How To Sail Videos include Sailing & Cruising Tips, Sailing Instruction, Maintenance & Boat Repair, and Boat Projects. Our productions are created by professional filmmakers and talented amateurs who want to share their knowledge of sailing and boats with you. Our instructors include legendary sailors like Gary Jobson, Don Street, and Lin & Larry Pardey. We are constantly adding new how-to sail and boar maintenance videos to our library. If you come across a video that you believe others might enjoy, let us know through our contact form.

  • Sailing Cruising Tips

    Sailing Cruising Tips (22)

  • Sailboat Maintenance

    Sailboat Maintenance (5)

  • Boat Projects

    Boat Projects (6)

  • Singlehanded Docking Sail Trim - Singlehanded Docking Sail Trim

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    Featuring Capt. Jack Klang Running time: 53 minutes In Singlehanded Docking Sail Trim, Capt. Jack Klang combines innovative classroom models with real world sailing situations to explain the skills and techniques required for singlehanders to dock with confidence in any wind or current, trim sails for power and speed, and retrieve a mooring alone. See Sailing Instruction with Capt. Jack Klang to get both Cruising Tips and Singlehanded Docking & Sail Trim at a discounted price.

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    Featuring Capt. Jack Klang Running time: 64 minutes The complete collection of 30 Cruising Tips with Captain Jack Klang. This is a must for those who want to learn sailing basics and brush up on their sailing skills. How-to topics include sail trim, docking, and anchoring. Jack combines innovative classroom models with real world situations to show how things work so everyone can understand. See Sailing Instruction with Capt. Jack Klang to get both Cruising Tips and Singlehanded Docking & Sail Trim at a discounted price.

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  • Cruising Under Sail - Annapolis Book of Seamanship Video Series Annapolis Book of Seamanship Video Series

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    A video series based on the popular book by John Rousmaniere.

    Running time: 5.5 hours. Teaches seamanship and basic sailing skills. Based on John Rousmaniere's famous book and hosted by the author, this award-winning instructional sailing DVD series is now available as a Digital Download. As the old salt says, "rocks don't move." Though made nearly 15 years ago, Rousmaniere's milestone series teaches techniques handed down by generations of sailors. A must for newbies and a solid reference for those who want to freshen up and improve their seamanship and sailing skills. "Will help Sailors be more confident and even enjoy sailing in heavy weather." - Gary Jobson.

    RECOMMENDED: Rent or Download-to-Own the series through Vimeo. Individual volumes available separately.

    About Sailflix-Vimeo VOD ABOS Series Vimeo Rent All $39.38 Buy All $78.70

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  • Circumnavigation - Pardey Off-Shore Sailing Pardey Offshore Sailing Series

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    A video series by Lin and Larry Pardey Running time: 6.5 hours. Lin & Larry Pardey's Offshore Sailing Series is a collection of 5 videos about the skills required to become a safe and confident blue water sailor. Lin & Larry Pardey are among America's (and the world's) most knowledgeable and recognized cruising sailors. They are known as "America's first couple of cruising." The series includes: Get Ready to Cruise; Get Ready to Cross Oceans; Storm Tactics; Cost Control While You Cruise; and Cruising Has No Limits.

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    Featuring Capt. Jack Klang Running time: 53 minutes Capt. Jack Klang combines innovative classroom models with real world sailing situations to explain the skills and techniques required for singlehanders to dock with confidence in any wind or current, trim cruising sails for power and speed, and retrieve a mooring alone. See Sailing Instruction with Capt. Jack Klang to get both Cruising Tips and Singlehanded Docking & Sail Trim at a discounted price.

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  • CLICK ABOVE FOR TRAILER, MORE INFO & VIMEO PURCHASE

    Featuring Capt. Jack Klang Running time: 64 minutes The complete collection of Capt. Jack Klang's 30 Cruising Tips. This is a must for those who want to learn sailing basics and brush up on their sailing skills. How-to topics include sail trim, docking, and anchoring. Jack combines innovative classroom models with real world situations to show how things work so everyone can understand. See Sailing Instruction with Capt. Jack Klang to get both Cruising Tips and Singlehanded Docking & Sail Trim at a discounted price.

