Watch Sailing & Boating Adventures Around the World – Page 8 of 14

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.

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Boat Life: Leave the Dirty Jobs for Brittany – Lazy Gecko Sailing VLOG 211
Lazy Gecko Sailing & Adventures

Boat Life: Leave the Dirty Jobs for Brittany – Lazy Gecko Sailing VLOG 211

We're pulling the anchor up and headed for the Hudson River! It's finally time to repair the damage from our hit and run boater, in the meantime we'll do some much needed maintenance on the boat as well as explore New York City in the fall! Come along for the adventure and make sure t...
Two Girls…Two Lessons. –  Lazy Gecko Sailing VLOG 210
Lazy Gecko Sailing & Adventures

Two Girls…Two Lessons. – Lazy Gecko Sailing VLOG 210

We're going sailing and Tara, our new crew member, is hoisting the sails! We'll sail towards New York where we'll anchor off of a famously haunted island where we end up having a spooky visitor come aboard Calypso. I'll try out my brand new HH gear and we'll sit down to get ...
Sailing the British Virgin Islands for FREE! – Ep 84
Sailing Jibsea

Sailing the British Virgin Islands for FREE! – Ep 84

This week we sail from St. Martin/Sint Maarten to the British Virgin Islands in big seas and big waves! We anchor in the deepest water to date and show you how we cruise the BVIs on a budget. We heard that it's quite pricey to sail in the BVIs due to mooring ball fees and it being a popular cha...
Tara Takes One for the Team! – Lazy Gecko Sailing VLOG 209
Lazy Gecko Sailing & Adventures

Tara Takes One for the Team! – Lazy Gecko Sailing VLOG 209

I take Tara to a pub where she decides to take one for the team...She's slurping it down so we can enjoy a cold one! Then we're sailing to a favorite local anchorage where we'll hit a few fun spots. I'll toss on one of my favorite bikinis...It's time for some maintenance so ...
Sailing to Anchor for the First Time – Ep 82
Sailing Jibsea

Sailing to Anchor for the First Time – Ep 82

After sitting tight in an anchorage waiting out high winds, we finally move our sailing monohull over to another bay in St Martin, on the French side of The Caribbean island. We sail to where the party's at over in Tintamarre, a popular remote island amongst day tours and charter boats in St M...
Naked Shots!! – This S#!T is going to be Delicious! – Lazy Gecko Sailing VLOG 208
Lazy Gecko Sailing & Adventures

Naked Shots!! – This S#!T is going to be Delicious! – Lazy Gecko Sailing VLOG 208

We're in Montauk, New York waiting out a big blow. We'll go exploring which turns into day drinking in one of America's most lovely towns! Come see all the craziness unfold. Then it's back to Calypso for some more wild times! Check out our NEW webpage at www.lazygeckos.net Othe...
Jeeping It on Some Island Somewhere…Totally Our Style! – Lazy Gecko Sailing VLOG 207
Lazy Gecko Sailing & Adventures

Jeeping It on Some Island Somewhere…Totally Our Style! – Lazy Gecko Sailing VLOG 207

We're on Block Island in the Northeast U.S., we meet some amazing new friends who offer us their sweet classic Jeep for a day of exploring! Come experience this amazing island with us, Jeep style! We'll see amazing sights, lighthouses, funny animals and more! Music Credit: Instagram @Tayl...
UPDATE, ANNOUNCEMENT: Boat Sale, Our Next Adventure – Ep 80
Sailing Jibsea

UPDATE, ANNOUNCEMENT: Boat Sale, Our Next Adventure – Ep 80

This episode, we share an update what we've been up to, the sale of our monohull sailboat, our sailing plans, what's next for us and what to expect for Jibsea in the upcoming future. NEW VIDEOS EVERY FRIDAY! Please subscribe and share our videos - every bit of support is much appreciated,...
Seasick Nanny – Will She Make It? – Lazy Gecko Sailing VLOG 206
Lazy Gecko Sailing & Adventures

