East Quogue Sailing: Luxury Charters to Shelter Island & Greenport

A four-hour private charter on Bonnie Lynn gives you space to set a relaxed pace: there’s time to sail out toward Gardiner’s Island or explore Great Peconic Bay, anchor for a swim if your group is under 12, or stage a multi-course meal aboard. Operators note the format is popular for photo shoots, micro-weddings, and staff retreats where the goal is unhurried time on the water. The listing specifies a starting price of $2,650 for up to 10 guests, with per-guest rates for larger groups and optional extra half-hours by arrangement.

For luxury travelers who want a long afternoon without committing to a full day, the four-hour charter strikes a balance between sailing time and on-board hospitality. You can bring a private chef, choose a local caterer, or serve your own provisions while the crew handles service and navigation. Practical note: the operator requests guests arrive 15 minutes before departure.

The Fourth of July Fireworks Charter aboard Selina II is a two-hour private outing designed around the season’s main event: a front-row view of the fireworks from the water. The operator frames this as a premium, festive cruise that sells out; the description recommends booking early and lists optional add-ons such as a charcuterie board, flower arrangements, and professional photography packages.

If your travel dates include national holidays, this specialized charter converts an evening on the water into a curated celebration—no land-based crowds, just an intimate group, the yacht’s personality, and fireworks reflected on the sea. Operators emphasize the atmosphere and scenic vantage point; because availability is limited, treat this as a time-sensitive booking.

Selina II’s full-day private charter is positioned as the ultimate sailing day for small groups. Limited to six guests, the eight-hour itinerary can include circumnavigation of Shelter Island, stops to anchor and swim, and options to disembark for a shoreline meal if desired. The operator highlights the yacht’s classic wooden construction and invites guests to participate in hands-on sailing if they wish—an appealing blend of learning and leisure.

The listing also offers several curated add-ons to round out the day: charcuterie boards, floral arrangements, photographer packages, and playlist assistance are noted as extras. For those who want a private, immersive experience—time to explore multiple coves, a planned picnic, or a slow coastal transit—this full-day format provides breadth and the tactile feel of traditional yacht sailing.

Bonnie Lynn’s three-hour private sail is aimed at groups that want a full meal experience without the commitment of a full day. The operator suggests this duration is ideal for a multi-course dining experience, and for smaller groups (12 or fewer) there is typically time to anchor for a swim. The published starting price is $2,050 for up to 10 guests, with an additional per-guest fee for larger parties and a service charge for parties over eight.

This option is practical for celebrations, corporate outings, or a refined afternoon with family and friends. Bringing your own food is acceptable, or you can coordinate a caterer from the operator’s suggestions—either way the crew handles service so you can focus on the view and the company.

The Surprise full-day sail emphasizes a relaxed, discovery-driven itinerary for up to six guests. The operator notes a seven-hour duration and a clear meeting point: 1100 Manhasset Ave, Greenport, NY. Included items—ice, bottled still and sparkling water, service ware, towels, and blankets—reflect an attention to onboard basics so guests can travel lighter and enjoy a day of exploring, swimming, and coastal scenery.

Practical suggestions from the listing include bringing removable footwear (Surprise is a shoes-off boat), non-aerosol sunscreen, a warm layer, and cash tips for the crew. For travelers who want a day of low-key exploration with essentials handled, this charter balances comfort with the freedom to plan anchor stops or a picnic ashore.

The two-hour Bonnie Lynn sail is the shortest private option included here, suitable for a morning or evening outing focused on coastal views. The operator highlights exceptional views of Shelter Island and Bug Lighthouse within the itinerary, and the listing notes a starting price of $1,450 for up to 10 guests with per-guest fees for larger parties. Two hours is a compact window for photography, short swims (on smaller groups), or a sunset cruise.

This format suits travelers who want a taste of local waters without a long commitment—an easy complement to a day on shore or an elegant way to close out an evening. As with other Bonnie Lynn charters, operators request guests arrive 15 minutes before departure.