Winter Park is like the chic, cozy cousin of Orlando—where charm meets sunshine and every corner feels like a story waiting to be discovered. Swap the crowds and chaos of traditional Orlando hotels for cobblestone streets, boutique shops, and lakeside cafés that beg you to linger over a latte. Here, you can stroll through art-filled museums, hop on a scenic boat tour, and nibble your way through farmers’ markets—all without jostling for a spot on a rollercoaster. Winter Park isn’t just a place to stay—it’s a playful, slower-paced escape that makes Orlando feel unexpectedly magical.
Dine at AVA MediterrAegean
Photo: AVA MediterrAegean
AVA MediterrAegean brings a transportive dining experience inspired by the flavours and coastal spirit of the Mediterranean. With warm lighting, effortless elegance and beautiful décor, as you step into the restaurant, you feel as you are miles away on an ancient Greek island indulging in the best of the best. Located on Park Avenue, AVA MediterrAegan’s menu features elevated mezze, fresh seafood, and beautifully executed wood-fired dishes—perfect for a long, indulgent evening in Winter Park’s culinary scene.
Explore the Charles Hosmer Morse Museum of American Art
Photo: Charles Hosmer Morse Museum of American Art
Home to the world’s most comprehensive and stunning collection of works by Louis Comfort Tiffany, the Morse Museum is the perfect stop for anyone ready to upgrade their cultural bucket list. Wander through galleries filled with Tiffany lamps, stained glass, jewelry, and architectural treasures that make you feel like you’ve stepped into an artist’s dream world. It’s a serene and inspiring escape for travelers who love art, design, and craftsmanship. Bonus: it’s basically impossible not to imagine your own home with one of these beauties on every table.
Shop Along Park Avenue
Photo: Park Avenue District
We’re a sucker for palm tree-lined streets, beautiful boutiques and irresistible cafés. Spending the afternoon strolling and shopping Park Avenue was a favourite memory of ours as we love wandering through curated shops that pique our interest with beautifully decorated windows. From local jewelry, to gourmet treats (visit the legendary Peterbrooke Chocolatier of Winter Park) and curated gifts (visit frank. for that!) for all, the street’s charming atmosphere makes browsing (and buying!) a perfect experience.
Take a Scenic Canal Boat Tour
Photo: Winter Park’s Scenic Boat Tour
Winter Park’s Scenic Boat Tour is one of the area’s most iconic and peaceful activities. Glide through narrow canals and across shimmering lakes as your incredibly knowledgeable tour guides shares about the region’s history, architecture, and lush landscapes. As the sun cascaded down, we were mesmerized by the gorgeous waterfront estates and overhanging tropical greenery while cruising through the unique canal system on Winter Park. A true must do for all.
Spend a Day at SeaWorld Orlando
Photo: SeaWorld Orlando
Though just outside Winter Park, SeaWorld Orlando adds a dynamic dose of adventure to the itinerary. With its lineup of world-class coasters, marine-life encounters, and seasonal events, the park balances Winter Park’s relaxed vibe with big-energy excitement. It’s the perfect way to round out your trip with a thrill-filled day before returning to the area’s more laid-back charm.
