Orlando Date Night Ideas | Our favorite ideas for your first, second, and third date along with your anniversary, first getaway, and proposal

Plan the perfect first, second, and third date, anniversary celebration, first getaway, and proposal in Orlando

Dinner at the same old restaurant followed by a movie at the closest theater just isn’t going to cut it this time. Whether you’re planning your very first date or are ready to pull out all the stops for a memorable first getaway, there’s a date night in Orlando to suit every occasion.

We’ve rounded up some of our favorite Orlando date night ideas for your first, second, and third dates along with your first getaway, anniversary, and the perfect proposal. Never get stumped on an idea for date night again.

First Date

Budget: SAK Comedy Lab
Fill your first date night with laughter and put your first date jitters at ease by heading to a comedy show. SAK Comedy Lab in downtown Orlando has live improv shows nearly every night of the week. Weekend shows include Duel of Fools, a comedy competition with audience judges, and King of the Hill, which relies on audience voting to decide who stays in the show.

Budget: Food Trucks
Food trucks make a wonderful first date. There’s no pressure to agree on a restaurant and the casual atmosphere is way less intimidating than committing to a formal sit down meal. The fact that it’s budget-friendly is icing on the cake. We love Tasty Takeover (Tuesdays in the Milk District) and the Orlando Food Truck Bazaar (dates vary monthly). Read our post on planning a food truck date for more ideas.

Food Truck Date Night: Tasty Tuesdays in the Milk District
Tasty Takeover in the Milk District

Splurge: Chef’s Table
Reserving a chef’s table is an impressive alternative to an intimate table in a fancy restaurant. The pressure to fill every moment with conversation is off since you’ll have regular check-ins from the chef as each dinner course arrives. Plus, you’ll get serious bonus points for planning a date that’s fun, filling, and educational.

Here are a few of our favorite chef’s table experiences:

Victoria & Albert's

Get loads more first date ideas in this post –> 50 First Dates in Orlando

Second Date

Budget: Leu Gardens Movie Night
Nothing says romance quite like watching a movie under the stars. Leu Gardens hosts a wallet-friendly movie night on the first Friday of each month. You’re free to bring outside food, beer, and wine with you. The gardens open at 6pm, so arrive early for prime parking and a stroll around the manicured gardens before the movie starts. Admission is $6 per person, or free if you're a member. The Audubon Park district offers plenty of options for a pre-movie bite.

Budget: Lake Eola Swan Boats and Orlando Farmers Market
Every Sunday, Lake Eola Park is abuzz with the arrival of the weekly Orlando Farmers Market. Share a beverage served in a pineapple or coconut, grab a bite to eat from one of the many food vendors, and then take a stroll through the expansive market which is akin to a lively street festival. After fueling up on market eats, make your way to the opposite side of Lake Eola and rent your own romantic swan paddleboat. You can paddle around the lake and explore the fountain up close for $15 per half hour. This is a date day must-do, at least once!

Lake Eola Swan Boats

Splurge: Take a Class
A cooking or cocktail class sets the stage for a playful date within a structured environment. The demonstration style cooking classes at Publix Aprons Cooking School (Dr. Phillips and Winter Park) provide the best bang for your buck. You’ll have plenty of time for conversation in between course demonstrations, and the set up is like watching a live cooking show. 

If you’re both craft cocktail lovers, splurge on the cocktail class at The Woods (offering private classes) or The Courtesy (public classes on the 1st and 3rd Saturday of each month) to learn some mixologist tricks together. You’ll learn how to craft cocktails in a lively environment with an experienced bartender as your teacher. 

Third Date

Budget: Enzian + Eden Bar
Do dinner and a movie with a twist at Enzian Theater in Maitland. Rather than screening the latest blockbusters, Enzian shows a mix of classic and independent films. Tip: arrive early to snag one of the prime couch seats in the theater. The on-site bar and restaurant, Eden Bar, is a great spot for dinner and drinks before or after the flick. Tickets to most shows are $8/person, and menu items are $15 or less.

