Watch Sailing & Boating Adventures Around the World – Page 4 of 25

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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Sailing Two Wooden Boats & Saltwater Fly Fishing in the Ten Thousand Islands
Acorn To Arabella

Sailing Two Wooden Boats & Saltwater Fly Fishing in the Ten Thousand Islands

In this week’s episode, we say goodbye to Sanibel Island and the beautiful “Ding” Darling Wilderness, and we set sail for Florida’s Ten Thousand Islands, an archipelago just north of and adjacent to the Everglades. It felt great to raise the sails after so much motoring. We enjoyed a lively, advent...
Transom Repairs on Victoria: Boat Work is Better in Boca Grande & North Captiva
Acorn To Arabella

Transom Repairs on Victoria: Boat Work is Better in Boca Grande & North Captiva

Get an exclusive 15% discount on Saily data plans! Use code ARABELLA at checkout. Download Saily app or go to -------------------------- We’ve sailed our beautiful wooden sailboat all the way from Maine to Boca Grande, where it’s time to stop and give our tender, Victoria, a little TLC. Her trans...
Fixing the rudder and painting the boat!
Sampson Boat Co

Fixing the rudder and painting the boat!

Support TALLY HO; Become a Patron; ---- EPISODE 214 In this episode we identify and fix the problem that led to a binding rudder, although we are left with some unanswered questions about corrosion. We also scrape, sand, and paint the bottom of the boat to get her ready to re-launch, and re-va...
Cruising Cabbage Key & Cayo Costa: Finding a Hidden Paradise
Acorn To Arabella

Cruising Cabbage Key & Cayo Costa: Finding a Hidden Paradise

Use this link to subscribe and save $20 off your first subscription of AG1 -------------------------- This week, Arabella exits the Caloosahatchee River and sails towards the Gulf of Mexico, dropping anchor in Cape Coral to provision the boat and head in to Rumrunners for a nice dinner on the water...
After a 7 year project, people think this is an entirely different boat.
Sampson Boat Co

After a 7 year project, people think this is an entirely different boat.

Support TALLY HO; Become a Patron; ---- EPISODE 213 In this bonus episode I address some questions which have been asked a lot recently; What exactly is left of the original Tally Ho? Why didn’t I just build a new boat - and wouldn’t that have been easier? —— To become a Patron - To d...
Cruising the Okeechobee Waterway from East to West
Acorn To Arabella

Cruising the Okeechobee Waterway from East to West

Join us (and a tree full of pelicans) as we begin cruising east to west on the Okeechobee Waterway. Not many sailboats our size have the ability to cruise the Okeechobee Waterway. Because we are gaff-rigged, our masts are shorter, giving us the clearance we need to pass under the many bridges and po...
Cruising the Intracoastal Waterway East Coast Florida: Saint Augustine to Fort Pierce
Acorn To Arabella

Cruising the Intracoastal Waterway East Coast Florida: Saint Augustine to Fort Pierce

This week, we continue cruising the Intracoastal Waterway down the east coast of Florida. We miss sailing, but offshore waters were calling for sloppy seas and light winds. With few safe harbors to duck into in the case of emergency, we decided to stay grounded in the ICW. And when we say “stay grou...
The 3 Best Decisions I Made While Building My Own Sailboat
Acorn To Arabella

The 3 Best Decisions I Made While Building My Own Sailboat

Throughout the process of building my own wooden sailboat, I had to make several important decisions. Some of these decisions were met with massive support, others…not so much. One important consideration was marine diesel engine maintenance—I wanted it to be as easy as possible! In this week’s epis...
A Boat In Desperate Need of Some Paint – Episode 335 – Acorn to Arabella: Journey of a Wooden Boat
Acorn To Arabella

A Boat In Desperate Need of Some Paint – Episode 335 – Acorn to Arabella: Journey of a Wooden Boat

