Church Street District Date Night Itineraries

With its history dating back to the 1800s, the Church Street District is one of Downtown Orlando’s most iconic areas. The district centers around Orlando’s original train station, Church Street Station, formerly known as The Old Orlando Railroad Depot. Today, Church Street Station is home to several restaurants and is a popular event venue. The district is jam-packed with dining and drinking options in addition to fun activities for date nights. Come explore with us!

Church Street District Restaurants

The Bao Spot

54 West Church Street #140

Local family owned food concept, The Bao Spot opened the doors for the first time December 1, 2023 on Church Street in Downtown Orlando. The menu offers a number of appetizers, including Fried Brussel Sprouts and Honey Bacon, plus Fried Pork Dumplings. It's one of the best new restaurants in Orlando.

You'll find one of the nerdiest, most creative atmospheres here – and excellent Asian-inspired eats. We love downtown Orlando restaurants, including The Bao Spot.

Artisan’s Table

55 W Church Street, Suite 128

If you want high-quality food but aren’t in the mood for a super fancy environment, Artisan’s Table has a perfect balance. This is one of the pricier places to eat in Downtown Orlando, but still has an airy and light atmosphere. You don’t have to show up in a suit and tie, but you’re guaranteed to get fresh cuisine and upscale flavors.

Their entrees have a diverse range of culinary influences, from pan-seared salmon to quinoa bowls to fried shrimp tacos. You can even split some short rib poutine and wash it down with a signature cocktail. With the location of this restaurant, you will truly feel the heart and pulse of Downtown Orlando.

Southern gourmet food at The Artisan's Table
Southern gourmet food at The Artisan's Table | @artisanstable

Related Post: Downtown Orlando Restaurants We Love For Date Night

Hamburger Mary’s

110 West Church Street

You’ll never be bored or have the same dining experience twice at Hamburger Mary’s. From gourmet burgers like the Barbra-Q Bacon Cheeseburger (spicy-sweet BBQ sauce, bacon, cheddar and jack cheese, onion ring and Mary’s special sauce), Mary Mac & Cheese Balls (house made breaded mac & cheese balls fried and served with Mary-nara sauce) and their mind-blowing do-it-yourself Mary Tyler S’mores, Mary knows her food.

For the complete Mary’s experience, The “Dining with the Divas” show on Fridays or Saturday night’s Leigh Shannon’s Cabaret Dinner Show is a must. Reservations are required, so be sure to call ahead and put your names down! Friday and Saturday aren’t the only nights where you can have an extra good time here, as Tuesdays are Twisted Sisters Bingo, Wednesdays are Trivia Night, and there is a special Broadway Brunch Show on Sundays.

Image credit: Hamburger Mary's Orlando

Kres Chophouse

17 W Church Street

Kres Chophouse has a dark, classic steakhouse vibe and the food does not disappoint in the least. Kres won a Diner’s Choice award in 2017 for Best Restaurant in Downtown Orlando and was voted Best Steakhouse in Orlando by USA Today. Go all out by dressing up in your date night best, ordering a few cocktails, and indulging in a fancy meal.

Image credit: Kres Restaurant

Related Post: Orlando’s Most Romantic Restaurants

Irish Shannon’s

41 W. Church Street

Energetic haunt for Irish pub grub & beer, plus TV sports & live music on an indoor/outdoor stage. With the Irish theme, this place gives off a great game-day vibe.

Drinks are priced at half off before and during any Orlando City soccer match. There is also a match day drawing for a pair of FREE tickets to the game. Finally, end your night with live music on Saturdays beginning at 10pm.

Cucina Pizza & Bar

54 W Church St #151

Enjoy delicious dishes from modern Italian cuisine paired with great service, generous portions, and a warm atmosphere. Cucina draws inspiration from Southern Italy to create a menu, wine list, and atmosphere that blends Italian tradition with a modern twist.

This unique blend of old and new keeps guests coming back for an authentic dining experience that is truly one-of-a-kind.

Solita Tacos & Margaritas

222 S Orange Ave (Corner of Orange and Church)

At Solita, they like things to be casual and fun. Hang out by the patio fire pit with a hand-crafted margarita; or kick back at our friendly bar, grab some tacos, and explore our ever-changing collection of premium tequilas and mezcals. Enjoy a leisurely dinner in their spacious dining room, designed to evoke the industrial feel of an old tequila distillery. The happy hour deals here are great for gathering with friends!

