Orlando, Florida, is known for its theme parks and attractions, but the City Beautiful is so much more than its roller coasters and characters. In fact, the city is seeing a sort of renaissance, with more and more travelers exploring outside of its attraction corridor. While it has always been a magnet for those looking for outdoor adventures since it’s on the headwaters of the Florida Everglades, increasingly it has become a hotspot for art aficionados as well as foodies, thanks to a slew of Michelin stars and honors over the past two years.
If you’re thinking about a weekend getaway to Orlando, you should also know that it’s easier than ever to get to the city with the new Brightline train that goes from Orlando down the state to Miami, as well as a new airport terminal that recently opened at its international airport.
Keep reading for the perfect itinerary for a 48-hour trip to Orlando.
Where to stay: The Alfond Inn
Located in the heart of the historic Winter Park neighborhood is The Alfond Inn. This boutique hotel recently completed a $36 million renovation and expansion that added 71 new guest rooms along with a complete overhaul of its existing 112 rooms. Along with spacious accommodations, the resort has two pools and a spa to enjoy. Plus, it’s a short walk to some of the best entertainment and restaurants in Orlando.
Day 1
For the sake of our 48 hours, we’re going to assume that you arrived late the night before your adventure so you could wake up refreshed and ready to explore the city for the next two days.
9 a.m.: Breakfast at Barnie’s Coffee & Tea Co.
Just a short walk away from the hotel is Barnie’s Coffee & Tea Co. The specialty coffee shop is known for its signature blend, Santa’s White Christmas, a bag or two of which you can even bring home. While the coffee is superb, don’t miss out on their scrumptious breakfast, with stand-out menu items including French toast, huevos rancheros, and the breakfast burrito. For something lighter, consider the baked goods and avocado toast.
10 a.m.: Winter Park Scenic Boat Tour
After breakfast, take a five-minute walk to the boat dock for the Winter Park Scenic Boat Tour, which has been operating since 1938. This leisurely tour is run every hour, on the hour, from 10:00 a.m. until 4:00 p.m. The fully narrated, 45-minute tour takes passengers through a series of canals and lakes to show off the beautiful homes of Winter Park — including one that belonged to Mr. Rogers — along with local wildlife and the chance to enjoy the bright Florida sunshine.
Pro tip: The boat tours are loaded up on a first-come, first-served basis, so be sure to arrive about 15 minutes before the tour starts to ensure you get a spot.
11 a.m.: Visit The Charles Hosmer Morse Museum of American Art and stroll down Park Avenue
Just up the street from the boat launch for the Winter Park Scenic Boat Tour is The Charles Hosmer Morse Museum of American Art. The museum is renowned for its collection of works by Louis Comfort Tiffany, with lamps, pottery, windows, and his world-famous chapel interior for the 1893 World’s Columbian Exposition in Chicago. The chapel alone is worth a visit to the museum thanks to an impressive amount of detail that takes several minutes to take in. To get through the majority of the exhibits in the museum takes about an hour to an hour and a half.
After you’ve gotten your fill of the museum, head over to Park Avenue, which is the main thoroughfare in Winter Park. The street is lined with cute cafes, restaurants, and shops. Explore the boutiques and storefronts as you wait for your table at lunch to be ready.
1 p.m.: Lunch at Prato
One of the most popular places to eat in Winter Park is Prato, which serves Italian cuisine made with seasonal ingredients. Lunch is served Wednesday through Sunday from 11:30 a.m. until 3 p.m. and reservations are recommended.
The restaurant has an industrial-chic vibe with exposed brick, and the menu is filled with tasty dishes like the chopped chicken salad, brisket panini, and sweet potato ravioli with brown butter. For a splurge, try the black diamond pizza, which has a base of truffled cheese and is topped with freshly shaved black truffle (their wood-fired pizza ovens are imported from Italy).
2:30 p.m.: Visit the Orlando Museum of Art
After lunch, you likely won’t want to do anything too taxing, so make your way to the Orlando Museum of Art. The museum rotates exhibitions throughout the year, and often features special activities such as art classes, private tours, and yoga in the art galleries. Be sure to check the event calendar to see what’s planned for the day you’re visiting. It usually takes about one to two hours to see everything in the museum.
4:30 p.m.: Take a dip at the Orlando Beer Spa
One of the most unique activities in Orlando is the Orlando Beer Spa, and it’s exactly what it sounds like. Upon entering the beer spa, you’ll be shown your locker, which has a robe to change into. The spa has multiple rooms, including one for couples and a larger room for friends if you’re looking to share the experience with others. Upon entering the room, you’ll see a large soaking tub that’s full of water and beer ingredients like hops and yeast (you’re not soaking in actual alcohol), plus an infrared sauna, a hay lounge, and a private bathroom. Everyone also gets unlimited beer on tap while there. The experience here is fun and relaxing, and your skin ends up being super soft. Most sessions last about an hour.
