SHELTER ISLAND HEIGHTS SAILING FIELD GUIDE

Selina II: A Four‑Hour Private Sail Through Shelter Island Heights

A relaxed, private 4‑hour charter aboard a classic wooden yacht that explores Shelter Island, Dering Harbor, Greenport and Peconic Bay—this guide explains what to expect and how the outing is tailored to your group.

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Selina II: A Four‑Hour Private Sail Through Shelter Island Heights.

Duration

4 hours

Location

Shelter Island Heights

Operator

Sail Selina NY

Outing Highlights

THE ROUTE

Shelter Island, Dering Harbor and Greenport

The charter moves through sheltered waterways—calling on Shelter Island coves, Dering Harbor and the Greenport waterfront—so you see quiet anchorages and the character of the North Fork shoreline in a single, flexible outing.

THE VESSEL

A classic wooden yacht made private

Selina II is presented as a classic wooden yacht offering a private experience: cushioned seating and cozy blankets create a relaxed, intimate atmosphere for your group.

THE PACE

Flexible sailing, swimming and picnicking

The charter’s pace and route are tailored to each group; you can anchor to swim or sunbathe and enjoy a personalized picnic onboard while the crew handles navigation and shares local stories.

What the day feels like

What the half‑day feels like

Four hours aboard Selina II feel deliberately unrushed: the crew sets a flexible pace that alternates sailing, quiet drifting in coves and time at anchor for swimming or a picnic. Guests can take part in traditional seamanship—raising sails and learning lines—or simply stretch out on cushioned seating, stream a playlist via Bluetooth and toast with chilled bubbly for a personalized afternoon on the water.

Suitability

Who it's for

Who this private half‑day suits

Active beginners and aspiring sailorsGuests who want to learn hands‑on will find opportunities to help raise the sails and learn traditional seamanship from the crew.

Couples or small groups seeking relaxationThe cushioned seating, blankets and private nature of the charter make it well suited to groups who prefer a laid‑back afternoon of swimming, sunbathing and a picnic.

Swimmers and beachgoersBecause the boat anchors in quiet coves for swimming, this outing matches travelers who want water time as part of a short cruise.

Music and food loversGroups that want personalized music and onboard refreshments will appreciate the Bluetooth playback option and the ability to enjoy a catered or brought‑along picnic and chilled bubbly.

Practical planner

Details to review before reserving

Onboard amenities

Selina II provides cushioned seating and cozy blankets for passenger comfort; guests can stream music via Bluetooth and enjoy a personalized picnic and chilled bubbly onboard.

What to bring

Plan for swimming and sun time if you intend to anchor—bring whatever personal items you prefer for that (note: the charter emphasizes onboard comfort with provided seating and blankets).

Booking Notice

Review cancellation policies before reserving.

Frequently asked questions

Planning Your Outing

How long is the charter?

The private charter is a 4‑hour outing.

Which waters and stops does the sail cover?

The route explores Shelter Island, Dering Harbor, the Greenport waterfront and Peconic Bay.

Is this a private experience?

Yes — the listing describes a private charter aboard the classic Selina II for your group.

Can guests take part in sailing the boat?

Guests can help raise the sails and learn traditional seamanship from the captain and crew, or opt to relax while the crew handles navigation.

Are there opportunities to swim and picnic?

Yes — the charter anchors in quiet coves for swimming, sunbathing and a personalized picnic onboard.