Orlando Neighborhoods After Five: The City Beautiful

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For many, Orlando is synonymous with theme parks, tourism and conventions. But what a lot of people don’t know is Orlando is bustling with small and interesting neighborhoods that are great for exploring after 5 p.m. Here are our suggestions for feeling like an Orlando local while visiting The City Beautiful for work.

Mills 50

This eclectic neighborhood provides the ultimate Orlando local experience. From the local businesses, unique mix of cultures and quality eateries, there is surely something for everyone in this area.

Go for a Run

Sometimes when traveling it can be hard to maintain your exercise routine. Thankfully, the Sunshine State provides endless opportunities to get outside. In the Mills 50 area, local running store Track Shack hosts a weekly run on Wednesday evenings down the Orlando Urban Trail. There are two routes available – roughly two and three miles respectively – and the event is free. Be sure to stick around after your run for refreshments and giveaways.

Quantum Leap Winery

If you are looking to relax and sample some interesting wines, check out Quantum Leap Winery. For just $5(!!) you can sample either four white wine or red wine samples. The samples are generous and the staff are very friendly and knowledgeable about their wines. There is seating inside as well as on their outdoor patio. They also periodically hosts events, so check their Facebook page too!

Sample Unique Eats

There are plenty of restaurants in Mills 50 that can satisfy any palate. A local pizza staple, Lazy Moon, serves up vegetarian or vegan pizzas. Tako Cheena serves up Latin-Asian inspired tacos and burritos that are a huge hit with locals. Looking for Cuban food? Check out Black Bean Deli. They have weekly specials and a great menu that makes you feel like you are in Miami or Havana.

Thornton Park

Situated just a block or two from Lake Eola in downtown Orlando, the Thornton Park district has an inviting, neighborhood-type feel and is bustling with young professionals. Check out the neighborhood’s website to see events happening when you are in town.

Graffiti Junktion

While this is a chain restaurant, Graffti Junktion truly feels like walking into your neighborhood bar. The burgers are amazing and there are plenty of drink specials throughout the week. It’s a great spot to watch a game or even play along during trivia nights.

Thornton 2nd Thursday Wine & Art Walk

Held every month on the second Thursday, this wine and art walk is very popular with locals. Check out local art, enjoy some tricks and take in the community that makes up Thornton Park. The starting location changes each month, but you can check the Thornton Park District’s Facebook page for more details. One important thing to note – the cost is $15 and it is cash only. You’ll receive a map of all of the participating business along with a wristband.

Walk Around Lake Eola

Orlando’s Lake Eola Park is in the heart of Downtown Orlando. If you are looking to get a run in after work, the entire loop is just shy of a mile. The shaded sidewalks also make it a great place to get out for a walk – especially during the summer when the days are long. Lake Eola is known for its swans – just be sure not to feed them, they can get a bit feisty. If you want a different perspective, rent a Swan Boat and cruise the lake! The rental costs about $15 for half an hour and depending on the day the tours run until 10 p.m.


If you are looking for a place with the quintessential American small town feel, then a visit to Celebration should definitely be on your list. The brick-lined streets of downtown allow for easy window shopping and there are plenty of food options to fill you up.

Columbia Restaurant

Columbia Restaurant has been owned and operated by five generations over 110 years. The original location, opened in 1905, is the oldest restaurant in Florida and is still in operation today in Tampa’s Ybor City serving Cuban and Spanish cuisine. Celebration’s Columbia Restaurant opened in 1997.

A few of the highlights to order include The Original 1905 Salad, the original Cuban sandwich or the paella. A trip to Columbia Restaurant would not be complete without a mojito or sangria!

Wonderland Cookie Dough Co.

Once you got your fill at Columbia Restaurant, take a short walk over to Wonderland Cookie Dough Co. Their cookie dough is made fresh daily with no added preservatives, using top-notch ingredients and is egg free, so it’s 100% safe to eat. An added bonus is the store is open until 10 p.m. every day.

Bohemian Hotel Celebration

This beautiful boutique hotel is an elegant addition to Celebration’s downtown. After taking a nice stroll around the lake, head inside to grab a drink at the Lakeside Bar + Grill Lounge. You can eat al fresco or head inside to listen to live music. There are daily features as well from Martini Monday where select martinis are $10 to Burger Thursday where featured burgers are $14.

Dr. Phillips

The Dr. Phillips neighborhood is chock full of restaurants. If you are looking for a great happy hour or a nice meal, then Sand Lake Road is going to be your destination.

The Whiskey

If you love a good Old Fashioned, then you need to try one from The Whiskey. When it comes to food, you have to try one of their unique burgers. From the Impossible burger to elk and bison and everything in between, there is sure to be a burger for your taste buds. Our favorites? The Southerner is topped with a fried green tomato, bourbon bacon and pimento cheese. The Smoked Brisket Grilled Cheese is not to miss either. The brisket is smoked for 20 hours and topped with Gruyere cheese and Kansas-style BBQ sauce on garlic toast.

The Pharmacy

Despite the name, The Pharmacy is a speakeasy that harkens back to the Prohibition Era. The restaurant is a little bit hidden but look for a green button next to a pair of elevator doors. Their happy hour runs from 5-6:30 p.m. where the entire dinner menu and select craft cocktails are half priced.

World of Beer

If you are looking to watch a game or play some trivia, then World of Beer is a great destination. Besides the fun events throughout the week, World of Beer boasts a great menu and an extensive beer list that covers local, domestic and international brews.

International Drive

International Drive, also known as I-Drive, is packed with fun activities. Think of it as Orlando’s version of the Las Vegas strip. Since there is so much to do, we’ve broken down this area by categories to help point out even more.

Orlando Activities

Do you want to hit the links after work but there’s a Florida shower? Not to worry! Head over to Top Golf, just off of I-Drive, where you can hit some golf balls, enjoy a drink and have a meal.

Looking for something with a little more speed? Try go-karts. There are several options up and down I-Drive, but we recommend Andretti Indoor Karting & Games and NASCAR I-Drive because both of these locations offer indoor go-karting which is nice if it’s hot outside or raining.

If you want to get an awesome view of Orlando, head over to ICON Orlando to take a ride on the tallest observation wheel on the East Coast of the United States. At 400 feet tall, you can get breathtaking views that will make for awesome photos. ICON Orlando is also home to SEA LIFE Aquarium, Madame Tussauds Orlando, lots of restaurants and shopping. It’s a great one-stop shop!

Orlando Restaurants

While there are a lot of chain restaurants on I-Drive, there are some really great options when it comes to dining and it really depends on what kind of mood you are in. If you are looking for dinner and a show (and don’t mind a loud environment), then head over to Mango’s Tropical Cafe for a Las Vegas-style show or Tapa Toro to watch a flamenco dancer while eating delicious paella and tapas.

If you are looking for something a bit more unusual, head over to Cafe Tu Tu Tango where food meets art. For a more low-key night, head to Shake Shack or listen to live music at Tin Roof.

Guest Writer

Jessica Bohlman | The Orlando Duo | Instagram | Pinterest | Twitter | Facebook

Besides the theme parks, Orlando has many great neighborhoods to explore. Miles 50 has unique cultures and eateries. Thornton Park is great for young professionals to experience art. Celebration has many great food options to fill you up. Dr. Phillips gives you a variety of themed restaurants. International Drive has go-karting and restaurants as well. There\'s plenty of activities to offer in Orlando Neighborhoods at night.

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