The Whole Enchilada in Winter Garden

Pleasant temperatures and sunny weather throughout the year mean an abundance of options when it comes to outdoor dining in Orlando. To help you sift through the options and pick the perfect restaurant for your next date night outing, we've put together this comprehensive outdoor dining guide.

Let's kick off with our quick picks for the best outdoor dining in Orlando:

  • Boxi Park
  • Boca Winter Park
  • Chroma Modern Bar + Kitchen
  • Eden Bar
  • Hillstone
  • Luke's Kitchen and Bar
  • Prato
  • Santiago’s Bodega
  • Sixty Vines
  • Wine Bar George
  • The Old Jailhouse
  • The Waterfront Orlando
  • The Yardery

This outdoor dining guide is updated periodically throughout the year so check back to see what's new. Latest update April 2024.

Orlando Outdoor Dining Guide

Keep reading for a comprehensive guide for Orlando restaurants with outdoor seating.
Options are categorized based on the type of outdoor dining:

OPEN AIR PATIOS

À La Cart
Outdoor mini food truck park with permanent + rotating trucks, great craft beer selection
609 Irvington Ave., Orlando (second location in SoDo slated to open Spring 2024)
(407) 776-4693

Boxi Park
Shipping container food truck park with gourmet quick-service dining, award-winning beer, live entertainment, and more.
6877 Tavistock Lakes Blvd., Orlando

Soft Serve Ice Cream at Boxi Park
Soft Serve Ice Cream at Boxi Park – Dani Meyering

Bulla
Happy hour, weekend brunch, and a curbside patio out front.
110 S Orlando Ave., Winter Park
(321) 214-6120

Eden Bar
This all-outdoor restaurant and bar connected to Enzian Theater is one of my favorite spots for cocktails and light bites. The ambiance is extra romantic at night, thanks to twinkle lights setting the towering live oaks aglow. Stick around for a movie after dinner and drinks.

1300 S Orlando Ave, Maitland
enzian.org/food

Eden Bar patio dining in Orlando
Image credit: Enzian Theater

Eleven at Reunion Resort
Rooftop restaurant with indoor/outdoor seating on the 11th floor of Reunion Resort serving tapas and craft cocktails, live entertainment with a DJ every Friday and musician every Saturday.
7593 Gathering Dr, Kissimmee
(833) 258-0472

READ MORE: Orlando's Best Rooftop Restaurants and Bars

Grape & The Grain
Dog-friendly, food trucks Friday – Saturday nights, live music select nights, heaters and fans on the patio for all kinds of weather!
1110 Virginia Dr, Orlando
(407) 674-6156

Hamilton’s Kitchen
Brunch 7 days a week, delicious food, in-house sommelier, chef-driven cuisine, located inside The Alfond Inn
300 E New England Ave, Winter Park
(407) 998-8089

Propagate Social House
Coffee, wine, plants, and brunch all with a gorgeous backyard setting
40 E. 5th. Street, Apopka
(407) 703-2696

The Acre
Gorgeous outdoor wedding venue that becomes an outdoor hangout spot with pop-up markets and more
4421 Edgewater Dr, Orlando, FL 32804
[email protected]

The Acre Orlando Pizza with Meat and Cheese Platter
The Acre Orlando Pizza with Meat and Cheese Platter – Image by Dani Meyering

The Pinery
Upscale craft cocktails and delicious bites with a curbside open-air patio overlooking Ivanhoe Village
295 NE Ivanhoe Blvd Suite A, Orlando
(407) 377-7576

The Yardery
The ideal outdoor destination for a fun date or getting together with friends. Dog-friendly and kid friendly with a casual food menu and outdoor games
415 E. 4th St., Sanford, FL 32771
(407) 878-2179

The Hampton Social

This eatery in Pointe Orlando boasts a spacious outdoor dining area with comfy patio chairs and love seats, tables, and coastal vibes. Check it out for dinner or visit on the weekend for brunch, paired with signature rosé, frosé, and fun cocktails, of course.

