Some Hamptons days are for the beach chair. Others call for getting out on the water properly — a crewed yacht, a cooler of something cold, and the coastline sliding by from the best seat in the region. A private charter turns one afternoon of your stay into the story everyone tells afterward.
Staying on Dune Road makes it easy. Marinas sit minutes away on the bay side, so boarding a boat is a short hop rather than a half-day of logistics. Here's how a charter day works, and how to build one into your stay.
Bay cruise or ocean run?
Charters here come in two flavors. A bay cruise keeps you on the calm, protected water behind the barrier island — flat seas, easy swimming stops, and relaxed cruising past the marshes and beach houses. It's the right call for mixed-age groups, anyone prone to seasickness, and days when the ocean is lumpy.
An ocean run trades that calm for open-Atlantic drama: long views of the dune line, deeper blue water, and the option to range east along the South Fork. Experienced captains read the forecast and steer you to whichever side of the island is having the better day.
The sunset cruise
If you charter only once, make it the golden hour. A sunset cruise on the bay catches the water at its calmest and the light at its best, with the sky doing things over the western horizon that no restaurant view can match. Most crews are happy for you to bring drinks and food aboard, so a simple spread and something to toast with is all it takes.
The timing works beautifully with a stay at the house: step off the boat at dusk, and you're back on your own oceanfront deck — or in the hot tub — twenty minutes later.
Celebrations on the water
Charters shine for occasions. Milestone birthdays, anniversaries, proposals, a toast to the whole family being in one place — an afternoon afloat gives the celebration a centerpiece without any of the hosting work. Pair it with a private chef dinner back at the house the same evening and you've built a full celebration day out of two phone calls.
For multi-family groups, the boat day is also a natural way to split the party: half the crew cruises while the other half holds down the pool and the beach, then everyone swaps stories over dinner.
What group sizes work
Here's the practical wrinkle: many crewed charter boats are licensed to carry up to six passengers, a common limit for smaller charter vessels, while larger certified boats can take bigger parties. Since our homes sleep 12 and 16, plan around that — book a larger vessel, run two boats side by side, or split the group into a morning trip and an afternoon trip.
None of that is a problem if it's arranged ahead of time; it's only a headache if it's discovered the week of. Tell us your headcount early and the right boat, or boats, can be matched to your group.
Arranging it with your stay
Private yacht charter is available as an add-on when you book direct with us — along with the no-booking-fee rate you get for skipping the middlemen. Summer weekends book out first, so raise it with your inquiry rather than after you arrive, and include your group size, preferred day, and whether a sunset cruise or a full day appeals most.
Request it when you book one of the homes — the 8-bedroom at 915 Dune Road for groups up to 16 or the 6-bedroom at 819 for up to 12 — or call +1 201-888-1170 and we'll coordinate the charter around your dates.
Common questions
How many people can join a yacht charter?
Many crewed charters carry up to six passengers under common licensing limits, while larger certified vessels take bigger groups. With a full house of 12 or 16, plan on a larger boat, two boats, or split trips — all easy to arrange with notice.
How far in advance should we book a charter?
For summer weekends, request it when you book your stay. Shoulder-season and weekday charters are more flexible, but early notice always means better boats and better time slots.
Where do charters depart from?
From marinas on the bay side, minutes from both homes — the village is about five minutes away, so the trip from your door to the dock is one of the shortest in the Hamptons.
Can we do a sunset cruise and dinner at the house on the same evening?
Yes, and it's one of the best evenings you can build here. Step off the boat at dusk and have a private chef dinner waiting back at the house — both can be arranged as add-ons with your booking inquiry.
Last updated August 10, 2026.
Stay oceanfront on Dune Road
Our 6 and 8 bedroom homes sit directly on the beach in Westhampton Beach, with heated pools, hot tubs, and private beach access.



