Watch Sailing & Boating Adventures Around the World tagged “Macgregor”

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 1-24 of 74 results
🪙 Cap’n finds Booty at the Reef🪙😜
Sailing And Fun

🪙 Cap’n finds Booty at the Reef🪙😜

🚩🚩🚩Socials links below https://linktr.ee/sailingandfun Here's one of those beautiful snorkeling days in Key West Florida we promised. We hit a new mooring out at Eastern Dry Rocks and have the perfect setup of sun, low tide at noon, great water c...
🏝️An Undiscovered Island!!!🏝️sailing and fun🏝️
Sailing And Fun

🏝️An Undiscovered Island!!!🏝️sailing and fun🏝️

🚩🚩🚩Socials links below https://linktr.ee/sailingandfun After years in the Keys you would think there was no island left undiscovered by us but we are excited to be surprised by a jewel in the middle of the crystal clear waters near Key West Flor...
😧Exercise Caution – Advised 🦈🛟sailing and fun 🛟
Sailing And Fun

😧Exercise Caution – Advised 🦈🛟sailing and fun 🛟

🚩🚩🚩Socials links below https://linktr.ee/sailingandfun After a fun and educational little tour of our marina, we head out to the furthest reef in the Florida Reef Tract, well the furthest that we've been to, Western Dry Rocks. We've read that we...
The Hot🔥 and Cold ❄️of it – Key West – Sailing & Fun
Sailing And Fun

The Hot🔥 and Cold ❄️of it – Key West – Sailing & Fun

🚩🚩🚩Socials links below https://linktr.ee/sailingandfun We hit the Mud Keys on a day when we might should have stayed anchored closer in. Day two brings us luck with the brilliant sunshine as we make our way out to the reef. Unfortunately there...
100 Ways to get Hurt 🤕- plus CAT update⛵
Sailing And Fun

100 Ways to get Hurt 🤕- plus CAT update⛵

🚩🚩🚩Socials links below https://linktr.ee/sailingandfun We set sail in the beautiful sunshine to hit up one of our favorite little private islands. We have it to ourselves for half the day at least so we do some exploring, paddle board over to th...
Fortified Fun 🏰 Key West Beach – 🩴sailing and fun
Sailing And Fun

Fortified Fun 🏰 Key West Beach – 🩴sailing and fun

🚩🚩🚩Socials links below https://linktr.ee/sailingandfun We love going to historical places and this fort was not a disappointment. Fort Taylor in Key West is not just a captivating place to soak up history but it's also surrounded by a beautiful ...
Barley a spot not Stung!😧sailing and fun
Sailing And Fun

Barley a spot not Stung!😧sailing and fun

🚩🚩🚩Socials links below https://linktr.ee/sailingandfun We are hitting up Eastern Dry Rocks off the coast of Key West today and unfortunately this vast reef lives up to its name in that there's little living coral and many rocks - at least in th...
1 leak, 2 leak 3 leak More😢😭sailing and fun?
Sailing And Fun

1 leak, 2 leak 3 leak More😢😭sailing and fun?

🚩🚩🚩Socials links below https://linktr.ee/sailingandfun We try not to let rain stop the fun as we turn cloudy skies into a day of sailing the coast of Key West.
Motorless & Drifting in the Atlantic!⛵
Sailing And Fun

Motorless & Drifting in the Atlantic!⛵

🚩🚩🚩Socials links below https://linktr.ee/sailingandfun Motorless, sail-less and drifting in the Atlantic... and it is awesome! We sail over a myriad of ocean green waters, cruise by the Key West harbor and enjoy a lazy river day on a open ocean ...
💃🏻What makes a good dance floor?💃🏻 Adventures with Sailing and Fun
Sailing And Fun

💃🏻What makes a good dance floor?💃🏻 Adventures with Sailing and Fun

🚩🚩🚩Socials links below https://linktr.ee/sailingandfun After checking out an aerial map, I spotted a place that I thought would be perfect for a day of relaxation, swimming, cocktails and a little bit of dancing.
🦈BIG SPLASHES are NOT Good at the Reef🦈
Sailing And Fun

🦈BIG SPLASHES are NOT Good at the Reef🦈

🚩🚩🚩Socials links below https://linktr.ee/sailingandfun We are starting off this series in the Keys with a visit to our favorite place, The Reef! I get to break in my extra long dive fins and test my ability to get down to the very bottom as many...
🌊⛵Tossed at Sea – Bad Karma?⛵🌊adventures with Sailing & Fun
Sailing And Fun

🌊⛵Tossed at Sea – Bad Karma?⛵🌊adventures with Sailing & Fun

🚩🚩🚩Socials links below https://linktr.ee/sailingandfun We set out on a few “blown up" adventures - winding our way through the beautiful Low Country marsh as well as out in the Atlantic in both Charleston and the Florida Keys.
🪸😀The Best Way to spend a Weekend😀 🪸Sailing and Fun
Sailing And Fun

