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36 Hours in Orlando (Not at the theme parks)

July 3, 2018 1 Comment

This is a guest post by Katie Tschopp of the lifestyle blog, The Best Thing. She is a California transplant, hailing from Orlando but also having lived in NYC. Her blog highlights the fact that she is truly the domestic goddess I could onyl hope to be one day. The blog is equal parts healthy cooking & baking, travel to unforgettable destinations, and spot on recommendations for books & culture, with a little hint of mindfulness practices mixed in.  Once we met and I found out she was from Orlando I knew that I had to ask her do a guest post since I will be traveling there in October for a conference. Nothing beats a local’s recommendations! Be sure to check out her blog (read my guest post on true crime podcasts) and help me in welcoming her to SoCal. 

Orlando has a reputation as the land of Disney World, alligators and humid as heck weather. But, the central Florida city is gaining popularity as a destination for travelers who aren’t interested in princesses or roller coasters.

Ask any local (I am one, I lived in Orlando for the first 18 years of my life and return regularly to visit my parents), and you will hear how Orlando has so much more to offer than the tourism industry would have you believe. From downtown Orlando through picturesque Winter Park, here is a suggested itinerary for anyone visiting Orlando and not wanting to face the crowds at Disney, Universal, SeaWorld etc.



Start your day with a trip to the Winter Park Farmer’s Market. This outdoor local food + arts market is nestled in the heart of Winter Park, which is the perfect neighborhood to spend your first day exploring. Grab a bagel from Davis Bakery & Co inside the main building to eat while you explore the fresh fruit and vegetable stands along with the gourmet food options. Be sure to grab a bag of the famous kettle corn before you leave. You won’t be able to miss it, there’s always a line!

Casa Feliz


Shop along Park Avenue, a pretty tree-lined street just across the train tracks from the Farmer’s Market. Sip on a latte from Mon Petit Cheri Café while you window shop and step into any stores that catch your eye. Sultre Boutique has eye-catching pieces for special occasions (it’s on the pricey side), The Impeccable Pig always has fun clothing at great prices and Writer’s Block is a great indie bookstore. There are also about a dozen cute little boutiques on off-shoot streets that you can explore to your heart’s content! If you may it to the far end of Park Avenue, you can check out Casa Feliz, a beautiful historic home that is open to the public several days of the week. If it’s not open- the outside is just as stunning to look at.


A short walk from Park Avenue is Hannibal Square where you will find tons of cute restaurants with outdoor seating. Stop into Rifle Paper Co on the way to grab a few cards- this is the flagship store of the popular brand. Sit outside at Armando’s and order one of their delicious pizzas while you sit back and people watch.


Kick back and relax on a pontoon boat as part of the Winter Park Scenic Boat Tour ($14, cash only). This hour-long tour takes you by the mansions on three lakes in the area that are all connected by canals and it serves as part nature tour as you cruise past cypress trees, palms and perhaps a crane or even an alligator. After the tour, it’s time for an afternoon pick me up! Head to Foxtail Coffee, which may be the prettiest coffee shop in all of Orlando- if not all of Florida.


Time for happy hour! Head to Ravenous Pig for locally brewed $3 beers and a yummy selection of appetizers. This stylish gastro pub also boasts a great cocktail list.


When you’re ready for dinner, head back to Park Avenue to eat at Prato where you’ll find a seasonal, modern spin on classic Italian.  The meatballs are popular here and all their pasta dishes are incredible.


If you’re not ready to turn in yet- Red Light Red Light is great for after-dinner drinks. Or you could catch a comedy show at SAK Comedy Lab. And no matter where you are staying for the night (though I recommend staying at The Alfond Inn), you should at least stop by this boutique hotel to enjoy the artwork lining the first floor walls and sit in the garden out back to enjoy a post-meal drink.



Kick-off your Sunday at East End Market– a neighborhood market filled with local food options. People rave about the pastries and croissants from Olde Hearth Bread Co, or if you’re in the mood for something lighter, order a fresh juice or smoothie from SkyeBird.


Head less than a mile east to Leu Gardens, an expansive botanical garden that’s open daily. Spend an hour or so walking about the gorgeous gardens- which are a popular local wedding venue too.


Next, hit up fun local shops at Lake Ivanhoe Row. Grab a funky, vintage piece of jewelry from Dora Mae or a little gift or cute card from Paper Goat Post, all while strolling along, enjoying the lake views. If you’re hungry, grab lunch before you go at the neighborhood bistro, White Wolf Cafe and Bar.


Head a little south to downtown Orlando and rent bikes through the city’s bike share company Juice. You can bike around downtown, cruise through the historic Thornton Park neighborhood with charming brick streets and take a break to enjoy the breeze by Lake Eola. Make sure to swing by Church Street Station- a historic train station in the heart of downtown. There are tons of bars to grab a drink for happy hour if you’re in the mood.

Hunger Street Tacos


Time for tacos! Orlando has some great Mexican restaurants that have popped up in recent years. Hunger Street Tacos is a favorite for authentic, creative tacos and Reyes Mezcaleria is super cute and has a great tequila/mexcal list!


End your night with drinks at The Matador– a popular spot that has a dive bar feel with plenty of seating and a fun cocktail list.

I hope this guide helps anyone traveling to Orlando and not wanting to visit the theme parks- or I think doing a day at the parks and a day in Winter Park/Orlando would be perfect! Shiloh and I would love to know if you have any other must-dos in Orlando or the nearby areas- let us know in the comments!

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1 Comment

  • Katie Tschopp July 3, 2018 at 11:30 am

    I had so much fun doing this swap with you! Loved getting your recs on podcasts! Can’t wait to listen to them all:)

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    Dr. Shiloh

    Travel has always been a part of my life and I have found the key to making it a part of my professional experience. Expect recaps of great destinations, advice on incorporating travel into your work & tips on making travel with a family easier. Cheerio!


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