Entrance To The Villas of Grand Cypress Golf Resort in Orlando, Florida
Resort Activities

The Adventurist

When simply “seeing” a destination just won’t do.

FEATURE ADVENTURE: Scotland in Florida

It’s the closest thing you’re going to get to playing the famed Old Course at St. Andrews in Scotland – without having to leave American soil. Designed by Jack Nicklaus, the New Course at Villas of Grand Cypress was built to model the Scottish links masterpiece. While the entire course isn’t an exact copy of St. Andrews, it certainly has the feel with double greens, stone bridges and walls, gorse mounds, burns, and pot bunkers as deep as 12 feet. Holes number 1 and 18, however, are replicas – hole 18 is a dogleg right that replicates the legendary Road Hole, while hole 1 includes a drive across a stone bridge. 

Discovery Cove

SeaVenture Tour | Discovery Cove

WALK ON THE WILD SIDE

After shimmying into wet suits and easing into a man-made coral reef consisting of 1.2 million gallons of saltwater, a dive helmet is lowered over you, feeding oxygen as you wander along the bottom of the reef floor. During the 20-minute experience, you’ll come eye-to-eye with sharks, pet velvety rays, and cut through schools of fish like Moses parting the Red Sea.

Airboat Cruise | Boggy Creek Airboat Rides

SPEED THROUGH THE SWAMP

Four unique airboat adventures soar up to 45 miles per hour atop the swamp water around Lake Tohopekaliga in Kissimmee, then slow to sashay through canals and marshlands to take in views of exotic birds, turtles, and the Florida alligator wallowing in their natural environment. Daily 30-minute, 45-minute, and one-hour tours are available.

 

Orlando Watersports Complex

Wakeboarding | Orlando Watersports Complex

GET UP GUARANTEE

Whether you're learning to get up for the first time or trying to master advanced tricks, a one- to four-hour lesson at Orlando Watersports Complex is guaranteed to take your ability to the next level. Regardless of your skill, a wide range of different cables allows even the most seasoned riders a challenge.

Like a Local

Quirky, under-the-radar highlights only a local could recommend. 

Celebration’s Town Center

Originally built by Disney as a planned community in the ’90s, the town of Celebration is a little bit like walking into the movie Pleasantville. The downtown area is meant to evoke the nostalgia of small-town USA with a host of quaint shops, sidewalk cafés, taverns, and movie theater housed in neo-traditional architecture. Regular evening events range from “snowy” Christmases to Food Truck Fridays to exotic car shows.

The Pharmacy 

What looks to be just an average elevator door within a breezeway inside Dr. Phillip’s Dellagio Plaza building is actually the unmarked entrance to Orlando’s trendiest speakeasy. Designed to mimic a 1920s apothecary, the establishment serves two kinds of menu items: “elixirs,” hand-crafted prohibition-style drinks, and “prescriptions,” an ingenious way of saying good-for-you farm-to-table fare. 

La Nouba 

Even if you don’t attend a show, a trip to see this striking theater located on the west side of Disney Springs – an outdoor shopping, dining, and entertainment complex – is a must. Constructed especially for Cirque du Soleil, the freestanding permanent structure resembles an enormous ivory circus tent. Inside, an elaborate mechanical stage includes movable glass cages, transporting you to a world of color, sound, and illusion. 

Café Tu Tu Tango

Plenty of restaurants like to display the work of local artists. This vibrant, bohemian tapas joint takes that one step further by also physically bringing in the artists to work among the diners, encouraging interaction and conversation about the creative process. Think of it as dinner and a show.

Artegon Marketplace

Inspired by famous marketplaces, like Seattle’s Pike Place, the London Flower Market, and Boston’s Faneuil Hall, this former shopping mall was renovated and rebranded in 2014 as the “anti-mall.” While you’ll find a few mainstream brands, like Bass Pro Shops, the heartbeat of this marketplace is the 100 artisans who sell eclectic goods, from hand-painted ostrich eggs to freshwater pearl necklaces.

