Close your eyes and think of Orlando. What’s the first thing that comes to mind? For the majority of people, it’s visions of tourists donning Mickey Mouse T-shirts or Wizarding World of Harry Potter robes. While the attractions are intrinsically woven into the fabric of Central Florida, there are multiple facets to the area—more Michelin than Marvel and more cosmopolitan than comic book—that speak to a luxury experience one may not expect from such a bustling tourism hub. 

Having been born and raised in Orlando, I can vouch that the city has had a serious rebrand over the last few decades. What started as a small cow town known for its orange groves has exploded into a sprawling metro with decidedly more discerning tastes, first-class theme parks included. Want an all-in-one resort with award-winning restaurants, a kickass pool and elegant rooms? Check. How about an urban adventure where you can try all the foodie eats and craft cocktails your body can handle? Check, check. Or maybe you want an idyllic escape with Disney’s Main Street, U.S.A. vibes, yet shopping and dining on par with Miami or New York? Check, check, check.

Forget Googling where to go ever again. We’ve got your cheat sheet for choosing your own authentic (and upscale) Orlando getaway. We’ll leave packing the mouse ears up to you.

The “I Want To be Near the Parks but Not Feel Like It” Vacation

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As an Orlando native, I understand my hometown’s park appeal (Even my high school prom was at Epcot!). If you want to hit up the attractions, it only makes sense to stay somewhere close. According to Visit Orlando, there are over 480 hotels, resorts and inns in the area, but as a local who has many staycations under her belt, there’s one that truly stands out among the rest: The Four Seasons Resort Orlando at Walt Disney World Resort. 

The 26-acre property has impeccable accommodations, a world-class spa, highly-lauded dining, golf and a sprawling pool area with a splash zone, slides, a lazy river and an adult-only pool. The best part: It’s situated less than 10 minutes from the parks. Put simply, it has everything you can expect from a Four Seasons resort with a little extra Mickey magic sprinkled in. 

While adults will appreciate the first-class service and dining options—just take the Michelin-starred Capa, a rooftop steakhouse known for its unparalleled Spanish-inspired cuisine and gorgeous views—the resort can really roll out the red carpet for families. In the spa, there’s a Magical Moments for Kids service where children are transformed into their favorite princess or a dashing knight. At Ravello, another one of the hotel’s on-site restaurants, there’s a Good Morning Breakfast with Goofy & His Pals on select days. Additionally on select nights, Ravello has a Pasta & Play program where after dinner, kids will be escorted to the nearby lawn by Kids For All Seasons team members for some supervised fun until 9 p.m., allowing
parents to finish their meal or bottle of wine in peace. Talk about a true luxury. 

The resort’s hands-on approach to hospitality also means there’s nothing you can’t make happen. Fable boutique, located on the resort’s lobby level, offers elevated gifting options and the chance to order a princess or space ranger tent with on-theme accessories to be set up in your room for little ones to play in. If you’re looking for a truly extravagant experience, you can rent out an entire floor of the hotel, Capa restaurant or even the spa. Private character meet-and-greets are also available upon request. 

Dine + Drink

Explore beyond the hotel’s premises by resort-hopping over to Victoria & Albert’s. The opulent, Victorian-styled restaurant, located in Disney’s Grand Floridian Resort & Spa, has been a AAA Five Diamond Award winner each year since 2000 and recently earned its first Michelin star—a first for a Disney restaurant—along with the 2024 Michelin Guide Florida Service Award, won by sommelier Israel Perez. Victoria & Albert’s is known for its innovative tasting menu and pairings with fine wines, zero-proof options or other beverages from an extensive drink list that includes an entire page dedicated to still water. Yes, it’s that posh.

Another option is the Bull & Bear, situated at the Waldorf Astoria Orlando, which is an ode to the original Bull & Bear Prime Steakhouse in New York City. It’s worth a stop if you’re looking for a reinvented take on steakhouse staples without compromising on service. While they serve up perfectly executed pieces of meat and plates with just the right amount of creative flair, like the escargot and gnocchi or the veal oscar, the restaurant also has top notch tableside experiences—from a smoked old-fashioned served out of a bull decanter to a liquid nitrogen dessert.

