Ram's Head Inn

Dating back to 1929, this Shelter Island gem offers sweeping waterfront views that are romantic 24/7/365. The journey to get here — a ferry ride across to Shelter Island — is part of the magic, transforming an ordinary dinner into a true escape.

For Valentine's weekend, they're pulling out all the stops with special prix-fixe menus featuring locally-sourced seafood, prime cuts, and seasonal ingredients from North Fork farms. The perfect escape for couples seeking classic elegance over crowds.

The restaurant occupies a beautifully restored 1920s building with original architectural details, warm wood tones, and picture windows framing the water. In warmer months, the outdoor terrace is pure magic — but even in February, the sunset views through those massive windows make every table feel like the best seat in the house.