There's More To Orlando Than Theme Parks. Skip Planning With My 3-Day Itinerary

Orlando, Florida, is one of those cities that everyone sees as a gateway to Disney and Universal. Sure, these Florida tourist attractions are popular, but too often they overshadow the city itself. Orlando has a ton to offer on its own. Perhaps you want to check out the big-name concert in the Kia Center or watch the NBA's Orlando Magic. Maybe your love of sports makes you want to visit the Camping World Stadium to catch a championship game. Or maybe you just want an easy exploration, checking out local antiques and other shops.

I lived in Orlando for more than a year and spent 25 years as a Florida resident, making regular visits to this city full of creative people. Whether you're flying into Orlando International Airport (MCO) or even Tampa International Airport (TPA), considered the top airport for food and travel, I wanted to develop a guide to some of my favorite Orlando highlights. With this three-day itinerary, you will have a chance to explore the best parts of Orlando without needing to spend a ton of time and money on a week-long vacation. I designed it to be specific while also appealing to a majority of visitors, so you will see a variety of activities and modes of transportation.

Luckily, the "City Beautiful" is a buzz of activity all year. But the best times to visit are in the spring and fall. Temperatures are a little less oppressive in those seasons and, even better, the Atlantic hurricane season (which spans June 1 – November 30) isn't regularly churning out aggressive tropical weather. You can do this itinerary for about $100 per day per person, plus a hotel stay around $180 or so per night at the EO Inn. Please note that this is a full three-day itinerary, so you should plan to arrive the night before and leave the morning after, making your hotel stay 4 nights in total. Following this four-night, three-day itinerary will cost you around $1,000 in total, but if you choose a cheaper hotel, you can get the price down further. Whatever the reason for your visit, the city offers plenty to keep you busy, entertained, fed, and engaged. 

First things first. You need a home base during your stay, and the EO Inn is exactly where you want to start your day. Located within downtown's Lake Eola District, this boutique hotel is one of the most relaxing places I've ever stayed, and its hotel/spa vibe immediately helps you unwind. Rooms start at $180, and its location makes your first day of exploring super easy. Also, parking can be a nightmare in Orlando, so plan on using rideshare services like Uber and Lyft to get around when walking is just too far or Florida weather throws you a curve ball. Or if the weather is nice, renting a bike is also a great way to explore the city.

8 – 10 a.m.: For a truly "Orlando experience," start your day with a visit to the appropriately named I Love Orlando Café, a 10 minute walk from the hotel. From a light croissant and breakfast pastries to my favorite tower of waffles, there is no lack of options to accompany your morning coffee. Both locals and tourists dine there, so it's a great way to get a feel for the city's friendly and welcoming vibe.

10 a.m. – 12 p.m.: After breakfast, take your time and explore Lake Eola Park and the famous fountain at its center that has become the official emblem of Orlando. Florida is the Sunshine State after all, so take advantage of the weather by following along the beautiful, shaded pathway dotted with picnic tables along the downtown lakefront. The paved path helps make the park accessible to those with disabilities, and young ones in your group can enjoy the play areas. If weather permits, anyone can get out on Lake Eola on the rentable swan-shaped boats to catch amazing photo ops with great views of the city. I've spent a lot of time browsing some of the boutique shops nearby and recommend you do the same, since each one offers a collection of artisan-created pieces that are uniquely Orlando.

Bad weather Alternative: Book a massage at EO Inn, solve puzzles at The Great Escape Room, or experience thrills at Epic Axe Throwing.

12 – 1 p.m.: After a morning around Lake Eola, grab lunch at the Outpost Neighborhood Tavern. This fun and welcoming space serves big portions of southern comfort food while offering events and entertainment, whether that be a sports game on TV or a drag show. Personally, I've never not enjoyed a meal at this downtown staple.

