Nantucket's cobblestone streets, candlelit restaurants, and stunning sunsets create the perfect setting for romance. Here are our top picks for a memorable date night.
The Chanticleer
Most Romantic Overall
Rose-covered cottage in Sconset serving French-inspired cuisine. Garden dining in summer is pure magic. This is special-occasion dining at its finest.
Sunset Sail
Most Memorable Experience
Watch the sun drop over the island from a classic sailboat. BYOB on most cruises. Book a private charter for extra romance.
Dune
Most Intimate
Tiny, sophisticated restaurant with creative cuisine. The small space creates an intimate atmosphere. Reserve well ahead.
Cru
Best Waterfront
Oysters, cocktails, and harbor views at sunset. Start here for drinks even if dinner is elsewhere.
Ventuno
Best Late Night
Sophisticated Italian with a lively bar scene. Perfect for dinner, or come late for cocktails and jazz.
The Club Car
Best Piano Bar
Classic cocktails and live piano in an elegant setting. After-dinner drinks here are a Nantucket tradition.
Madaket Sunset Picnic
Best Low-Key Romance
Pack cheese, wine, and a blanket. Watch the legendary Madaket sunset together. Simple and unforgettable.
Topper's at The Wauwinet
Best Splurge
Elegant dining at a secluded luxury hotel. Take the hotel's launch from town for a truly special experience.
Perfect Date Night Itineraries
Classic Romance
Sunset sail → Walk through town → Dinner at The Chanticleer → Nightcap at The Club Car
Casual & Fun
Cisco Brewers afternoon → Madaket sunset → Millie's for fish tacos → Stroll downtown
Foodie Evening
Oysters at Cru → Walk to Ventuno for dinner → After-dinner jazz at the bar
Date Night Tips
- Make reservations 2-4 weeks ahead in summer
- Request outdoor seating for waterfront restaurants
- Sunset timing varies - check before planning evening
- Dress is smart casual at most restaurants
- Walk between dinner spots - the evening stroll is part of the romance