7 Day Cultural Immersion Itinerary in Orlando, FL

• Day 1: Start the day with a visit to the Cornell Fine Arts Museum for a dose of art and culture. After this, head over to Winter Park's Farmers market for a variety of local produce and crafts. For lunch, grab a bite at the locally-owned The COOP for some classic southern comfort food. End the day with a thrilling performance at Cirque du Soleil located in the heart of Disney Springs.
• Day 2: Begin the day by learning about the history of Orlando at the Orange County Regional History Center. Next, walk over to the Cathedral Church of St. Luke for a stunning view of the church's architecture and quiet prayer. For lunch, grab some authentic Cuban food at Versailles Cuban Bakery in Winter Park. End the day with a visit to the internationally renowned Orlando Ballet.
• Day 3: Visit The Charles Hosmer Morse Museum of American Art to see the world's most comprehensive collection of works by Louis Comfort Tiffany. After this, go on a picturesque boat ride at the Winter Park Chain of Lakes. For dinner, head over to The Ravenous Pig, Winter Park's most awarded restaurant known for their innovative southern cuisine.
• Day 4: Begin the day with a visit to the The Harry P. Leu Gardens for a relaxing stroll through several botanical gardens. Next, head over to the Athletic Museum at the Amway Center to learn about Central Florida's sports history. For lunch, grab some delicious tacos from MX Taco in downtown Orlando. End the day at the Dr. Phillips Center for the Performing Arts to experience a mix of theatre, music and dance.
• Day 5: Start the day with a visit to The Holocaust Memorial Resource and Education Center, a sobering museum filled with educational content relating the history of the Holocaust. Next, go on a relaxing boat tour of the Winter Park Chain of Lakes, which lasts around 2 hours. For lunch, grab a freshly-made sandwich or salad at The Sanctum Cafe, known for their organic and locally-sourced ingredients. End the day with a scenic stroll around Lake Eola Park, with stunning views of the city skyline.
• Day 6: Spend the day exploring Disney's Epcot, a global cultural celebration! The park is filled with different pavilions representing many countries and diverse cultures. Epcot is also known for its innovative rides, flower and garden festival, and fireworks display.
• Day 7: Start the day with a visit to the Orlando Museum of Art to explore their extensive collection of American art ranging from contemporary to ancient. Afterwards, head over to The Madeline Bistro & Venue to enjoy brunch with a side of live music. End the day with an immersive performance at the Orlando Shakespeare Theater.

Time and Costs Estimates

• Cornell Fine Arts Museum - 2 hours - Free admission
• Winter Park Farmers Market - 2 hours - Free admission
• The COOP - 1.5 hours - $15-$20 per person
• Cirque du Soleil - 2.5 hours - $60 or more per person
• Orange County Regional History Center - 2 hours - $8 per person
• Cathedral Church of St. Luke - 30 minutes - Free admission
• Versailles Cuban Bakery - 1 hour - $10-$20 per person
• Orlando Ballet - 2 hours - $35 or more per person
• The Charles Hosmer Morse Museum of American Art - 2 hours - $6-$20 per person
• Winter Park Chain of Lakes - 2 hours - $13 per person
• The Ravenous Pig - 2.5 hours - $50 or more per person
• The Harry P. Leu Gardens - 2 hours - $10 per person
• Athletic Museum - 1.5 hours - $10 per person
• MX Taco - 1 hour - $10-$15 per person
• Dr. Phillips Center for the Performing Arts - 2.5 hours - $40 or more per person
• The Holocaust Memorial Resource and Education Center - 1.5 hours - Free admission
• The Sanctum Cafe - 1 hour - $15 or more per person
• Lake Eola Park - 2 hours - Free admission
• Disney's Epcot - Full day - $109 or more per person
• Orlando Museum of Art - 2 hours - $15 per person
• The Madeline Bistro & Venue - 1.5 hours - $30 or more per person
• Orlando Shakespeare Theater - 2.5 hours - $25 or more per person
• Total Costs: $535 or more per person

Transportation

To get around, renting a car is the most convenient option. Alternatively, Uber and Lyft has a strong presence in the city. Many points of interests are easily walkable- especially Winter Park!.

Links to Key Attractions/Restaurants/Points of Interest

• Cornell Fine Arts Museum
• Winter Park Farmers Market 
• The COOP
• Cirque du Soleil
• Orange County Regional History Center
• Cathedral Church of St. Luke
• Versailles Cuban Bakery
• Orlando Ballet 
• The Charles Hosmer Morse Museum of American Art
• Winter Park Chain of Lakes
• The Ravenous Pig
• The Harry P. Leu Gardens
• Athletic Museum 
• MX Taco
• Dr. Phillips Center for the Performing Arts
• The Holocaust Memorial Resource and Education Center
• The Sanctum Cafe
• Lake Eola Park
• Disney's Epcot
• Orlando Museum of Art
• The Madeline Bistro & Venue 
• Orlando Shakespeare Theater

Tips:

If you want to include more parks/attractions/activities in the itinerary, consider adding more days to your trip. Conversely, if you want to have a more relaxed trip, consider removing a few of the more time-consuming activities from the itinerary.