Solita operates four other locations, all of which are in California. The company has established fresh roots in Florida but hasn’t strayed from its laidback Cali vibes. The restaurant’s menu features Baja-style fare prepared in the kitchen’s oak-fired grill and smoker

Cocktail toast
Solita's Hpuse Margarita + Whimsical Creamsicle. | Photo by Nancy DeVault

Birria1983 Mexican Bar & Grill

54 W Church Street, Suite 141

Birria1983 started as a food truck in 2020 and has now expanded into a permanent location in the old Graffiti Junktion space at the Church Street Market. Birria1983, is an L.A.-style Mexican restaurant, serving all things birria — from quesabirria to birria ramen to birria pizza. Not a fan of birria? Birria1983 also serves street corn, rice bowls, fajitas, quesadillas, burritos, Mexican pizzas, churros and more. 

Things to Do in the Church Street District

SAK Comedy Lab

SAK Comedy Lab has reopened in their new location on Church Street!

Nowhere else in Florida will you find a place like SAK Comedy Lab. Since 1991, their professional ensemble of improv actors has entertained audiences with our unique brand of live improvised comedy. They take your suggestions and make up characters, scenes, and songs on the spot. Their comedy is fun and edgy for adults, but also widely enjoyed by our younger fans.

SAK Comedy Lab

High-T Orlando

23 West Church Street

Finding High T can be like falling down the rabbit hole. There is a door on Church Street for High T, but the experience is all on the second floor of the building.

The themed environment inside High-T is incredible. You'll be amazed by the beautiful Alice in Wonderland environment. The cocktails are expensive, but they are hand-crafted and each one has its own special drinkware and presentation.

Please be aware the staff is very discerning when it comes to the dress code, and the policy is not always consistent from one person to the next. So to be on the safe side it is highly encouraged to dress up.

High-T is so special, in fact, it is one of our favorite ideas to celebrate a birthday in Orlando.

a bartender serves up creative Cocktails at High T Alice in Wonderland Bar Downtown Orlando
Birthday Adult Cocktails at High T Alice in Wonderland Bar Downtown Orlando – Dani Meyering

Fringe ArtSpace

54 W Church Street Suite 201

Fringe ArtSpace is a year-round venue and a hub for Orlando’s arts community where you can view traditional theatre, participate in learning experiences, and where you’ll find affordable rehearsal and performance space, designed for art makers and art lovers. Our events range from free (with a recommended Pay What You Can donation) to $25.

CMX Cinemas Plaza Café 12

55 S Orange Ave Level 2

CMX Plaza Cinemas Cafe features 100% reserved tiered stadium seats, all digital projection and a Dolby digital audio system. The concession stand offers classics such as popcorn, candy, and beverages along with our in-house kitchen & beer/wine bar, offering made-to-order snacks, sandwiches & hot off the grill items. We dig visit dine-in theaters like this one for a rainy day idea.

Self-Guided Walking Tour

A great way to connect with your love is to explore the rich history the Church Street District possesses. You two can go on a self-guided walking tour of the historic buildings along Church Street together.

Even more helpful is that the Downtown Orlando office itself offers walking tours throughout the year!

Downtown Orlando Parking and Tips

Let’s be honest–parking in the Downtown Orlando area can be a total pain. However, the City of Orlando does offer a Diner’s Rate in most of their parking garages.

If you park in one of the applicable garages between 6:00 P.M. and 10:00 P.M., it’s only a $6 flat fee. This is not valid in the GEICO garage or the 1st floor of the Jefferson St. garage.

Downtown Orlando parking garages and public parking lots include:

  • Amelia St. Garage: 355 Alexander Place, Orlando, FL, 32801
  • Bank of America Center Garage: 390 North Orange Avenue, Orlando, FL, 32801
  • Livingston Lot: 388 West Livingston Street, Orlando, FL, 32801
  • Wells Fargo Garage: 20 North Orange Avenue, Orlando, FL, 32802
  • Church Lot: 100 East Washington Street, Orlando, FL, 32812
  • Central Boulevard Garage: 53 West Central Boulevard, Orlando, FL 32801

Don’t forget to ask your restaurant to validate your parking ticket if needed.

More Orlando Main Street District date night ideas:

Feature image credit: Church Street District