Winter Park Holiday Favorites: Dining & Shopping & Events
Winter Park glows with holiday cheer as local boutiques and eateries roll out festive offerings. Whether you’re hunting for a unique gift or looking for a cozy family meal, these hometown spots deliver warmth and nostalgia this season. From handcrafted jewelry to seasonal fare and decadent chocolates, each business brings its own sparkle to the holidays.
AJ Chocolate House is Winter Park’s luxury chocolate cafe and patisserie. Its flagship shop – often filled with the “forever-lingering smell of fresh chocolate” – offers more than 150 handcrafted European sweets. You can indulge in warm waffles, creamy gelato, or a decadent slice of cake alongside their coffee. For holiday shopping, AJ’s is a dream: choose from artisanal chocolate gift boxes, chocolate-dipped fruits, or a mix of truffles beautifully packaged in velvet boxes. Whether you’re creating a sweet childhood memory with your family or bringing home an elegant box of chocolate for hostess gifts, AJ Chocolate House turns holidays into a delicious celebration.
Almut Belote Jewelry is a Winter Park studio where master goldsmith Almut Belote handcrafts fine jewelry. Each piece is designed by Almut herself, reflecting her artsy Austrian background and decades of experience. In her Winter Park workshop, Almut creates original solid-gold bracelets, rings, and pendants, building each with exquisite detail. These heirloom-quality jewels make special holiday gifts: consider a gold cuff bracelet or gemstone ring as a timeless present. With such personal craftsmanship, any gift from Almut Belote – be it a pair of elegant earrings or a custom necklace – becomes a cherished holiday keepsake.
The Atelier Home + Design is Winter Park’s boutique for luxury home décor and one-of-a-kind gifts. It features “an ever-evolving selection of furnishings, decor, gifts, and statement pieces” that add personality and style to any space. During the holidays, shoppers can browse festive ornaments, artisanal candles, cozy throw blankets, and quirky barware perfect for hostess gifts. The Atelier’s curated interior-design vibe makes holiday shopping feel indulgent – imagine finding a bold decorative pillow or handcrafted trinket tray that transforms your home for the season.
Be On Park Fine Jewelry is Winter Park’s premiere jeweler for elegant, designer pieces. During the holidays, Be On Park’s warm showroom is filled with fine gemstones and precious metals. You can shop for classic diamond earrings, a sapphire pendant, or a custom gold ring – all perfect for making this season extra memorable. Whether you’re proposing on New Year’s Eve or gifting a timeless necklace to a loved one, the expert staff will help you find just the right sparkler for the occasion.
Boca Restaurant offers a warm, inviting atmosphere and creative American cuisine ideal for holiday gatherings. Think hearty bowls of shrimp & grits, flavorful flatbreads, or fresh seafood, each dish uses the season’s best local ingredients. Boca’s cozy industrial-chic dining rooms and fireplaces make it perfect for family dinners or celebratory brunches. Sip on a handcrafted cocktail and savor a festive meal with loved ones; the thoughtful details and friendly service ensure every holiday moment here feels unforgettable.
Dear Jane is a bright and playful women’s boutique that’s “a one-stop shop for trend seekers”. The shop feels like stepping into a celebrity’s stylized closet – colorful and chic. Inside, you’ll find “trendy boutique clothing, delicate intimates, and luxe jewelry” alongside modern home gifts and high-end candles. It’s the perfect place to pick out a holiday outfit or a sweet gift. Browse racks of cozy sweaters, elegant party dresses, and cute accessories, or grab a luxury bath set for stocking stuffers. During the holidays, Dear Jane decks the store with festive decor, turning holiday shopping into a stylish, feel-good experience.
Flûtes Champagne Bar puts a bubbly spin on holiday nights. This upscale lounge is “celebrating the timeless art of champagne”, with a “curated selection of exquisite champagnes” and a lively, modern vibe. Flûtes offers endless bubbly options from French Champagne to sparkling French wines along with elegant small plates. It’s the perfect place for a holiday toast or a girls’ night out. Decked out with festive lights and energetic music, Flûtes makes any winter evening feel like a celebration. Raise a glass of champagne or sip a sparkling flight with friends and family to make this season sparkle a little brighter.
Monkee’s is a large women’s boutique located in Hannibal Square. Holiday shoppers love Monkee’s for its friendly atmosphere and endless choices. You can easily outfit everyone on your list here – from stylish boots and cozy outerwear to sparkly jewelry and chic handbags. Think warm scarves, glittery sweaters, or a cute holiday dress. Monkee’s helpful staff will make sure you leave with the perfect look or gift, whether it’s a festive ensemble for a party or a luxurious scarf to wrap up on a chilly winter night.
Rifle Paper Co. is an internationally beloved stationery and lifestyle brand born in Winter Park’s Hannibal Square. Its flagship store carries the full Rifle collection of hand-painted, floral-themed designs. Around the holidays, Rifle’s boutique is filled with festive paper products, think whimsical holiday cards, illustrated wrapping paper, and chic ornaments. It’s the ideal spot to find creative gifts, like a set of artistic notecards or a cozy printed blanket. Every item makes even the simplest holiday greeting feel extra-special thanks to Rifle’s signature artistic flair.
The Vintage Vault lives up to its name with an “elevated wine experience” perfect for the holidays. This wine shop and tasting room offers a curated collection of fine wines, gourmet cheeses, artisanal olives, and handmade jams. Stop by to relax with a glass of red by the fireplace and a house-made charcuterie board, or stock up on holiday provisions. Need last-minute gifts? The Vault has it covered: pick unique bottles for the wine lovers on your list, plus pantry gifts like olive oil or hot sauce. In short, Vintage Vault provides everything you need for festive dinners or gift baskets – all in one cozy, spirited space.
Each of these local businesses adds its own special charm to Winter Park’s holiday scene. Visiting them not only means finding the perfect gift or meal but also supporting our community’s local spirit. This season, wander the twinkling streets of Winter Park and discover festive treasures in every shop, all while making warm memories with the ones you love.