Destination
Fishers Island
The quietest island on the East End.
Fishers Island is a small favor. Technically part of New York but only accessible by ferry from Connecticut, it stays quiet in a way that no other East End destination does. There is no arrival scene, no dock crowd, no bars on the water. We run day trips here from Montauk or Greenport, and it is our top pick for a group that wants to disappear for eight hours. The east end of the island has a beach club and a golf course that you cannot get into without a member, so we do not chase that. What we do is anchor off the south side, swim, have a slow lunch aboard, and cruise the coast. On overnights, we tie up in West Harbor. Fishers is not for a first charter. It is for a group that has done the sandbar day and wants something quieter. Bring layers. The evening breeze is real.
Top routes from Fishers Island
A calm-water day crossing with a swim off the south side.
West Harbor overnight with a chef aboard.
A slow cruise past the lighthouse and back.
A sample day in Fishers Island
- 9:30 amBoard in Montauk.
- 10:30 amAnchor off the south side for a swim.
- 12:30 pmSlow lunch aboard, cruise the coast.
- 3:00 pmRace Rock Light photos.
- 5:00 pmReturn to Montauk.
Boats that depart from here
Local FAQ
Can we get off the boat on the island?+
Mostly no unless you are a member of the club. Everything we do here is on the water.
Is it too far for a day trip?+
Not from Montauk. It is a real day on the water, but the crossing is easy on flat days.
Best time to go?+
Weekdays in June or September. It stays quiet.
We are Carter and Sean, local captains out of Sag Harbor. Fishers Island is off the radar for most people who visit the East End, and that is exactly why we love it. It sits in Fishers Island Sound, quiet and low key, with some of the prettiest water in the region. A Fishers Island yacht charter is a longer run and takes planning, but the payoff is worth it.
Why charter out of Fishers Island
Fishers Island has a small, private feel. There are no big crowds, no busy ferry lines, and no packed marinas. The island itself is mostly residential, with a small village and quiet beaches. West Harbor on the north side is the main harbor for visiting boats. Isabella Beach on the south side is a favorite anchor spot on a calm day.
A Fishers Island yacht charter with us is a full day. We leave early, cross Block Island Sound or Fishers Island Sound depending on the pickup, and spend the middle of the day at anchor. If you want a quiet day away from the busy South Fork scene, this is the trip.
We are USCG licensed and insured. Every trip has a captain. See the for boats.
Top routes and stops from Fisherss Island
Route one is West Harbor. This is the main harbor on the north side of the island. Well protected, easy to anchor, and close to the village if you want to go in for a walk.
Route two is the Isabella Beach anchor. On the south side of the island, Isabella Beach is a quiet stretch of sand. On a calm day we can anchor off shore, drop the ladder, and enjoy a full afternoon of swimming and drifting.
Route three is the Fishers Island Sound cruise. We work along the shoreline, past the classic old estates, and get a full view of the island from the water. It is a scenic run with almost no boat traffic.
A sample day departing from Fishers Island
8:00 am. Meet at the dock in Sag Harbor or Montauk. Early start.
8:30 am. Lines off. Cross the sound.
10:30 am. Arrive at Fishers Island. Anchor in West Harbor.
11:00 am. Optional dinghy into the village for a walk.
12:30 pm. Cruise around to Isabella Beach. Lunch and a swim.
2:30 pm. Second swim and drift.
4:00 pm. Cross back toward Montauk or Sag Harbor.
6:00 pm. Return to the dock. Long day, good day.
Best boats for Fishers Island
Fishers Island is an open water run, so we use our bigger boats. Mid size cruisers and up. Ask us for the current recommendation based on the forecast and your group size. For a private event, the 122 ft event yacht is a great option. See .
Boarding,parking, and logistics
We board Fishers Island charters in Sag Harbor or Montauk depending on the day. Montauk is a shorter run to the island, so it is often the better pickup. We share the exact spot after booking. Give yourself 20 minutes to load in.
Bring layers, sunscreen, hats, and soft soled shoes. We supply ice, water, towels, and a clean head. Motion sickness meds are smart if the forecast is a little bumpy.
Best time of year and weather notes
Late June through early September is prime for Fishers Island. We watch the wave forecast for Block Island Sound and Fishers Island Sound. A short chop can make the ride long, so calm days are ideal. If the weather is not right, we reschedule.
What locals do vs. what tourists ask for
Tourists ask for the party dock scene. Fishers Island is not that. Locals come here to escape the crowd. Locals anchor, swim, read a book, take a nap, and cross back at a slow pace. The whole point of a Fishers Island day is to slow down. If you want big crowds and a loud scene, this is not the trip. If you want quiet water and a private feel, this is the one. Also see our Block Island and Montauk pages.
Frequently asked questions
How long is the ride to Fishers Island?+
From Montauk, about 60 to 75 minutes on a calm day. From Sag Harbor, closer to two hours. Depends on the boat and the sea state.
Is a Fishers Island boat rental a full day trip?+
Yes. It is a full day because of the run time. Plan on at least eight hours door to door.
Can we dock at Fishers Island?+
There are some moorings and dockage at West Harbor. Availability is limited, so we plan ahead.
Do you offer private boat tours around Fishers Island?+
Yes. All charters are private. Just your group with your captain.
What is the vibe on Fishers Island?+
Quiet, private, and slow. That is the appeal.
What if the weather is not right?+
We reschedule at no cost. Safety and comfort come first.