Destination
Montauk
Big water, big fish, the lighthouse at the end.
Montauk is a different day than the rest of the East End. Real ocean, real fish, and the lighthouse at the tip that everyone wants a photo in front of. Charters out of Montauk lean either fishing or the classic east-to-west ocean run past the cliffs. We work with a small group of captains here who grew up chasing striped bass, and if you want to fish, this is where we send you. If you would rather cruise, we like the run from Montauk Harbor out to Gin Beach, then east along the bluffs to the Point. The lighthouse from the water is worth the trip on its own. Montauk gets busy in July. We can meet you at a private slip in Star Island or Gosman's Dock and have a plan for parking that will not ruin your morning.
Top routes from Montauk
Two hours around Montauk Point with a swim off Gin Beach.
Four hours chasing striped bass. Rods, tackle, bait included.
Push east twelve miles for lunch at Ballard's, back by sunset.
A sample day in Montauk
- 9:00 amBoard at Montauk Harbor with coffee and pastries.
- 9:45 amCruise east past Gin Beach and Shagwong Reef.
- 11:00 amPhotos at the Montauk Point Lighthouse.
- 12:30 pmAnchor for lunch in Fort Pond Bay.
- 3:00 pmReturn to Montauk Harbor.
Boats that depart from here
Local FAQ
Do you offer fishing charters?+
Yes. We work with two USCG captains in Montauk who specialize in bass and fluke.
What if the ocean is rough?+
We check the marine forecast the morning of. If it is not a good day for your group, we reroute inside or reschedule.
Boarding location?+
Star Island Marina or Gosman's Dock depending on the boat. We confirm the day before.
We are Carter and Sean. Montauk is The End, and we know it well. From Sag Harbor we can be in Lake Montauk in about 45 minutes, or we meet you right at the dock in Montauk to save time. If you want fishing, a sunset cruise, or a full day around the Point, we set it up.
Why charter out of Montauk
Montauk gives you a mix you cannot get anywhere else on Long Island. On one side you have Fort Pond Bay and Lake Montauk, both calm and easy. On the other side you have the open Atlantic and the rip off Montauk Point, which is famous for fish. In between you get Gin Beach, Navy Beach, and miles of coast that most people only see from the road.
A Montauk yacht charter with us is built around what you want. Some folks want to drop lines and chase striped bass. Others want a cocktail cruise at sunset with the lighthouse in the background. Some want a swim at Gin Beach followed by a bite at Gosman's Dock. All fair game.
We are USCG licensed and insured, and every trip has a captain. Fleet details on .
Top routes and stops from Montauk
Route one is the lighthouse loop. We run out of Lake Montauk, head east along the coast, and swing around Montauk Point Lighthouse. The lighthouse from the water is a totally different view than the one from the road. On a calm day we can get close in.
Route two is the Gin Beach and Shagwong run. Gin Beach is on the north side, right by the Lake Montauk inlet. Calm, clean, and great for a swim. From there we work west along Shagwong Point and drift over some of the classic fishing spots. Even if you are not fishing, the view is huge.
Route three is Fort Pond Bay and Navy Beach. We come in from the west side and drop anchor off Navy Beach. This is the sunset spot. You can dinghy in for a drink or stay on the boat and watch the sky turn pink. Very Montauk.
A sample day departing from Montauk
9:00 am. Board at Lake Montauk. Coffee and safety brief.
9:20 am. Lines off. Head out the inlet.
10:00 am. First fishing drift or a swim at Gin Beach, your call.
12:00 pm. Lunch on the boat, or a quick stop at Gosman's Dock for a bite.
1:30 pm. Cruise east to the lighthouse. Photos, drone if you brought one.
3:00 pm. Work back west along Shagwong for a second swim or another drift.
5:00 pm. Return to the inlet and back to the dock.
Best boats for Montauk
Montauk water can get bigger than what you find inside the bays. For open water days we like our mid size cruisers with more freeboard. For a fishing trip, ask us about our center console setup. For a party or an event, the 122 ft event yacht can meet you in the deeper spots. See for the full list.
Boarding, parking, and logistics
Boarding is at a marina inside Lake Montauk. We share the exact slip after booking. Parking is easier than the village of Sag Harbor, but the marina lot fills up in July and August. Give yourself 20 minutes. If you are driving out from the city, allow time for summer traffic on Route 27.
Bring layers. It gets breezy off the Point even on a warm day. Sunscreen, hats, sunglasses, and soft soled shoes. We supply water, ice, towels, and a clean head.
Best time of year and weather notes
Late June through early October is the sweet spot in Montauk. Water is warmest in August. Fishing gets very good in September and October when the bait pushes through. Wind out of the southwest builds every afternoon in summer, so morning trips are usually the smoothest. Fog can roll in fast off the ocean. If we see it coming, we adjust the route to safer water.
What locals do vs. what tourists ask for
Tourists want the party dock scene. That is fine, and we can drop you there. Locals want the quiet swim at Gin Beach at 11 am before the crowd shows. Locals fish the rip at first light, come in, eat, and take a nap. Locals watch the sunset from a boat off Navy Beach with a drink and no rush. Tell us your speed and we will match it. Also check our Amagansett and Block Island pages for related trips.
Frequently asked questions
Can I book a Montauk fishing charter?+
Yes. We run light tackle and inshore fishing trips. Let us know your target and skill level. We match you with the right captain and boat.
How long does it take to reach Block Island from Montauk?+
About 90 minutes at cruise speed on a calm day. It is a full day trip and depends on the weather.
Where do we board a Montauk boat rental?+
At a marina inside Lake Montauk. We share the exact slip after you book.
Do you offer private boat tours of Montauk Lighthouse?+
Yes. Lighthouse cruises are one of our most requested trips. Best done in the morning or at sunset.
Is it safe to go around Montauk Point?+
On the right day, yes. The rip can get rough when wind and tide fight. We only run the point when conditions are safe.
Can we bring drinks on board?+
Yes. Just no glass on the swim deck if we can help it, and we ask that guests drink responsibly.