05/24/2026
Jackie O’s Guide to Memorial Day Weekend in Newport, Rhode Island 🤍⚓️🎾
Summers here still feel touched by Jackie Kennedy—salt air, white hydrangeas, harbor views, tennis whites, and effortless elegance.
If I were planning your Newport weekend inspired by Jackie O, here’s exactly where we would go:
⚓️ Stay & Stroll
• Check in to the + check out the rooftop harbor views
• Cruise Ocean Drive for the iconic shoreline + stop at Castle Hill Inn for the views
🍽️ Where to Eat
Flora at Gardiner House — Newport’s buzziest reservation for a reason. Mediterranean-inspired with notes of Marbella, Saint-Tropez & Capri, Rhode Island seafood, beautiful interiors, and harbor views that feel impossibly chic.
The Vanderbilt Dining Room— brunch here is a Newport must. Classic Auberge elegance and one of the prettiest ways to start the day. #
🎾 Jackie-Era Newport Musts
• International Tennis Hall of Fame — tennis whites encouraged
• St. Mary’s Church — where JFK & Jackie were married
• Bellevue Avenue + mansions (The Breakers is iconic)
• A short Cliff Walk for ocean views + Gilded Age architecture
• Ocean House in Watch Hill for sunset cocktails or brunch—the kind of grand seaside New England glamour Jackie would have loved.
⛵️ The Newport Experience
• On Watch Sailing around the harbor
• The Vanderbilt yacht for a harbor cruise
• Browse Thames Street + stop into Kiel James Patrick
🤍 For Jackie fans
Drive by Hammersmith Farm — Jackie’s childhood summer home and where her wedding reception was held. Even from outside, it feels special.
✨ My ideal Newport weekend:
✓ Vanderbilt brunch
✓ Harbor/yacht time
✓ Ocean Drive + Castle Hill
✓ Bellevue + one mansion
✓ Cliff Walk
✓ Tennis Hall of Fame
✓ Thames Street shopping
✓ Ocean House sunset cocktails
Newport somehow feels polished and relaxed at the same time—old money charm, sea breeze, tennis whites, and a little Jackie magic. Let’s go ✨
NewEnglandSummer