Watch Sailing & Boating Adventures Around the World – Page 7 of 30
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 Homecoming We’ve All Been Waiting For | Returning to VA After 8 Months Away l Episode 322
Welcome back to another episode of WE|Sail! After eight long months away, it's finally time - we're heading back to our boat VA in Fiji! But first, one last stopover in French Polynesia for an incredible Patreon charter through Bora Bora, Raiatea, and Tahaa. This homecoming doesn'...
Splash Day Gone Wrong!
After 6 months of work, our 40ft sailboat is finally ready to go back in the water after 4 years of being on the hard, but not everything goes to plan. Our new 460Ah FogStar Batteries - Check out FogStar and everything they have to offer here - 🚢 Join Our Crew on Patreon - Want to support our ...
DOMINICAN REPUBLIC! We made it behind the VIP walls of Puerto Plata #dominicanrepublic #puntaplata
We arrive by boat at Ocean World Marina Puerto Plata and quickly realize this is no ordinary marina. From clearing in and exploring Puerto Plata’s old fort and Umbrella Street to discovering what’s hidden behind the resort’s massive walls, this is the real cruiser’s view of the Dominican Republic. I...
From Boat Shows to Bahamas: Setting Sail with 10 Strangers in the Exumas l Episode 321
Welcome back to another episode of WE|Sail! We're BACK in the Bahamas! Fresh off the boat show in Annapolis, we're diving straight into hosting our Patreon charter with 10 incredible people from all over the world. What happens when strangers meet on a sailboat in paradise? Pure magic! ...
Welcome Back to Boat Life! Annapolis Show, Dream Catamaran & Next Steps for WE|Sail – Episode 320
Welcome back to another episode of WE|Sail! Erica's finally on her way back to VA! After months of recovery, we're easing back into boat life one step at a time, and what better place to start than the Annapolis Boat Show. This year's show felt extra special - like a true reunion w...
We Finally Made it the San Blas “Swimming Pool”
We’re a family sailing full-time, exploring the Caribbean and Central America aboard our sailing catamaran Big Lost. New episodes every Tuesday at 10:30 AM ET. In this episode aboard Sailing Big Lost, we finally trade the noseeums of Snug Harbor for sunshine, clear water, and one of the most iconic...
LUXURY on the WATER: Inside Hammock Beach MARINA! Ep-198
-We head into Hammock Beach Marina for the week and it might just be one of the best marina stays we’ve ever had! From the moment we tied up, we were blown away by the amenities—both at the marina and at the incredible Hammock Beach Golf Resort & Spa. During our stay, we got access to it all: 🏖...
How WE Met? | The Story WE’ve Never Told | A Sailors Love Story – Episode 319
Welcome back to another episode of WE|Sail! This weeks episode is a little different. The story we've never told. After seven years of documenting our sailing adventures around the world, we're finally sharing the story that started it all- how WE became we. Before the ocean, before th...
Rained Out in San Blas
We’re a family sailing full-time, exploring the Caribbean and Central America aboard our sailing catamaran Big Lost. New episodes every Tuesday at 10:30 AM ET. We’ve had rain off and on since arriving in Panama, and as we begin exploring the San Blas—now learning their true name, the Guna Yala Isla...
Living the Dream in Greece: Crystal Water, Beaches & Pure Freedom • S5Ep5
Welcome back to Greece! In today’s sailing episode, we sail into what might be the most beautiful hidden anchorage we’ve ever found — tucked inside the north side of Kalamos Island. Crystal-clear shallows, empty beaches, wake-surf sessions, underwater dreamscapes… and even a hike to a medieval castl...
The Current Nearly Defeated Us… Ep-197
Join us as we sail up the ICW and explore some of Florida’s most charming coastal towns — Cocoa Village, Titusville, and New Smyrna Beach. We soak in the sunshine, discover new spots, and even spot manatees for the very first time (a total dream moment!). But later in our journey, things take a tur...
WE|Sail’s Favorite VIDEOS | Happy Thanksgiving
Ahoy WE|Sailors!!!! This week we are skipping out on an episode and making sure everyone spends some time with family for the holiday. This is a time to give gratitude and we have so much to our family, friends and sailing community who have supported us through all these years. WE promise we wil...
