Destinations
Nine ports we know by heart.
From Sag Harbor to Fishers Island, every one has its own weather, dockmasters, and best time of day.
Home port. Whalers' town turned quiet harbor.
Three Mile Harbor, quiet mornings, long light.
Big water, big fish, the lighthouse at the end.
Shinnecock, sand bars, and quiet coves.
Beach launches, small charters, low-key days.
In between everywhere. Ferries and hidden coves.
Wineries, a working harbor, and quiet cruising.
A day trip that feels like a week.
The quietest island on the East End.
The East End of Long Island is one of the best charter playgrounds on the East Coast. From our home port in Sag Harbor, we can reach nine distinct destinations, each with its own character. Some are quick 20 minute runs. Some are half day crossings. All of them are worth the trip.
Here is a quick tour of every spot we run to, plus notes on which destinations pair well together.
Sag Harbor
Home port. Historic whaling village. Long Wharf, cedar shingle houses, and one of the best small town restaurant scenes in the state. Most of our charters start and end here. Popular short trips include a two hour harbor cruise, a sunset run past Cedar Point Lighthouse, and a dinner drop off at Long Wharf.
Highlights: Long Wharf, Havens Beach, Sag Harbor Cove, and the Turtle Cove anchorage.
East Hampton
A 30 minute run from Sag Harbor. Best known for the ocean beaches, but the bay side offers Three Mile Harbor, Gardiner's Island views, and Napeague Harbor. Great for sunset cruises past Louse Point and lunch stops at Bostwick's on the Harbor.
Highlights: Three Mile Harbor, Gardiner's Bay swim spots, Cedar Point beach, and Sammy's Beach.
Montauk
The end of the island. About an hour from Sag Harbor by fast boat. Home to the best offshore fishing on the East End and some of the wildest scenery. Popular runs include a lunch stop at Duryea's Lobster Deck, a Ditch Plains swim stop, and offshore trips for tuna and mahi.
Highlights: Montauk Point Lighthouse, Fort Pond Bay, Ditch Plains, and the offshore canyons.
Southampton
A little quieter than East Hampton, and prettier from the water than most people realize. We run into Shinnecock Bay for family days, and along the ocean side for beach cruises. Great option for guests staying west of the canal.
Highlights: Shinnecock Bay, Cold Spring Pond, and the North Sea beaches.
Amagansett
A 45 minute run from Sag Harbor into Napeague Harbor. The sandbar off Napeague is one of the best summer anchor ups on the East End. Shallow, sandy bottom, warm water, and easy walking. Great for family days and low key group trips.
Highlights: Napeague Harbor, Napeague sandbar, and Lazy Point beach.
Shelter Island
The gem in the middle of everything. A short run from Sag Harbor. Coecles Harbor for lunch at 18 Bay or Sunset Beach. Dering Harbor for shopping and a walk. Crescent Beach for a swim stop. This is our most requested destination for a half day trip.
Highlights: Coecles Harbor, Dering Harbor, Sunset Beach, Crescent Beach, and Ram's Head Inn.
Greenport and North Fork
About 45 minutes from Sag Harbor by boat. Historic waterfront, great restaurants, and easy dockside access to North Fork wine country. Popular full day trip: dock at Mitchell Park Marina, taxi to two wineries, and return for a Claudio's dinner.
Highlights: Mitchell Park Marina, Claudio's, Little Creek Oyster Farm, and the Greenport carousel.
Block Island
The big crossing. About two hours from Sag Harbor across Block Island Sound, weather dependent. Best done on a calm summer day with an early start. Lunch at the Oar. Beach afternoon at Ballard's. Bike the island. Return for a sunset cruise home.
We do not run to Block Island in rough weather. If we cancel for conditions, you get a full refund or reschedule.
Highlights: New Harbor, Ballard's Beach, Mohegan Bluffs, and the Southeast Lighthouse.
Fishers Island
The quietest of our destinations. About 90 minutes from Sag Harbor. Fewer boats, cleaner water, and a real old money New England vibe. Great for guests who want to escape the summer crowds. Dock at West Harbor and walk to lunch.
Highlights: West Harbor, Isabella Beach, and the Fishers Island Club (guests only).
Cross Town Routes That Work
Some of our best days are combos. Here are a few multi stop routes our guests love.
The Sunset Loop
Sag Harbor to Cedar Point Lighthouse to Shelter Island for a Sunset Beach dinner, then a slow ride home under the stars. 4 hours.
The Sandbar And Swim Day
Sag Harbor to Napeague sandbar for a long anchor up, then over to Coecles Harbor for a late lunch, then back. 8 hours.
The Full East End
Sag Harbor to Greenport for lunch, then over to Shelter Island for a swim, then back through Gardiners Bay for sunset. 8 hours.
The Montauk Push
Sag Harbor to Montauk with a Ditch Plains stop and lunch at Duryea's, then run home along the ocean side of Napeague. 8 hours.
The Block Island Crossing
Sag Harbor to Block Island for the day, return by sunset. Weather dependent. 10 hours.
How To Pick A Destination
If you are not sure, start with these questions.
- How long is your day? Short trips stay close. Long trips can push out to Montauk or Block Island.
- Are there kids? Sandbar days and calmer bay trips work best.
- Is this a special occasion? Sunset routes and dockside dinner drop offs are the move.
- Do you want to fish? Montauk. Every time.
- Do you want to swim? Shelter Island, Amagansett, or Gardiners Bay.
Take the quiz for a matched recommendation. Or email us and we will plan the day.
Ready To Explore?
Pick a destination above or let us pick for you. Most guests find that the best days combine two or three spots. That is what having a local captain unlocks.
email us
Frequently asked questions
Which destination is best for a first time charter?+
Shelter Island. It is close to Sag Harbor, has calm water, easy dock access, and great lunch spots. Perfect for a first day out.
Can we do Block Island as a day trip?+
Yes, weather permitting. It is about a two hour run each way from Sag Harbor. We recommend an early start and a full day charter. If conditions turn, we can substitute Shelter Island or Greenport at no extra cost.
What is the best sandbar in the Hamptons?+
Napeague, off Amagansett. Shallow, sandy, warm, and easy to anchor. On summer weekends get there by 11 am to grab a spot.
Can we do a wine country day by boat?+
Yes. We dock in Greenport and arrange a car to take your group to two or three North Fork wineries. Return to the boat for a sunset cruise home. Very popular with adult groups.
Are there quiet destinations that avoid the crowds?+
Yes. Fishers Island, the north side of Shelter Island, and Gardiners Bay stay quiet even in July. Tell us you want off the beaten path and we will pick a route almost no one else is running.