Destination
Block Island
A day trip that feels like a week.
Block Island is a real crossing, but on the right day it is worth every minute. From Montauk it is about twelve miles of open water to the harbor, and once you are in Great Salt Pond the whole feel of the day changes. The island stays quiet even in July, the beaches are wide and empty on the north end, and the moped culture makes the whole thing feel like a different country. We plan Block Island days on a weather window. If the forecast is not clean, we reroute or push a day. When it is right, we leave Montauk in the morning, tie up in New Harbor, get a car or bikes into town, do lunch at one of two places we like, spend the afternoon at Mansion Beach, and head back before the wind builds in the afternoon. Overnights on Block are one of the best things we do.
Top routes from Block Island
Nine-hour full-day charter. Crossing, lunch, beach, and back.
Two-night mooring in New Harbor. Everything included.
For groups willing to sit at Ballard's and skip the rest.
A sample day in Block Island
- 8:30 amBoard in Montauk. Coffee and provisions ready.
- 10:00 amArrive Great Salt Pond, tie to a mooring.
- 10:45 amBikes or car into town.
- 12:30 pmLunch at Dead Eye Dick's or Winfield's.
- 2:30 pmBeach afternoon at Mansion.
- 5:00 pmReturn to Montauk before the afternoon wind.
Boats that depart from here
Local FAQ
How long is the crossing?+
About forty-five minutes to an hour from Montauk on a good day.
Can you do it from Sag Harbor?+
Yes, but it becomes a long day. We recommend leaving from Montauk when possible.
What if the weather turns?+
We check the forecast at 5 am the morning of. If it is not a clean window, we reschedule at no cost.
We are Carter and Sean, local captains out of Sag Harbor. Block Island is a bucket list day for a lot of our guests. We run out of Montauk to cross Block Island Sound and spend the day on the island. It is a full day trip that depends on the weather. When conditions line up, it is one of the best runs of the summer.
Why charter out of Block Island
Block Island sits about 14 miles off Montauk Point. The island is small, walkable, and full of character. Great Salt Pond is a huge protected harbor on the west side. Old Harbor is the classic ferry landing with shops and restaurants. Mohegan Bluffs on the south side are some of the most dramatic cliffs on the East Coast.
A Block Island yacht charter is different from our bay day trips. It is a longer run, so we plan the day around the weather. We watch the forecast all week. If the sea state looks good, we go. If not, we reschedule. Safety first.
We are USCG licensed and insured. Every trip has a captain. See the for boats.
Top routes and stops from Blockk Island
Route one is Great Salt Pond. This is the big protected harbor on the west side. Well marked entrance, plenty of room to anchor, and easy access to the town via dinghy or launch. Most of our charters anchor here for lunch.
Route two is the Old Harbor and Mohegan Bluffs cruise. From Great Salt Pond we can run around the south side of the island to see Mohegan Bluffs from the water. The cliffs are massive. On a calm day this run is unforgettable. Old Harbor is on the east side, near the ferry dock and the main town.
Route three is a full loop of the island. Weather permitting, we run all the way around. You get every angle of Block Island in one day. This is a long trip, so we plan the fuel and the timing.
A sample day departing from Block Island
8:00 am. Meet at the dock in Montauk. Early start for a Block Island day.
8:30 am. Lines off. Out the inlet and across the sound.
10:00 am. Arrive at Great Salt Pond. Anchor in a good spot.
10:30 am. Dinghy or launch into town for coffee, a walk, or the bluffs.
1:00 pm. Back on the boat. Lunch and a swim.
2:30 pm. Cruise the south side of the island for the bluffs view.
4:00 pm. Head back across the sound.
5:30 pm. Return to Montauk. Home in time for dinner.
Best boats for Block Island
Block Island is an open water crossing, so we use our bigger boats with more freeboard. Mid size cruisers and up are the right call. Ask us for the current recommendation based on the forecast. For a group event, the 122 ft event yacht is set up for the run. See .
Boarding,parking, and logistics
We board Block Island charters at a marina in Montauk. Early start is important, usually by 8 or 9 am, so you get a full day on the island. Park in the marina lot. Give yourself 20 minutes.
Bring layers, sunscreen, hats, and soft soled shoes. Cash for the launch or dinghy fees on the island. We supply ice, water, towels, and a clean head. Motion sickness meds are a good idea if you are prone.
Best time of year and weather notes
Mid June through mid September is prime for Block Island. Calm days are the goal. We watch the wave forecast, not just the wind. A short chop on the sound can make the ride long. If the forecast is not right, we reschedule at no cost.
What locals do vs. what tourists ask for
Tourists want to hit every spot on the island in one day. That is possible, but it makes the day feel rushed. Locals pick one anchor, one town stop, and one long swim. That is the best Block Island day. Save the rest for the next trip. Also see our Montauk and Fishers Island pages.
Frequently asked questions
How long is the ride from Montauk to Block Island?+
About 90 minutes at cruise speed on a calm day. Longer if the sea state is up.
Is a Block Island yacht charter safe?+
Yes, when the weather is right. We only run the crossing in safe conditions. If the forecast is off, we reschedule.
Can we dock at Block Island?+
Yes. There are docks and moorings in Great Salt Pond and Old Harbor. Availability is tight in July and August, so we plan ahead.
Do you offer private boat tours around Block Island?+
Yes. A full loop of the island is one of our best day trips when the weather cooperates.
Can we do Block Island as a half day?+
No. It is a full day trip because of the run time. Expect at least eight hours door to door.
What if the weather turns during the day?+
We watch the forecast the whole time. If it changes, we head back early. Safety first, always.