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Our weekend guide to Orlando’s neighbor, Lake Nona, a perfect day-trip destination.

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To dine where the locals go, Sand Lake Road is a quick drive away. This stretch is a regular haunt for residents of the neighboring Windermere and Doctor Phillips communities. While there’s a restaurant for every craving, Kabooki Sushi is a standout with its lively atmosphere and Japanese fare. 

And if you want to get competitive without breaking a sweat, head to Stadium Club in the Caribe Royale Resort. Not only does this immersive sports bar have electric energy and eats, but it also has pro-level sports simulators so you can swing, shoot, throw and kick without the humidity. 

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First off, if going to the attractions is on the agenda, remove the stress of planning with guided VIP experiences at the Walt Disney World and Universal Studios Florida parks. Although if it were up to me, dip out before the late-night crowds and head to a (slightly) less crazy tourist haven, Disney Springs. Besides having better food options than the parks (try Jaleo by José Andrés for delectable tapas), there’s plenty to do in this retail and dining hub from catching Cirque du Soleil’s “Drawn to Life” show (try booking their new Page To Stage Signature Experience for an intimate behind-the-scenes look) or bowling at Splitsville Luxury Lanes. Don’t want to miss the fireworks? Easy. Book a nighttime Fireworks Cruise that lets you soak up the spectacle from the water sans having to stand shoulder-to-shoulder with countless others. 

While there’s no shortage of shopping options, The Mall at Millenia is a notch above the rest. Its considerable concentration of luxury boutiques, ranging from Dior and Rolex to Hermès and Chanel, puts it on par with other luxe retail districts in Miami and Palm Beach. They even offer complimentary delivery to hotels and residences within a 40-mile radius, and as long as you plan ahead, you can reserve an appointment at their Personal Stylist Suite, where you work one-on-one with a personal stylist to edit and enhance your wardrobe. 

Like the rest of Florida, Orlando is also known for its collection of premiere golf courses. Arnold Palmer’s Bay Hill Club & Lodge is the most iconic thanks to its namesake golf legend, but you’re only able to play the greens if you’re a guest of a member or staying on property. Instead, try the Ritz-Carlton Golf Club course designed by Greg Norman. Not intimidated by driving a little further? Hit the road for a few hours to play a course with character at Cabot Citrus Farms or Streamsong Golf Resort.

The “I Want To Explore a City” Vacation

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What many people don’t realize is that Central Florida’s main tourism hub is a solid 20- to 30-minute drive from what’s considered true downtown Orlando. Dubbed “The City Beautiful,” its urban sprawl has a little bit of everything: top-notch food, craft cocktails, professional sports teams, a state-of-the-art performance center and plenty of swans. 

After undergoing a recent $18 million renovation project, the Grand Bohemian Hotel Orlando is the chicest place to rest your head. Its eye-catching art deco design paired with a striking color palette of black, white and rich jewel tones is woven into every aspect of the property, from the lobby to the guest and meeting rooms. 

While the attractions are intrinsically woven into the fabric of Central Florida, there are multiple facets to the area—more Michelin than Marvel and more cosmopolitan than comic book—that speak to a luxury experience one may not expect from such a bustling tourism hub. 

On the ground floor, the sounds of live music and lively conversation lure you into the Bösendorfer Lounge, named for the bar’s signature piano. It’s a watering hole for guests and locals alike. Across the hall is The Boheme, the property’s main restaurant with a menu dedicated to European-inspired cuisine, along with an all-encompassing Sunday Jazz Brunch spread. For a more Zen getaway, head a few stories up to the Poseidon Spa and the recently opened Altira Pool + Lounge, where you can take a dip while enjoying the views of the city skyline no matter the time of day. 

