Top 10 Sailing Films and Best Documentaries Of All Time

As a massive fan of the water, if I’m not on a boat, I’m often reading of sailing adventures, planning a trip, or losing myself in a sailing related movie. In no particular order, here’s my run down of some of the best sailing related films and documentaries out there.

The Top 10 Sailing Films and Documentaries…


Adrift – Based on a true story after facing a Category 4 hurricane on a sailing trip, Tami Oldham and Richard Sharp face the unimaginable in the Pacific Ocean. A harrowing tale, with a MASSIVE plot twist, this is a must see sailing film.

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Highlights – Starfish and Family

Since we’ve had Ruby May back we’ve enjoyed a couple of short sails in our local waters. I wanted to share a couple of brief notes on two of those passages.

The first thing I wanted to share was a strange highlight from a night on anchor in Stangate Creek on the River Medway. A beautiful night on-board and our first night in local waters. In the morning when we pulled the anchor up, it came up with hundreds of worm-like Starfish attached to it. Without a doubt, the strangest ‘anchor-experience’ I’ve had! Take a look at the pics here…

Don’t worry, just after I shot this they were all thrown back in!

A family day on the water

On bank holiday Monday we got to take my Dad and his girlfriend for a cruise around the Montgomery wreck. I’ve not had the opportunity to sail with him before, and due to COVID-19 restrictions we’ve not spent much time together in the last year. So, it was particularly special and was very fun. It was a windy day (F7 by the end of the day), but we had a great day and it was a pleasure to have our first guests on-board. Here’s a couple of pics…

To see more pictures from our recent sailing trips – go to

Ruby May’s Homecoming, Sailing From Milford Haven to Chatham

After far too may months, restrictions finally eased sufficiently to allow us to sail our much loved new boat home. We’d done various bits of prep on-board, such as fitting a new radar reflector, adding new safety gear, fixing the AIS, and fitting a new log. We’d also had a brief shakedown sail to Skomer Island and finally the day had arrived for us to bring her home.

On this passage we had Dolphins and Puffins, huge waves and flats seas, lots of wind and no wind! We also got to know our boat and had an awesome week on the water with the kids. Grab a cuppa, this blog is my diary from that week…

A Dolphin escorting us on our passage
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