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Sharing our passion since 2011

About Us

Read up about On Watch Sailing and our boats. As an established small business, we are fully insured. Our boats are well maintained and we have a safety record second to none.

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About On Watch Sailing

On Watch Sailing was founded using Lyra in 2011 by Captain Green in order to bring the joys of sailing and being on the water to you. At that time, Green, his wife Jen, and two young children lived aboard Lyra in Newport harbor. Ultimately, Lyra was day chartered while being a full time home for 7 years! Now that the family lives ashore, Lyra is a full time charter vessel. It may not have been the easiest path to creating a small business, but it’s been a rewarding one. Captain Sam and Wren joined On Watch Sailing in 2021.

Our focus on our private customers can be seen and felt, from the moment you join us. We take great pride in providing a unique and guest-tailored experience for each trip. On Watch is always happy to field any questions you may have and endeavor to communicate in a timely fashion if something that may impact your trip (typically weather related) comes up.

Your privacy is respected at all times and we will never share your personal information without your permission, although a good photo or video may go to the website or social media unless you ask us not to post. As a small business, your enjoyment and general safety is our greatest goal. We will adapt our sailing trip or charter to your requirements!

About The Boats

Both Lyra and Wren can accommodate up to 6 passengers, from 1.5-hour to full-day charters. Feel free to bring your own music, some light snacks, and a tasty beverage (no hard alcohol please!). Options include sailing, tours, general relaxation, and (on the longer trips) swimming and anchoring.

Lyra is a Reliance 44, launched in 1980. Under previous ownership, she completed an 11 year circumnavigation and an Atlantic circle. Green and Jen found her in 2008. They brought a young family up on her for nearly 10 years, summering in Newport and sailing her south to Florida and the Bahamas for two of the winters. She has been the cornerstone of On Watch Sailing since 2011.


Wren was acquired by Captain Sam in February of 2021. He chose her for her sweet lines and for the sterling reputation of the Allied built sailboats. She can comfortably seat four guests in the cockpit and six if the her deck space is used. There’s lots of great space to spread out in for guests that opt to go on deck. After a stem to stern refit in the spring of 2021 by Captain Sam, Wren went on to cruise through a fabulous summer season at On Watch Sailing. Follow her journey on her personal Instagram account and look for her in the reviews at TripAdvisor! Be sure to ask Captain Sam about his ultimate plans for the boat.