10 Ideas for Date Night in Maitland

Tucked between Winter Park and Orlando and bordering Seminole County, Maitland is a bustling suburb of Orlando. It has become a popular residential destination thanks to the amount of corporate offices nearby and an impressive collection of parks, restaurants, and other recreational activities. Turns out, it's also got a ton to offer date nighters. Whether you’re a Maitland resident or exploring Central Florida at large, we’ve got some great ideas for your next date night in Maitland.

Things to Do in Maitland

1. Visit the Maitland Art Center

W Packwood Ave., Maitland | artandhistory.org
Hours: Museum: Tuesday – Sunday, 11am – 4pm, Last Wednesday of each month 5:30-8:00pm; Garden:
Tuesday – Sunday, 11am – 4pm
Cost: $6 per person

The Maitland Art Center is a true beauty that is often overlooked. Couples looking for a unique wedding venue often find themselves here. But you don't need such a special occasion to appreciate one of Maitland’s signature offerings.

concrete angels and intricate artwork at Outdoor Chapel at Maitland Art and History Museum
Outdoor Chapel at Maitland Art and History Museum – image by Dani Meyering

Maitland Art Center was founded as an art colony in 1937 by American artist and architect, André Smith (1880-1959). Inside, there are permanent collections as well as special exhibits. The Art Center is actually part of a collection of five Maitland art and history museums, so spend a full afternoon exploring them all. 

For added date night fun, check out the periodic Date Night at Maitland Art Center event which includes snacks and an art project for couples with beer and wine available for purchase.

Check the events calendar for upcoming dates.

2. Go ice skating at Orlando Ice Den

8701 Maitland Summit Blvd., Orlando | orlandoiceden.com
Hours: Afternoon Sessions: 12-4:45pm, Evening Sessions: 7-8:45pm
Cost: $17 during the week and $20 for Friday Night, Saturday, and Sunday, including tax and skate rental.

Ice skating isn't an obvious Central Florida activity, but it's fun. Orlando Ice Den hosts regular public ice skating sessions for all skill levels, along with learn to skate 4-week and 8-week sessions. You can rent ice skates directly at the rink. It is cold inside so dress warm with good socks, and make plans to snuggle up after to warm each other up. It does get busy on Friday and Saturday nights so be prepared for a crowded rink.

3. Sample sweets at Maitland Chocolate Factory

445 S Orlando Ave, Maitland | maitlandchocolate.com
Hours: Monday – Friday, 11am – 8pm and Saturday, 11 am – 5pm

This family-owned chocolate shop is located in the Shoppes of Maitland shopping center in between Lake Lily and the new Maitland City Centre. Enjoy a wide variety of chocolate treats including truffles, chocolate covered strawberries, chocolate bars, and more. Each weekday a different chocolate covered item is on special, like chocolate covered pretzels, potato chips, or fruit. For a romantic treat, ask about their personalized items.

While you're in this shopping plaza, check out Athena's Roasted Chicken for one of the best values in town! Or Kos Coffee and Wine.

4. Dine at a local eatery

Antonio’s is a landmark restaurant in Maitland bringing three unique concepts together. An Italian market and casual cafe are offered downstairs and a more refined dining experience is offered upstairs. The food is authentic and fresh. A fun date night idea is to dine in the downstairs cafe amid the imported Italian goods, then peruse the market.

Antonio's Maitland - Italian Market and Cafe with red tomatoes and other produce in the foreground and a deli case in the background
Antonio's Maitland – Italian Market and Cafe – Dani Meyering

The shelves are stocked with imported foods from Italy and an impressive selection of Italian wines add temptation. You can pick up some dessert to go for a sweet touch, or take them across the street to enjoy in Lake Lily Park.

Located across the street from aforementioned Antonio’s, Luke's Kitchen and Bar is owned by the same restaurateurs that brought us Prato on Park Avenue. This corner location sat in need of a development after the longtime Steak and Ale closed (shout out to those old enough to remember Steak and Ale).