🪸😀The Best Way to spend a Weekend😀 🪸Sailing and Fun

Learn how to make the most of your weekend getaway by exploring Charleston's picturesque coastline and pristine waters through our top sailing adventures. From sunsets to snorkeling, we've got you covered!
We Broadsided 2 Boats!😧⛵🫣adventuress with Sailing and Fun
Sailing And Fun

We Broadsided 2 Boats!😧⛵🫣adventuress with Sailing and Fun

Experience an exciting day on the water with Sailing and Fun as we explore Charleston's picturesque marina, attempt an unexpected sail, encounter a boating accident, head to the beach, and brave the chilly marina pool!
Seeing the Light😎sailing adventures with Sailing and Fun
Sailing And Fun

Seeing the Light😎sailing adventures with Sailing and Fun

Join Sailing and Fun on an exciting journey to visit one of the oldest lighthouses in the world! Experience dolphins, discover hidden beaches, and immerse yourself in a breathtaking maritime adventure at Morris Island Lighthouse.
🎡You know what the best thing is… adventures with Sailing and Fun🎡
Sailing And Fun

🎡You know what the best thing is… adventures with Sailing and Fun🎡

🚩🚩🚩Socials links here https://linktr.ee/sailingandfun After a quick look back at the latest season, we finally head to Charleston, SC. This start is just to familiarize ourselves with the surroundings and get settle at our marina - the nicest on...
Last Look Before We Leave 😎 sailing adventures with Sailing and Fun
Sailing And Fun

Last Look Before We Leave 😎 sailing adventures with Sailing and Fun

🚩🚩🚩Socials links here https://linktr.ee/sailingandfun A quick last visit to our fav private island and a bit-o-sailing before we head to a new destination!
Careful – They can hear you🤫adventures with Sailing and Fun
Sailing And Fun

Careful – They can hear you🤫adventures with Sailing and Fun

🚩🚩🚩Socials links here https://linktr.ee/sailingandfun There's another fun day to be had at alligator reef but this time we fit in a little bit of smooth sailing and get to mingle with a group of sharks.
Banging in our Boat 😜adventures with Sailing and Fun⛵
Sailing And Fun

Banging in our Boat 😜adventures with Sailing and Fun⛵

🚩🚩🚩Socials links here https://linktr.ee/sailingandfun A marina right in the heart of Key West is our home for the next couple days while we try to sort out some motor issues. Fortunately it's only a seven mile run out to Sand Key, a beautiful re...
Island Girl 👙( and boy ;)🩳Sailing adventures with Sailing and Fun
Sailing And Fun

Island Girl 👙( and boy ;)🩳Sailing adventures with Sailing and Fun

🚩🚩🚩Socials links here https://linktr.ee/sailingandfun We hit up this private island once before and we couldn't resist coming back. We'll probably come as often as we can - as long as it stays private at least. The goal is to do it all, relax, e...
The Slide that Untied… my Bikini ;)🧜‍♀️ Sailing adventures w/ Sailing and fun🧜‍♀️
Sailing And Fun

The Slide that Untied… my Bikini ;)🧜‍♀️ Sailing adventures w/ Sailing and fun🧜‍♀️

🚩🚩🚩Socials links here https://linktr.ee/sailingandfun It is said that when you're on a boat, everything should have a dual purpose and in this case even the paddleboard takes on a new role. We are hitting up another reef in this little film but ...
Crunch!??💦Rescue & Repair Outboard Experience 🌊⛵ Sailing and Fun – Adventures in the Florida Keys!
Sailing And Fun

Crunch!??💦Rescue & Repair Outboard Experience 🌊⛵ Sailing and Fun – Adventures in the Florida Keys!

🚩🚩🚩Socials links here https://linktr.ee/sailingandfun When cruising the beautiful waters in the Florida Keys, the shallows have us grounded. We show you what happened miles from help and what we did to diagnose and repair our outboard motor. Key ...
👙 🤿 Wild Life – Take a walk on the Bayside – Sailing and Fun in the FL Keys 👙 🤿
Sailing And Fun

👙 🤿 Wild Life – Take a walk on the Bayside – Sailing and Fun in the FL Keys 👙 🤿

The wind is up and so are the waves so we set a course for adventure on the bay side of the FL Keys. Our Socials https://linktr.ee/sailingandfun
7 – Is it a Lucky Number??
Sailing And Fun

7 – Is it a Lucky Number??

Super high winds land us on a sand bar with 7 ( probably more ) sharks and a manatee! Plus a Navy fly by :) Uncensored & Exclusive Content https://linktr.ee/sailingandfun In this video, we rushed to launch off the boat trailer in the Florida Keys to ...
Epic water experiences, one click away.

Something AWESOME is coming!
Be the FIRST to know⛵

Sign up for exclusive updates and be the first to hear when we go live!
Get sneak peeks, exciting announcement, and special content straight to your inbox!

We don’t spam! Read our privacy policy for more info.


WeBoating
Logo
Shopping cart