Watch Sailing & Boating Adventures Around the World – Page 2 of 2

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 25-41 of 41 results
#45: The Tunnel of Doom
HaveWindWillTravel.com

#45: The Tunnel of Doom

Prepping our boat for the fiberglass job took a lot of cleaning, a lot of a plastic and a lot of tape, cut mostly by my teeth! Pretty cool to see her all ready for surgery, though. Lookout rot! Here we come!
#43: Removing the Shrouds: How Many Lawyers Does it Take?
HaveWindWillTravel.com

#43: Removing the Shrouds: How Many Lawyers Does it Take?

Two apparently! Removing these shrouds required some hefty plumbing wrenches and a few bad lawyers jokes but we finally got them off! Enjoy!
#38: Here Comes the Crane!
HaveWindWillTravel.com

#38: Here Comes the Crane!

Just a few last detachments (just a few, I swear!). This mast pull prep is no effin joke. But all that's left now are the rods holding her up. Here comes the crane!
#37: Here Comes the Boom!
HaveWindWillTravel.com

#37: Here Comes the Boom!

You guys watch closely, because we're counting on you to help us put all of this crap back together. Preparing the boat to pull the mast turned into one heap of a mess, but don't let it get you down! Getting that stringer fixed will get us one step closer to sailing south! Follow along ...
#35: Time to Replace the Old (B)rods
HaveWindWillTravel.com

#35: Time to Replace the Old (B)rods

The only really bad thing about rod rigging is that she doesn't show her age, but we knew, at 30+ years, our original rods were getting up there. If we wanted to sail south next season, a re-rig was in high order. Let the debate begin ... rod versus wire.
#33: Havana Daydreaming
HaveWindWillTravel.com

#33: Havana Daydreaming

We've got a TON of projects coming up kids, so I wanted to give you a little glimpse of what it is that motivates us when we're doing all of this scraping, cleaning, sanding and prepping. Plenty of cruising vids at
#32: When Rigging Fails
HaveWindWillTravel.com

#32: When Rigging Fails

Because sometimes it just does, although our takeaway here was: check your chafe points. But, we were surprised to see our mast (even with a rotten base) stood up to some of the heaviest forces she has ever seen. This was, easily, our worst sail ever on the boat.
#27: Where Are You Going?
HaveWindWillTravel.com

#27: Where Are You Going?

Cuba! I'm kidding (sort of). Maybe. There and 1,000 other places. I'll share our (very vague) plans but we're less than a year out and--believe me--that's not near enough time. (But it never is.) A big shout-out to just a few of the other wanderlusts who inspire us: Dani &a...
#26: Where Have You Been?
HaveWindWillTravel.com

#26: Where Have You Been?

Before we tell you where we're going, I thought it might help to know where we've been. In fact, I wrote it all down for you in my first sailing book -- SALT OF A SAILOR (FREE TODAY on Kindle): Happy Thanksgiving followers!
#25: What is Your Story, Annie?
HaveWindWillTravel.com

#25: What is Your Story, Annie?

Time to get real people. I've had a great time making entertaining videos but it seems folks want to know the REAL STORY. Well, this is it. The story of me. Stay tuned for the Keys to the Kingdom book launch at
#14: Brandon Makes Us Dock Under Sail!
HaveWindWillTravel.com

#14: Brandon Makes Us Dock Under Sail!

Come along as our good friend and boat repair expert Brandon with comes out for a day sail to teach us a few sailing tips aboard our 1985 Niagara 35 and bets us we can't dock under sail. "What would you do if the engine went out?" he asked. It's friends like Brandon that make ...
#12: Aerial Silks on a Boat — The Reward
HaveWindWillTravel.com

#12: Aerial Silks on a Boat — The Reward

Now that you know how to rig it up, it's time for your reward: an aerial silks routine on-board. Silk at your own risk people and enjoy more boat silking videos at
#11: Aerial Silks on a Boat – The Rigging
HaveWindWillTravel.com

#11: Aerial Silks on a Boat – The Rigging

Want to know how to rig the silks on the boat? I'll show you! WARNING: Kids - do not try this at home (try it on your boat!). Hang at your own risk. Silk carefully people! More silking videos at
#10: Sailing Dragon, Hidden Lessons
HaveWindWillTravel.com

#10: Sailing Dragon, Hidden Lessons

Join us for a fun day-sail aboard our Broker-Turned-Boat-Buddy, Kevin's, Pearson 36 cutter, PanDragon where we share some lessons and some "YouTube crazy" good times.
#4: Tour of Our Niagara 35 – Topside
HaveWindWillTravel.com

#4: Tour of Our Niagara 35 – Topside

Seems the first tour I did I forgot entirely we even HAD a topside. You might want to see the--you know--sails and rigging and stuff. So, here 'tis. Tour of zee boat, topside! More photos and write-ups about our beautiful boat under "The Boat" tab at
#3: Tour of Our 1985 Niagara 35 – Below Decks
HaveWindWillTravel.com

#3: Tour of Our 1985 Niagara 35 – Below Decks

Virtual tour of our 35 foot live aboard sailboat, a Canadian-built 1985 Niagara 35 designed by Mark Ellis and built by Hinterhoeller with one stateroom, a separate stand-up shower stall, and a spacious but functional interior. Perfect cruising vessel for a couple. Also, Video Annie says embarrassi...
Come Aboard — Experience the Cruising Lifestyle!
HaveWindWillTravel.com

Come Aboard — Experience the Cruising Lifestyle!

A few years ago I was a lawyer, working 10 hours a day, headed for partnership, but I quit my job because I wanted to work to live not live to work. Get inspired. Get on board, and cruise with us. Subscribe for videos on sailing, cruising, boat repair, re-rigging our boat, kite-surfing, aerial si...
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