9101 International Dr., Orlando
(689) 800-6760; thehamptonsocial.com/orlando

The Hampton Social's signature frosé

Pigzza
Forget traditional and jump into a marvelous mashup of BBQ and Italian. From the minds behind Pig Flloyds, you're sure to leave satisfied.
1050 N Mills Ave, Orlando, FL 32803
(407) 704-8223

Plantee's Burgers
Delicious burgers and “chicken” sandwiches that you won't believe are plant-based with outdoor seating that gives all the Mills50 vibes
1030 N Mills Ave, Orlando
(321) 206-4271

Luke’s Kitchen and Bar
Twinkle lights, cozy patio seating, great food and cocktails, Sunday brunch
640 South Orlando Ave, Maitland
(407) 674-2400

Plant Street Market
Pet-friendly outdoor patio, live music, market with multiple food vendors and a craft brewery
426 W Plant Street, Winter Garden
786) 671-1748

Sixty Vines
Small outdoor patio that feels exclusive, ideal for wine lovers and fresh cuisine
110 S Orlando Ave Suite 12, Winter Park, FL 32789
(407) 410-8005

STK Orlando
Rooftop terrace, awesome happy hour from 3-6:30pm Monday – Friday and 3-5:30pm Saturday – Sunday, located at Disney Springs
1580 E Buena Vista Drive
(407) 917-7440

Sugar Factory
Small patio out front, over-the-top milkshakes and desserts, brunch menu available Saturdays and Sundays, located at ICON Park
8371 International Drive  #70, Orlando
(407) 270-7082

The Whole Enchilada

Find this Tex-Mex eatery in the heart of Downtown Winter Garden. The margaritas are some of the best in town (I recommend the prickly pear and the mango), especially when sipped on the colorful rooftop terrace. If you prefer to dine curbside, there's another smaller patio downstairs.

129 W Plant St., Winter Garden
‭(407) 347-9699‬;  www.twefreshmex.com

The Whole Enchilada Plant Street Winter Garden
Image credit: Stephanie Patterson

COVERED PATIOS

Check out these great restaurants in Central Florida with lovely covered patios.

Armando’s
Italian eatery with multiple covered outdoor dining areas including curbside tables in Hannibal Square
463 West New England Ave Winter Park
(407) 951-8930

Artisan’s Table
Covered patio out front, globally-inspired eats and craft cocktails
55 W Church St Suite 128, Orlando
(407) 730-7499

bartaco
Spacious pergola-covered patio out front, check social media for “secret” taco options
7600 Dr. Phillips Boulevard, Orlando
(407) 801-8226

Bem Bom on Corrine
Mexican & Portuguese fusion cuisine, recently covered patio, weekend brunch
3101 Corrine Dr, Orlando
(407) 960-5101

Bites and Bubbles
Incredible wine and cheese selection, brunch, choose from the lovely covered patio, or the open-air upstairs bar and dining area
1618 N. Mills Avenue, Orlando
(407) 270-5085

Café Tu Tu Tango
Bottomless brunch Saturdays and Sundays, tapas, artful space, live entertainers on weekends
8625 International Drive, Orlando
(407) 248-2222

MORE: International Drive Restaurants with Outdoor Dining

Chroma Modern Bar + Kitchen

Chroma is a stylish Lake Nona staple with a bright interior, colorful accents, a spacious outdoor patio and tapas-style menu perfect for sharing. Pair your tapas with one of the refreshing seasonal cocktails. For extra date night fun, visit on a Friday evening to coincide with Lake Nona's weekly Art After Dark event from 6-9pm.

6967 Lake Nona Blvd, Orlando
(407) 955-4340; chromalakenona.com

Guide to Outdoor Dining in Orlando - Chroma Lake Nona covered patio
Image credit: Chroma Modern Bar + Kitchen

Cocina 214
Tex-Mex eats, weekday happy hour, Sunday brunch
151 E Welbourne Ave, Winter Park
(407) 790-7997

Cowfish at Universal CityWalk
Sushi and burgers with craft cocktails, vibrant atmosphere, the covered patio out back is a great way to get seated faster.
6000 Universal Blvd, Orlando, FL 32819
(407) 224-3663

READ MORE: The Best Restaurants at Universal Orlando for Date Night

DOMU – Dr. Phillips
Bright, pergola-covered patio out front, rotating soft-serve ice cream flavors
7600 Dr. Phillips Blvd #14, Orlando
(407) 630 – 6163

