Long Island’s sailing scene offers practical options for every type of mariner.
Two standout choices top our list: boat rentals from Sag Harbor, The Hamptons, or Montauk ($1,990/8 people), and the excellent Port Washington private tours ($475/6 people).
We especially like the Port Washington experience for its intimate setting and knowledgeable local guides who share fascinating maritime history.
The Hamptons rentals earn our recommendation for their well-maintained vessels and flexibility to explore at your own pace.
Let’s explore these outstanding sailing adventures in detail.
Key Points
- Sag Harbor, The Hamptons, and Montauk offer boat and yacht rentals starting from $1,990 for up to 8 people, with equipment provided and flexible booking.
- Private yacht charters in The Hamptons, Montauk, or Sag Harbor start from $2,390 for up to 10 people, with a 5-star rating and captain provided.
- Captain Steve’s Sailing Experience in Port Washington offers a private tour for up to 6 people at $475, with beautiful views and friendly service.
- Sailing experiences in Long Island may not be accessible for individuals with certain health conditions, such as back problems, heart conditions, or pregnancy.
- Sailing experiences in Long Island offer various options in terms of group size, pricing, and locations, allowing visitors to choose the best fit for their needs.
Boat or Yacht Rental in Sag Harbor, The Hamptons, or Monatauk
Renting a boat or yacht in Sag Harbor, The Hamptons, or Montauk is a fantastic way to experience the scenic waterways of Long Island.
Yacht Hampton Boat Rental, located in Long Island, USA, offers a range of vessels for your sailing adventure. Prices start from $1,990.00 per group (up to 8 people), making it an affordable option for a group outing.
The meeting point is at 10 Wharf St, Sag Harbor, NY 11963, USA, and the activity ends back at the same location. The rental includes the use of all equipment the vessel of your choice provides, though a fuel surcharge may apply.
Service animals are allowed on board. Booking is easy, with confirmation received within 48 hours, and free cancellation up to 24 hours before the experience starts. The Reserve Now and Pay Later option is also available.
While the activity isn’t wheelchair accessible, most travelers can participate. Infants must sit on laps, and the location is near public transportation.
With an overall rating of 5.0 from 4 reviews, this sailing experience is sure to be a hit.
Read our full review: Boat or Yacht Rental in Sag Harbor, The Hamptons, or Monatauk Review
Book now: Check availability
Private Yacht Charter in The Hamptons, Montauk or Sag Harbor
Unlock the splendor of Long Island’s waterways by chartering a private yacht in The Hamptons, Montauk, or Sag Harbor. This exclusive experience, recommended by 100% of travelers, offers the perfect way to explore the region’s stunning coastline.
With a perfect 5.0-star rating from 10 reviews, you can trust that this charter will exceed your expectations. Priced from $2,390.00 per group (up to 10 people), the charter includes a fuel surcharge and a captain to navigate the vessel.
Enjoy the flexibility of free cancellation up to 24 hours before the start and the convenience of a reserve now, pay later option. The private tour departs from 10 Wharf St, Sag Harbor, NY 11963, USA, and returns to the same location.
Although not wheelchair accessible, the charter welcomes service animals, and most travelers can participate, including infants who must sit on laps. Confirm the start time with the local provider in advance to ensure a seamless experience.
Read our full review: Private Yacht Charter in The Hamptons, Montauk or Sag Harbor Review
Book now: Check availability
Captain Steves Sailing Experience on Long Island
Captain Steve’s Sailing Experience on Long Island offers a unique and personalized way to explore the scenic waterways. For $475, your group of up to 6 can embark on a private tour led by the knowledgeable Captain Steve.
The meeting point is in Port Washington, NY, where you’ll find the boat docked at the end of a long pier. While there’s no parking on the hotel and marina property, you can use the nearby public lots.
The tour isn’t wheelchair accessible, but strollers are welcome. Infants must sit on laps, and those with back problems, heart conditions, or pregnancy are advised against joining. A moderate fitness level is required.
Upon booking, you’ll receive confirmation, but keep in mind there are no refunds for cancellations.
With an impressive 5-star rating from 6 reviews, customers highlight Captain Steve’s friendly service, beautiful views, and comfortable atmosphere. This sailing experience provides a memorable way to soak in the natural beauty of Long Island’s coastline.
Read our full review: Captain Steves Sailing Experience on Long Island Review
Book now: Check availability
Recap
Explore the best sailing experiences on Long Island by renting a boat or yacht in Sag Harbor, The Hamptons, or Montauk. Indulge in a private yacht charter in these picturesque destinations. Alternatively, embark on Captain Steve’s Sailing Experience for an unforgettable time on the water. With these options, you’ll discover the beauty of Long Island’s coastline and create cherished memories.