Luke’s immediately gained a reputation for elevated American classic cuisine and craft cocktails. In the dining room and patio, you'll find locals taking out-of-towners here, professionals dining with clients, and of course couples enjoying a date night together.

Entrance to Luke's Kitchen and Bar in Maitland with brick wall and ivy
Luke's Kitchen and Bar in Maitland – image by Dani Meyering

And near Luke's and Antonio's you'll find Lazy Moon Pizza has just opened a new location. Lazy Moon in Maitland takes over for a former Einstein Bagel's location, which gives plenty of space for everyone to enjoy the MASSIVE slices of pizza offered at Lazy Moon. Don't overlook their salads either! You'll find a lovely outdoor patio area too for the days that the weather cooperates. And Lazy Moon is open pretty late for your late-night pizza cravings!

Lastly, Kappy’s likes to call themselves “Maitland’s Tastiest Landmark” and it certainly is. You can’t miss Kappy’s as you drive down 17-92. Come lunch time, the place is usually packed. When the weather is nice, sit outside and watch the comings and goings of Maitland. Or take it to go and head to one of the nearby parks. Kappy’s has been serving up subs since 1967 and you’ll feel those classic lunch counter vibes when you step up to order or sit down at the inside diner counter.

Some menu items are creations of customers, and are therefore named after them. You can get a traditional cheesesteak, or you can get it Kappy’s style which is chopped ground beef – a Maitland classic! Split one of their made from scratch milkshakes.

Kappy's subs in Maitland
Kappy's Subs – image by Dani Meyering

Just Opened: Fast-casual restaurant, The Great Greek Mediterranean Grill, is now open in Maitland in the new Trelago development near I-4 (701 Maitland Blvd., Suite 100), and more businesses will join the line up soon!

NEW: Maitland Social on Horatio Avenue, is home to local favorites Wave Asian Bistro & Sushi, Pizza Bruno, Foxtail Coffee Co., and Thriving Cocktails. The space features indoor and outdoor seating. A few of the vendors have opened as of June 2024, with more coming soon!

5. Meet birds of prey at the Audubon Center for Birds of Prey

1101 Audubon Way, Maitland | fl.audubon.org
Hours: Tuesday – Sunday from 10am-4pm
Cost: $10

This unique find is a special place to have in Central Florida. Here you'll experience old Florida by getting up close with incredible birds of prey like ospreys or maybe even a bald eagle. This rehabilitation and release facility offers monthly educational experiences and is open to the public year round.

Speaking of birds, Blackbird Comics and Coffee in Maitland is one of my absolute favorite coffee shops in the Orlando area. It's affordable, the serve their drinks in actual ceramic mugs (not paper cups), and the comics store and board games mean it attracts a friendly crowd.

6. Check out Lake Lily Park

701 Lake Lily Drive, Maitland | itsmymaitland.com/Facilities
Hours: 8am – dusk

At Lake Lily Park, you’ll be able to walk hand in hand with your honey along Florida's oldest brick road. This 5-acre park holds a lot of treasures including two historic homes, a great playground, and an annual Rotary Club Art Festival.

Lake Lily Park - Historical Marker and old brick road in Maitland Florida - image by Dani Meyering
Lake Lily Park in Maitland Florida – image by Dani Meyering

For a complete date, start with drinks and appetizers at Luke’s Kitchen. Walk across the street to Antonio’s for entrees and dessert. Then take an evening stroll around Lake Lily Park. All three of these spots are located facing each other.

7. Cruise along a bike trail

The City of Maitland has done a great job of incorporating bike trails into their city, with future plans to expand. For a DIY ride, follow this bike route to explore local parks, residential and commercial areas.

