Sail Greenport & Long Island with Surprise Sailing Yacht Charters

Surprise Sailing Yacht Charters — Greenport Sailing Experiences

Surprise Sailing Yacht Charters operates from Greenport, New York, offering a focused set of sail experiences on Long Island’s North Fork. Trip options include a Two Hour Day Sail (morning and afternoon), a Two Hour Sunset Sail, a Half Day Sail, a Full Day Sail, and themed wine tasting cruises with named events.

Popular sails and durations

• Two Hour Day Sail — A 2-hour excursion available in morning or afternoon.
• Sunset Sail — A 2-hour evening sail timed for sunset views.
• Half Day Sail — A half-day outing for swimming, sunbathing, and coastal cruising.
• Full Day Sail — A full day on the water aboard the yacht Surprise.
• Saltbird/Chronicle Wine Tasting Cruise — A 2-hour tasting with winemaker Robin Epperson-McCarthy on August 17 and a Chronicle tasting on September 6.

Each offering departs from Greenport and highlights coastal scenery, time on the water, and clear trip durations to match guest plans.

What to expect

Guests booking these sails will find concise schedules and event dates listed for each trip. Public and private sailing options are presented so visitors can select the right length and format. Themed wine cruises pair sunset sailing with guided tastings on specified dates.

Why choose sails from Greenport

Selecting a sail departing from Greenport places guests on Long Island’s North Fork with direct access to local waters. Surprise Sailing Yacht Charters lists multiple tour lengths that fit short visits or full-day explorations. Named cruises and event dates help travelers plan seasonal experiences.

Practical details

• Departure point: Greenport, New York.
• Vessel: Surprise (used for full‑day and other sails).
• Trip lengths: two-hour sails, half-day sails, and full-day sails.
• Special events: Saltbird tasting on August 17; Chronicle tasting on September 6 with winemaker Robin Epperson-McCarthy.

Booking and planning tips

Check published schedules and reserve in advance for specific event dates. Choose the Two Hour Day Sail or Sunset Sail for a concise experience, the Half Day Sail for swimming and relaxation, or the Full Day Sail for extended time aboard Surprise.

Detailed trip highlights

• Half Day Sail: Experience swimming, sunbathing, and relaxed time on the water during a half-day outing designed for leisure and small-group memories.
• Two Hour Day Sail: A focused two-hour route that showcases coastal scenery from morning or afternoon departures, ideal for a brief nautical experience.
• Sunset Sail: A timed two-hour sunset cruise that emphasizes evening light and coastal views.
• Full Day Sail: A full-day voyage aboard Surprise that allows extended exploration of local waters and the open sea.
• Wine Tasting Cruises: Saltbird and Chronicle wine tastings pair two-hour sails with guided tastings; the Saltbird tasting features Robin Epperson-McCarthy on August 17, and the Chronicle tasting is scheduled for September 6.

Ideal for

• Families and friends seeking accessible, on-water experiences.
• Visitors to Greenport and Long Island’s North Fork wanting coastal scenery.
• Small groups looking for public or private charter options.

Event dates & partners

Saltbird wine tasting: August 17. Chronicle wine tasting: September 6. Robin Epperson-McCarthy leads the Saltbird tasting event.

Booking notes

Schedules, durations, and specific event dates are published for each offering so travelers can plan. Departure is from Greenport, New York, with options that include two-hour sails, half-day sails, and full-day sails aboard Surprise.

For Greenport visitors seeking a memorable on-water day, consult published schedules and reserve a Two Hour Day Sail, Half Day Sail, Sunset Sail, Full Day Sail, or wine tasting cruise today from Greenport.