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VRBO Suggestion – Heart of the Gulch
Day 1 (evening arrival) Drinks/Bites in Printers Alley Skulls Rainbow Room for Burlesque Show 11pm – Printers Alley Day 2 Coffee at Barista Parlor Walk around Centennial Park & visit the Parthenon Lunch at Edley’s BBQ or The Local Explore the Gulch Dinner Harper’s Steakhouse Drinks at Twelve Thirty Club (Justin Timberlake’s high end bar with live music, all day long starting at 10am) Nightlife at Luke Combs Bar – line dancing and iconic bathroom photo op Kid Rock’s Big Honky Tonk – live bands Day 3 Breakfast at Pancake Pantry OR Milk & Honey – honey lattes and biscuits Prince’s Hot chicken – lunch Explore 12 South – Hit the Murals (I believe in Nashville) , playdate bar (fun slide moment) Dinner Ellington’s (sophisticated southern) OR Dinner at Hampton Social Drinks at Patterson House – speakeasy Bar hopping: Eric Church’s Bar (Chief’s) – Must-try burnt ends for a snack. Morgan Wallen’s This Bar Jelly Roll’s Bar – Goodnight - Laid-back vibes and live music. Lainey Wilson’s Bar – Bell Bottom’s Up -Great wings + fun piano bar downstairs Day 4 Brunch White Limozeen (Dolly Parton Inspired rooftop) Dinner at Etch Drinks at The Bobby Hotel Rooftop House of Cards (magic & Upscale Dinner Show) Day 5 Coffee & Donuts at Five Daughters Bakery Other ideas: Losers Bar (Midtown) – Riley Greens Spot with surprise performances The Local – Great lunch spot Visit Arrington Vineyards for wine tasting – 32 min drive from the Gulch Jack Daniel’s Distillery (2.5 hours away)
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Restaurants
1. Delaire Graff Estate (Stellenbosch)
Why: Known for Bordeaux blends & stunning mountain views. Must-Try: Cabernet Sauvignon Reserve, Delaire Graff Rosé. Bonus: Art gallery, spa, and two award-winning restaurants. 2. Babylonstoren (Franschhoek) Why: Iconic Cape Dutch farm with organic gardens and a holistic experience. Must-Try: Mourvèdre Rosé, Babel Red Blend. Bonus: Garden-to-table dining at Babel and The Greenhouse. 3. Waterford Estate (Stellenbosch) Why: Renowned for its Wine & Chocolate Pairing experience. Must-Try: Kevin Arnold Shiraz, Waterford Estate Jem. Bonus: Beautiful Mediterranean-style courtyard and cellar tours. 4. Tokara (Stellenbosch) Why: Modern architecture, mountain views, and award-winning wines. Must-Try: Chardonnay, Director’s Reserve Red. Bonus: Restaurant Tokara offers exceptional fine dining with a view. 5. Creation Wines (Hemel-en-Aarde, near Hermanus) Why: Elevated tasting experiences & food pairings w/ panoramic valley views. Must-Try: Pinot Noir, Viognier. Bonus: One of the most innovative wine and food pairing menus in SA. 6. Rust en Vrede (Stellenbosch) Why: Historic winery producing world-class red wines. Must-Try: Estate Red, Syrah. Bonus: Intimate fine dining restaurant with a seasonal tasting menu. 7. Klein Constantia (Constantia Valley) Why: Legendary producer of Vin de Constance, a world-famous dessert wine. Must-Try: Vin de Constance, Sauvignon Blanc. Bonus: Serene estate nestled in Cape Town’s oldest wine region. 8. Beau Constantia (Constantia) Why: Boutique winery with glass-encased tasting room overlooking the valley. Must-Try: Lucca Red Blend, Cecily Viognier. Bonus: Chef’s Warehouse restaurant on site—perfect for lunch. 9. Stark-Condé Wines (Jonkershoek Valley, Stellenbosch) Why: Peaceful and romantic setting with a tasting room on a lake. Must-Try: Syrah, Three Pines Cabernet Sauvignon. Bonus: Intimate and off-the-beaten-path with incredible mountain views. 10. Bouchard Finlayson (Hemel-en-Aarde, near Hermanus) Why: Specialists in Burgundian-style Pinot Noir and Chardonnay. Must-Try: Galpin Peak Pinot Noir, Missionvale Chardonnay. Bonus: Stunning hiking trails on the estate. WEEK 1: CAPE TOWN - CITY & COAST
Day 1-3: Arrival & City Immersion Stay: Ellerman House – Clifton Highlights:
Stay: Ellerman House Highlights:
Stay: Move to The Silo Hotel – V&A Waterfront Highlights:
Day 8-10: Stellenbosch Serenity Stay: Delaire Graff Estate Highlights:
Stay: La Residence – opulent vineyard retreat Highlights:
Day 15-17: Hermanus – Ocean Meets Wine Stay: Birkenhead House Highlights:
Stay: The Strandloper Ocean Boutique Hotel Highlights:
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