Those of us with kids know this dilemma: when you book a sitter for three hours, a one-hour dinner doesn't cut it but there's no way to fit in dinner plus a movie. So, Marc and I have figured out a way to make dining out not only longer but also more engaging. We do progressive dinners.

The concept for this moveable feast is simple: we pick an area of Orlando where there is a solid cluster of good restaurants in walking distance from each other and then we eat one dish at each of three or four places.

We usually sit at the bar rather than getting a table with a dedicated server (who probably would hate this idea). We might get an entree to share or two small appetizers. And we always finish somewhere that offers an ooey gooey dessert. The entire experience takes about two hours or more, depending on how long we linger at each place.

Progressive dinners have given us the chance to scope out restaurants we might like to enjoy for a full, three-course meal. We love sitting at the bar and chatting with the bartender, who, unlike servers, has time to talk and give us the low-down about the chef and the food. And we love being on the move between each course. It gives the night a cosmopolitan feel.

Thanks to our blossoming Main Street districts in and around Orlando, we have a ton of restaurant clusters that are ideal for progressive dinner date nights. Here are a few of our favorites:

Hannibal Square
This quieter cousin to Park Avenue stretches along bricked New England Avenue in Winter Park and houses several great restaurants, including Mynt (excellent Indian cuisine), Armando's, Chez Vincent and Hannibal's on the Square, which features a delicious chocolate souffle for dessert.

Armando's in Hannibal Square

Thornton Park
This tiny corner of downtown Orlando near the south east side of Lake Eola Park has really hit its stride lately thanks to the addition of two new restaurants and the consistency of one longstanding sushi spot. Favorites in this area include Soco and Eola Wine Company.Thornton Park is also home to The Pop Parlour, an artisan ice pop shop where you can get several eclectic ice pops, including some made with beer or liquor. Keep in mind that with Lake Eola right there, you can easily add a swan boat paddle to your date night.

Grande Lakes Resort
Home to The Ritz-Carlton and JW Marriott Orlando, Grande Lakes is a sprawling 500-acre+ property in south Orlando. With lots of amenities like spas, golf and lazy rivers, it's an ideal place to spend a weekend but it's also a fantastic spot for a progressive dinner. Start by self-parking at the JW Marriott and you'll have the $20 self-park fee waived as soon as you dine at any of the JW's restaurants. Then you can start munching and sipping your way through four outstanding restaurants: Primo, Whisper Creek Farms: The Kitchen and Highball & Harvest and Norman's at The Ritz-Carlton. We recently experienced this progressive dinner for our anniversary and while it was definitely a splurge, we absolutely loved every minute of it.

H&H bar 2 660
Highball & Harvest

Mills 50
Lovers of international eats will appreciate the variety of restaurants that call the Mills 50 District home. Not only will you find lots of affordable options here but you'll also find several fun bars to check out, too. Tako CheenaHawkers Asian Street Fare, and Pig Floyd's are Mills 50 favorites and translate into a 7-minute walk if you dine in this order. Strand is great, too. For bars, try Lil Indie's, and Quantum Leap Winery; they're all solid bets.

tako cheena
Tako Cheena features a variety of asian inspired “takos” like this Panko Crusted Cod Tako

Church Street
Ceviche and Kres Chophouse are two terrific reasons to do a progressive dinner in the Church Street District. Be sure to plan dessert at Kres and order the amazing White Chocolate Bread Pudding, which is drizzled with a ridiculous Jack Daniels sauce. If the night is still young, head over to the Grand Bohemian to hear some live jazz in the Bosendorfer Lounge on Friday and Saturday nights. By the way, you can valet at Kres Chophouse for $15 – $20, but if you go inside and have dinner or even just a drink, you’ll get a discount and pay only $8-$10 to valet.

Park Avenue
An obvious option for sure, but not all of Park Avenue's restaurants are ideal for a progressive dinner. Our picks are Boca, Prato, The Wine Room, which serves charcuterie and cheese platters, small plates and flatbreads. All of these are easy to get in and out of and have a fun vibe. For dessert, I'd recommend going to The Alfond Inn where you can have dessert and a nightcap either inside by the fire or outside by the fire pits.

Prato (small)
Photo credit: Prato

SunRail: Park Avenue to Church Street
You can really rack up some mileage by adding SunRail to your progressive dinner date night. You'll want to start in Winter Park since it's much easier to park your car near the Winter Park SunRail station than near the Church Street station. SunRail runs Monday to Friday only and the last northbound train from Church Street to Park Avenue leaves at 10:30pm. You can see the full schedule here.

College Park
This area is a little more spread out along Edgewater so you might want to jump in your car to hit all the hot spots. Our favorites incude K Restaurant, RusTeak, Paxia and Adriatico Trattoria Italiana. If you're timing is right and K is hosting its Friday Night Flights event, definitely start there. You'll get pours of 5 – 6 wines plus appetizers and live music for $20 per person. Follow K Restaurant's Facebook page to stay updated.

K Restaurant & Wine Bar
K Restaurant & Wine Bar

Audubon Park
Kick off this feast at East End Market with a cheese and wine tasting at La Femme de Fromage. You can call ahead to book it (407-571-9947). From there you have your choice of a few Audubon Park District restaurants, including Sushi Lola's, Txokos (soon to be re-imagined by a new owner) and Bikes, Beans & Bordeaux. Plan for dessert at P is for Pie, which is open until 8pm on Fridays and Saturdays, or head to Kelly's Homemade Ice Cream for an ice cream flight. Are you a beer lover? Don't miss Redlight Redlight where you'll find one of the biggest beer selections in Orlando.

A few other areas to try…

  • Baldwin Park
  • Ivanhoe Village
  • Downtown Sanford
  • Celebration Town Center
  • Disney Springs
  • Universal's CityWalk
  • Disney's BoardWalk

Have you had a memorable progressive dinner? Tell us about it in the comments section!