by Jessica Giles | February 28, 2020

A Complete Guide to Historic Downtown DeLand

Looking for a charming weekend getaway? Here are all the places you should shop, eat and explore in DeLand

Illustration by Leslie Chalfont
  1. ATHENS THEATRE The storied building has been a vaudeville theatre, movie palace and video game room in its past lives, but now it’s restored to its former glory as a stage for local productions, concerts and lectures. 124 N. Florida Ave.
  2. SANTORINI GREEK CUISINE There’s a reason you’ll always see a crowd outside this incredibly authentic Greek eatery. Arrive early to grab one of the few tables inside and enjoy the best gyros, moussaka and spanakopita in the state. 210 N. Woodland Blvd.
  3. DELAND WINGS You’ll have to journey off the beaten path to find this Instagram-worthy mural by local artist Erica Group, but it’s well worth the detour. Hint: look in the alley behind No. 9 on the list. Persimmon Lane
  4. SKYDIVE DELAND Thrill-seekers from around the world flock here to this skydive training capital of the world. Free fall over scenic downtown DeLand or grab a seat at the on-site restaurant and observation deck to watch the jumpers. 1600 Flightline Blvd.
  5. BOSTON COFFEHOUSE With its exposed brick interior, delicious breakfast menu and hidden garden in the back, this cozy coffee shop is the perfect place to start your weekend. Tip: order the Yankee doodle. 109 E. New York Ave.
  6. SPEC MARTIN MEMORIAL STADIUM Watch the Stetson Hatters and the DeLand Bulldogs football teams punt and tackle under the Friday night lights at this stadium: the same one that Adam Sandler plays on in the 1998 film The Waterboy. 260 E. Euclid Ave.
  7. CHICAS CUBAN CAFE This cafe is nestled inside the historic Artisan Hotel. Don’t fill up on croquettes until you’ve tried the signature Chicas chicken. 215 S. Woodland Blvd.
  8. PERSIMMON HOLLOW BREWING CO. Drink sensibly but get a little weird at this downtown brewery with quirky flavors like  the Daytona Dirty Blonde and the Tipsy Friar. 111 W. Georgia Ave.
  9. THE HIVE BOUTIQUE Shop trendy women’s clothing, accessories and local brands at this adorable spot on the main strip, formerly known as Dressed. 108 S. Woodland Blvd.
  10. STETSON MANSION Wander around the luxurious estate of famous hat magnate John B. Stetson. It’s the only Gilded Age mansion in Florida. 1031 Camphor Lane
  11. HONTOON ISLAND STATE PARK Hike, bike and fish at this secluded island on the St. Johns River. Be on the lookout for remnants from the original Mayaca Native American inhabitants, including a 10-foot owl totem pole. 2309 River Ridge Road
  12. DE LA VEGA Chef Nora De La Vega serves up exceptional Latin fusion dishes at this charming downtown restaurant. Snag a seat on the patio and sip on sangria while you people-watch. 128 N. Woodland Blvd.
  13. SIDECAR HOME MARKET Is it a bar? Is it a vintage furniture store? Both! Browse repurposed furnishings and goods by Florida artisans like FinchBerry soaps and Rifle Paper Co. all with a cocktail in hand. 100 S. Woodland Blvd. 
  14. RODEO WHIP This family-owned ice cream shop has been around since 1983, and the homemade swirls often draw a drive-thru line that circles the building. Insider’s tip: order the small; the scoops are huge. 1250 S. Woodland Blvd. 

Looking for more city guides? Check out our Bird’s Eye View archive.

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