Grand Old House has been standing strong since 1908, originally built as a plantation home on Petra Plantation. Over the years, it’s been everything from a hospital and Sunday school to a beauty parlour and shelter during hurricanes. A doctor even once performed surgery on a dining table.
The house became a restaurant in 1969 and hasn’t looked back since. Despite the changes, it’s held onto its soul and added a few extras along the way, like the 5,000 square foot oceanfront deck where you can now toast to history with a perfectly chilled glass of wine.
It’s where you come for food with a view, and stay for the wine and conversations.
What to Sip
Taste new varieties
Grand Old House has a knack for sourcing unique wine varieties from little-known vineyards and grower producers. The result? Grand Old House offers Cayman unique, high-quality wines not found elsewhere in the world. The artisan champagnes and wines stocked are produced by the estate that owns the vineyards where the grapes are grown. This allows for a transparent and traceable source of products from farmers who are dedicated to sustainable farming methods and innovative practices. The farmers carry out all vineyard duties from vinification and bottling to aging.
Taste history in a glass
Wines here don’t just impress. They tell stories. Take a look at what’s come through the tasting room in the past:
- 1990 Antinori “Tignanello” – Once dubbed one of the greatest Tignanellos ever made, this Super Tuscan has earthy notes and just enough fruit to remind you of its star status.
- 1993 Prunotto Barolo Bussia – Barolo is famous for aging gracefully, and this one still has structure with firm acidity and a sense of place.
- 1995 Masi Amarone “Mazzano” – Rich, velvety, and full of dark fruit, this Amarone ages beautifully. With its deep structure and elegant finish, tasters are left wondering how incredible it might be in another 15 years.
Taste the big pours
When it comes to big pours, nothing tops Grand Old House’s Goliath. At 27 liters – the equivalent of 36 standard bottles – it’s ready to serve 200 guests. Priced at $20,000, it’s less a bottle and more a showstopper, because sometimes a regular pour just won’t do.
Where to Sip
You’ve got options. Want to sit outside and catch the ocean breeze? Prefer an air-conditioned nook with a view? From the grand Colonial Room with its own bar, the outside decks, or the private rooms tucked away in the heart of the house, every corner has its own vibe. Each wine room comes adorned with its own personality, story, and shelves stacked top to bottom with bottles. Here’s a taste of what you’ll find in each wine room:
- Jeroboam Room
This room is full of big, bold character. Just like the Californian Cabernets and Spanish reds it showcases. Think rich flavours, deep tradition, and plenty of personality. - Sassicaia Room
Inspired by Tuscany’s iconic Super Tuscans, this room is all about elegance. A perfect place to indulge in Italian reds and to pretend you’re sipping your way through Bolgheri. - Balthazar Room
Champagne dreams? This one’s for you. Decked out with a hand-painted Italian ceiling and a sparkling lineup of bubbles from France and Italy, it’s a celebration in a glass. - Melchior Room
The “go big or go home” room. Featuring large-format bottles — from Jeroboams to Melchiors — this one’s perfect for collectors or anyone who just likes making a statement with their wine. - Patio
The oceanfront patio is the buzz of Grand Old House. With space for up to 300 guests, it’s where sunset cocktails meet sea breezes and unforgettable dinners under the stars. Enjoy panoramic Caribbean waters that shift from gold to indigo as the sun sets, paired perfectly with fresh island dishes.
Beyond the sip
From the ocean and on the fire
The menu begins with ocean-to-table and farm-to-table principles. Local ceviche, lobster, conch, salmon, scallops, coconut prawns with mango salsa, and braised local goat offer a taste of Cayman’s freshest ingredients. Larger dishes such as seared scallops, seafood pasta, and blackened mahi-mahi continue the theme, each reflecting the same signature freshness of the Caribbean breeze.
Bold, fresh flavors and smoky aromas come alive in the outdoor kitchen, where the culinary team showcases the art of live-fire cooking with the daily barbecue special.
Sweet endings
To finish, desserts are crafted with the same attention to detail as the main courses. Guests can indulge in a crisp lime shell crust served with pineapple sauce or rich brownie delights paired with espresso and vanilla ice cream.
Refresh and relax
The specially created South Sound Breeze—a refreshing blend of cucumber, ginger, and mint—offers a non-alcoholic option that embodies the spirit of the neighborhood.
Yes, the food is excellent. And yes, the sunsets are spectacular. But for those in the know, Grand Old House is also home to one of the most unique and impressive wine experiences in the Caribbean. Here’s your wine guide on how to sip at Grand Old House.