Seasick Nanny – Will She Make It? – Lazy Gecko Sailing VLOG 206

We've pulled the anchor up and departed for an offshore sail to Block Island! Tara immediately learns what it means to have a sailboat moving under you, come see how it goes! Then we will take you exploring where we'll find historic, beautiful locations all before we get invited to a local...
We had to see this for ourselves – Ep 79
Sailing Jibsea

We had to see this for ourselves – Ep 79

Thanks to Skillshare for sponsoring this episode. The first 1,000 people to use the link or our code sailingjibsea will get a 1 month free trial of Skillshare: It's another boat life birthday this week in Caribbean Dutch island of Sint Maarten. We visit the famous and popular Maho Beach in P...
Rookie Mistake Made by Brittany! – Lazy Gecko Sailing VLOG 205
Lazy Gecko Sailing & Adventures

Rookie Mistake Made by Brittany! – Lazy Gecko Sailing VLOG 205

Tara, the new nanny, is onboard! We get her settled in, fix some boat issues, and visit a local historic destination before setting sail for Martha's Vineyard! Come explore a beautiful town with us! Then we realize that Brittany has made a major rookie mistake...Come find out what it is! Music...
Liveaboard Family Brings in a Full-Time Nanny! – Lazy Gecko Sailing VLOG 204
Lazy Gecko Sailing & Adventures

Liveaboard Family Brings in a Full-Time Nanny! – Lazy Gecko Sailing VLOG 204

After our weekend in Provincetown we sail 20 miles south to the Cape Cod Canal where we deal with high currents and bridges. Then we're off to get our watermaker fixed as well as pick up a brand new crew member! You'll meet Tara, our new liveaboard Nanny! Come meet the new crew! Check out...
REEL EXCITING 80nm SAIL to St. Martin & Sint Maarten – Ep 76
Sailing Jibsea

REEL EXCITING 80nm SAIL to St. Martin & Sint Maarten – Ep 76

Join us as we sail our monohull sailboat 80 nautical miles from Barbuda to Saint Martin, a french Caribbean Island. Fishing, big waves, ocean to table, conch horns, sunset and all that good stuff the sailing lifestyle is all about! NEW VIDEOS EVERY FRIDAY! Please subscribe and share our video - ...
Think We Might Miss the Islands! – Lazy Gecko Sailing VLOG 203
Lazy Gecko Sailing & Adventures

Think We Might Miss the Islands! – Lazy Gecko Sailing VLOG 203

We're sailing to an historic town in America! We'll grab some fuel, deal with another crazy boater, get the most expensive mooring ball ever and explore a beautiful town! All before having a little fun back onboard Calypso during sunset! Check out our NEW webpage at www.lazygeckos.net O...
Sailing Antigua to BARBUDA: Endless Beach, Foraging, Pink Sand, PARADISE. – Ep 75
Sailing Jibsea

Sailing Antigua to BARBUDA: Endless Beach, Foraging, Pink Sand, PARADISE. – Ep 75

We sail our monohull from Antigua to Barbuda and enjoy endless miles of amazing beachfront. It's a few windy days here but an amazing time nonetheless exploring pink sand beaches, foraging for food and drink on this gorgeous island before enjoying an amazing Caribbean sunset. NEW VIDEOS EVERY...
When you’re STRANDED by your Dinghy! – Lazy Gecko Sailing VLOG 202
Lazy Gecko Sailing & Adventures

When you’re STRANDED by your Dinghy! – Lazy Gecko Sailing VLOG 202

We're moving on...From a month of bad events, we've set sail and are headed east. Come hang out in a couple of Long Island Sound anchorages with us as we catch a stowaway, check for damages, do some maintenance and get stranded by Taco, our dinghy! Check out our NEW webpage at www.lazyge...
Boat Crash: We’re HIT by another boater…and they RUN! – Lazy Gecko Sailing VLOG 201
Lazy Gecko Sailing & Adventures