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Explore O-Town’s districts

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Dine + Drink

One of the unique things about Orlando is that it’s made up of different districts, all of which are situated close to downtown. While there are plenty of eateries that are walkable within downtown proper—from Artisan’s Table to Kres Chophouse—the true foodie finds are slightly outside the city center. Take Tori Tori and Moderne for example, two bar/restaurant hybrids that are as aesthetically pleasing as they are appetizing. 

They’re located in Mills 50 district, a pocket of Orlando less than two miles from downtown and known for its standout Asian cuisine. While both bars garner a visit for the drinks alone, their similarities diverge from there when it comes to food. Tori Tori specializes in yakitori (skewered chicken) and inventive bar bites, while Moderne has a more expanded menu of shareables from tuna kobachi to Rangoon dip to fire roasted duck. 

A few hundred feet from Tori Tori is Edoboy, but if you don’t know what to look for, you’ll miss it. The unassuming eight-person standing sushi bar is tucked in a parking lot, but with sushi so good, who needs a flashy street front? Within the hour time slot (reservations are released every Monday at noon), choose 12 pieces of nigiri or handrolls to be made directly in front of you. 

Cap off the evening by heading to Mathers Social Gathering, a true Prohibition-era speakeasy. Sip
meticulously crafted cocktails like the Bathtub Gin (served in an actual miniature bathtub) and snack on light bites such as the Prohibition milk and cookies which comes with a shot of bourbon. Then, visit their general store for absinthe shots and, on certain nights, enjoy live entertainment, such as burlesque performances, music and magic shows. 

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Located across the street from the Grand Bohemian is the Dr. Phillips Center for the Performing Arts. The state-of-the-art entertainment and cultural hub hosts Broadway musicals, concerts, stand-up comedy shows, ballets and more. Their latest music venue, Judson’s Live, is the perfect way to see what the Dr. Phillips Center is all about if you’re not in town during a major show. The intimate space has table seating, so you can sit back and enjoy a 50-minute performance while drinking and dining off a curated, scratch-kitchen menu.

While the Orlando Magic NBA team may be the city’s most well-known professional sports organization, the Orlando City Soccer Club has one of the most devoted fanbases in town and have dubbed themselves the Ruckus. The Major League Soccer team plays in Inter&Co Stadium alongside the women’s team, the Orlando Pride. Join up with the Ruckus for a pregame tailgate behind Broken Strings Brewery or in their dedicated section in the stands, known as the Wall. However, if loud chants, drums and general rowdiness aren’t appealing, opt for premium seating options, ranging from private suites to the Terrace, which boasts outdoor tables with complimentary food and beverage service. 

If you need a way to wind down on Sunday, walk over to Orlando Farmers Market at Lake Eola Park. It’s one of the most enjoyable, low-key ways to spend a weekend, with a variety of local food and craft vendors. I personally recommend grabbing a fresh coconut to sip on while you stroll around and watch the swans glide on Lake Eola—and if you’re really feeling adventurous (or want a leg workout), take a spin on one of the lake’s iconic swan paddleboats. 

The “I Want a Charming Weekend Away” Vacation

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Winter Park was chartered in 1887 as a vacation destination for wealthy northerners who wanted a reprieve from cold weather, so it’s no wonder it has a distinct New England feel. While I may be partial to Winter Park’s quaint vibe, since I grew up here (and subsequently moved back after a decade away), it’s truly a place that doesn’t fit the Orlando stereotype. 

Park Avenue, the brick street lined with boutiques and restaurants, anchors the city, so it’s fitting that the The Alfond Inn at Rollins is just a two-block jaunt away. It’s the brainchild of Rollins College, the neighboring liberal arts school that also happens to be the Sunshine State’s first recognized college. Since it opened in 2013, the hotel directs net operating income to support Rollins scholarships and has garnered a reputation as the premiere place to stay in Winter Park.  

Part of its unique appeal is its dedication to the arts. The Alfond Collection of Contemporary Art includes more than 600 pieces, spanning from paintings to mixed media to sculptures, with most showcased on the inn’s premises, highlighting both established and emerging contemporary artists. On the first Wednesday of each month, there’s even a happy hour art tour where you can grab a drink from the hotel’s restaurant, Hamilton’s Kitchen, and subsequently be guided around by a Rollins Museum of Art staff member. 