1 – 5 p.m.: As the sun reaches higher into the Florida sky, it pours heat into the city. In summer, heavy downpours of rain can suddenly appear in the afternoons without much notice. Whether you are escaping heat or rain, afternoons are a good time to take the 15-minute walk (or 5-minute ride) to the nearby Orange County Regional History Center, housed in a former courthouse that was the site of the 1980 trial of serial killer Ted Bundy. The history center has multiple floors that take visitors back to the early days of Florida and includes exhibits on rocket launches, theme parks, trials, and more. To fully appreciate the exhibits, plan on exploring for around two or three hours. I spent at least an hour in the room dedicated to space travel. Afterward, take a 10-minute Uber ride to the Orlando Museum of Art (or OMA, as it's called by the locals) and spend a couple of hours exploring. I was blown away by its collection of huge art pieces. It sits near the lake and offers both permanent and rotating exhibits throughout the year.

5 – 7 p.m.: Stomachs are likely rumbling by now, which means it's time to find some local fare. Take a 10-minute Uber from OMA to Se7en Bites, created by chef Trina Gregory, who happens to be my former coworker! After gastric surgery in 2007, she was limited to only seven bites per meal. This led to her philosophy that if you only get seven bites, "it better be the best damn 7 bites ever!" Featured on several Food Network shows like "Diners, Drive-Ins, and Dives," this comfort food restaurant serves the best chicken pot pie you've ever put in your pie hole — to take a phrase from the restaurant's signage.

8 p.m. – 12 a.m.: For a lighthearted night out, take a walk or catch a short ride to Sak Comedy Lab in downtown's Church Street Station entertainment district. There, improvisational comedy thrives and every single show is different. I also found the live music accompaniment a nice and hilarious touch. This comedy club is also known for producing some big stars, from Wayne Brady to writers, actors, and producers who found careers on "Saturday Night Live" and beyond. There's a reason this hot spot was awarded best comedy by Orlando Weekly in 2023.

Approximate cost for the day per person: $100 – $125 (around $300 including hotel)

8 – 10 a.m.: After a night's rest at EO Inn, begin your second day in Orlando with a short, 15-minute Uber ride to nearby Winter Park, less than 5 miles away. While there are tons of beautiful towns in Florida worth visiting for a weekend getaway, this upscale shopping district is located just to the northeast of downtown Orlando where you will find cobblestone streets, uniquely Florida shops, restaurants, and gorgeous outdoor spaces. Think of it as Main Street U.S.A. outside of the Magic Kingdom. When you arrive, enjoy a fresh breakfast at Croissant Gourmet. This French restaurant offers coffee alongside freshly made pastries. Be sure to grab one of my favorites, the breakfast crepe, and thank me later! But the quiches and croissants are equally delicious. It's located in the heart of Winter Park, making it a great starting point to begin your adventure in the city's Park Avenue District.

10 a.m. – 12 p.m.: The best way to experience Winter Park's Park Avenue District is to simply wander through its beautiful streets. This collection of eclectic shops offers everything from kitchen essentials and high-end fashion to handcrafted gifts and historic sites. But don't miss The Ancient Olive. As the cook in my family, I always found this store's gourmet food an inspiration. With a focus on unique olive oils and vinegars, you can grab some interesting flavors to experiment with back home. Just 4 minutes away on foot is Arabella, a that is a favorite among my friends. It focuses on women's clothing with a vintage, boutique charm.

12 – 1 p.m.: Finding food is easy on Park Avenue, but locals love the experience within Tabla. This Indochinese fusion restaurant is often called "Secret Garden" by those in the know because it's nestled next to a beautiful tree and a koi pond. The restaurant specializes in Indian and Thai cuisine, and the affordable lunch specials are particularly good value (and tasty, of course). 

1 – 4 p.m.: If you've had your fill of boutique shopping, take a short walk to the Charles Hosmer Morse Museum of American Art, home to the world's most comprehensive collection of Tiffany glass. Tiffany glass is high-quality glass art developed by Louis Comfort Tiffany in the late 1800s. Permanent and temporary exhibits are on display there, and I personally spent a full afternoon wandering through the galleries. Give yourself at least two to three hours to explore it all. If you have time after, take the 6-minute walk to see Casa Feliz, an incredible historic home that we history nerds love! It's also a museum that dates back to the Great Depression. The attraction is open for tours, but only on Tuesdays, Wednesdays, and Thursdays, so plan accordingly if you want a glimpse inside.

