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The On Watch Experience
The highlight of your visit to Newport RI, we consistently offer the highest quality private sailing trips in the area. We work hard to make sure you have an amazing experience with On Watch Sailing.
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EXCELLENT 96 reviews![]()
Jason Mullenix10/07/2025 We had an amazing, relaxing, peaceful time on our charter with On Watch Sailing. Capt. Jack was friendly and knowledgeable, and made a family of sailing rookies at home. Absolutely recommend to anyone!! Thanks again! Anne Hilton06/07/2025 Yesterday’s sailing trip was an absolute delight! The sparkling, crystal-clear water provided a stunning backdrop, making every moment visually spectacular. The boat itself was fantastic—well-maintained, spacious, and perfect for soaking in the serene atmosphere. Greene and Katie were the true stars of the day. Their warmth and enthusiasm made the experience unforgettable, especially for my two boys. They were incredibly engaging, ensuring the kids were entertained and felt included throughout the trip. Their knowledge and passion for what they do shone through, making the watch-selling process seamless and enjoyable. Overall, it was a perfect blend of breathtaking scenery, a top-notch vessel, and exceptional hosts. Highly recommend this experience to anyone looking for a unique and memorable outing! Rachel Kosky30/06/2025 We had the best private sail experience with Green and his co-captain aboard the Lyra. Hope to do it again soon! Georgi Dye27/06/2025 Excellent customer service! We were visiting from out-of-state for one day and they accommodated all our needs! Highly recommend this company. Happy sailing⛵️ Bonnie Levins26/06/2025 We had such an amazing time sailing with you guys. So professional, informative of the area and what was best to see . Our kids and their friends all ages 17 and 18 had a blast! We would do it again in a second.. and will! See you next time! Hillary Knaebel24/06/2025 We had the most incredible sailing trip with Captain Green and Jack. Incredible service, very friendly and knowledgeable about the area, and an all around amazing adventure around Jamestown. Would highly recommend booking with Captain Green! Melody Alger16/06/2025 I try to book a trip with On Watch at least once per summer. The guys are great - as interactive or unobtrusive as you'd like. They have a wealth of knowledge as to Newport history, activities in and around the harbor and the landmarks along the shore. A beautiful, relaxing sail with a chill crew! Dianna Pereda21/05/2025 Absolutely Amazing! Lovely sail, great views, and great tour! We got to sail the boat ourselves which was pretty cool and the charter was private to our group of friends. Green and Jack were the sweetest! They provided great recommendations and gave us brief history backgrounds while on the sail, super supportive of our photo shoots and great company. If you want a private sail this is the place! Jake Slender05/05/2025 Great experience overall…Super friendly crew, and did everything they could to make sure everyone on board felt safe and was having a great time. I would highly recommend these guys, and will definitely use them again!Load more