August 02, 2025
Living in South Florida has its perks with sunshine, beaches, and endless palm trees, but sometimes you crave a change of scenery. That’s exactly what inspired our recent getaway to Winter Park, Florida. Tucked just outside of Orlando, Winter Park is an artsy, walkable, and refreshingly charming town with tree-lined streets, vibrant dining, and a pace that invites you to slow down and explore.
We’d heard glowing things about Winter Park for years but had never taken the time to visit. So, we packed a bag, hopped in the car, and in just over three hours, we found ourselves transported into a completely different vibe - think historic Southern elegance meets college-town culture with a healthy splash of modern flair.
Our home base for the trip was The Alfond Inn, and let’s just say it set the tone for the entire weekend. Located right in the heart of town, this boutique hotel isn’t just a place to sleep; it’s a cultural experience. Owned by Rollins College, The Alfond Inn operates as a philanthropic property, with all net profits going toward student scholarships. That alone would’ve earned our admiration, but the hotel also dazzled with its beautiful design and curated collection of contemporary art displayed throughout the property.
We checked in and immediately felt immersed in the hotel’s unique blend of modern comfort and artistic charm. The conservatory, a light-filled space with lush plants and architectural details, was a dreamy place to relax with a coffee or cocktail. Outside, the courtyard offered a quiet, green retreat that felt like an urban oasis. We also made time for the elevated pool, a lovely rooftop spot with great views and comfy loungers perfect for unwinding in the late afternoon sun.
For our first meal, we headed to Cocina 214, a contemporary Mexican and Tex-Mex kitchen just a short stroll from the hotel. The vibe was upbeat and welcoming, and we were happy to find vegan options clearly marked on the menu. We ordered the vegan tacos, which were fresh, flavorful, and perfectly portioned, and of course, we couldn’t resist the chips and guacamole - simple, but done right.
The drinks at Cocina 214 were the real showstoppers. I went bold with the Swirl El Diablo, a frozen margarita swirled with sangria - a tangy, sweet, and dangerously smooth concoction. Bill chose the Cocina Guavarita, their Margarita Contest Winner made with Don Julio Blanco, Cointreau, and guava. Let’s just say there were no regrets.
After lunch, we set out to explore Park Avenue, Winter Park’s main thoroughfare. This district has it all: tree-canopied streets, upscale boutiques, art galleries, sidewalk cafés, and the kind of small-town charm you usually only see in movies. The town itself dates back to 1882, and its roots are evident in the historic architecture and brick-paved walkways. Every block offered something new, from hidden bookshops to artisan chocolate stores.
We took our time ducking into shops and admiring the local art scene. One of the joys of Park Avenue is that it’s walkable with no traffic stress and no need to rush. It’s the kind of place that invites lingering.
Later that afternoon, we headed back to the hotel for some pool time before freshening up and strolling over to Garp & Fuss for happy hour. Tucked just behind Park Avenue’s main drag, Garp & Fuss is a local favorite for good reason. The atmosphere was relaxed and social, with an interior that blended cozy vintage touches with modern flair.
The drinks were well-crafted, the servers friendly, and the overall vibe was perfect for winding down after a day of exploring. Whether you're seated inside or out on the patio, it feels like you’ve discovered a local secret.
We were pleasantly surprised by how vegan-friendly Winter Park turned out to be. For dinner, we tried Orchid Thai Cuisine, and it did not disappoint. The crispy spring rolls were light and packed with veggies, while the orchid salad brought a beautiful mix of colors and flavors to the table. We ordered the Pad Thai and was thrilled that they were able to accommodate our dietary needs without hesitation.
The staff was warm and helpful, and the entire experience felt like dining at a neighborhood gem that truly values both food and hospitality.
Of course, no evening is complete without dessert, so we stopped by Gelato-go Orlando, where we were delighted to find vegan chocolate gelato on the menu. Creamy, rich, and intensely chocolaty it hit the spot.
With cups in hand, we took a post-dinner stroll through the Rollins College campus, located just steps from downtown. Founded in 1885, this private liberal arts college sits on the shores of Lake Virginia and is one of the most beautiful campuses we’ve seen in Florida. Picture Spanish-Mediterranean architecture, live oaks draped in moss, and a lakeside view that glows at sunset. It felt like a perfect ending to a perfect day.
Before heading back home, we had one final meal at New General Café, a cozy and modern spot known for its clean, wholesome cooking. Everything is made from scratch, and they proudly cook without seed oils or overly processed ingredients.
We shared the vegan brekkie sandwich, which was an explosion of savory flavors - almond-crusted tofu, house-made lentil sausage, kale dressed in buttermilk ranch (vegan, of course), and spicy aioli on a soft brioche bun. We also split the pineapple pancakes, made with oat flour and layered with pineapple cashew cream and compote, topped with caramelized pineapple and served with a side of organic maple syrup. Add in two oat milk lattes, and we were officially in brunch heaven.
Even though our visit was short, Winter Park left a big impression—and a growing list of things we still want to do next time.
• The Charles Hosmer Morse Museum of American Art
This museum is home to the world’s most comprehensive collection of works by Louis Comfort Tiffany, including his iconic stained-glass windows, lamps, and jewelry. It also houses American decorative art from the 19th and early 20th centuries. The exhibits are known to be immersive, rich in detail, and full of stories from America’s artistic heritage. It's a must-see for art lovers.
• Scenic Boat Tour of the Winter Park Chain of Lakes
We can’t wait to hop on one of the scenic boat tours that glide through the canals and lakes surrounding Winter Park. The one-hour narrated tour covers Lake Osceola, Lake Virginia, and Lake Maitland, and offers stunning views of waterfront homes, tropical plants, and the lush Rollins College campus. It's said to be one of the best ways to see the town’s natural beauty and we’re all in.
Winter Park was everything we hoped it would be - walkable, friendly, full of history, and deliciously indulgent in all the right ways. Whether you’re into food, art, nature, or just relaxing in a beautiful place, this Central Florida gem checks all the boxes.
It’s incredible that in just a few hours' drive from South Florida, you can discover a place that feels entirely new. We’ll definitely be back—with more time to explore and a growing list of places to eat, sights to see, and memories to make.
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