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  • Singlehanded Docking Sail Trim - Singlehanded Docking Sailing Instruction with Capt. Jack Klang

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    Featuring Capt. Jack Klang Running Time: 1 hour 58 minutes. 2-Video Series for crews and singlehanders. Includes both Cruising Tips with Capt. Jack Klang and Singlehanded Docking & Sail Trim. From sail trim to docking, Capt. Jack combines classroom models and real world situations to help you become a better sailor. Capt. Jack Klang is a US Coast Guard certified skipper and long-time consultant to Quantum Sails. Capt.

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  • Yoga Onboard Book and eBook Yoga Onboard

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    Featuring Sailor & Yoga Instructor, Kim Hess-Stone Running time: 35 minutes Yoga for Sailors Onboard is a practical guide for cruisers and liveaboards. Sailor and Yoga instructor, Kim Hess, shows you how to adapt traditional yoga postures, or asana, using various parts of the boat as props to create a yoga practice that works for your vessel. Some of the benefits of a regular yoga practice include increased strength and flexibility, restored energy, and harmony between the body and mind--benefits that all sailors, especially on longer voyages, will appreciate.

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  • Sailvation Sailboat Charter Briefing Scenic Sailvation Sailboat Charter Briefing

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    A film  by Incila Oezmert Running Time: 39 minutes. Sailvation Sailboat Charter Briefing walks you through a typical charter boat hand-over. The video is not designed to replace your live hand-over. However, with the information it provides, you'll be better equipped to understand the hand-over process, ask more detailed questions, and make your next charter cruise more enjoyable and trouble-free.

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  • Building the Frames Episode 1 The BIG Sailboat Project Boat Building

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    A video series by Sandra Sims Running time:4 hours 25 minutes Ten years in the making, The BIG Sailboat Project tracks the gritty effort of two gals as they pursue their dream of building and cruising a 43 foot steel sailboat. Located a 1000 miles from the coast in rural Alberta, Canada, the duo decide on steel as their building material, which they shape into a Bruce Roberts designed 43 MKII Long Keel Cutter.

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  • Batten pocket Repair Sail Repair with Wally Moran

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    A Series featuring Wally Moran Running Time: 53 minutes. In this 5-part video, sailing writer and charter skipper, Wally Moran, tackles his first sail repair project using a Sailrite Ultrafeed LSZ-1 sewing machine. Each year, Wally transits the Intracoastal Waterway from Canada to the Bahamas, and sometimes to Cuba (He’s a Canadian – he can!) And along the way, Wally maintains his boat, and now he’s doing his own sail repairs and planning some canvas projects too.

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    A Film by Charles Croft with Don Street Running time: 47 minutes Filmed in Martinique aboard Iolaire, Don Street's 46 ft engineless wooden yawl. Master sailor Don Street teaches you and your crew everything you need to know about sailors' knots, line handling and throwing in just 50 minutes. Don has decades of ocean sailing experience. Check him out at street-iolaire.com.

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  • Streetwise Tips Vol. 1 The Complete Don Street

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    A video series with Don Street Running time: 5 hours 45 minutes. For the first time, TheSailingChannel is offering all five Don Street sailing videos in one economical package: Streetwise, Vol. 1 and Vol. 2; Sailors' Knots & Line Handling, which contain dozens of sailing tips; Transatlantic with Street, a primer on blue water sailing; and Antigua Race 1985, a classic Caribbean racing documentary.

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  • Boat Maintenance DYI - Diesel Maintenance Pt. 1 Boat Maintenance Tips DYI

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    A video by Rob Dubin Running time: 76 minutes. From the Sailing Quarterly Video Magazine library. Boat Maintenance Tips DIY delivers a wealth of information for the do-it-yourselfer. Boat maintenance professionals explain and demonstrate: Diesel Engine Maintenance & Troubleshooting, How to Clean a Winch, Rigging Checks from Masthead to Deck, Fiberglass Repairs, How to Fix a Marine Head, and Varnishing. (M1Z)

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  • Sail Racing Tactics - The Role of the Tactician Trailer Sail Racing Tactics with Gary Jobson Video

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    A video by Rob Dubin hosted by Gary Jobson Running time: 66 minutes. From the Sailing Quarterly Video Magazine library. In Sail Racing Tactics, America's Cup champion, Gary Jobson demonstrates techniques that will improve the performance of your boat in both fleet and match races. Many of these sail racing tactics tips will also help cruisers make faster passages. (R2Z)

