Destination
Greenport / North Fork
Wineries, a working harbor, and quiet cruising.
Greenport is a real working harbor, and the town has kept its shape. The docks in front of Claudio's are our regular pickup on the North Fork, and from there you can cruise east to Orient Point, west toward Robins Island, or hop over to Shelter Island in ten minutes. The North Fork has become the wine country of the East End, and we can arrange a car service from the dock to two or three tasting rooms and back. Cruising here is calmer than the ocean side, and the bay water warms up early in the season. Greenport is a great starting point if your group is coming from the North Fork or Riverhead and wants to skip the drive down 27. Boarding here is quick, parking is easy, and the town is a five-minute walk from the slip.
Top routes from Greenport / North Fork
A slow cruise east with a swim stop.
Dock, car to a winery, back on the water for sunset.
Two hours across the bay. Meet the rest of the group in Sag.
A sample day in Greenport / North Fork
- 10:30 amBoard at Mitchell Park Marina.
- 11:00 amCruise east toward Orient Point.
- 12:30 pmAnchor for lunch.
- 2:00 pmOptional dock and drive to a winery.
- 5:00 pmReturn.
Boats that depart from here
Local FAQ
Where do we board?+
Mitchell Park Marina, in front of Claudio's. Five-minute walk from the ferry.
Can you arrange a winery visit?+
Yes. We book a car service and two tasting rooms based on what you like to drink.
Overnight?+
Yes. Greenport is a great overnight base with easy dining ashore.
We are Carter and Sean, local captains out of Sag Harbor. The North Fork is a totally different world from the South Fork, and we love running charters over there. Greenport Village is a great stop, and the waters around Orient Point and Sterling Harbor are some of the most scenic on the East End. Boats from 22 ft to 122 ft with a captain on every trip.
Why charter out of Greenport
Greenport is a working village on the water. It has a real main street, a good harbor, and easy dock access. From the harbor you can reach Shelter Island in minutes, Orient Point in about half an hour, and the wine country of the North Fork right from the dock. It is a completely different feel than the South Fork. Slower, more local, and rooted in farming and fishing.
A Greenport yacht charter with us is often a dock and dine day. We tie up in the village, walk to lunch at a waterfront spot, and head back out. Some guests want the wine day, where we cruise the bay and stop for a bite near the wineries. Others want a full day out to Orient Point and back. All fair game.
We are USCG licensed and insured. See boats at .
Top routes and stops from Greenport
Route one is the village and Sterling Harbor loop. We come in past the Greenport waterfront, swing through Sterling Harbor, and tie up in the village for lunch. Easy and scenic.
Route two is the Orient Point run. We head east from Greenport, past the north side of Shelter Island, and out to Orient Point. The lighthouse view from the water is a highlight. On a clear day you can see across to Plum Island and beyond.
Route three is the Peconic Bay wine country cruise. We work west along the bay side of the North Fork. You can see the vineyards from the water. We can arrange a lunch stop at a spot near the wineries so you get both the boat day and the wine day.
A sample day departing from Greenport
10:00 am. Meet at the dock. Load in, safety brief.
10:20 am. Lines off. Cruise past the Greenport waterfront.
11:00 am. Anchor off Shelter Island for a first swim.
12:30 pm. Head back to the village. Tie up and walk to a waterfront restaurant for lunch.
2:00 pm. Push east toward Orient Point. Lighthouse views.
3:30 pm. Second swim in calm water.
5:00 pm. Return to the dock in Greenport.
Best boats for Greenport
Any of our boats work well out of Greenport. For a small group, the 22 ft or 28 ft is quick and easy. For a group of eight to twelve, our mid size cruisers are a great pick. For a wedding or a party, the 122 ft event yacht is set up for big groups. See .
Boarding,parking, and logistics
We board most Greenport charters at a marina in Sterling Harbor or right at the village docks. Parking in the village is manageable in the off hours and tight in July and August. Give yourself 15 minutes to load in. If you take the LIRR to Greenport, the station is a short walk to the dock, which is a huge plus for city guests.
Bring layers, sunscreen, and soft soled shoes. We supply ice, water, towels, and a clean head.
Best time of year and weather notes
May through October is our Greenport season. The North Fork stays busy well into September, when the wineries hit their harvest. Wind out of the south builds in the afternoon. Peconic Bay can chop up, but the water inside Sterling Harbor stays calm.
What locals do vs. what tourists ask for
Tourists ask us to cross from the South Fork and go straight to a famous dockside spot. Fair enough. Locals go slower. They start with a swim off Shelter Island, then ease into the village at 1 pm when the lunch rush has cleared. Locals often pair a boat day with a stop at a winery for the sunset. That combo is hard to beat. Also see our Shelter Island and Sag Harbor pages.
Frequently asked questions
Can I book a Greenport boat rental for a wine day?+
Yes. We can plan the cruise around a stop near one of the wineries and time the tide so the tie up is easy.
How long is a typical Greenport yacht charter?+
Four to eight hours. Full days are popular in the summer.
Do you dock and dine in Greenport Village?+
Yes. The village has waterfront restaurants that take boat traffic. We handle the timing.
Do you offer private boat tours to Orient Point?+
Yes. Orient Point and the lighthouse are one of our most requested runs.
Is Greenport good for a family day?+
Yes. The village is fun for all ages, and the water around Shelter Island is calm and swim friendly.
Can we bring wine on board?+
Yes. Bring what you want. We supply ice and cups.