Dragonfly Robata Grill & Sushi
Fresh sushi, awesome happy hour, large covered outdoor patio
7972 Via Dellagio Way, Orlando
(407) 370-3359

Earls Orlando
Weekend brunch (happy hour brunch pricing from open to noon!), daily specials, happy hour food + drinks
4200 Conroy Road, Unit H246, Orlando
(407) 345-8260

The Glass Knife

This dessert-centric restaurant serves up some of the most photogenic sweets in town alongside savory food items available all day. For a real treat, visit during the weekend brunch available on Saturdays and Sundays. Arrive early so you can get your hands on one (or seven) of the eatery's infamous donuts.

While we're partial to the romantic date night booth inside, the covered patio is a nice alternative.

276 S Orlando Ave, Winter Park
(407) 500-2253; theglassknife.com

The Glass Knife outdoor dining in Orlando
Image credit: The Glass Knife

Graffiti Junktion Thornton Park
Casual spot for burgers, covered outdoor patio, themed trivia nights
900 E Washington St, Orlando
(321) 424-5800

Hunger Street Tacos
All outdoor eatery with a covered outdoor dining area, some of the best tacos, and authentic Mexican eats in town (pair your food with a glass of sangria)
2103 W Fairbanks Ave, Winter Park
(321) 444-6270

Market to Table
Farm-to-table cuisine, located in downtown Winter Garden, covered patio behind restaurant
146 W Plant St, Winter Garden
(407) 395-9871

Mia’s Italian Kitchen
Authentic Italian eatery, endless family-style dining option, daily happy hour, covered patio
8717 International Drive, Orlando
(407) 601-7130

Pig Floyd’s
A cozy patio now has a marvelous new cover providing shade that pairs great with modern fusion BBQ
1326 N Mills Ave, Orlando
(407) 203-0866

Discover: Kids Eat Free Restaurants in Orlando

The Pub Orlando
Weekday happy hour M-F from 3-7pm, located at Pointe Orlando
9101 International Dr. Suite 1003 Orlando
(407) 352-2305

Townhouse Restaurant
A landmark in Oviedo, Townhouse Restaurant has been serving the locals since the 1950's. A hidden patio in the back is great for some fresh air and home-cooked food. There is a covered portion of the patio as well as open-air with umbrellas. Breakfast is a must here.
139 N Central Ave, Oviedo, FL 32765
(407) 365-5151

Townhouse Restaurant in Oviedo for outdoor dining
Townhouse Restaurant in Oviedo for outdoor dining – Dani Meyering

Reyes Mezcaleria

Feast on Mexican-inspired fare while sipping margaritas and sangria at Reyes Mezcaleria. The restaurant’s pet-friendly outdoor patio is spacious and covered to keep you cool. Check it out for happy hour and weekend brunch.

821 N Orange Ave. Orlando
407-868-9007; reyesmex.com

Image credit: Reyes Mezcaleria

Rodizio Grill
Brazilian steakhouse at Pointe Orlando
9101 International Dr # 1220, Orlando
(407) 593-4422

Soco Thornton Park
Covered curbside patio in Thornton Park District, weekend brunch (try the housemate pop tarts!), happy hour
629 E. Central Blvd., Orlando
(407) 849-1800

Tap Room at Dubsdread
Clubhouse fare with a covered patio, located on the Dubsdread golf course
549 W Par St, Orlando
(407) 650-0100

Teak Neighborhood Grill – Orlando

This MetroWest hangout has all of the elements of a solid neighborhood hangout: a rotating craft beer list, a famous burgers list (OMG! the “glazed donut burger”) and a great outdoor seating area. It's also pet-friendly, so feel free to bring along your furry family members. The Maitland location also features outdoor patio seating.

