By Sarah Grafton
There’s a special kind of magic that settles over Winter Park during the holidays. The oaks along Park Avenue are strung with beautiful lights, the air carries the scent of fresh greenery and citrus, and everywhere you turn, there’s a sense of joy and community. Whether you’re visiting from out of town or planning a festive staycation, here’s how to spend 36 unforgettable hours in the heart of Winter Park’s Park Avenue District.
Friday: Festive Finds & Holiday Magic
Begin your weekend with a cozy stop at New General, where creamy hot chocolate and expertly brewed coffee set the tone for the day. Grab a seat by the window or sip as you stroll Park Avenue’s twinkle-lit sidewalks. The boutique-lined avenue is full of local gems, perfect for holiday browsing.
Head to The Chapman for brunch or a late lunch—the French toast is a must-try: golden, soft, and perfectly sweet. Afterward, treat the family to a spin on the Holiday Carousel, a nostalgic delight for children and families!
To experience Winter Park from a new perspective, hop aboard the Scenic Boat Tour. Ron and his team will guide you through quiet lakes and canals, past historic estates and moss-draped trees, sharing stories and secrets only locals know.
As the sun begins to set, visit the Charles Hosmer Morse Museum of American Art. On Friday evenings in December, enjoy free admission from 5 to 8 p.m., complete with live music. The museum features the world’s most comprehensive collection of Louis Comfort Tiffany’s works—jewelry, glass, pottery, and more.
After your museum visit, take an enchanting stroll through the Cathedral of Light, a breathtaking tunnel of twinkling holiday lights that makes the evening feel like a dream. Just a few steps away, pause by the towering Christmas Tree, beautifully lit and perfect for photos or simply soaking in the spirit of the season.
Before dinner, make your way to The Imperial, one of the district’s newest treasures. Tucked inside the 200 block, this cozy wine bar offers boutique wines, craft beers, and a small but flavorful appetizer menu. Charcuterie, anyone?
For dinner, Winter Park serves up something for every craving. Craving bold, comforting flavors? The fajitas at Cocina 214 bring Tex-Mex to life with sizzling flair. Prefer Italian-inspired fare? Prato is known for its wood-fired flatbreads and fresh pastas—perfectly paired with a glass of wine. The meatballs are a local favorite and the bar is always a festive after-hours spot!
When it’s time to wind down, check into The Alfond Inn. Just steps from the Avenue, this elegant boutique hotel combines comfort with culture. Explore the inn’s thoughtfully curated contemporary art collection or book a late-night spa treatment. With luxury accommodations and a distinctly Winter Park touch, it’s the perfect home base for your holiday weekend.
Saturday: Style, Strolls & Sweets
Begin your day with breakfast at Barnie’s Coffee & Tea Co., where the avocado toast is as delicious as it is Instagram-worthy. Then take a peaceful morning walk through Central Park, where holiday decorations and fresh air make the perfect start to your day.
Dedicate the rest of your morning to discovering some of Park Avenue’s most iconic and unique retailers. Explore stylish pieces at Tuni, Be on Park, and Savannah Taylor, or shop elevated menswear at John Craig. Find timeless gifts at Siegels, statement pieces at Through the Looking Glass, timeless pieces at Reynolds Jewelers, and curated treasures at Arabella on Morse—each shop offers something special you won’t find anywhere else.
Need a treat? Swing by Peterbrooke Chocolatier for a scoop of creamy gelato. Before you leave, grab a bag of their famous chocolate-covered popcorn—it’s the perfect souvenir or road snack.
As you wander, take note of the hidden art galleries sprinkled along the Avenue. These quiet, creative spaces showcase works from local and international artists and add an extra layer of inspiration to your weekend. Whether you’re browsing familiar brands like Williams Sonoma or uncovering one-of-a-kind specialty shops, Park Avenue delivers variety, quality, and charm!
Whether you’re soaking in the culture, indulging in delicious bites, or simply enjoying the sights and sounds of the season, a holiday weekend in the Park Avenue District is the perfect mix of luxury, tradition, and small-town magic—wrapped in lights and tied with a highly curated bow.
