Watch Sailing & Boating Adventures Around the World – Page 2 of 15
Explore sailing, boating, and water sports through our curated video archive. From epic sea voyages to serene diving escapes, discover unforgettable adventures from top YouTube creators. Start your journey. Dream big. Sail far.
Showing 25-48 of 342 results
Last Day in The Isle of Skye, Scotland | DrakeParagon Sailing
****VIDEOS ALWAYS COMMERCIAL FREE ON PATREON!**** A stunning anchorage with easy access to land and good amenities...with no other boats! What is this hidden gem? We sailed to Loch Harport in The Isle of Skye and enjoyed a week in this beautiful anchorage (in July!) that we practically had to ourse...
We Have Some BIG NEWS! – S4EP13
Check out the BRNKL System here: In this episode we share some big news - we are SELLING Gypsy Moon. It's been an emotional roller coaster to come to this decision, but it is the only way we can move forward to something new. We also take you through the full install of our BRNKL Security syst...
A secluded and wild anchorage in Scotland – Loch Claidh in the Western Isles | DrakeParagon Sailing
If you’d like to watch this episode commercial free, please consider joining our community on Patreon. No cell, no wifi, no people...just our boat and a good friend. This is Loch Claidh in the Western Isles of Scotland. We tuck into this beautiful anchorage and enjoy a solitude that can only come wh...
Spend 36 Hours at Sea with Us! – S4EP12
Blu3 Nomad portable diving system: In this episode we set sail on a 36 hour passage to St.Martin! We had an amazing sails with beautiful conditions, but our autopilot fails on route leaving us to hand steer for 24 hours. Upon arrival we have to navigate through a busy, narrow and shallow bridge to...
Goodbye’s Never Get Any Easier😢 – S4EP11
In this episode we explore Martinique by sea and by land - we rent a car to be able to drive around and see more of the island for Cass' last day. The sad day comes to drop her off at the airport and say goodbye after an amazing time spent together. She is the best crew and best friend I could ...
Her FIRST OVERNIGHT Sail – S4EP10
In this episode we set sail from Bequia to the french island of Martinique! As this would be Cass' first overnight sail we take time to prep everything like food and filling up with water before setting off. We were blessed with amazing conditions for this sail, that is until the wind picked up...
Good Times with Friends in the Caribbean – S4EP8
Get 10% off your first month of therapy with my sponsor BetterHelp: In this episode we leave Canouan and sail back south to Union island to meet up with our good friends @OddLifeCrafting and enjoy a ton of waters ports together! Thanks for watching! Be sure to give the video a thumbs up and SUBSC...
Life On Solid Ground – S4EP7
In this episode we switch things up a bit and stay on solid ground for a couple of days! After a few sickeningly rolly nights on anchor due to high winds we took refuge in the beautiful Atlantic Breeze Apartments in Canouan. If you are interested in booking this Airbnb click here: Or you can conta...
We Found The Most AMAZING Spot On This TINY Island – S4EP6
In this episode we officially check into a new country! We explore the Grenadines with our buddy boat @SailingSunday and have a ton of fun on the water. We then have some BIG NEWS as Kiki and I let ya'll in the loop about our recent engagement. After discovering this cool sailor friendly resort...
She’s BACK Sailing Her Boat Alone! ⛵️
IM BACK! After a 7 month hiatus, im finally back! I went through 6 months of non stop rain in California, and some personal losses in my family. It’s been a tough few months but I’m finally back where I am the happiest, on the BOAT! In this video I attempt to fix a patch in my dinghy, and then get t...
24 Hours of Raw, Unfiltered BOAT LIFE – S4EP5
In this episode we take you along for what 24 hours of REAL boat life looks like - and reality check... it's not always sunshine, cocktails and bikinis! There are also times where nothing seems to go right. Living on a boat means constant repairs and often things break at the WORST times. But w...
