Favorite Sailing Documentaries

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. We have another page dedicated to the best sailing movies.

How to Watch These Documentaries

Some of these are free documentaries on Youtube or Vimeo. When they are, I’ll link to them. Almost all of these can be easily watched for free with an Amazon Prime free trial.

I love free things, like anyone else. I also like to help support creators, especially our fellow sailors, so I’m usually happy to pay for these documentaries when necessary.

Coyote: The Mike Plant Story

I found this fantastic sailing documentary on Amazon. It was a total surprise; I’d never heard about it before. I highly recommend it!

We debated whether to rent this or not, and are really glad we gave it a watch. In retrospect, I wish I’d paid a few dollars more and bought it. It’s a very well-produced film, directed by Thomas M. Simmons, Mike Plant’s nephew.

Mike was a legendary sailor who lived life to the absolute fullest, which included making dangerous decisions. In his adventures, he hitchhiked overland to South America, briefly spent time in prison for drug smuggling, built a boat and became a legendary sailor, racer and multi-time circumnavigator. I’m embarrassed to say I’d never heard of Mike before watching Coyote, but am glad I do now. I’m excited to read the book, which was written by his sister. It apparently explores Mike’s life in more balanced nuance.

Coyote: The Mike Plant Story


Kekoa is the story of two sailors –brothers, and best friends– who live life to the fullest.

Although they have no experience with wooden boat building, they teach themselves to build a beautiful, luxury wooden catamaran, from scratch.

They use Kekoa as a platform to build truly adventurous, beautiful lives. They, and Kekoa, attract a community of like-minded friends and family in the U.S. virgin islands. Today they use Kekoa to run a sailboat charter business out of the USVI.

This story is a must-watch! It’s available to watch free on Youtube.

Following Seas

Following Seas is an absolute gem of a sailing film!

I give Following Seas my strongest recommendation. There are too many amazing nuances to detail here, so I won’t try to cover everything. I highly suggest you just give it a watch!

ir?t=flguide 20&language=en US&l=li3&o=1&a=B075FX7MGDIn short: Following Seas is the story of an adventurous sailing family.

With young children aboard, they sailed the world over a span of 20+ years, and raised their family along the way. I loved the simplicity, resilience and incredible seamanship embodied by this crew.

They built their own ferrocement boat and used it to circumnavigate 3 times; once via the canals, once via the capes, and once around Antarctica. They were the epitome of absolute simplicity, professionalism and self sufficiency.

This film sparked a lot of thought and discussion for our family. It’s fascinating to consider the advances in yachting technology over the decades, and in the cruising lifestyle. The Griffith family navigated by a sextant, and all of their gear was simple and robust.

I enjoyed seeing the similarities between this family’s adventure and their modern peers, like SV Infinity. The Griffith family apparently financed their voyages by selling photography and film footage. In many ways this family was a predecessor to the popular Youtube sailors of today.

I highly recommend this documentary! If I were a film critic I’d probably give it 9.5/10 rating.

You can watch it easily online; you can rent or buy Following Seas on Vimeo, or on Amazon. You can also watch it for free with a free Amazon Prime trial or a membership.

Following Seas

Between Home

I love this story. I followed it in real-time as it happened, and still follow Nick all of these years later.

The story of Between Home is that of a young adventurer, Nick Jaffe. Nick 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 Jaffe is proof that it’s the spirit of adventure that counts, not the size of a boat, or budget.

Between Home: Full version and trailer


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.

Here is a sad, recent update on Laura Dekker’s boat, Guppy. It was published in Lats and Atts magazine. This Lats and Atts issue has been made available online — you can access the full version free.

Maidentrip: Full version and trailer

Hold Fast

Hold Fast is one of the best free sailing movies online.

It was created by the legendary Moxie Marlinspike.

A group of young, counter-culture friends buy an old sailboat and cruise the Caribbean. This movie is hilarious, 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

I love this film.

Chasing Bubbles tells the story of Alex Rust; a restless Chicago options trader who leaves his old life behind to search for something more. Alex 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; it carries profound life lessons. This great, free sailing documentary is also available in its full version, free to watch on Youtube.

Sea Gypsies: Far Side of the World

I first heard about Infinity through this great 59-North podcast episode, which is fantastic!

Note: At the time of this writing this documentary is available to watch for free on Amazon Prime. If you don’t have it you can easily use a free trial.

This documentary shares one journey aboard the sailboat Infinity. Infinity is a 120 ft. ferro cement boat, salvaged from the scrap yard, and then taken on an epic, never-ending voyage.

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 Sea Shepherd 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.

There is more information about Infinity 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.

Sea Gypsies Far Side of the World: Full Version and Trailer

180 Degrees South

A group of young sailors, rock climbers and adventurers travel to Patagonia in South America.

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.

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.

180 South full-length movie and trailer 

Hot Boats Cold Water (1983)

This sailing documentary is free to watch on Youtube. It captures the heyday of sailing and comes highly recommended by many sailors.