Ferry Ride: Exploring the Hamptons, Shelter Island, and Fire Island from Southold

Why Heaven Off Main is the perfect launch point for your coastal adventures

One of the best things about staying at Heaven Off Main in Southold is how effortlessly connected you are to some of the most beautiful destinations on the East End. While the North Fork is known for its peaceful vineyards and farm stands, it’s also a perfect jumping-off point for exploring the Hamptons, Shelter Island, and even Fire Island.

The local ferry system makes it incredibly easy. You can start your day with a coffee in Southold and be wandering the shops in Sag Harbor or walking the dunes on Fire Island by early afternoon. It’s simple, scenic, and surprisingly quick.

Here’s how to do it:

- Drive or bike to Greenport. It’s just a 10-minute ride from Heaven Off Main.
- Take the North Ferry to Shelter Island. It runs every 10 to 15 minutes and takes just 5 minutes.
- Cross Shelter Island at your own pace.
- Take the South Ferry to North Haven and you’re in the Hamptons. From there, you’re just minutes from Sag Harbor, East Hampton, or Amagansett.

Want to visit Fire Island?
You can also head west from Southold and take the ferry from Sayville or Patchogue. It’s an easy day trip that brings you straight to the car-free boardwalks, beaches, and charm of Fire Island. Perfect for a sunny beach day or a sunset stroll by the water.

Pro tip: Bring a picnic, pack light, and let the ferries do the work. You’ll get the best of both worlds — the tranquility of the North Fork and the adventure of island hopping all in one stay.

Let me know if you’d like a printable ferry guide or recommendations for what to do in each spot!