8. Meander through Jim Houser Azalea Garden

700 Old Horatio Ave, Maitland | itsmymaitland.com/Facilities
Hours: 8am – dusk

This roadside park doesn't look like much when driving by, but if you take the time to visit you’ll find a winding path through bundles of azalea bushes planted beneath shady oaks. The park is dedicated to former Maitland mayor Jim Houser. In the center of the park are two benches facing each other; one is dedicated to Mr. Houser, the other to his wife, making this a romantic little spot.

Located next to the park you'll find Cover Bridge Park, which is home to one of Florida’s few covered bridges open to vehicular traffic.

Jim Houser Azalea Garden Maitland
Image credit: @thisfloridalife

9. Enjoy dinner and jazz

164 Lake Ave, Maitland | jazztastings.com
Hours: Tuesday – Thursday: 5-11pm, Friday and Saturday: 6pm-1am

Dine on delicious meals like bronzed salmon, lamb chops, or calamari and sip on refreshing cocktails or an exquisite glass of wine, all while enjoying live jazz music.

Jazz Tastings is an impressive date night destination with an artful menu and live music nightly. They are closed Sundays and Mondays. Be sure to check their event listings ahead of time to make sure your date night hits a high note.

10. Catch a flick at Enzian Theater

1300 South Orlando Ave, Maitland | enzian.org
Hours: Theater: Vary; Eden Bar: Monday & Tuesday: 4-11pm, Wednesday, Thursday & Sunday: 11am-11pm, Friday & Saturday: 11am-1am
Cost: $12.50 per person

Offering a film experience like no other, Enzian Theater is a small, charming theater tucked beneath a canopy of old Southern oak trees with a bright marquee that shines in the evening sky. Here you can catch the latest buzzworthy independent film or a cult classic. Enzian’s lineup is always changing so be sure to check their calendar well in advance. Ordering tickets ahead of time is also recommended.

The sole auditorium offers seating at dining tables and in comfy retro chairs and couches. A full food and drink menu is available inside the theater as well as outside at Eden Bar. You'll want to get in line to enter the theater ahead of time as tables with the best views are reserved for theater members and the remaining seats are first come first served.

Start off your evening with a round of drinks and an appetizer at Eden Bar. Or, visit after your film to have a nightcap and discuss the movie’s finer points. This Florida-themed bar is completely outdoors and is always buzzing. 

Enzian Theater Maitland
Enzian Theater. Image credit: Stephanie Patterson

11. Shop and Dine at Maitland City Centre

190 Independence Lane, Maitland | http://maitlandcitycentre.com

This mixed use development combines upscale urban apartments with dining and shopping plus a gathering area for events. Highlights include Houndstooth Kitchen & Eatery and live entertainment and vendors on the first Friday of the month. Exciting developments include the addition of a Maitland outpost of Sanford Brewing Company, plus more dining options like sushi, several cafes, and more.

Pro-Tip: Turci Pasta – a popular eatery on Edgewater Drive that is known for fine dining, fresh, handmade pasta and quaint atmosphere – will open a second restaurant with an additional wine bar inside Maitland City Centre this year, along with a new Kelly’s Homemade Ice Cream.

12. Take a Trip to Permanent Vacation Tiki Bar 

106 Lake Avenue, Maitland, FL 32751 | permanentvacationfl.com
Hours: Tuesday & Wednesday: 5-11pm, Thursday – Saturday 5pm–1am
Reservation strongly recommended – book a reservation here

Take your date on a little vacation with a visit to Permanent Vacation inside the Copper Rocket. Like other traditional tiki bars, the menu indicates the potency of each drink. Symbols on the menu show the strength and alcohol level. Plus your bartender or server will gladly steer your ship in the right direction based on what you're looking for.

Any night out at a tiki bar requires fuel. Permanent Vacation tiki bar has a great food menu including flatbreads and appetizers.

Predator Cocktail and Low and Slow Mocktail at Permanent Vacation maitland florida
Predator Cocktail and Low and Slow Mocktail at Permanent Vacation – Dani Meyering

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Feature image credit: Maitland Art Center