Sailing Into Guna Yala: From Puerto Obaldía to Isla Pinos
We’re a family sailing full-time, exploring the Caribbean and Central America aboard our sailing catamaran Big Lost. New episodes every Tuesday at 10:30 AM ET. We’re a family sailing full-time, exploring the Caribbean and Central America aboard our sailing catamaran Big Lost. New episodes every Tue...
3 MAJOR Sailboat UPGRADES in One Week
In this weeks video we have 3 major upgrades happening which means we are finally able to plan out splash date. Come and check out what we have been up to from increasing our power set, fitting new fabric and a big install below the sailboat. Our new 460Ah FogStar Batteries - Check out FogStar and...
Don’t Buy a Sailboat Until You Watch This – 5 Costly Mistakes New Sailors Make
Quiet Power: Electric and Hybrid Propulsion at Annapolis: Thinking of buying your first offshore sailboat? Before you hand over your life savings, watch this video. In it, we break down the 5 biggest mistakes new sailors make when buying their first cruising boat — and how to avoid them. From fal...
S1E30 . Refitting My Old Sailboat in Crazy Wind | Real DIY Boat Life, Storage Fixes & Splicing Wins
Refitting this old sailboat feels a little like therapy… if therapy involved heat waves, glue guns from the 90s, and a boat heeling like it wants to buck me off. Today I’m tackling more interior fixes: templating new shelves, building out bathroom storage, dealing with rogue cabinet doors, and addin...
Navigating Shallows With NO Depth Sounder 😬 Ep-196
ICW boating, shallow water navigation, Fort Pierce to Vero Beach — in today’s episode we motor up the Intracoastal Waterway with a broken depth transducer, making every mile sketchy as we pass through Vero Beach, Melbourne Beach and Eau Gallie. Along the way we spot playful dolphins and explore beau...
First Time Up the ICW! | Big Comfort Upgrades on Escapade! Ep-195
We’re heading up the ICW for the very first time! 🚤 From Stuart to Fort Pierce, it’s a whole new kind of adventure for us aboard Escapade. Along the way, we’re showing off a few small upgrades that are making a huge difference — including our new electric table leg that transforms our salon into a c...
Another Day, Another Problem: Final Sail to Hawaii – Episode 318
Welcome back to another episode of WE|Sail! Get some merch from our new collection: 🔔 SUBSCRIBE for our continuing journey: FOLLOW our day-to-day updates: Instagram: Facebook: ⚓ Support us on Patreon and join our sailing charters: 📆 Want to come Sail with us for the next WE|Sa...
S1E29 . DIY Boat Life: Sweat, Sawdust, and a Few Regrets.
It started simple — just mount the tender, test the davits, and clean up a few things. Fast forward to midnight, and I’m covered in sawdust, sweating through my shirt, and wondering what went wrong 😅 This is real DIY boat life — no scripts, no sponsors, just hard work and questionable decisions on ...
I Fell Asleep and Crashed Into the Rocks
Get The Book → The True Story Behind the Night I Almost Lost Everything—and What It Taught Me About Command at Sea. Two boats. Two oceans. Two mistakes I’ll never forget. This is the night I fell asleep under full sail and ran my boat straight into the reef—twice. It’s not about drama; it’s about...
SAILBOATS, SECRETS, AND SHENANIGANS – ANNAPOLIS BOAT SHOW 2025! Ep-194
Go to and use code ESCAPADE to get 10% on Holafly plans for the first 12 months or 5% off on any other Holafly eSIM This isn’t your typical boat show vlog — we’re taking you behind the scenes of what it’s really like to be cruising creators at the Annapolis Boat Show! From creator meetups and af...
Crossing the Equator: Neptune’s Ceremony | Tahiti to Hawaii Delivery – Episode 317
Welcome back to another episode of WE|Sail! We're back! Sorry for the two-week hiatus – charters and boat shows took over our lives, but we promise it's still all about the sailing. In this episode, we're five days into our catamaran delivery from Tahiti to Hawaii, and it's be...