Watch Sailing & Boating Adventures Around the World

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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Did Our Charter Gambit Work? | Mid Season Update
BoatFools Sailing

Did Our Charter Gambit Work? | Mid Season Update

@boatfools #sailboatcharter #bareboatcharter #morgan382 #morgan384 #sailingmaine Did Our Charter Gambit Work? | Mid Season Update Was putting our own sailboats into charter a brilliant idea—or a terrible mistake? We're halfway through our first charter season, and it's time for an hone...
Which dream vacation is right for you? Here is ours!
Sail Stillwater

Which dream vacation is right for you? Here is ours!

If you’ve ever dreamed about sailing through the Caribbean, waking up in a new island paradise every day, and skipping crowded resorts… this is your sign to make it happen. In this video, we break down exactly why booking a sailing charter in the British Virgin Islands (BVI) might be the best vacat...
Skippering our first sailing regatta in Antigua
Sail Stillwater

Skippering our first sailing regatta in Antigua

Join us on a sailing adventure through the beautiful Caribbean, as we explore Antigua while sailing in the Chasing Bubbles Regatta. This sailing regatta was an unforgettable experience, filled with stunning sunsets and group gatherings. Discover the joys of boat life with us as we journey through th...
Sailing in Paradise | Chasing Bubbles Regatta- Antigua
Sail Stillwater

Sailing in Paradise | Chasing Bubbles Regatta- Antigua

We recently had the incredible opportunity to skipper a Beneteau sailboat in one of the coolest sailboat regatta events to ever hit the Caribbean! We were able to learn from some amazing skippers all while sailing in a new area to us around the island of Antigua. Sailing with the group is not a trip...
Charter Chat Podcast episode 1. Why the BVI? w/ Alex Cena
Sail Stillwater

Charter Chat Podcast episode 1. Why the BVI? w/ Alex Cena

In this episode, we chat about yacht charters and sailing charters in the British Virgin Islands, the world-renowned mecca of sailing charters. We discuss the ultimate BVI charter itinerary, highlight the best anchorages and hot spots in the British Virgin Islands, and explain why the BVI continues...
Fish ON! Sailing the deep waters of St. Croix. Day #2
Sail Stillwater

Fish ON! Sailing the deep waters of St. Croix. Day #2

Sailing Charter Day 2 | St. John to St. Croix | Rough Seas, Fishing & Christiansted Harbor and Boardwalk. Day 2 of our Virgin Islands sailing charter takes us offshore as we leave St. John, USVI and sail across deep open water to St. Croix. With rough seas and steady wind, this passage was a t...
The most underrated sailing itinerary in the Caribbean! The USVI and SVI
Sail Stillwater

The most underrated sailing itinerary in the Caribbean! The USVI and SVI

Join Brian and the crew as they sail a Bali catamaran through the USVI and SVI, taking on high seas, remote islands, and one of the most adventurous routes in the Caribbean. This isn’t your typical charter itinerary—it's rougher, wilder, and absolutely unforgettable. From offshore fishing (we ...
BVI mooring ball failure = DISASTER!
Sail Stillwater

BVI mooring ball failure = DISASTER!

In this video we dive into the question: Are mooring balls safe in the BVI? We take a close look at the incident involving The Wandering Hillbilly, when his boat broke free from a mooring ball and ended up drifting and grounding — a dramatic reminder that mooring balls aren’t automatically “safe.” ...
Before we sail. Boat prep & provisioning
Sail Stillwater

Before we sail. Boat prep & provisioning

⛵️ Sailing Charter in the BVI | Boat Prep, Checkout & Provisioning Welcome aboard! In this video, we take you behind the scenes of our sailing charter adventure in the beautiful British Virgin Islands 🇻🇬. From prepping the boat and completing the charter company’s checkout process, to provision...
36 hours in St. Thomas. Best things to do!
Sail Stillwater

36 hours in St. Thomas. Best things to do!

: 🌴 36 Hours in St. Thomas, US Virgin Islands | Top Things To Do 🌴 Join us on a 36-hour adventure while we explore St. Thomas, USVI — one of the most beautiful islands in the Caribbean! Whether you're here on a quick getaway or a cruise stop, this guide covers the must-see spots, breathtaking...
Tour the Bali 4.8. Luxury charter catamaran in the BVI
Sail Stillwater

Tour the Bali 4.8. Luxury charter catamaran in the BVI

Welcome aboard the Bali 4.8 sailing catamaran- On a Whim – our largest charter boat yet! In this video, we give you a full Bali 4.8 walkthrough tour, highlighting the spacious design, luxury features, and everything that makes this catamaran charter yacht one of the most popular choices for sailing...
Exploring the British Virgin Islands by boat. Why this trip should be on your BUCKET LIST!!!
Sail Stillwater

Exploring the British Virgin Islands by boat. Why this trip should be on your BUCKET LIST!!!

