SHELTER ISLAND HEIGHTS SAILING FIELD GUIDE
A Day Aboard Selina II: Classic Wooden Sailing Through Shelter Island and Peconic Bay
An eight-hour private charter from Sail Selina NY that lets up to six guests swim, learn traditional sail handling, enjoy a curated picnic, and explore Shelter Island, Greenport, and the calm waters of Peconic Bay.
A Day Aboard Selina II: Classic Wooden Sailing Through Shelter Island and Peconic Bay.
Step aboard Selina II, a classic wooden sailing yacht, for the ultimate sailing day around Shelter Island, Greenport and the Peconic Bay. The private, full-day charter mixes hands-on sailing or relaxed sun-soaking with opportunities to anchor and swim, a curated picnic option, and flexible drop-off at local restaurants with prior coordination.
Highlights
Outing Highlights
Historic Wooden Yacht
Experience the charm of traditional yacht sailing aboard Selina II, a classic wooden sailing yacht that sets the tone for a tactile, timeless day on the water.
Hands-On or Hands-Off Sailing
Guests can take part in raising sails and learning the rhythms of classic yacht sailing, or simply relax while the crew handles every detail—this option is built into the private charter experience.
Calm Bays, Anchor Swims, and Sun Time
Shelter Island and Peconic Bay offer calm, scenic waters ideal for anchoring to swim, soak up the sun, and enjoy a private picnic on board.
What the day feels like
What the Day Feels Like
Over an eight-hour private charter on Selina II you’ll move between sheltered coves and open bay, alternating short sailing passages with slow drifting at anchor for swimming, picnicking, or shore drops. The pace is deliberately unhurried: hoist and trim sails if you choose, listen to your playlist through the boat’s Bluetooth connection, and take in the low-rise North Fork shoreline and the quiet inlets around Shelter Island.
Suitability
Who it's for
Who this trip suits—and who should look elsewhere.
Practical planner
Details to review before reserving
Full-day private charter: 8 hours aboard Selina II.
Swimsuit and towel if you plan to swim; sun protection and layered clothing for changing conditions; a phone or device if you want to use the boat’s Bluetooth music connection. Pack food only if you don’t opt for the curated picnic add-on.
Operator: Sail Selina NY. The charter is private and limited to six guests; the crew can coordinate a curated picnic or arrange a drop-off at a local restaurant with prior notice.
Review cancellation policies before reserving.
Frequently asked questions
Planning Your Outing
How long is the Full-Day Private Charter?
The charter runs eight hours.
How many people can be on the charter?
The private charter is limited to six guests, giving the trip a private, small-group feel.
Can I participate in sailing the boat?
Yes—guests are welcome to participate in raising sails and learning the rhythms of classic yacht sailing, or they can relax while the crew sails.
Is food provided?
You can bring your own picnic, or the operator can coordinate a curated picnic for you as an add-on.
Can you drop us off at a restaurant?
Yes—the crew can arrange to drop you off at a local restaurant in the area with prior coordination.
Will we have time to swim?
Yes—there are plenty of opportunities to anchor and swim in the calm waters around Shelter Island and Peconic Bay.