The Weekender

How to spend 36 hours in Orlando, with Villas of Grand Cypress as your base camp. 

Friday

5 p.m. | Bike & Dine around Villas of Grand Cypress

Get your bearings of this 1,500-acre golf resort by borrowing a bike from the pool and taking it for a spin around the grounds (there are designated bike trails). Finish with dinner at The Club. Cap off the night relaxing by the pool that is central to the villas.  

Saturday

11 a.m. | Pontoon Tour with Scenic Boat Tours

These hour-long pontoon-boat cruises bring a little bit of Venice to Florida. Starting on Lake Osceola in Winter Park (just a few miles from downtown Orlando), you travel through two different narrow man-made canals – one into Lake Virginia to the south; the other into Lake Maitland to the north – passing azalea gardens, cranes, and multi-million-dollar mansions on the way.

12 p.m. | Afternoon on Park Avenue

Leave your car in the Scenic Boat Tour parking lot, and walk the two blocks west to Park Avenue, Winter Park’s classy shopping and dining district. The tree-lined 10-block stretch is home to more than 100 shops, from upscale national retailer Williams-Sonoma to modern-boho styles of the one-of-a-kind Forema Boutique. Grab lunch at one of the many sidewalk cafés (some of our picks: Prato, Luma on Park, Boca).

 

7 p.m. | A Show in the Church Street District

Head to Orlando’s historic downtown, home to the city’s top entertainment venues, fine dining, and nightlife, for a 7:30 show at Mad Cow Theatre. Photos from more than 100 productions – a mix of classics, contemporary plays, and musicals – from 15 seasons grace a colorful wall in the lobby. While a small theater, that just means you’re that much closer to the stage.

 

9:30 p.m. | Kasa Restaurant & Bar

The kitchen of this restaurant just a block down from Mad Cow doesn’t close until 11, so if you haven’t had dinner or just want a quick tapas plate or two after the show, this is the place. The menu – boasting Spanish and Asian influences, as well as a raw bar – is as fresh as the decor’s mix of warm wood and cool aquamarine.

Sunday

10 a.m. | Lounge Out at the Villa Pool

The beauty of the Villas at Grand Cypress is that you’re right on the edge of Disney World, yet you couldn’t feel further away. Relish the serenity at this pool, reminiscent of a natural lagoon that weaves through tropical vegetation and rocks. Drinks are brought to your lounge chair under the shade of palm trees.

Crooked Can Brewing Company

Crooked Can Brewing Company

It’s not easy to find good craft beer at $4 to $5 a pop, but Winter Garden’s new microbrewery has done it with 16 taps serving beers only brewed in-house, ranging from stouts to IPAs to amber ales. The best part? Crooked Can is located inside the Plant Street Market, a cluster of artisan shops, so you can actually walk around and peruse the other stores with a beer in hand. 

 Erin McKenna’s Bakery NYC

ERIN MCKENNA’S BAKERY NYC

Indulgent edibles are around every corner in Disney. However, this bakery, which opened in 2015 in the Disney Springs shopping district on the edge of the park parameters, filled a hole in the dessert roster: It only serves vegan and gluten-free items, including some of the best cookies, cupcakes, focaccia, and cinnamon rolls that even non-gluten-free patrons have said they’ve ever had.

 

Quantum Leap Winery

Quantum Leap Winery

Central Florida’s first urban winery has a two-fold mission: to make good wine from grapes from around the world, but to do so in an environmentally friendly way. All raw, unrefined wines are imported not in bottles but large plastic vessels to their Ivanhoe Village location, where – after aging, blending, and finishing – they’re packaged in kegs, pouches, or boxes – all low-carbon-footprint vessels. 

Scoops

Based in a historic building in downtown Winter Garden, Scoops is the old-fashioned ice cream shop of your childhood dreams with classic wooden counters and stools and checker-topped tables for a game of chess. Flavors range from key lime to cappuccino to salted caramel and include sorbets, sundaes, and milkshakes, but what the spot is really known for is its generous portions; one scoop is technically the size of three at only $2.50 to boot.

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