Set sail with us for an unforgettable week in the British Virgin Islands! 🌊🏝️ From the stunning rock formations of The Baths to the vibrant underwater world at The Indians and Norman Island’s caves, every stop on this journey is a dream come true. Explore the charm of Cooper Island, the lively vibe ...
Sailing the BVI. Willy T and the Indians
Sail Stillwater

Sailing the BVI. Willy T and the Indians

Join us as we explore the legendary Norman Island in the beautiful British Virgin Islands! 🌴 We kick off our adventure snorkeling the famous caves, teeming with vibrant marine life and hidden treasures. Then, we make our way to the iconic Willy T floating bar, where fun and unforgettable moments aw...
Sailing the BVI. North Sound Virgin Gorda
Sail Stillwater

Sailing the BVI. North Sound Virgin Gorda

On day 2 of our bare boat charter in the British Virgin Islands, we bring you along with as we leave Cooper Island and head to North Sound on Virgin Gorda. On the way we stop at Great Dog, which is known for being a popular snorkeling spot in the BVI. Once to North Sound we heads to Bitter End yac...
Sailing the BVI. Setting sail for Cooper Island
Sail Stillwater

Sailing the BVI. Setting sail for Cooper Island

Our BVI sailing adventure kicks off with an exciting Day 1! We set sail from Nanny Cay, enjoy the beauty of the open water, and arrive at the picturesque Cooper Island. After settling in, we wrap up the day with a delicious dinner at the Cooper Island Beach Club, surrounded by stunning views and isl...
Sailing the BVI. The Baths National Park on Virgin Gorda
Sail Stillwater

Sailing the BVI. The Baths National Park on Virgin Gorda

Join us as we head out on an adventure in an open air pickupas we explore the island of Virgin Gorda, one of the most stunning islands in the British Virgin Islands! In this video, we take you to the famous Baths, a unique and breathtaking natural wonder known for its massive granite boulders, cryst...
Sailing the British Virgin Islands
Sail Stillwater

Sailing the British Virgin Islands

Join us as we start our BVI bareboat charter adventure with an overnight stay at Nanny Cay marina on Tortola. This charter we will be on Limin, a 45' Fountaine Pajot catamaran from Navigare Yachting. In this video we introduce you to our amazing crew, explore the marina and share a glimpse of...
Sailing charter almost ruined by tropical storm…
Sail Stillwater

Sailing charter almost ruined by tropical storm…

In the days leading up to our recent bareboat sailing charter in the British Virgin Islands, the weather forecast predicted severe conditions, including a low-level hurricane. We flew into St. Thomas and took a ferry to Tortola a few days before our charter was set to begin. Fortunately, the weather...
We fell in love with sailing… How it started vs where its going!
Sail Stillwater

We fell in love with sailing… How it started vs where its going!

Here’s a revised and longer version of your YouTube video description: In this video, we share the story of how we fell in love with sailing and the profound impact it has had on our lives. From the first time we set sail to becoming passionate about life on the water, sailing has not only transfor...
Things to know before you go on your sailing charter
Sail Stillwater

Things to know before you go on your sailing charter

Before you set sail here are 5 tips on things to know, before you go on a bareboat sailing charter. We'll talk a little bit about what and how to pack, how much money to plan for, being flexible with your itinerary, how to enjoy living on island time, and how to plan ahead so you dont sweat the...
SEASICKNESS what is it? and how to PREVENT it
Sail Stillwater

SEASICKNESS what is it? and how to PREVENT it

People often ask us about our sailing trips and whether or not we have people that get seasick. So we decided to make a video so hopefully people can have a basic understanding of what seasickness is, how to prevent it, and if they are affected how they can remedy it. Links to products mentioned: ...
CHARTERING A CATAMARAN (AKA, try before you buy!)
Gone with the Wynns

CHARTERING A CATAMARAN (AKA, try before you buy!)

Our boat is still a couple of months away from us being able to sail away.  So, we decided to do something we have never done before. Charter a boat. ❤ Join Our Crew! ❤ For exclusive content, behind the scenes & Q&A's: ☝Full Scoop On The Blog 📷 Photo & Video Gear 📷 📱 UPDAT...
AQUILA 42 YACHT Foiling Option Luxury Liveaboard Power Catamaran Yacht Tour
NautiStyles

AQUILA 42 YACHT Foiling Option Luxury Liveaboard Power Catamaran Yacht Tour

AQUILA info & contact: Follow Us Building an Explorer Yacht @NautiGuys This is BIG!!! You guys are the first to see this Beauty! As the official World Premiere for this AQUILA 42 YACHT is this week at the Miami Boat Show. I have said about 5 times on this tour: "I could have totally li...
Wrapping up an awesome year!
Boating Journey

Wrapping up an awesome year!

What a year we have had! Merry Christmas to all of you! We're looking forward to 2023!! Visit our blog at boatingjourney.com for gear and recipes. #boatingjourney #boatlife #boatingadventures #FortLauderdale #caribbean
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