Destination
Shelter Island
In between everywhere. Ferries and hidden coves.
Shelter Island sits between the North and South Forks and is the most convenient island in the country for someone with a boat. From Sag Harbor you can be at the sandbar off Shell Beach in fifteen minutes. From Greenport it is a five-minute crossing. We use Shelter as the anchor for a lot of days that start and end elsewhere, because it lets a group swim, eat, and rest between two harbors without a long ride. The Ram's Head, Sunset Beach, and Crescent Beach are all reachable by tender. Docking on Shelter itself is limited, but we can arrange a mooring off Coecles Harbor or a dinghy in to Sunset Beach for lunch. If your group is split between the North Fork and Sag Harbor, this is where we meet in the middle.
Top routes from Shelter Island
Anchor on the west side of Shelter for a swim afternoon.
Dinghy in to Sunset Beach for a slow lunch, then cruise.
Quiet cruise around Ram Island and back.
A sample day in Shelter Island
- 12:00 pmBoarding at Sag Harbor or Greenport.
- 12:30 pmAnchor at Shell Beach.
- 2:00 pmDinghy in to Sunset Beach for lunch.
- 4:30 pmCruise around Ram Island.
- 6:00 pmReturn.
Boats that depart from here
Local FAQ
Can we dock on Shelter?+
Limited transient slips. We usually anchor or moor off and tender in.
Are the ferries a problem?+
Not at all. We know the schedule and stay clear of the runs.
Best time of day?+
Late afternoon. The west side of Shelter for sunset is one of the best light shows on the East End.
We are Carter and Sean, local captains out of Sag Harbor. Shelter Island sits right across the bay from our home port. On a fast boat we are there in ten minutes. It is one of the most relaxed spots on the East End, and we run charters here all summer. Boats from 22 ft to 122 ft with a captain on every trip.
Why charter out of Shelter Island
Shelter Island is a slower pace. The traffic is lighter, the docks are quieter, and the water around the island is easy to love. You have Coecles Harbor on the south side, Dering Harbor on the north side, and Crescent Beach on the west. In one afternoon you can hit all three and still have time for dinner.
A Shelter Island yacht charter with us usually starts in Sag Harbor and crosses the sound, or we meet you at a dock on the island. Either way you get the best of both worlds. Restaurants and shops in Sag Harbor and quiet coves and beaches on the island.
We are USCG licensed and fully insured. Every charter has a captain. See the for boats.
Top routes and stops from Shelterr Island
Route one is the Crescent Beach and Sunset Beach loop. Crescent Beach is on the west side of the island. The water is calm and the sand is soft. Sunset Beach the restaurant is nearby, and the sunset view from the water is one of the best around.
Route two is the Dering Harbor and Ram Island run. We come around the north side, ease into Dering Harbor for a look at the old estates, and swing east past Ram Island. Ram Island is small but pretty. The channel between the two is a fun cruise.
Route three is the Coecles Harbor drift. Coecles is on the south side of the island. Big, open, well marked, and a favorite for anchoring. Great for a long swim stop with the group.
A sample day departing from Shelter Island
10:00 am. Meet at the dock. Load in, safety brief.
10:20 am. Lines off. Head to Crescent Beach for the first swim.
12:00 pm. Cruise around to Dering Harbor. Dock and dine if you want, or eat on the boat.
2:00 pm. Push east to Ram Island and drift along the shore.
3:30 pm. Second anchor in Coecles Harbor. Toys off the back.
5:00 pm. Return to the dock. Or push back to Sag Harbor for dinner in the village.
Best boats for Shelter Island
Any of our day boats work well around the island. For a small group, the 22 ft is fast and fuel friendly. For a bigger group, the mid size cruisers give you shade and room. For events or big groups, the 122 ft event yacht can host in deeper water. See .
Boarding,parking, and logistics
We can board in Sag Harbor and cross to the island, or meet you at a marina on the island. Ferry traffic can be busy in July and August, so if you are coming from the mainland, plan on the ferry lines being slow. If you are staying on the island, we make it easy. We come to you.
Bring layers for the boat ride, 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 Shelter Island season. Water warms up by late June. July and August are peak. The channels around the island can get busy on weekends, so mid week trips are our favorite. Wind out of the south builds in the afternoon. We work the calm side of the island when it does.
What locals do vs. what tourists ask for
Tourists ask for a stop at the busy west side scene. Fair enough, and we can do it. Locals go the other way. They anchor in Coecles, swim, nap, and drift with the tide. Locals know the little sandbar on the north side that shows up at low tide. Locals also know that a sunset cruise off Crescent Beach on a calm evening is one of the best hours in the summer. Also see our Sag Harbor and Greenport and the North Fork pages.
Frequently asked questions
Can I book a Shelter Island boat rental if I am staying on the island?+
Yes. We meet you at a marina on the island. Just tell us where you are and we work out the pickup.
How long does it take to cross from Sag Harbor to Shelter Island?+
About ten minutes at cruise speed. Very short hop.
Do you offer private boat tours around Shelter Island?+
Yes. A full loop of the island is one of our most requested trips.
Is Coecles Harbor good for swimming?+
Very good. Big, calm, and easy to anchor. One of our favorite swim stops.
Can we dock and dine on Shelter Island?+
Yes. There are a few waterfront restaurants that take boat traffic. We handle the timing and the tie up.
What is the vibe on Shelter Island?+
Slow, quiet, and easy. That is why locals love it.