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Grand Cypress Golf Club

Orlando’s Legendary Golf Retreat

Gemstone Collection

Explore The Property


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


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


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


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. 

Disney Springs

Disney Springs is an outdoor shopping, dining, and entertainment complex at the Walt Disney World Resort in Bay Lake, Florida, near Orlando. The complex offers a great mix of unique shops, one-of-a-kind restaurants, lively entertainment, and activities for the entire family, while couples enjoy quality-time and business travelers relish time away from work. 

Scenic Boat Tour

Winter Park, famous for being one of the most scenic small towns in America, is home to Scenic Boat Tour, a leisurely one-hour boat ride through the Winter Park Chain of Lakes. During the tour on the 18-passenger pontoon boat, you will enjoy spectacular local scenery, including views of extravagant waterfront mansions and Florida wildlife. 

Paddleboat at Lake Eola

Escape from Orlando’s busiest attractions with a fun paddleboat ride on Lake Eola. Better yet, head out on a Sunday to pair it with stroll through Lake Eola’s renowned Farmer’s Market, featuring much more than your average farmer’s market, including seasonal fresh produce, unique drinks, home-cooked barbeque, and much more.

Winter Garden Farmers’ Market

Voted the number one farmers’ market in the nation by the American Farmland Trust, this downtown gem occupying a massive four blocks every Saturday from 10 a.m. to 2 p.m. is known for its variety of vendors. We’re talking everything from Indian chutneys at Nisha’s Flavors of India, smoked fish dips from Captain Jo’s, herbs and spices from Cacao n’ Spices, and the best pickles you’ve ever had from Mr. and Mrs. Pickles. With transportation to and from the market provided by the Villas of Grand Cypress ($10 per person), there’s no excuse not to visit.

Tibet-Butler Nature Preserve 

Located on the shore of Lake Butler, this 440-acre wildlife haven within earshot of Disney World is a bit of real Florida wilderness among the dense urban sprawl. A dream for nature lovers, photographers, and hikers, a trail system loops through a variety of habitats, including pine forests, swamps, and a cypress-lined shoreline, offering peeks at local flora and fauna like barred owls, ospreys, lizards, tortoises, and more. Complimentary transportation is offered by the resort with reservations.  

The Weekender

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


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.  


10 a.m. |  Breakfast in Bed
No rush to get dressed and head to breakfast. Simply order in-rooming dining from the on-site restaurants and have breakfast delivered. Choose from an array of options, including fresh waffles, lemon brioche French toast, omelets, and more.

12:30 p.m. | Check out the Winter Garden Farmers Market
Browse the nation's premier farmers’ market, located in downtown Winter Garden and offering everything from local crafts to baked goods to artisan food items. Of course, it wouldn’t be a farmers’ market without produce, of which you’ll find scores of golden beets, rainbow carrots, massive mangoes, and sweet bell peppers under the city pavilion.

2 p.m. | Lunch at The Whole Enchilada 
Located within easy walking distance of the farmers’ market on Plant Street, this Tex-Mex restaurant offers a rooftop patio and bar for open-air eats. The menu features nachos, salads, tacos, burritos, and, as the name implies, enchilada platters, plus a variety of margaritas.

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. | Late Dinner at Kres Chophouse
The kitchen of this steakhouse, located across the street from Mad Cow, doesn’t close until 12 a.m., so if you haven’t had dinner or just want a quick drink after the show, this is the place. Housed in a historic 1930s building, the steak house bills itself as“modern while still honoring the classics,” with prime beef aged in-house, hand cut to order, and ultra-fresh Florida fish delivered daily. 


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.

1 p.m. | Stroll the Tibet-Butler Nature Preserve 
The 2.6-mile Tibet-Butler Nature Trail at this 440-acre wildlife haven loops through a variety of habitats, including pine forests, swamps, and a cypress-lined shoreline, offering peeks at local flora and fauna like barred owls, ospreys, lizards, tortoises, and more. Complimentary transportation is offered by the resort with reservations.  


Flavor of…

The best food artisans, farms, and local markets.

Courtesy of 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. 

Courtesy of 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. Have a craving? The resort offers free transportation to the district. 

Courtesy of 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. 


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.


If looking to take advantage of your room’s fully equipped kitchen, this is your market to stock up at (the resort even offers complimentary shuttle service to and from). Located in the Crossroads shopping center, the hometown grocery rolls a full-service pharmacy, bakery, deli, seafood supplier, and general market shopping experience all into one. Check out their sushi – it's made fresh throughout the day by the on-site sushi chef. 

A Gemstone Collection Hotel

Grand Cypress Golf Club, One North Jacaranda, Orlando, Florida 32836   P: (407) 239-1909   Toll Free Reservations: 800-233-1234