Where to Stay in Orlando

Two luxury hotels: one a convenient oasis near Disney; the other a hidden gem of art-filled charm a world away
Orlando
Hyatt Regency Grand Cypress Resort, Aerial ViewPhoto Courtesy of Hyatt Regency Grand Cypress Resort

Orlando is an escape to a wonderland of entertainment and dining unique in this world. “Where to stay” is obviously integral. It’s the launchpad from which to experience it all. More than comfort and convenience, we seek an escape within an escape; accommodations that are not only comparable to our experience, but elevate it. After all, Orlando is the “Theme Park Capital of the World,” Where Imagination Takes Flight.

1. Hyatt Regency Grand Cypress Resort

Orlando
Hyatt Regency Grand Cypress ResortPhoto Courtesy of Hyatt Regency Grand Cypress Resort

The hotel itself is a vacation; it’s Orlando without a queue. Set around its own private lake and sprawling tropical grounds, the Hyatt Regency Grand Cypress Resort feels surprisingly removed from the theme-park frenzy just beyond its gates. Here, we plan for a day in which we deliberately remain at the hotel to enjoy the enormous lagoon pool, water sports on the lake, golf, rock climbing, bikes, mini-golf and dining.

One big draw is the pool, not typical of a hotel. A lagoon-style complex is punctuated by 800,000 gallons of water in which twelve waterfalls, two hot tubs, a splash pad and waterslide stream through rock formations that encompass a destination unto itself. There are caves to swim through and secluded corners where the experience begins to feel less like a hotel swimming pool and more like an aquatic playground.

Orlando
Exterior Pool Waterfalls, Hyatt Regency Grand Cypress ResortPhoto Courtesy of Hyatt Regency Grand Cypress Resort

From the balcony of our bright and cozy suite we ovelook the 21-acre Lake Windsong where we can kayak, paddle-board, canoe, sail, paddle boat and even hydro-bike. Disney World is minutes away, but we are content relaxing on the beach.

Just off the beach, the LakeHouse Restaurant & Bar is where our breakfast of Florida Pink Shrimp and grits with linguica, onions, tomato and a poached egg is our scrumptious palette opener to the day.

Orlando
Shrimp and Grits, Lakehouse Restaurant and Bar, Hyatt Regency Grand Cypress ResortPhoto by Adam Waxman/DINE magazine

The main dining event, however, is the headline restaurant, Four Flamingos, A Richard Blais Florida Kitchen. Chef Blais makes dining exciting as his menu reflects the tropical ambience and conviviality of service that encapsulates the Orlando vibe with panache and flare.

Oysters & Pearls at Four Flamingos
Oysters & Pearls at Four FlamingosPhoto courtesy of fourflamingosorlando.com

Hyatt Regency Grand Cypress Resort, 407-239-1234, 1 Grand Cypress Blvd, Orlando, FL

2. The Alfond Inn

Orlando
The Alfond Inn, OrlandoPhoto Courtesy of The Alfond Inn

The other side of Orlando challenges what we think we know about Orlando. Winter Park is a charming neighbourhood that does not feel like the Orlando we expect.

North of the theme parks, a canopy of live oak trees line brick streets of boutiques, cafés and restaurants. Tucked just off of Park Avenue the personality of the boutique Alfond Inn is immediately apparent, as we feel like we’ve checked into an art gallery.

Orlando
The Alfond Inn, LobbyPhoto Courtesy of The Alfond Inn

Part contemporary art museum, it is an extension of the Rollins Museum of Art, with works from the Alfond Collection of Contemporary Art displayed throughout its public spaces. Wandering through the hotel is part of the experience as corridors and lounges are all galleries.

In fact, the hotel is owned by Rollins College, stewarded by the Rollins Museum of Art, and its net operating income supports scholarships for Rollins students. This creates an unusual proposition where ordering a cocktail can feel almost philanthropic.

Orlando
The Alfond Inn, SuitePhoto Courtesy of The Alfond Inn

Our room continues the hotel's approach to luxury through art, creating a hip vibe that is comfortable, modern and chic. It is such a pleasure to wake up within this palette of colours. Every accoutrement beckons our curiosity and sets a whimsical tone for our stay. Our balcony overlooks a quiet pool and sun deck on which to make one of life’s great decisions: cocktail or nap? There are two pools and a spa with sauna and steam.

Orlando
The Alfond Inn, Spa PoolPhoto by Adam Waxman/DINE magazine

From amidst the elegant southern charm of The Alfond Inn we enter the hotel’s signature restaurant, Hamilton's Kitchen, which harmonizes the lush surroundings in the courtyard with a menu inspired by Florida and the American South. Happy and relaxed, we are a world away.

Peaches and Southern Fare at Hamilton's Kitchen
Peaches and Southern Fare at Hamilton's KitchenPhoto courtesy of www.hamiltonskitchen.com

The Alfond Inn, 407-998-8090, 300 E New England Ave, Winter Park, FL

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