6 p.m.: Take a break
Take about an hour's break back at your hotel to get ready for dinner.
8 p.m.: Dinner at Capa
Capa at the Four Seasons Resort Orlando at Walt Disney World is the closest you’re going to get to a theme park on this trip as the one Michelin-starred restaurant overlooks Magic Kingdom. The signature dish here includes the sharable 32-ounce porterhouse steak, which you can pair with sides like fried eggplant or potatoes with brown butter. Additionally, the restaurant is known for its cocktails, the highlight of which is the Capa Gin Tonic, a light and refreshing drink that’s almost too pretty to consume.
During the nightly fireworks at Magic Kingdom, the restaurant pauses service so guests can go out to the balcony to see the show before returning to their next course.
Fun fact: Capa’s chef, Malyna Si is the only female chef to lead a Michelin-starred restaurant in Florida.
Day Two
8 a.m.: Head to Kelly Park and Rock Springs
Get up bright and early so that so you can make it into Kelly Park and Rock Springs in time. The park opens at 8 am, but in the warmer summer months you should be in line to enter no later than 6 a.m. because the park often reaches capacity within the first hour of opening. Kelly Park is popular because of its free-flowing natural springs that are a cool 68 degrees throughout the year. Besides soaking in the springs the best thing to do here is go tubing down the river, with tube rentals available from vendors outside of the park. The tube run is about 25 minutes long, but you can go over and over again or just enjoy swimming around the park’s bright blue waters.
12 p.m.: Lunch at Pig Floyd’s Urban BBQ
After a morning of swimming and tubing you’ve likely worked up an appetite, so head straight for Pig Floyd's Urban BBQ in the Mills 50 neighborhood. The fast-casual restaurant dishes out everything from classic BBQ plates with meats and sides to more unique BBQ bento boxes and towering sandwiches. But real foodies will want to try a few of the tacos, each of which is sold individually. The pork belly taco is a taste of BBQ meets Asian fusion, with a shell loaded with pork belly, citrus, peanut slaw, teriyaki sauce, and sesame seeds. For something a little more spicy, try the butter chicken taco, where jasmine rice, chicken, tikka masala sauce, and a Greek yogurt drizzle are topped with jalapeños and cilantro for a trip straight from Orlando to foodie heaven.
1:30 p.m.: Take a break
Because of the early morning wake-up call and the likely food coma that follows lunch at Pig Floyd’s, you’re probably ready for a break back at the hotel. Take a shower and crawl back into bed for an afternoon nap before getting ready to head back out for the evening.
4 p.m. or 6 p.m: See a show at the Dr. Phillips Center For The Performing Arts
The two-block Dr. Phillips Center For The Performing Arts is right in the heart of the action in downtown Orlando. Throughout the year, the sprawling concert hall hosts a variety of events like plays, concert movies, and the Orlando Ballet. I suggest trying to get tickets for a matinee showing before 4 p.m., or for one of the early evening shows around 6 p.m. This is also a great excuse to dress up.
Fun fact: Its Steinmetz Hall opened in 2022 and is rated one of the world's most acoustically perfect spaces.
Depends on your showtime: Dinner at The Pinery
The Pinery is a Michelin-recommended restaurant in the Ivanhoe Village neighborhood, about a 10-minute drive from the Dr. Phillips Center. The restaurant pays homage to the history of the district it's in since Ivanhoe Village was once the center of the country’s pineapple industry. The dining room is warm and welcoming, and the menu feels elevated thanks to the use of local ingredients and fresh seafood. The house-smoked fish dip is a Florida staple that can’t be missed, as is the pineapple-marinated chicken sandwich and the fried chicken dinner in which the meat has been brined in Southern-style sweet tea.
9 p.m.: Nightcap at The BANDBOX
The BANDBOX is Orlando’s first spirit-free speakeasy, and it’s just a short drive from The Pinery. The 1920s-themed bar has everything from non-alcoholic beer and cocktails to wine, shrubs, and CBD drinks. The bar does require a reservation for indoor table service, and each reservation is for one hour only. Because of its speakeasy theme, the bar encourages its guests to dress up in order to make the experience feel more glamorous and special. Inside the lounge, there are a few tables, a black and white photo booth, and period music to listen to while enjoying conversations with your travel mates.
