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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The Charter Captain everyone wants, in the BVI
Sail Stillwater

The Charter Captain everyone wants, in the BVI

Join us for an inspiring conversation with Captain Jason Geyser, one of the most requested yacht charter captains in the British Virgin Islands (BVI). In this episode, Jason shares his journey into the world of luxury yacht charters, his lifelong passion for sailing, and the hospitality-first minds...
Sailing from St Croix to Culebra. USVI-SVI  Day 4
Sail Stillwater

Sailing from St Croix to Culebra. USVI-SVI Day 4

Day 4 of our Caribbean sailing adventure in the VIRGIN ISLANDS on a bareboat charter through the U.S. and Spanish Virgin Islands! Today we sail from St. Croix (USVI) to the island of Culebra, Puerto Rico, a favorite stop for cruisers and sailors traveling between the Virgin Islands and Puerto Ric...
Best beach to visit in the Virgin Islands. Sailing adventure day 3
Sail Stillwater

Best beach to visit in the Virgin Islands. Sailing adventure day 3

Today we leave Christiansted, St. Croix and sail to Buck Island, one of the most beautiful spots in the U.S. Virgin Islands. We drop anchor and spend time enjoying Buck Island’s incredible beach, crystal-clear water, and relaxed island vibes. From there, we continue sailing toward Frederiksted, St....
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...
Sailing Bahamas to USA, crossing the Gulf Stream
Igor Stropnik

Sailing Bahamas to USA, crossing the Gulf Stream

Sailing from Ragged Islands, Bahamas to USA, crossing the Gulf Stream on Leopard 50 Sailing Catamaran.
Package Delays & Island Days | USVI Boat Life
Sailing Big Lost

Package Delays & Island Days | USVI Boat Life

After our 7-day passage to the USVI, we find ourselves in island time — waiting on delayed packages before we can continue our journey south to Saint Martin for hurricane season. While we wait, it’s a week of boat projects and island adventures! We spend time troubleshooting a radar that won’t acti...
Sailing from Caribbean to Bahamas
Igor Stropnik

Sailing from Caribbean to Bahamas

Sailing from Caribbean to Bahamas on Leopard 50 Sailing Catamaran.
Sailing Caribbean Islands
Igor Stropnik

Sailing Caribbean Islands

Sailing St. Martin, Anguila, St. Barths and Antigua on Leopard 50 Sailing Catamaran.
Sailing British Virgin Islands (BVI)
Igor Stropnik

Sailing British Virgin Islands (BVI)

Sailing BVI, British Virgin Islands on Leopard 50 Sailing Catamaran.
Sailing Bahamas to Caribbean
Igor Stropnik

Sailing Bahamas to Caribbean

Sailing from Bahamas to BVI on Leopard 50 Sailing Catamaran.
Sailing Bahamas, Exumas
Igor Stropnik

Sailing Bahamas, Exumas

Sailing Exumas on Leopard 50 Sailing Catamaran.
Crossing the Gulf Stream
Igor Stropnik

Crossing the Gulf Stream

Crossing the Gulf Stream to Bimini and Exumas from Florida. Sailing on Leopard 50 Sailing Catamaran.
Does this NEW ALUMINUM DINGHY live up to THE HYPE?! | Honest Review of GoDu Dinghy – Ep 234
Sailing Jibsea

Does this NEW ALUMINUM DINGHY live up to THE HYPE?! | Honest Review of GoDu Dinghy – Ep 234

Aluminum dinghies are becoming more popular with sailors and cruisers and after months of full-time sailing the Caribbean with our GoDu Adventure aluminum dinghy, we're sharing a real world review. We cover how a hard dinghy compares to an inflatable dinghy, how it handles, beach landings, towi...
CHASING BUBBLES around the Virgin Islands! ⛵️ Let’s Bring Her Back WITH A BANG!  🎉  l ep.61
Spear It Animal

CHASING BUBBLES around the Virgin Islands! ⛵️ Let’s Bring Her Back WITH A BANG! 🎉 l ep.61