6400 Times Square Avenue, Orlando
(407) 313-5111; teakorlando.com

Glazed Donut Burger | Image credit: Teak Neighborhood Grill

Terralina Crafted Italian
Italian eatery located at Disney Springs, outdoor covered bar and patio seating area
1650 E Buena Vista Dr, Lake Buena Vista
(407) 934-8888

Vanbarry’s Public House
Casual hangout with fun menu items like tableside s'mores and creative drinks
4120 S Orange Ave
(407) 704-8881

Vines Grille & Wine Bar
Upscale eatery along Restaurant Row in Dr. Phillips, covered outdoor patio, happy hour
7533 Sand Lake Rd, Orlando
(407) 351-1227

Wine Bar George

Owned by Master Sommelier George Miliotes, this wine-focused restaurant is one of my personal favorites at Disney Springs. There's limited outdoor seating upstairs on a narrow covered terrace. For something extra special, visit the counter service window downstairs, The Basket. Indulge in fun options like a build your own picnic to-go and frozen wine concoctions available to go (baskets are not included, please bring your own).

1610 E Buena Vista Dr, Lake Buena Vista
(407) 490-1800; winebargeorge.com 

Wine Bar George patio terrace - outdoor dining in Orlando guide
Image credit: Wine Bar George

Wekiva Island
Super casual island eats, sit along the river or at a picnic table at the covered pavilion
1014 Miami Springs Dr, Longwood, FL 32779
(407) 862-1500
$5 admission on peak holidays and weekends

LIVE MUSIC

Hollerbach’s Willow Tree Cafe
Open-air rooftop and covered ground-level patios, German eats, live music Thursday – Sunday
205 E 1st Street, Sanford
(407) 321-2204

House of Blues Orlando
Live music in the courtyard out front, daily happy hour, revamped weekend brunch (bottomless beverages!), located at Disney Springs
1490 E Buena Vista Dr, Orlando
(407) 934-2583

Maxine's on Shine

Maxine's on Shine is an Orlando staple, and a MICHELIN Guide recognized restaurant. There's live music on the weekends and the popular brunch is served Fridays-Sundays. Dinner is served Weds-Sat from 5-9pm. Don't leave without snapping a pic together in front of the “Love You to the Moon and Back” mural on the side of the building. They recently opened a brand new covered patio for dining.

337 N Shine Ave, Orlando
(407) 674-6841; maxinesonshine.com

Ole Red Orlando

Blake Shelton's eatery at ICON Park gives Orlandoans a spot to enjoy Southern fare and daily live music. While the main stage is located indoors, the restaurant features multiple outdoor dining areas upstairs and downstairs. And, because the music from the main stage is piped through the speaker outdoors, you won't miss any of the entertainment by sitting outside.

8417 International Dr, Orlando
(321) 430-1200; olered.com/orlando

Outdoor dining in Orlando - Ole Red Orlando patio
Image credit: Ole Red Orlando

Raglan Road

This is our go-to spot at Disney Springs. We've been dining and drinking here since the Downtown Disney days. It's also a fantastic spot for live music and was recently awarded Best Live Music in Orlando Magazine‘s 2020 Dining Awards. The outdoor patio is just as energetic as indoors and features live music most days beginning at 6pm.

1640 E Buena Vista Drive, Lake Buena Vista
(407) 938-0300; raglanroad.com

Outdoor dining in Orlando with live music - Raglan Road
Image credit: Raglan Road Orlando

Tin Roof Orlando
Lively bar with live music and bar bites, located at ICON Park
8371 International Dr, Orlando
(407) 270-7926

A Sunset Walk Pub + Live Music Crawl at Margaritaville Resort Orlando

CURBSIDE/AL FRESCO

Boca
Curbside patio dining, farm-to-table cuisine, weekend brunch with bottomless mimosas and Bloody Marys
358 North Park Ave., Winter Park
(407) 636-7022

Bosphorous
Turkish restaurant with locations in Winter Park, Dr. Phillips, Lake Nona, and Winter Garden, curbside patio dining
108 S Park Ave, Winter Park
(407) 644-8609

Braccia
Italian + Brazilian fusion eatery with crispy thin-crust pizzas, outdoor patio tables, cozy vibe
153 E Morse Blvd, Winter Park
(407) 636-9918

Briarpatch
Popular breakfast and brunch spot along Park Avenue, curbside tables
252 Park Avenue North, Winter Park
(407) 628-8651

Eola Wine Company

This local wine bar is located just steps from Lake Eola Park. Pull up a seat on the curbside, covered patio to watch the comings and goings in Orlando's Thornton Park District. Come for the extensive list of boutique wines and craft beer, stay for hearty charcuterie boards, and weekend brunch (with mimosa flights!) on Saturdays and Sundays.