5 – 7 p.m.: Wrap up your day in Winter Park with a very cool and offbeat dining experience at Bosphorous, a favorite among my friends. This restaurant offers Turkish cuisine, and it was recognized as a Tripadvisor Travelers' Choice in 2025, not to mention past accolades.

7 p.m. – 12 a.m.: Depending on when you visit, there are various events happening in the Park District of Winter Park. There are special outdoor events that happen in November and December, often focused on the holidays. And if you are visiting in the warmer months, check the schedule at the Winter Park Playhouse. This theater company offers musicals, plays, cabarets, festivals, and a whole lot more throughout the year. Each time I've seen a show there I'm incredibly impressed by how well the productions are put together.

Approximate cost for the day per person: $100, depending on what grabs your attention at these eclectic shops (around $280 including hotel)

8 – 10 a.m.: It's your third and final day in Orlando! Time to explore the more offbeat, vintage, and retro side of the city. Less than 2 miles away from your home base at EO Inn is Ivanhoe Village. Ridesharing is the fastest way to make the short trek to this "unapologetic neighborhood," but if it's a beautiful day, consider renting a bike or taking the 30-minute walk.

A morning stop at the White Wolf Café is great for a hearty breakfast that includes breakfast sandwiches, jumbo cinnamon buns, and more. French toast is a popular choice, but I personally love the biscuits and gravy. You can get your food to-go, so feel free to find a warm spot outside in the morning sun to eat and soak up the unique atmosphere of Ivanhoe Village.

10 a.m. – 12 p.m.: Bring your coffee with you on a stroll through Ivanhoe Village and take in the local street art on the retail district's buildings. Be sure to stop in Diversion Orlando for incredible, rare, and sometimes hilarious vintage finds. If you're crafty or have younger travelers with you, consider a visit to the Craft Table, which offers workshops, antique supplies, and people actually working on their next creative project.

12 – 1 p.m.: Hungry? Gnarly Barley is a prime choice for a delicious no-fuss lunch along the lakefront. This fun restaurant is known for its "sammis" (delicious sandwiches) and beer, but it also serves up tacos and salads.

1 – 5 p.m.: For true treasure hunters and the curious, A T Furniture & Antiques is a must-see stop in Ivanhoe Village. My first time through the decorative storefront shocked me when it gave way to a massive two-story warehouse of furniture, knick-knacks, antiques, and surprises. It's an intriguing way to escape the Florida heat (or rain), but give yourself at least 2 hours to explore every nook and cranny. For more upscale and personalized accessories and home goods, visit the guys at Maffrey's just a 6-minute walk away. Both of these businesses offer a wide selection of "good goods," which are products made with the intent to improve life and the planet.

5 – 7 p.m.: If you've wrapped up your shopping and the sun is starting to fade, make your way back to Ivanhoe Lake across the street from Maffrey's. From there, you can catch spectacular views and photos of the sunset reflecting off the water.

One of my favorite places to grab dinner in this part of town is at the City Food Hall, which is Ivanhoe Village's food hub. Multiple vendors offer varieties of food to tempt every palate in your group. But save room for dessert because Better Than Sex, A Dessert Restaurant is just an 8-minute walk and the right spot to top off your last meal of the day. Plan ahead though, since reservations are encouraged to make for a very special (and romantic!) dessert dining experience.

7 p.m. – 12 a.m.: The best way to wind down after a day of exploring (and to cap off a three-day adventure in Orlando) is a stop at the Imperial Wine Bar, also in Ivanhoe Village. This neighborhood bar offers a welcoming atmosphere and specializes in boutique wines while playing host to live music throughout the week. And don't stress about your flight out of Orlando Airport the next day — the airport is less than 30 minutes away from EO Inn.

Approximate cost for the day per person: $80 – $100, not accounting for any treasures you might find along the way (around $280 including hotel)