Boat Crash: We’re HIT by another boater…and they RUN! – Lazy Gecko Sailing VLOG 201

We're relaxing in a new anchorage when a seemingly intoxicated boater comes and slams into Calypso right before a storm hits. There's a struggle to get them free as they're tangled in our bridle, revving their engine and yanking on our boat/tackle in the process. Even the police get i...
Unmarked Anchorage, Beautiful Beaches, Pranks and Instant Karma in Antigua – Ep 74
Sailing Jibsea

Unmarked Anchorage, Beautiful Beaches, Pranks and Instant Karma in Antigua – Ep 74

Thanks to Skillshare for sponsoring this episode. The first 1,000 people to use this link will get a 1 month free trial of Skillshare: We sail our monohull into an uncharted anchorage spot and swim to shore and bask in the pristine beaches that line the Antiguan coast. Travis thinks it'll be...
1 in 2 Million Chance of THIS Breaking on our Boat? – Ep 73
Sailing Jibsea

1 in 2 Million Chance of THIS Breaking on our Boat? – Ep 73

It's catch and cook on our monohull sailboat this week! You'll never guess what we found in the belly of our snapper that we caught while trolling on our sail to Jolly Harbour in Antigua! We stop in Jolly Harbour tackle a boat project and repair and trying to figure out how to fix a broken...
Things Are Falling Apart…Death and Damage – Lazy Gecko Sailing VLOG 200
Lazy Gecko Sailing & Adventures

Things Are Falling Apart…Death and Damage – Lazy Gecko Sailing VLOG 200

We JUST got hit by a Hurricane, come see the aftermath. We notice we have some damage, then we try to get off the dock when we get some terrible news..all followed by a hit and run. This is just great.... Check out our NEW webpage at www.lazygeckos.net Other Links: Server: Visit our private serve...
Big Rolly Seas! – Sailing to a Remote Private Island in Antigua – Ep 72
Sailing Jibsea

Big Rolly Seas! – Sailing to a Remote Private Island in Antigua – Ep 72

This week we sail our monohull to the east coast of Antigua and explore a the private and uninhabited Green Island, and go on a dinghy adventure to Devil's Bridge. There's no shortage of waves, beautiful coast lines, super yachts and mega yachts here and we send our drone up to get the be...
Sailing to the Yachting Capital of the Caribbean & DIY BOWSPRIT SEAT – Ep 71
Sailing Jibsea

Sailing to the Yachting Capital of the Caribbean & DIY BOWSPRIT SEAT – Ep 71

This week we sail from Guadeloupe to the yachting hub of the caribbean where there's no shortage of luxurious mega yachts and super yachts. We explore Antigua and get the best view of English Harbour. NEW VIDEOS EVERY FRIDAY! Please subscribe and share our video - every bit of support is much...
When Nightmares Come True…We Get Hit by a HURRICANE! – Lazy Gecko Sailing VLOG 199
Lazy Gecko Sailing & Adventures

When Nightmares Come True…We Get Hit by a HURRICANE! – Lazy Gecko Sailing VLOG 199

It's a snoozy morning that gets destroyed by a Hurricane! We're hunkered down for what turns out to be way worse of a storm than anyone could have guessed. We're forced to ride it out...How did it turn out? Come see! Check out our NEW webpage at www.lazygeckos.net Other Links: Ser...
Sailing to TEENY TINY ISLANDS we Never Knew Existed in GUADELOUPE! – Ep 70
Sailing Jibsea

Sailing to TEENY TINY ISLANDS we Never Knew Existed in GUADELOUPE! – Ep 70

Thanks to Skillshare for sponsoring this episode. The first 1,000 people to use this link will get a 1 month free trial of Skillshare: We enjoy a beautiful sail our Hunter sailboat to a group of small (and some uninhabited) islands we never knew existed! We hike, explore ruins, penitentiaries and...
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