For months, Steve and Robin have been moving Arabella south, waiting for warm enough weather to haul her, and give her a fresh coat of paint. The time has finally come. Arabella is getting hauled out, and—in this episode—we’ll detail the hard work that went into scraping and painting their homebuilt...
The Oldest City In the US – Episode 334 – Acorn to Arabella: Journey of a Wooden Boat
Acorn To Arabella

The Oldest City In the US – Episode 334 – Acorn to Arabella: Journey of a Wooden Boat

Robin finally returns to Arabella after spending a few weeks dealing with work stuff. Steve takes the opportunity to handle some housekeeping and tame Akiva’s mane while waiting for Robin to return. Once Robin arrives, Steve takes her on a tour of the oldest city in America. St. Augustine was found...
Followed by Dolphins On the Way To Florida – Ep. 333 – Acorn to Arabella: Journey of a Wooden Boat
Acorn To Arabella

Followed by Dolphins On the Way To Florida – Ep. 333 – Acorn to Arabella: Journey of a Wooden Boat

After a few challenging (and expensive) days on a dock in the fancy town of Hilton Head, Jack finally catches a flight home, and Steve’s friend, Jeff, makes his way into town to take his place. Steve provisions the boat, and cleans the rest of the snow and ice off the deck. Before heading 20 miles ...
Boat Life During an Historic Southern Winter – Ep. 332 – Acorn to Arabella: Journey of a Wooden Boat
Acorn To Arabella

Boat Life During an Historic Southern Winter – Ep. 332 – Acorn to Arabella: Journey of a Wooden Boat

Surprise, surprise. It’s STILL not warm for Arabella and crew, which is anchored in Charleston, SC. Annie B. heads back home, and Jack and Steve continue on. “Beaufort to Buford” is the war cry! The first challenge for Jack and Steve is Elliot Cut, a notoriously tricky section of ICW south. With th...
START TO FINISH – Rebuilding a big wooden yacht!
Sampson Boat Co

START TO FINISH – Rebuilding a big wooden yacht!

REBUILDING TALLY HO - WATCH FROM THE BEGINNING —— To become a Patron - To donate or support - My Wishlist For sneaky previews of what’s going on in between episodes, follow my FACEBOOK and INSTAGRAM MANY THANKS! Music; County Farm - Wayward Jane Who's Using Who? - The Min...
Will We Ever Get A Break From The Cold?? – Episode 331 – Acorn to Arabella: Journey of a Wooden Boat
Acorn To Arabella

Will We Ever Get A Break From The Cold?? – Episode 331 – Acorn to Arabella: Journey of a Wooden Boat

Thanks to Lumen for sponsoring! To get 20% off go to and start improving your health today. -------------------------- A friend in need is a friend indeed—especially if your friend is also on a wooden boat! This week’s episode opens with Steve tendering out to the Schooner Hindu, where his friend...
Dragon Dancing for a Happy New Year – Episode 330 – Acorn to Arabella: Journey of a Wooden Boat
Acorn To Arabella

Dragon Dancing for a Happy New Year – Episode 330 – Acorn to Arabella: Journey of a Wooden Boat

This week, the journey resumes as Arabella and crew continue to sail south through North Carolina, heading towards warmer waters. A slower pace of life means an opportunity for some much-needed housekeeping. Steve tackles a clean-out of Arabella’s anchor locker from a quiet anchorage in Goose Cree...
The Great Dismal Swamp Canal – Episode 329 – Acorn to Arabella: Journey of a Wooden Boat
Acorn To Arabella

The Great Dismal Swamp Canal – Episode 329 – Acorn to Arabella: Journey of a Wooden Boat

This week, Arabella slows down and cruises through the Great Dismal Swamp, navigating her first lock—the Deep Creek Lock—and leaving a small reminder that they were there ;-) After a provisioning run at the local Food Lion, Steve and Robin venture deeper into the Great Dismal Swamp, which—despite i...
Cruising by the Largest Naval Base In the World – Episode 328 – Journey of a Wooden Boat
Acorn To Arabella

