Rollins makes our list because it’s the first recognized college in the state of Florida, founded in 1885. The college was originally slated to be in Sanford, but it ended up being on an 80-acre parcel on Lake Virginia in Winter Park instead. Currently home to around 3,000 Liberal Arts Students.
It’s also the most expensive college to attend in Florida, so while it’s not our demographic, it’s also nice to go out and see how the rich folks are living once in a while. If you go to visit Rollins, walk right up Park Avenue, and without a doubt, you’ll get a great idea of what the rich life is like.

Here are a few things to do while visiting Rollins:
- Visit Knowles Memorial Chapel
A beautiful, peaceful chapel in the center of campus. Whether you’re religious or love old architecture, it’s a nice, quiet stop that makes you feel like you’re in a southern storybook. - Grab a Rocking Chair on Mills Lawn
The large green lawn in the center of campus often has white wooden rocking chairs out front. Sit a spell. The view of the old Spanish-style buildings while the bells ring from Knowles Chapel is a vibe. On the way to Mills, make sure to check out Pinehurst Cottage along the memorial rock walk. Pinehurst Cottage is the oldest building remaining on campus and was built in 1886. - Walk the Campus Lakeside Path
Start with a stroll along Lake Virginia. The path behind the Cornell Fine Arts Museum offers some peaceful views and big oak trees with Spanish moss—feels a bit like home, just with a college backdrop. If you would like to walk a little more, make sure to hunt down the Mr. Rogers walking tour on campus. - Pop into the Cornell Fine Arts Museum (free admission!)
It’s small, charming, and right along the lake. The rotating exhibits are usually interesting, and the building itself is worth a peek. It’s a great mix of culture without being overwhelming. If you’re up for more art, visit the unique Rollins-owned Alfond Inn. The 5-star hotel features high-end art in every nook and cranny. - Heading Off-Campus: Take the Scenic Boat Tour
A real treat—this hour-long tour starts a block from campus and cruises through the Winter Park chain of lakes. It glides past the back of Rollins, under vine-covered bridges, and by some jaw-dropping homes. It’s like a swamp tour met HGTV. Stay tuned. This tour needs a full story on its own! I’ll link to it once I’m done. - After the Boat Tour: Finish with a Treat on Park Avenue
Head just across the street to Park Avenue—quaint shops, sidewalk cafés, and ice cream from Kilwins or a coffee from Barnie’s. It feels like a fancy small town.
So why is FSU saying they’re even older and founded in 1851? While FSU may be older, they didn’t become a college until 1901. Somebody contact me and clear up this mud for us.
Was there a St. John’s College of St. Augustine in the 1600’s? No. And even if so.. we’re not acknowledging it because it’s from Spain, not America.