If you’ve visited Winter Park before, then you already know how charming this city is. With its historical buildings, quaint shops and cobblestone streets, Winter Park, Florida, reminds me of Europe.
First-timer? You’re in for a real treat! I’ll be creating another day trip itinerary focused on outdoor activities later, but this one covers all the cozy indoor spots where you can enjoy amazing coffee, soak in the European-inspired atmosphere, and discover local art scenes that make Winter Park so unique.
Day Trip Itinerary
9:30 AM – Depart from your location
Depending on where you are, this trip should take you less than an hour (unless you are coming from Kissimmee). This takes me 20 minutes from Altamonte Springs
Estimated drive time: 30 minutes
Sip on Vietnamese Coffee
10:00 AM – Black Phin
Address: 1152 Harmon Ave
Cost: $8 – $12
This Vietnamese Coffee spot just opened not too long ago in the space inside Kiwi and Fern! They do have food such as Sandos and egg salad. If you love plants and delicious Vietnamese coffee, this is the spot you’ll want to check out!
Estimated drive time to next location: 10 minutes
Check out this Art Museum
11:30 AM – Morse Museum of American Art
Address: 445 North Park Avenue
Cost: $10 for adults, $1 students
This is such a beautiful museum and one you shouldn’t skip! Here you’ll find the world’s most comprehensive collection of works by Louis Comfort Tiffany. You’ll see a wonderful collection of stained glass among other things.
Estimated drive time to next location: 5 minutes
Have Lunch and Chocolates
1:30 PM – AJ Chocolate House
Address: 552 S Park Ave
Cost: $10 – $40
While this place is a bit on the pricey side, AJ Chocolate House offers the most decadent desserts and chocolates! Aside from that they do have a lunch menu and also a tea tower.
Winter Park has many lunch spot, so if you’re looking for something less pricey, check out this list : The Ultimate Guide: 25 Must-Visit Restaurants in Winter Park, FL
Instagram Reel: https://www.instagram.com/reel/C5OR2oTLxqg/
Estimated drive time to next location: 2 minutes (You could just walk)
3:00 PM – Rollins Museum of Art
Address: 1000 Holt Ave
Cost: Free
Located in Rollins College, the Museum of Art is such a hidden gem! While this is a small museum, it is free and their exhibits are usually quite interesting. While on campus, be sure to check out some of the other hidden gems such as The Benjamin Franklin Statue, Chapel Garden, Mister Roger’s Statue.
Instagram Reel: https://www.instagram.com/reel/C8cGqvZsMIE/
Estimated drive time to next location: 0 (You can just walk, no need to drive)
Stroll through European Charm
4:30 PM – Explore Downtown Winter Park and Hannibal Square
Address: 110 N Park Ave
Cost: Free unless you buy something
Since you’re already in the downtown area, might as well explore the rest! Downtown Winter Park is absolutely stunning with its historical buildings, lush gardens and cobbled streets. This is the city of arts and culture, and if you have some time check out Hannibal Square, which is the part that most tourists miss!
Instagram reel: https://www.instagram.com/reel/CvpdRb0rTuS/
Estimated drive time to next location: 5 minutes
Head to Dinner
6 PM – Bulla Gastrobar
Address: 110 S Orlando Ave
Cost: $8-$40, depends
There are plenty of food options in Downtown Winter Park, but if you’re looking for something different, Bulla Gastrobar is the way to go. With Tapas (Small Plates), cured meats, cheeses, and all sorts of Spanish dishes, you can’t go wrong.
Winter Park, Florida is a charming city you don’t want to miss out on. While this itinerary shows a glimpse of what you can do, there is still a lot more you can do in the area. I’ll be posting more itineraries for Winter Park, but if you’re looking for something specific let me know! I’d love to hear about it.
Notes:
- There is plenty of free parking space in Downtown Winter Park
- For most of these, you should be able to park and just walk to your next destination
- This is just one of many curated day trips! More Winter Park Day Trips to come soon
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