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Wine Tasting Sail NYC: Our Weekend on the Water

This weekend, Stacey and I went for a Wine Tasting Sail out of New York City's North Cove Yacht Harbor (near the World Trade Centre) on the Hudson River with Manhattan by Sail and it was freaking delightful!

After very kindly being gifted a ticket by friends from Australia, we finally got to booking and managed to pick (I think) the nicest day of the year this year to set sail. We're always looking for something slightly different to do and this one was beautiful:

Raise a glass and add a splash of class to an unforgettable evening on the Wine Tasting Sail in New York!

  • Board Manhattan's Shearwater  schooner for a remarkable 2-hour NYC Hudson River cruise.
  • Sip a curated collection of fine wines, perfectly paired with cheese and charcuterie.
  • Enjoy fresh air and uncontested views of famed New York City attractions.
  • This NYC sailing experience is fun for everyone, whether you're a local or visitor to the Big Apple!
  • Delight in one of the most memorable things to do in NYC with family, friends or a special date!

Four different wines (plus a “house” wine that you get between tasting wines) and a beautiful tasting plate of meats and cheeses will keep you busy for the whole two hours as you sail as close as I've ever been to the Statue of Liberty, and have plenty of opportunities to take a few beautiful photos!

Wine Tasting Sail NYC Stacey & Josh

There's also plenty of wine on the boat too, so safe to say it's good value for money!

If you're looking for something to do in these last few warm weekends, check it out! Shout out to Kathy & Bob who we met on our sail as well, they were great seat companions!

We booked through Cloud 9 Living. They have a HUGE range of delightful and delicious expeditions throughout New York and around the United States. You should check them out for other ideas and things to do!

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Josh Pugh

Josh Pugh

Josh Pugh is the founder and CEO of America Josh, the largest community for Australians living in the United States — a network of more than 75,000 members across all 50 states, grown in part through the acquisition of the Australians in the USA and Aussies International communities. Originally from South Australia, Josh moved to New York in 2017 and became a US citizen in October 2025 — so the advice he publishes comes from having personally navigated the whole journey, from the E-3 visa to citizenship. Through America Josh he has written hundreds of practical, first-hand guides on moving to and living in the US: visas and immigration, taxes, healthcare, banking, housing and settling into life in New York City. Josh is also President of Variety – the Children's Charity of New York and Founder & CEO of Fortnight Digital. He lives in the New York area with his wife Stacey and their two sons, Danny and Liam.View Author posts

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