Depart Manhattan under the skyline and sail out past the Statue of Liberty, turning north for Nova Scotia and Newfoundland. Track the New England shoreline through busy shipping lanes and tidal waters before crossing the Gulf of Maine on a proper offshore leg. Then head into colder, more demanding water. Nova Scotia brings fog, lobster pots and Atlantic weather systems, along with historic landfalls such as Lunenburg and Liverpool. From there the coastline grows wilder. Newfoundland offers deep inlets, exposed headlands and isolated fishing communities shaped entirely by the sea. Finish in St John’s having sailed from one of the world’s great cities into some of the most remote coastline in the North Atlantic

Don’t miss out – This trip runs for last time in 2026

What this voyage is really about

This is proper, remote adventure sailing. From the outset you are part of the working crew. Helming, standing watch, navigating, trimming sails and managing the boat as we move from busy waterways into genuinely isolated water. Expect shifting weather, night sailing, longer offshore legs and landfalls that feel a long way from anywhere. Quiet anchorages, working fishing towns and scattered communities define much of the route. Life on board is active and collaborative. Everyone contributes. The skipper and mate work alongside you throughout, building competence and confidence as the passage unfolds.

Why this route stands out

Few routes combine a departure from central Manhattan with classic New England sailing and a serious offshore leg between Nova Scotia and Newfoundland. Newport, Nantucket and Martha’s Vineyard give way to multi day passages across open ocean. Further north, the coastline becomes more exposed and more remote. Many harbours in Nova Scotia and Newfoundland are accessible only by sea. The route is shaped by tides, fisheries and Atlantic weather systems. No two seasons are identical.

Who this trip suits

You do not need previous offshore or high latitude experience, but you do need the right mindset. This passage mixes coastal sailing with remote offshore legs, night watches and several consecutive days at sea. Plans adapt to conditions. If you want fixed timetables and guaranteed stops, this is not the trip. If you want to move from Manhattan to Newfoundland under sail and earn every mile, it is.

What to do next

Check the Dates and Prices section for availability and joining details. You can reserve your place there, or schedule a call if you want to talk through the route and whether it is the right fit.

Interested in dates & availability?

To see when this trip runs, its start and end locations, price to join the crew and availability, click on the ‘Dates, Prices & Travel’ button up top.

Discretionary tipping of the Rubicon 3 crew

We’ve priced this trip 5-10% lower than we otherwise would to allow you the option, at the end of your adventure, to offer a discretionary tip to the Rubicon 3 skipper and mate if you feel they’ve provided exceptional service. A combined tip of 5-10% is suggested but is entirely at your discretion and based on your satisfaction with their performance. See our FAQs here.

Got Questions? We’re Here to Help!

We get it – joining a major sailing adventure is a big decision, and it’s natural to have lots of questions before you book. Wondering who else will be onboard? What the experience will be like? These and many more questions are completely normal. While our homepage and FAQs provide loads of info, we know sometimes it’s best to talk it through. Don’t hesitate to contact us by phone, email, or live chat (at the bottom of the screen). Better yet, we’d suggest you schedule a call. Most crew who join do and find it really useful. We can discuss your options, answer every question, and make sure you’re booking on the perfect trip for you.