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Unique Date Night in New York
  • Unique Date Night in New York
  • Wine Tasting Sailing Experience in NY
  • Romantic NYC Wine Tasting Sail
  • Scenic Wine Tasting Cruise on Hudson River
  • NYC sailing excursion

Romantic NYC Wine Tasting Sail

From: $199
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North Cove Yacht Harbor - New York, NY

May through August
Saturdays and Sundays - 4:30 PM
September through Early-October:
Saturdays and Sundays - 4:00 PM
Click here for Schedule

  • If you are looking for a unique date night, set sail with the wine experts for a fun and informative afternoon sail on the Hudson river in New York!

    • Discover the majesty of the Manhattan skyline from the serene waters of the Harbor and Hudson River on this 2-hour NYC sailing experience
    • Enjoy a delightful harbor adventure that will expand your palate as you pair great wines with cheese and charcuterie
    • Relish fresh air and uncontested views of famed New York City attractions from the deck of the Shearwater, a classic 1929 vintage sailboat
    • Each Wine Sail features an eclectic selection that may highlight differing countries, trends and themes
    • One of the most memorable things to do in NYC with that special someone!
    Full Description>
  • An unforgettable evening on the Hudson River awaits on this Romantic NYC Wine Tasting Sail!

    The wine experts will present a carefully curated selection of wines on each sail including both biodynamic and organic varietals. Step aboard and enjoy a delightful harbor adventure that will expand your palate as you pair great wines with cheese and charcuterie.

    You will be amazed by the vintage vessel that carries you on this exquisite NYC sailing excursion. The Shearwater is a meticulously-maintained 1929 classic schooner, spanning an 82-foot frame and departing daily from lower Manhattan.

    Expect to enjoy a 'themed' collection of varietals, perfect for sipping as your scenic wine cruise from New York gently glides past famed Manhattan attractions. All the while, you will delight in fascinating facts about the origins of the fine grape liquid that graces your glass with its presence.

    You'll never look at sailing in NYC the same way as you indulge in the history of the wines, no other attractions in Manhattan will quite compare to an evening of sipping and sightseeing!

    Key Info>
  • Essential Information

    • The sail is not narrated, however the crew is happy to answer your questions
    • The ship boards 10 minutes prior to departure
    • Although the boat holds up to 48 passengers, there is not enough bench seating available and some passengers will be required to either sit on the deck or stand. We recommend arriving early to ensure the best seat
    • Price includes a variety of wines dependent of the theme of that day's sail, as well as snacks and cheeses
    • Participants must be at least 21 years of age


    This sail will last approximately 2 hours.

    Maximum Participants

    This experience is shared by a total of 48 passengers.


    The wine tasting sail is only for those on the ship.

    Weather Dependent

    This an all weather outdoor experience and will sail in light rain. In the event of dangerous sailing conditions, your sail will be rescheduled. Always contact the experience provider with any questions regarding weather conditions.

    What To Wear

    Dress is typically casual. The temperature can be cooler out on the water, so dress accordingly. Passengers should wear only soft soled shoes such as sneakers, deck shoes, flip-flops or sandals. Heels and boots can scuff the deck. It is recommended to arriving at least 30 minutes before your scheduled time.

    Booking Information

    For this experience, it is recommended to request bookings at least 30 days in advance.

    Cancellation Policy

    Prior to scheduling/booking a date for this experience, Cloud 9 Living's standard return and exchange policy shall apply. Once you have scheduled a date and received a booking confirmation, no exchanges are allowed. Rescheduling is allowed up to 72 hours prior to the experience for a $20-30 per person fee payable directly to the experience provider. Failure to appear on your booked date or to reschedule in accordance with these terms will result in the loss of the value of your experience.

    Experience ID


    1. Is wine included?
      Yes, the wine tasting sail includes a variety of wines dependent of the theme of that day's sail.
    2. What if it rains?
      In the event of a cancellation by the Captain due to severe weather conditions or mechanical failure, customers will be rescheduled at no additional fee.
    3. Is there a restroom on board?
      Yes, the Shearwater does have a restroom on board. 
    4. What time do we need to arrive?
      Boarding starts 10 minutes prior to departure. It is recommended to arrive at least 30 minutes prior to ensure the best seats. Please keep in mind that there is not enough bench seating available and some passengers will be required to either sit on the deck or stand.
    5. Are gratuties included?
      Price for this sail does not include gratuity. It is customary to tip the crew if you enjoyed your experience and please remember to tip your server if you enjoyed the service provided.
    6. Will there be assigned seating?
      Seating is casual. You can pick a spot on one of the benches, hatch covers, cabin tops, or layout on the beautiful deck.
    7. Is this ship wheelchair accessible?
      Unfortunately, the Shearwater is not wheelchair accessible.