Get your free LMNT Sample Pack with any purchase at Also try the new LMNT Sparkling — a bold, 16-ounce can of sparkling electrolyte water. Join the Next Chasing Bubbles Regatta HERE (APRIL 9th, 2025)- You can charter a boat or sail in a vessel of your own...For more information and to keep up wit...
CRUISING ALUMINUM SAILBOAT: GOING WITH THE FLOW
Sailing Jibsea

CRUISING ALUMINUM SAILBOAT: GOING WITH THE FLOW

Join us on sailing adventure as we explore the stunning U.S. Virgin Islands (USVI) aboard our aluminum sailboat and sail to the British Virgin Islands (BVI) . In this episode, we were hoisting the sails in whichever direction where the wind takes us even if it means backwards or double the mileage. ...
The hardest week while living on a sailboat. Episode 29
Sailing Banana Pancakes

The hardest week while living on a sailboat. Episode 29

We got up early and sailed to the British Virgin Islands. We arrived in Tortola and headed to the Nanny Cay Marina. We got a slip for the night to get our boat hauled out the following day. The next morning they informed us that the lift had a flat tire so we waited around. It finally got fixed and...
Cliff Jumping (A week of fun sailing the USVI’s episode 28)
Sailing Banana Pancakes

Cliff Jumping (A week of fun sailing the USVI’s episode 28)

We were still anchored in Long Bay St. John of the US Virgin Islands. We were grateful that the sailboat was working, no problems, and we were taking a week off to just chill and enjoy the sailing life. Steve and Easton started their morning with a run and some father-son bonding. They stopped by...
Don’t Sit On Fire Coral (Sailing the British Virgin Islands) episode 27
Sailing Banana Pancakes

Don’t Sit On Fire Coral (Sailing the British Virgin Islands) episode 27

Hey Banana Family, In this episode we continue on our sailing journey adventuring all the islands of the US Virgin Islands and the British Virgin Islands. My sister and her family are still with us on the boat. We start the day off with a calm morning. We loaded up the dinghy and headed to White B...
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...
Sailing to St. John, US Virgin Islands (Episode 25)
Sailing Banana Pancakes

Sailing to St. John, US Virgin Islands (Episode 25)

In this episode we leave Salinas, Puerto Rico with a fixed engine! Finally! We have a nice sail to Vieques, Puerto Rico. We lift the sails, do some deep sea fishing, and our sailboat/catamaran is working perfectly! We set anchor and the kids enjoy surfing behind the dinghy for a few hours. Afterward...
The Spanish Virgin Islands and Puerto Rico
The Meri Crew

The Spanish Virgin Islands and Puerto Rico

We make the short sail from St. Thomas to Culebra, leaving the USVI and entering the Spanish Virgin Islands. We really enjoyed visiting both Culebra and Vieques, they both have a very laid back feel. From Vieques it was another short sail to Puerto Rico where we visited San Juan and spent time cr...
Cruising the USVI
The Meri Crew

Cruising the USVI

This is a shorter video. We weren't planning to make a video about the USVI but we were asked, and felt we maybe had enough material. Hope you enjoy it. We spent about three weeks and found we LOVED St. John's. We would like to spend some more time in St. Croix to explore it further -...
Sailing, Spearfishing, & Toxic Fish!!!!
Adventureman Dan

Sailing, Spearfishing, & Toxic Fish!!!!

It was an EPIC three weeks. The only way I can sum it up, is to say "Sailing, Spearfishing, & Ciguatera! Everything was great.... until it wasn't! But that's what adventure is. And sometimes, it can be deadly! We're all still feeling the affects of this toxic fish poisoning. ...
Cruising the British Virgin Islands
The Meri Crew

Cruising the British Virgin Islands

We weren't sure we would stop in the BVI, but the Salty Dawg's had a rendezvous so we decided to join in and it was a great time with some old friends. We spent another week cruising about on our own, with a fair amount of diving and as always lots of exploring.
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