• Updated with new information since originally published.
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  • Our editors recommend these diverse local experiences.

1. Charles Hosmer Morse Museum of American Art ⭐⭐⭐⭐⭐

Category: Museums & Culture for Couples
© Charles Hosmer Morse Museum of American Art

2. Albin Polasek Museum & Sculpture Gardens ⭐⭐⭐⭐⭐

Category: Weekend Activities & Fun Outdoors
© Albin Polasek Museum & Sculpture Gardens

3. Kraft Azalea Gardens

Category: Weekend Activities & Fun Outdoors
© Kraft Azalea Gardens

4. Bulla Gastrobar

© Bulla Gastrobar

5. Mead Botanical Garden

Category: Weekend Activities & Fun Outdoors
© Mead Botanical Garden

6. Casa Feliz Historic Home Museum

Category: Affordable Local Attractions
© Casa Feliz Historic Home Museum

7. Rollins Museum of Art

Category: Museums & Culture for Couples
© Rollins Museum of Art

8. Cady Way Trail, Winter Park, Florida

Category: Weekend Activities & Fun Outdoors
© Siam/stock.adobe.com

9. Hannibal Square Heritage Center

Category: Affordable Local Attractions
© Hannibal Square Heritage Center

10. Crealde School of Art, Winter Park, Florida

Category: Weekend Activities & Fun Outdoors
© Crealde School of Art

11. Winter Park Public Library

Category: Kids & Family Fun
© Winter Park Public Library

12. Ethos Vegan Kitchen, Winter Park, FL

Category: Weekend Activities & Fun Outdoors
© fahrwasser/stock.adobe.com

13. Hunger Street Tacos

© Hunger Street Tacos

14. Rollins College

© Rollins College

15. Winter Park Historical Museum

Category: Weekend Activities & Fun Outdoors
© Winter Park Historical Museum

16. Aloma Bowling Center

Category: Entertainment Near Me
© Aloma Bowling Center

17. WinterClub Indoor Ski and Snowboard

Category: Weekend Activities & Fun Outdoors
© JackF/stock.adobe.com

18. Winter Park Municipal Golf Club

Category: Weekend Activities & Fun Outdoors
© vladimirhodac/stock.adobe.com

Summary and Frequenly Asked Questions:

  • Five miles north of downtown Orlando in Central Florida’s Orange County, Winter Park is a leafy city with plenty of wide-open spaces, green urban parks, pristine golf courses, and balmy, year-round weather that make it a popular spot for outdoor recreation.
  • The quaint cobbled streets of the historic downtown area are lined with beautiful European-style buildings.
  • The city is home to interesting museums like the Charles Hosmer Morse Museum of American Art.
  • Explore antiquities and contemporary works at the Cornell Fine Arts Museum on the shores of Lake Virginia.
  • Enjoy an array of outdoor activities like hiking, water-based sports on the lake, or a game of golf on one of the many world-class golf courses.

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