The Speedy Stitcher Sewing Awl | Paragon’s Favorite Stuff Ep. 21
An extremely economical sewing awl that can fit on any boat and is robust enough to deal with whatever the cruising life has to throw at it? This is why the Speedy Stitcher is a must have on our boat! If you enjoyed this video, then give it a thumbs up, make a comment, share it, or support this do...
NEW CREW! Best Friends Reunited – S4EP4
In this episode we welcome a very special new crew member onboard!! Some of you might recognize her from our old Somerset Sailing videos, or past videos on my channel. Everyone welcome Cass! I'm so excited to be reunited with one of my best friends and get to spend some quality time together on...
Back to the Sea She Goes! – S4EP3
In this episode we return to Spice Island Marine ( ) in Grenada to get Gypsy Moon ship shape and ready for another season of cruising! We check a ton of things off our long to do list including a NEW BIMINI and installing our new Precision Sails Mainsail ( ). We make some new boatyard buddies, Ry...
Sailing From Stornoway, Scotland to The Faroe Islands – Part 2 | DrakeParagon Sailing
It’s been a rolly sail to the Faroe Islands with both too much wind and not enough. Now we just need to make our way through the fog and 3-4 knots of current before we reach our destination. Here we come Vestmanna! If you enjoyed this video, then give it a thumbs up, make a comment, share it, or su...
Leaving Santa Cruz | Sailing Avocet
Being able to spend an entire month in my hometown of Santa Cruz was wonderful, which is why leaving was so bittersweet. But before we cast off again Chris left us for Hollywood and Cleo and I (okay, just I) were left to tend to Avocet's to-do list. When Chris returned we got some biking in and...
Sailing from Stornoway, Scotland to The Faroe Islands – Part 1 | DrakeParagon Sailing
The first sail of the season and things don't quite go as expected. For a commercial free version check out ⬇️⬇️⬇️_________________________________ ⬇️⬇️⬇️ If you enjoyed this video, then give it a thumbs up, make a comment, share it, or support this documentary on Patreon or via Paypal with t...
2023 Voyage Plan and Our First Weather Window | DrakeParagon Sailing
Time to break out the Predict Wind app because the sailing season has officially begun on Paragon! After a winter in the Western Isles of Scotland, we're looking to sail north to the Faroe Islands and then head south. Waaaaaay south! If you enjoyed this video, then give it a thumbs up, make a...
REALISTIC Day in the Life of Liveaboard Sailors Cruising the Caribbean
Join us for a day living on our sailing catamaran, cruising the Caribbean! ⛵️ We wake up in a peaceful anchorage, go snorkeling, and take care of some general boat maintenance. Suddenly, a storm hits, but we weather it out despite being unprepared... We experimented with a new cocktail recipe to use...
Island Hopping in the Caribbean: Sailing, Snorkeling and Relaxing with Friends
Join us for a beautiful snorkel at the pier in Frederiksted, St. Croix, where Holly swam with turtles, spotted eagle rays, and hundreds of fish amongst diverse coral. After, we sail to Norman Island, BVI, where we meet up with friends to explore some caves, then show you a glimpse of an average nigh...
Day in the Life of Liveaboard Sailors: Cleaning, Snorkelling, and Sailing!
We started the week by catching up on chores in St. Thomas, a mundane but necessary task. Holly went for a swim/snorkel around the anchorage and saw some beautiful sea life. The arrival of a large cruise ship solidified our decision to head somewhere new, so we pulled up the anchor and sailed to St....
All Good Things Must Come To An END… S3EP18
TRAVEL WITH ME: In this episode we stop in the magical island of Dominica on our way south to Grenada. We finally make it to Grenada safe and sound just in time for our haul out date. We pack up the boat and prepare it for hurricane season on the hard at Spice Island Marine before saying our goodb...
BROKEN RUDDER! A Sailors Nightmare – S3EP17
In this episode we experience every sailors worst nightmare - a broken rudder! We have to haul out last minute and take you through the process of repairing it as quickly as we can. Thanks for watching! If you enjoyed this video be sure to like/leave a comment. Also don't forget to SUBSCRIBE! ...