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  • Sail Trim - Mainsail Trim Power & Speed Trailer Sail Trim and Performance Sailing with Gary Jobson Video

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    A video by Rob Dubin hosted by Gary Jobson Running time: 66 minutes. From the Sailing Quarterly Video Magazine library. In this how-to sailing video, America's Cup champion, Gary Jobson, provides tips on all aspects of sail trim that will help you improve the performance of your boat, wether you race or cruise.(R1Z)

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  • Seamanship 2 - Signaling Device Trailer Seamanship Training 2

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    A video by Rob Dubin Running time: 53 minutes. From the Sailing Quarterly Video Magazine library, this seamanship video addresses Safety-at-Sea, Safety Equipment, and Sail Performance. Tips include: Man Overboard Recovery, Emergency Signals, Power Generation, Radar, Outfitting, and Maximize Boat Performance. (C2Z)

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  • Seamanship V1: Anchor Holding Seamanship 1

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    A video by Rob Dubin Running time: 53 minutes. From the Sailing Quarterly Video Magazine library, this seamanship video includes tips covering Anchor Penetration and Holding; Weather Forecasting and Routing; Anchoring under Sail; Securing a Mediterranean (Med) Mooring; and a Man Overboard (MOB) Recovery demonstration by the U.S. Naval Academy Sailing Team. (C1Z)

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    Streetwise Tips Vol. 2 Don Street: Streetwise Tips Vol. 2 - Anchoring & Docking

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    A video by Rob Dubin with Don Street Running time: 66 minutes. From the Sailing Quarterly Video Magazine collection, this how-to sailing video is hosted by veteran charter skipper and sailing author, Don Street. It includes a treasure trove of anchoring & docking tips that will make your cruising safer and more comfortable. In Vol. 2, Don demonstrates anchoring techniques; ways to prevent chafe; instructions on handy knots and whippings; methods to get you afloat when you go aground; and shorthanded docking.

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    Streetwise Tips Vol. 1 - Using Drogues Don Street: Streetwise Tips 1 - Heavy Weather Sailing

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    A video by Rob Dubin with Don Street Running time: 56 minutes. This heavy weather sailing video with Don Street, legendary sailor and author, explains the preparation and tactics you need to take on boisterous seas. From the Sailing Quarterly Video Magazine library. In this 56-minute how-to sailing video, veteran charter skipper and sailing author, Don Street explains Heavy Weather Preparation and Sailing Tactics, Heaving To, Foredeck Work, Mainsail Flaking Systems, Emergency Sail Repairs, Distance Offshore & Simplified Celestial Navigation, and How to Rig Boom Preventers for jibe prevention.

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    Streetwise Tips Vol. 1 Transatlantic with Street Video

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    A film by Gavin Shaw Running time: 1 Hour 57 Minutes Classic trade wind 5,000 mile Transatlantic crossing shot in 1986 aboard legendary sailor/author Don Street's 1905 engineless 44 foot yawl, Iolaire. Documents Iolair's ninth Atlantic crossing from Ireland with eleven ocean islands along the way to Christmas in the Caribbean.

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    Sail Vicarious: Vicarious Sailing Sail Vicarious 6 Video Series

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    A video series by Spencer and Kathleen Bailey Running time: 8.5 hours. Join Spencer and Kathleen over a multi-year project as they locate the right cruising sailboat, make her ready for long range cruising. Then cast off with them as they cruise the U.S. eastern seaboard and venture offshore to the Bahamas and onto the Caribbean. You'll be there as they learn the hard way, correct mistakes, gain experience and confidence by doing, then reap the rewards of cruising aboard a well found vessel.

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    Circumnavigation - Pardey Off-Shore Sailing Lin and Larry Pardey Storm Tactics Video

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    A film by Lin & Larry Pardey

    Running time: 81 minutes. Lin & Larry Pardey Storm Tactics: Cape Horn Tested video delivers the skills you need to weather storms with confidence. It's the next best thing to having the Pardey's onboard, coaching you on storm tactics as the seas build and the rigging howls.

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    A film by Lin and Larry Pardey Running time: 90 minutes. Lin & Larry Pardey Ocean Sailing Tips Video demonstrates over two dozen ocean sailing skills on board their 29 foot wooden cutter, Taleisin, the boat that was their home for over 25 years and 100,000 miles of ocean sailing. Get ready to cross oceans with the Pardeys.

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