6 Date Itineraries in Orlando’s Iconic Church Street District

Orlando Date Night Guide is a free guide to the best of Orlando! We're supported by our advertisers when they buy digital ads, listings, content, and through affiliate links, so some things you read might be paid for or if you buy something thru a link on our site we might get a commission.
Church Street District Date Night Itineraries

With its history dating back to the 1800s, the Church Street District is one of 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 a number of restaurants and is a popular event venue, and the district is jam-packed with dining and drinking options in addition to fun activities for date nights.

Tacos & Tour

Who says you have to celebrate Taco Tuesday only on Tuesday? One of our favorite past times is going on a taco binge and capping it off with some refreshing adult beverages. Our first date in the Church Street District has a stop at the newly opened Pepe’s Cantina. You may be familiar with the name (and tacos) as their original location is by Hannibal Square in Winter Park. They offer food and drink specials Monday through Thursday, and have a fun Sunday Brunch menu.

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. This map provided by Downtown Orlando Walking Tours serves as a guide providing information on the origins of the buildings you’ll observe before finishing your mini tour at the iconic Church Street Station.

For Sports Lovers

Home of the Orlando Magic and the Orlando Solar Bears, a date at Amway Center is a must for Orlandoans. To up the cool factor, take your date to the O3 Bar, where you’ll have a prime view of the game while spending time together in a cool lounge and enjoying some drinks. Need a place to fuel up before the game? Market on Magnolia opened a few months ago and houses eateries 081 Pizza, Gnarley Barley, Da Kine Poke and the Market on Magnolia Bar all under one roof. The bar features craft cocktails, wine, 75 craft beers, and 26 TVs with NCAA and NFL packages. Whatever game you want to watch, you can do it here! Happy Hour is Monday-Friday from 2-7pm, with 1/2 off select drafts, and $1 off wine and craft cocktails. Their hours are also pretty awesome – even staying open til 2am Wednesday-Saturday.

If you and your significant other are into soccer, what better place to tailgate or watch a game than Lion’s Pride? This soccer haven is located in Church Street Station and is only a short walk away from the Orlando City Stadium. Watch a game while filling up on eats ranging from Fish Tacos to Churrasco Steak. The bar features a nice selection of wine, beer and Game Day specialty cocktails. There is theater style seating available upstairs at the Captain’s Lounge, and you two can even purchase some new Orlando Pride and Orlando City Lions merch!

7 Reasons an Orlando Solar Bears Hockey Game is a Date Night Must

Trivia and Dining with Divas

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.

Hamburger Mary's

Sophisticated Dinner

Tapas for Two
Ceviche Tapas Orlando brings Spanish charm to downtown Orlando, located in historic Church Street Station. The architecture will lure you in, and the ambiance and food will keep you. Their menu consists of a variety of small plates optimal for sharing. After your meal, head upstairs for a drink overlooking our City Beautiful. This downtown gem will be sure to impress your date and provide a gorgeous and romantic ambiance for you two to enjoy.

Dinner & A Show

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. There are several private dining options available if you're looking to make the evening extra special. Grab an early dinner to kick off your weekend before heading to the nearby Mad Cow Theatre for a night with the arts. Most showtimes start at 8pm Thursday-Sunday, with performances ranging from classic theatre to musicals.

Image credit: Kres Restaurant

Dinner & A Movie

Sometimes a classic date idea is just what you need to relax and unwind with your date. Lucky for you, Chela Tequila and Tacos and Cobb Cinema are so close to each other that if you want to skip the movie previews and enjoy some more quality time you won’t have far to go. After your meal, check listings for a great movie you’ve been wanting to see and take a few steps over to Cobb Plaza Cinema Cafe. Here, you can relax for a couple of hours and hold hands in the theater.

Cobb Plaza Cinema Cafe

More Orlando Main Street District date night ideas:

Feature image credit: Church Street District 
Arlene Laboy, Managing Editor of Orlando Date Night Guide


Arlene Laboy is the Managing Editor of Orlando Date Night Guide as well as a professional food and brand photographer. A wife and a mother, Arlene shares her love for adventuring around Florida through her Instagram account, @arlenemlaboy. Find out more about Arlene here.

Orlando Date Night Guide is a free guide to the best of Orlando! We're supported by our advertisers when they buy digital ads, listings, content, and through affiliate links, so some things you read might be paid for or if you buy something thru a link on our site we might get a commission.


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