, there remain vestiges of lower property values (mostly strip-mall entrepreneurial endeavors), but the area has cleaned up its winding lakeside thoroughfares and somewhat schizophrenic main streets (South Orange Avenue, Curry Ford Road, Michigan Avenue) to invite a burgeoning diversity that makes it all feel that much more authentic. Whether piloting a grumbling Harley or a silent Prius, you’re likely to find your place outside Lake Eola’s downtown splatter zone. You just need to know where to look.


La Fiesta Mexican Grill and Catering
2420 Curry Ford Road

Julie’s Waterfront Restaurant
4201 S. Orange Ave.

OLV Café
25 W. Crystal Lake St.

Mediterranean Blue
435 E. Michigan St.


Johnny’s Fillin’ Station and Other Side
2621 S. Ferncreek Ave.

The Gnarly Barley
7431 S. Orange Ave.

1912 S. Orange Ave.

The Rogue Pub
3076 Curry Ford Road


The Village Thrift Shop
888 E. Michigan St.

Apple Core Antiques and Gifts
2627 Curry Ford Road

Pink No. 5
2230 Curry Ford Road


Fort Gatlin Recreation Complex
2009 Lake Margaret Drive

Wadeview Park
2177 S. Summerlin Ave.
There are loads of green spaces and lovely walking paths throughout south Orlando, but with its lake views and picnic areas, this one is a real standout. It’s also adjacent to the Timucua White House.


St. Patrick’s Day at Claddagh Cottage
Claddagh Cottage Irish Pub
4308 Curry Ford Road
Where better to spend St. Paddy’s Day than at a traditional, cozy Irish pub? This place, located in a nondescript strip mall, opens its doors (and its parking lot) for a party in honor of Ireland’s patron saint.

Timucua White House
2000 S. Summerlin Ave.
This fantastic venue, which also happens to be the home of Cirque du Soleil conductor Benoit Glazer, brings some of the greatest experimental music in the area into a gorgeous three-story theater. For free, believe it or not. All you have to do to gain admittance is bring a bottle of wine to share. Don’t be shy – there are no strangers here, just friends you haven’t met yet.

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