Last updated on August 30th, 2020.
This page will feature the best sailing documentaries I’ve found over the years. If you think I should add something, please let me know! I’ll try to keep this page updated, as a helpful resource.
This page is dedicated to sailing documentaries. I have another page dedicated to the best sailing movies.
Some of these are free documentaries on Youtube or Vimeo. Some can be easily watched for free with an Amazon Prime free trial; others can be rented for a very low cost. I love free things, like anyone else. I also like to help support creators, especially when they’re our fellow sailors.
My Favorite Online Sailing Documentaries
A young adventurer, Nick Jaffe, buys a small, old Contessa 26 sailboat in Europe, and sails it home to Australia. This story is inspirational, as is Nick’s website. Nick’s story is truly inspirational, and is fun to watch. He is proof that it’s the spirit of adventure that counts, not the size of a boat, or budget.
The fantastic story of Laura Dekker, an amazing young woman who fought for her dream to sail around the world at the age of 16. She spent her childhood aboard boats with her father, who is also a sailor. Although she had significant sailing experience and expertise, she had to petition the Dutch court system to gain permission for her sail.
Hold Fast is one of the best free sailing movies online. It was created by the legendary Moxy Marlinspike. A group of young, counter-culture friends buy an old sailboat and cruise the Carribean. This movie is hillarious, inspiring and thought provoking. Moxie Marlinspike is a fascinating and inspiring person. He is making enormous, quiet impacts on our world, and is worth following.
Chasing Bubbles tells the story of Alex Rust; a restless Chicago options trader who leaves his old life behind to search for something more. He decides to buy a sailboat and learns how to sail around the world with a rotating cast of friends. He did this all, despite having no sailing experience. This is a beautiful, well-made film which carries profound life lessons. This great, free sailing documentary is also availble in its full version on Youtube.
Sea Gypsies: Far Side of the World
This documentary shares one journey aborad the sailboat Infinity; a 120 ft. ferro cement boat, on a never-ending voyag. Infinity is crewed by a young, adventurous family and an eclectic mix of sailors and wanderers. In this film, Infinity sails from New Zealand to Antarctica, and then to Patagonia. Along the way, they narrowly escape disaster and assist a SeaShepherd vessel with anti-whaling efforts. This is truly a must-watch. Infinity’s most recent expedition led the ship and crew through the Northwest Passage, which looks to be their next documentary release. I first heard about Infinity through this great 59-North podcast episode, which is also worth listening to! There is more information about Infiinity and the Antarctica voyage around the internet. Here is a nice piece from Infinity crewmember Andy Jamieson. Andy is also the crew member interviewed in the 59-North podcast.
A group of young sailors, rock climbers and adventurers travel to Patagonia in South America. Part of the journey is spent hitchhiking aboard a beautiful, custom steel sailboat. The sailing leg of their journey is cut short because the sailboat is dismasted at sea, forcing them to divert to Rapanui. This trip loosely retraces a 1968 overland travel expedition, undertaken by legendary adventurers Yvon Chouinard and the late Doug Tompkins; founders of Patagonia and The North Face, respectively. I love this film and highly recommend it.