Splurge: Walking Food Tour
Join a walking food tour and trade date night for a food-filled day date. There are several tours to choose from in Orlando, and most tours last about 3 hours. If you’re still feeling some getting to know you jitters, take comfort in the relaxed environment food tours provide. Your tour guide will keep you entertained along with each restaurant stop, and you’ll be in the company of others keeping the mood fun and relaxed. Locally, we love Sanford Food Tours.

The Sanford Food Tour

Splurge: Dr. Phillips Show and Dinner
You can’t go wrong with a swanky date night at Dr. Phillips Center for the Performing Arts. This cultural hub in downtown Orlando is hosting a spectacular lineup for the 2017/18 season, including Broadway shows we can’t wait to see. Arrive well before the show and make dinner reservations at a downtown restaurant – we recommend Kres Chophouse for an upscale, indulgent meal.

First Getaway

Anna Maria Island
This 7-mile island is a blissful stretch of paradise with serious romantic getaway potential. Book a stay at the Silver Surf Gulf Beach Resort or The Harrington House Beachfront Bed & Breakfast. The Waterfront Restaurant, Sandbar Restaurant, and Mar Vista provide date night ambiance. Laze the day away on the white sand beaches, snuggle up to watch the picture perfect Gulf sunsets, and play in the clear turquoise waters.

Boca Grande
This Old Florida getaway on Gasparilla Island is full of beach town charm and date night gems. The Gasparilla Inn boasts beachfront amenities and is located within walking distance of many of the village hotspots. Renting a bike is a peaceful way to explore the island, and you’ll get a mini workout too! Dining options are endless, but if you’re looking for special date night digs head to The Temptation. Tip: avoid going in August when much of the island is closed down. High season runs from December-March.

St. Augustine
St. Augustine is a quintessential getaway for any Floridian. Escape to a charming bed and breakfast near the central historic district, and then go for a walk to explore the city’s rich history. Hop on one of the sightseeing trolleys for a thorough overview of St. Augustine’s past. For date night, head to Ice Plant for savory fare and inventive craft cocktails with a Prohibition Era vibe.

Amelia Island
Another quintessential Florida escape, Amelia Island is a wonderful place to begin making vacation memories. The sprawling Omni Amelia Island Plantation Resort is an ideal home base for the weekend complete with oceanfront rooms, an oceanfront pool, and a spa with a dedicated couples suite. Adventure calls on Segway tours and horseback rides along the beach. The resort is full of quality dining options, or head off property to Fernandina Beach for the evening.

Image credit: Omni Amelia Island Plantation Resort

First Anniversary

Budget: St. Johns Rivership Dinner Cruise
Anniversary celebrations don’t have to be over the top in order to be special. It’s the thought and planning that count! The weekend dinner dance cruise along the St. John’s River in Sanford invites you onto the scenic river for an evening of drinks, dinner, and dancing. Cozy up at your own dining table, share a special meal, and dance the night away. Each cruise features live entertainment, and your meal is included in the ticket cost. The dinner dance cruise is $60.75/person.

Splurge: Ritz-Carlton Spa Day
Treat yourselves to the ultimate day of luxury at the spa at The Ritz-Carlton Orlando, Grande Lakes. Start with a relaxing couples massage or the signature hammock massage, then stay and play in the spa’s stunning waterfront pool. After a rejuvenating day, dress to impress in your date night best for a romantic meal while relishing the sunset view.

Ritz Carlton Orlando Spa - Over the Top Experiences for a Special Occasion

Splurge: Private Dining Room for Two
Commemorate the milestone by booking a private room at a local restaurant! You'll feel like you’ve got the whole restaurant to yourselves. There are a handful of options for an intimate setting, but our personal favorite is The Tennessee Truffle in Sanford. For $400, you can rent out the entire restaurant for the evening and share a custom 8-10 course meal.


Like the first date, preparing to pop the question is an incredibly exciting time in your relationship. Lucky for you, there are tons of unique and memorable ways to propose in Orlando. Here are a few of our favorite engagement ideas:

  • Get engaged while gliding above Central Florida in a hot air balloon on a private flight for two
  • Book the Glass Slipper dinner proposal package at Cinderella’s Royal Table
  • Step inside the Japanese pagoda at Lake Eola Park
  • Take a private champagne flight on The Wheel at ICON Park

Here are a few more perfect places to get engaged in Orlando.