Adding to its appeal is the hotel’s brand-new wing that opened last fall, featuring more guest rooms, a cafe and a long-awaited spa. The Spa is a 13,500-square-foot wellness oasis offering a comprehensive selection of treatments, many of which are named with Winter Park in mind, like the Mead Botanical Garden sculpting facial. There are also saunas, aromatherapy steam rooms, experience showers, a fitness center and an amenity space with a new pool surrounded by lounge chairs and private cabanas.

Dine + Drink

AVA MediterrAegean is Park Avenue’s latest it girl in terms of dining and drinking. Its menu, an artful mix of Mediterranean-inspired dishes and wow-worthy cocktails (like their Smoke and Mirrors tableside experience where a server carefully smokes an old-fashioned-inspired cocktail in front of you), sets it apart from neighboring establishments. Throw in its sleek, airy interior and MM, a members-only venue downstairs, and it’s no wonder there’s rarely an open table available.

For an equally buzzy scene, walk a few blocks down the avenue to Prato. Its long, centrally located bar is a communal gathering place, while their kitchen puts a signature touch on Italian mainstays. Order a wood-fired pizza or their cult-favorite mustard spaghettini “cacio e pepe.” 

Next time you’re craving a perfectly cooked steak, there’s only one place to go: Christner’s Prime Steak & Lobster. With wood-paneled walls, white tablecloths and top-notch service, it’s the epitome of a classic steakhouse, which is why it’s no surprise it’s been a Winter Park fixture for 30 years.

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Along with dining, Winter Park is equally a shopping destination, and it’s easy to spend an afternoon wandering through Park Avenue’s countless boutiques with a Barnie’s Coffee & Tea Co. drink in hand. If you’re not sure what you’re on the hunt for, Frank is a great place to start thanks to its elevated, yet expansive collection of gifts, from accessories and books to homeware and apothecary. Fine jewelry lovers will appreciate the curated selection of baubles at Be On Park that are begging to be worn, not tucked away in a jewelry box, and down the block, John Craig Clothier has everything the modern man needs to put his best-dressed-self forward. Other must-shops include the always adorable Tugboat & the Bird that’s part toyshop, part children’s boutique, and Siegel Clothing, a family-owned-and-operated Florida-inspired outfitter that’s been a staple on Park Avenue for over three decades.

A short walk away is Hannibal Square, home to Rifle Paper Co., the flagship store for the iconic stationary brand, along with Monkee’s of Winter Park, a womenswear boutique bursting with fun, head-to-toe party looks. Then over on Pennsylvania Avenue is Clementine and The Grove: the former a one-stop shop for the perpetual hostess who appreciates beautiful yet unique entertaining essentials and the latter offering clothes, accessories and gifts that embody a distinctly sunny state of mind.

While there may not be any beachfront properties in town, there are plenty on the lakefront. The best way to see the beauty of the Winter Park chain of lakes is by hopping aboard the city’s Scenic Boat Tour. These guided, hourlong pontoon voyages are narrated by local captains who navigate the canals that connect three of Winter Park’s seven lakes while cheekily narrating the city’s history and lore. Private charters are also available. 

There’s by no means a shortage of museums, so it’s easy to spend an afternoon getting cultured. The Charles Hosmer Morse Museum of American Art is home to the most comprehensive collection of Louis Comfort Tiffany glass in the world, displaying numerous exhibits dedicated to the famed artist, highlighting everything from his lamps to his chapel interior from 1893. To continue your enlightening museum crawl, venture over to the Rollins Museum of Art, followed by the Albin Polasek Museum & Sculpture Gardens. 

So now, when you close your eyes and envision a weekend in Orlando, trade the stereotypes for Michelin-starred menus, craft cocktails, designer shopping, boutique hotels, storied museums and world-class performing arts—oh, and the swans, don’t forget about the swans.  

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