430 E Central Blvd, Orlando
(407) 481-9100; eolawinecompany.com

Image credit: Eola Wine Company

RusTeak Thornton Park
Curbside hangout in Thornton Park, weekend brunch, fun cocktails, happy hour
101 S Eola Dr, Orlando
(407) 601-5219

Las Carretas Mexican Restaurant
Modern Mexican cuisine with colorful drinks served inside a vibrant dining room and an intimate curbside patio
4030 N Goldenrod Rd, Winter Park
(407) 335-4916

Mynt Fine Indian Cuisine
Go-to for authentic and artfully presented Indian cuisine in an upscale setting, several outdoor tables for dining al fresco
535 W New England Ave, Winter Park
(407) 636-7055

The Imperial – Winter Park
The gorgeous interior is hard to beat, but the covered curbside seating along Park Avenue is ideal for a relaxing evening
170 E Morse Blvd, Winter Park
(321) 972-9294

Discover more Winter Park Restaurants with Outdoor Dining

Pepe’s Cantina
Winter Park gem with happy hour, tableside guacamole, Tex-Mex eats, and rotating specials.
Locations in Winter Garden and DeBary have outdoor dining too.
433 W New England Ave, Winter Park
(321) 972-4881

Prato
Italian eats across the street from Winter Park's Central Park, several outdoor tables for al fresco dining
124 N Park Ave, Winter Park
(407) 262-0050

The Ravenous Pig
New American eats, craft beer, and cocktails, small patio with curbside seating, check out the weekly takeout dinners for two
*Don't miss the Beer Garden at The Ravenous Pig Brewery next door
565 W Fairbanks Ave, Winter Park
(407) 628-2333

Rome's Flavours
Authentic Italian eatery, housemade pizzas, and pasta, curbside seating just off of Park Ave, rotating dinner specials
124 E. Morse Blvd, Winter Park
(407) 951-8039

Rosallie French Cafe

Brunch is served all day at Rosallie, a charming curbside French cafe in the heart of Downtown Winter Garden. Satisfy your cravings with a variety of quiches, croissant sandwiches, and more with one of the cafe’s signature drinks (I love the rose mocha). Wine is also available by the glass or bottle.

141 W Plant St, Winter Garden
(407) 347-5507; Rosallie Facebook Page

Santiago’s Bodega
Beloved favorite for happy hour and brunch, located in the Ivanhoe Village Main Street District, shareable tapas
802 Virginia Dr, Orlando
(407) 412-6979

The Stubborn Mule
Fun cocktails (especially the Moscow Mule varieties), lively outdoor patio, popular weekend brunch, happy hour
100 S Eola Dr Unit 103, Orlando
(407) 730-3400

Yard House
Upscale sports bar vibe, small outdoor patio with peek-a-boo views of The Wheel at ICON Park, happy hour
8367 International Dr, Orlando
(407) 351-8220

WATERFRONT VIEWS

If dining on the water is your desire, jump over to our list of 15 Scenic Waterfront Restaurants Orlando.

Cabana Live
Head to Sanford for a casual and fun outdoor dining spot that's right on the water. You'll find happy hour specials during weekdays and a total party vibe on weekends. There's even a pool at Cabana Live, and as the name implies, cabanas you can book for dining and celebrations.
Address: 4380 Carraway Place, Sanford, FL 32771
(407) 878-3666

Fish Tacos Cabana Live Waterfront Restaurants Orlando Florida
Fish Tacos Cabana Live – image by Dani Meyering

The Boathouse
Waterfront eatery located at Disney Springs, complete your experience with a ride around the lake in one of the amphicars
1620 East Buena Vista Drive, Lake Buena Vista
(407) 939-2628

Canvas Restaurant & Market

With its bright interior, worldly menu, and waterfront patio, Lake Nona’s Canvas is ideal for a sunset meal with your love. The patio dining area features an assortment of tables overlooking the water so there isn’t a bad seat in the house. For weekend dining, visit during the popular Sunday brunch to feast on dishes like chilaquiles (my favorite), sweet and tart Meyer lemon pancakes, or go all in with the lobster Benedict. Enjoy live music on Wednesdays and Fridays.

