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Set sail from Greenport for a two-hour sunset cruise with Saltbird Cellars. This intimate tasting aboard Surprise pairs a winemaker-led flight with maritime views—perfect for wine lovers seeking a memorable evening on the water.
Set sail from Greenport for a two-hour sunset cruise with Saltbird Cellars. This intimate tasting aboard Surprise pairs a winemaker-led flight with maritime views—perfect for wine lovers seeking a memorable evening on the water.
Book with Surprise Sailing Yacht Charters
Verified experiences and guided adventures in the surrounding area.
Operated by Surprise Sailing Yacht Charters · Greenport, New York
Saltbird Cellars Wine Tasting Cruise drops the land-based tasting room and brings artisan wine straight to the water. Based in Greenport, New York on Long Island's North Fork, this 2-hour sail pairs a small-group sunset cruise aboard Surprise with an intimate tasting led by Robin Epperson-McCarthy, owner and winemaker at Saltbird Cellars. Up to six guests share close quarters on deck, where the sound of rigging and a breeze off Peconic Bay frame glasses of crisp whites and lighter reds.
The experience starts with a brief safety orientation and cast-off; then the sail eases into the harbor as the light shifts toward golden hour. Key features include the low-slung horizon over Peconic Bay, the boat's working sails, and a tasting flight curated by Robin that highlights regionally grown varietals and vinification notes unique to Saltbird Cellars. Because the tasting happens on deck, the setting amplifies tasting notes - briny sea air makes bright acidity sing, while a calm bay evening highlights subtler aromatics.
What makes this trip special is the combination of place and person: a winemaker who talks through technique and taste while guests look out at working waterfronts, lobsterman traps, and Greenport's historic wharves. The small size - six guests - creates a conversational, educational atmosphere rather than a staged tasting. For visitors to the North Fork, this outing offers a maritime perspective on local viticulture that you won't get in a tasting room.
This cruise is ideal as an early-evening treat or as a memorable capstone to a day exploring Greenport and nearby vineyards. Practical notes: the voyage lasts roughly two hours, minimum age is 21, and spaces are limited - book early for weekend sunsets. Weather dictates safety and comfort; windier evenings can be exhilarating but chill your drink and require layered clothing.
Why book it? If you want local wines presented by their maker and the quiet reassurance of a licensed small charter, this cruise blends hands-on winemaking insight with the elemental appeal of sailing. For photographers, the low light and reflective water create flattering portraits and saturated horizons. For wine lovers, Robin's firsthand descriptions connect grape to glass in a way that makes tasting notes tangible - salt on the tongue, sand on the mouthfeel, evening light in the glass. Saltbird Cellars Wine Tasting Cruise is short, social, and distinctively Greenport: a maritime sip that reframes both the wine and the place that made it.
Bookings are handled through Surprise Sailing Yacht Charters' online system and often fill weeks ahead in summer; a late-weeknight sail usually means calmer water and fewer boats. Pack a windproof jacket, non-marking shoes, and a camera with a polarizer. Minimum age is 21; tipping the captain and winemaker for excellent service is customary, and respectful behavior toward crew members.
easy.
2 hours.
Able to step aboard a small sailboat and stand or sit for two hours; moderate mobility recommended.
The sailing experience runs about two hours from cast-off to return.
Yes — the minimum age is 21 for this wine tasting cruise.
The cruise is weather-dependent; the operator will notify you and provide options—check the booking page via the referral link for specifics.
A tasting flight led by Robin Epperson-McCarthy is included in the experience description; confirm inclusions at booking via the referral link.
Policies vary by operator; contact Surprise Sailing Yacht Charters through the booking link to confirm allowances and restrictions.
Small sailboats typically require stepping over a high threshold and moving on narrow decks; contact the operator directly for detailed accessibility guidance.
Greenport is a historic maritime village with century-old wharves and a longstanding working harbor that shaped local fishing and boating traditions.
Pack out all trash, avoid single-use plastics on board, and follow crew guidance to minimize disturbance to wildlife and shoreline habitats.
Surprise Sailing Yacht Charters is a Greenport, New York-based charter company offering a range of day sails and special cruises aboard the yacht Surprise. They operate a selection of public and private sail experiences tailored for relaxation, sightseeing, swimming, and small-group celebrations. Core offerings include a Two Hour Day Sail (morning and afternoon departures), a Two Hour Sunset Sail, a Half Day Sail ideal for swimming and leisure, and a Full Day Sail for extended exploration of local waters. Special-event cruises feature curated wine tastings on board, including the Saltbird tasting with winemaker Robin Epperson-McCarthy on August 17 and the Chronicle tasting on September 6. These themed evening sails combine sunset views with guided tastings to create a seasonal, memorable experience. Reservations depart from Greenport, Long Island, and itineraries emphasize time on the water, coastal scenery, and flexible options for families and groups. The company lists clear trip durations for guests — two-hour sails, half-day outings, and full-day voyages — allowing travelers to select the right length for their plans. Booking pages list schedules, durations, and event dates so travelers can reserve Two Hour Day Sails, Half Day Sails, Sunset Sails, Full Day Sails, or Saltbird and Chronicle wine tasting cruises from Greenport, New York.
Book with Surprise Sailing Yacht Charters