A Summer Day in Greenport: Our Must-Do’s

One of our favorite ways to spend a summer day? Hop the ferry from Sag Harbor to Shelter Island, cruise across the island, and catch the next boat over to Greenport. It’s the kind of slow, scenic journey that reminds you why the East End is so special — water on every side, sea breeze in your hair, and something great waiting at every stop.

Greenport has become a go-to destination for locals and visitors alike, and it’s easy to see why. From harbor views and wine tastings to boutique shops and unbeatable seafood, this North Fork gem has everything you need for a perfect summer outing.

Here’s how we love to spend the day:

Catch the Ferry Ride (Yes, Both of Them)

Start your adventure in Sag Harbor and take the ferry over to Shelter Island — it's quick, charming, and gives you a front-row seat to the best coastal views. Drive across Shelter Island (bonus points if you stop at Marie Eiffel Market), then take the North Ferry into Greenport. It’s a ritual we never get tired of.

Lunch or Sunset Drinks at Claudio’s Waterfront

Once you land in Greenport, Claudio’s is a must. Located right on the harbor, this iconic spot has been serving up fresh seafood and good times for over a century. We had the honor of renovating Claudio’s Waterfront, blending its historic character with modern updates to match the vibe of a busy summer crowd. Whether you grab a table on the deck or a seat at the bar, it’s the perfect place to soak in the scene.

Wander the Village

Greenport is full of charm — cobblestone streets, indie bookstores, art galleries, and curated shops with that just-right coastal aesthetic. Stop by Lido for effortless summer pieces, grab an espresso at Aldo’s, or wander through the carousel park by the marina.

Local Tasting Rooms & Breweries

From sparkling rosé to hoppy IPAs, Greenport’s tasting scene is worth a detour (or a dedicated afternoon). Greenport Harbor Brewing Co. is a staple, and the North Fork’s vineyards are just a short drive away. Perfect for a relaxed afternoon or pre-dinner tasting flight.

Sunset at the Pier

Before you catch the ferry back, take a walk to the end of Mitchell Park Pier. It’s one of the best spots to watch the sky turn gold, boats drift in, and the village wind down. The perfect ending to a North Fork day, well spent.

Zappola Construction: Building Where We Live & Play

We love Greenport for days like this — and we’re proud to be part of its evolution. From restaurants like Claudio’s to custom homes and specialty builds across the East End, we bring the same care and craftsmanship to every project.