

Embarking from Greenport, NY, you’re setting sail along the picturesque North Fork of Long Island towards Montauk, NY. This journey offers a perfect blend of scenic views, opportunities for wildlife spotting, and safe anchorages, making it ideal for both experienced boaters and those looking to enjoy a leisurely cruise.
Starting your voyage at Greenport, a charming village with a rich maritime history, you’ll find the harbor well-equipped with amenities for supplies and dining. As you prepare to leave, check your vessel’s condition and monitor the weather forecast, particularly since you’re sailing along an area known for occasional swift changes in conditions. Ensure all necessary safety equipment is onboard, including life jackets, flares, and a first aid kit.
1. Initial Departure: As you exit Greenport Harbor, head eastward through the narrow channel while watching for local fishing boats. This area can be busy at times, so keep a lookout for navigational aids, especially buoys marking the channel's edges.
2. Shelter Options: If the waters turn rough or unpredictable, look to Peconic Bay and its numerous smaller inlets. This bay provides abundant shelter with various locations like Shelter Island or even Fort Pond Bay, where you can lay anchor until conditions improve.
3. Navigational Aids: Pay attention to markers as you navigate eastward. The Greenport Range Lights will guide you out of the harbor. After passing through the open waters, you'll need to keep an eye on the buoyage system along the way. Focus particularly on the entrance to Noyac Bay. The Noyac channel is well-marked, so stay within the designated areas as you move forward.
4. Point of Interest: Cedar Point County Park: Just past the entrance to Noyac Bay, you can consider dropping anchor off Cedar Point County Park. This area is perfect for a quick swim or picnic while enjoying scenic views of the Long Island Sound.
5. Continuing the Journey: As you progress towards Montauk, watch for the Point Montauk Lighthouse just before you enter the Montauk Harbor. This historic landmark is not only a picturesque sight but also signals that your next destination is just around the bend.
Upon arriving at Montauk, you’ll be greeted by its vibrant harbor where you can find numerous spots for fresh seafood dining and unique local boutiques. Montauk offers various activities from surfing at Ditch Plains Beach to exploring the scenic trails of the Montauk Point State Park.
While this trip promises delightful views and experiences, safety is paramount. Here are a few additional reminders:
This route is particularly suitable for recreational boaters who desire a relaxing yet attentive experience while enjoying the beauty of Long Island's coastline. Whether you are a seasoned sailor or a family looking for an adventure on the water, this trip from Greenport to Montauk will leave you with treasured memories and a connection to the rich seafaring culture of the area. Always remember, safety first, with adventure waiting just beyond the horizon.