13615 Sachs Avenue, Orlando
(407) 313-7800; canvaslakenona.com

A Culinary Map of Lake Nona Restaurants
Image credit: Canvas Restaurant & Market

Grills Lakeside Seafood Deck & Tiki Bar
Laid-back waterfront tiki bar near College Park, live music, huge patio and deck
4315 N Orange Blossom Trail, Orlando
(407) 291-8881

Hillstone

This romantic restaurant in Winter Park is one of Orlando's most beautiful places, especially at sunset. Treat your date to a special meal best enjoyed from the deck and patio overlooking Lake Kilarney. FYI: the dress code is formal, so make sure to wear your date night best.

215 S Orlando Ave, Winter Park
(407) 740-4005; hillstonerestaurant.com/locations/winterpark

Hillstone Winter Park
Hillstone restaurant in Winter Park by Kristen Manieri

The Waterfront
Waterfront seating overlooking Lake Jennie Jewel, delicious seafood, casual atmosphere, and brunch on Saturday and Sunday
4201 S Orange Ave., Orlando
(407) 866-0468

World of Beer – Downtown Orlando

Another casual option, sit on the patio to soak up scenic views of Lake Eola while you sip craft beer and indulge in bar favorites. Check it out during brunch (beer mimosas!) on the weekends, or happy hour Monday – Friday from 3-7pm.

431 E Central Blvd Ste B, Orlando
(407) 270-5541; worldofbeer.com/locations/downtown-orlando

Image credit: Stephanie Patterson

Even more waterfront options in our list of 15 Scenic Waterfront Restaurants Orlando.

COZY COURTYARDS

1921 Mount Dora
Sophisticated and art-spilled spot serving lunch and dinner, plus happy hour
142 East 4th Avenue, Mount Dora
(352) 385-1921

ABO Winter Park
Oyster and craft beer eatery tucked away in a secret courtyard in Winter Park just off Park Ave, happy hour Monday – Friday from 2-6pm
358 N Park Ave B, Winter Park
(407) 636-7021

Barnie’s Coffee & Tea
Winter Park coffee shop with courtyard dining tables, cafe fare, and brunch on the weekends
118 S Park Ave, Winter Park
(407) 629-0042

East End Market
Indoor market with multiple vendors, outdoor patio, and courtyard seating, check social media for details on occasional live music and local vendor pop-ups
3201 Corrine Drive, Orlando
(321) 236-3316

Goblin Market
Funky eatery in Mount Dora
330 Dora Drawdy Way, Mount Dora
(352) 735-0059

The Monroe
Social gathering place with a main dining room, bar, lounge/study, backyard patio, semi-private dining area, and daytime coffee bar
448 N Terry Ave., Orlando
(407) 734 2102

The Old Jailhouse

This unique restaurant in Historic Downtown Sanford specializes in delectable cuisine and top-notch cocktails, all served up in the former home of Sanford’s Old Jailhouse. You can literally dine behind bars as the owners have kept the building's charm intact. And, for an added dose of magic, the restaurant boasts a secluded outdoor dining space complete with string lights, perfect for your next fancy night out.

113 S Palmetto Ave, Sanford
(407) 548-6964; theoldjailhousesanford.com

Courtyard at The Old Jailhouse in Sanford - Outdoor Dining in Orlando guide
Image credit: The Old Jailhouse

Rocco’s Italian Grille
Italian eatery, romantic outdoor courtyard, live music select nights
400 Orlando Ave, Winter Park
(407) 644-7770

Yellow Dog Eats

This one is a bit of a hike (it's located in Windermere) but so worth it, especially for BBQ lovers. The spacious outdoor dining area is covered and dog-friendly, so bring along your friendly pup! We love it for the eclectic vibe, decadent desserts and sandwiches. Perfect for a casual lunch date.

1236 Hempel Avenue, Gotha
(407) 296-0609; yellowdogeats.com