Cruising by the Largest Naval Base In the World – Episode 328 – Journey of a Wooden Boat

Farewell, Annapolis. It's time for this handcrafted wooden sailboat to keep cruising South towards warmer weather. After visiting a few quiet anchorages in the Chesapeake, Robin, and Akiva stop for a few days in Seaford to get some "life stuff" done...but not before getting the boat ...
Into The Chesapeake with a Rainbow On Our Backs – Episode 327 – Journey of a Wooden Boat
Acorn To Arabella

Into The Chesapeake with a Rainbow On Our Backs – Episode 327 – Journey of a Wooden Boat

We hope everyone watching is in the middle of a great holiday season. All we want for Christmas is for you to tell your friends and family about our channel :-) After spending a few days pinned down with bad weather, Steve and Robin head out of Bivalve and up the Delaware River. With a rainbow mark...
100 Oysters Can Solve Most Problems – Episode 326 – Acorn to Arabella: Journey of a Wooden Boat
Acorn To Arabella

100 Oysters Can Solve Most Problems – Episode 326 – Acorn to Arabella: Journey of a Wooden Boat

The first 1,000 people to click the link will get a full year of Premium membership to Woodworkers Guild of America for only $1.49: How many jackets is too many? Arabella makes her way down the Jersey coast. Steve, Robin, and Peter (a friend from Boothbay, Maine) brace for colder weather, wearing ...
SYLFIA: The Untold Story of a One-of-a-Kind Expedition Vessel ⛵️
Expedition Drenched

SYLFIA: The Untold Story of a One-of-a-Kind Expedition Vessel ⛵️

Ahoy Fam!!!! This one is a very very raw and real story close to our heart, the story we never told about this beautiful vessel we call home. We hope that it helps explain a lot, no video could ever do justice to the amount of work that went into this boat or to really shed light on the man who meti...
Taking Our Home Built Boat Through NYC – Episode 325 – Acorn to Arabella: Journey of a Wooden Boat
Acorn To Arabella

Taking Our Home Built Boat Through NYC – Episode 325 – Acorn to Arabella: Journey of a Wooden Boat

Arabella makes her way through New York City! After setting the anchor in Glen Cove (Long Island, NY), Steve and Robin awake to an early alarm, like 4am-early, to time their arrival to the East River. Along the way, they enjoy incredible views of the Manhattan Bridge, Brooklyn Bridge, the Statue of...
How We Will Sail the Next 3000 Miles – Episode 324 – Acorn to Arabella: Journey of a Wooden Boat
Acorn To Arabella

How We Will Sail the Next 3000 Miles – Episode 324 – Acorn to Arabella: Journey of a Wooden Boat

Got local knowledge about our upcoming route? Let us know! Email us: [email protected] If you tuned into last week’s video, you may be aware that our engine died… Luckily, the engine itself turned out to be totally fine. There was an issue with water getting into the plugs that connect to t...
Sailing Out of Buzzards Bay – Episode 323 – Acorn to Arabella: Journey of a Wooden Boat
Acorn To Arabella

Sailing Out of Buzzards Bay – Episode 323 – Acorn to Arabella: Journey of a Wooden Boat

Learn more about the Elite 200V2 and visit our website for Black Friday gifts and discounts 👉 code: ACORN01 The journey continues! Ben joins the crew for a planned sail to Delaware. The hope is to be heading to Puerto Rico early December. Steve, Robin, and Ben have quite a few things to get done b...
Down The River and To the Sea – Episode 322 – Acorn to Arabella: Journey of a Wooden Boat
Acorn To Arabella

Down The River and To the Sea – Episode 322 – Acorn to Arabella: Journey of a Wooden Boat

This week, Arabella journeys to Mattapoisett, where she was first launched about a year and a half ago. The first leg requires sailing from Boothbay to Gloucester. The crew experiences heavy winds, sea sickness, and sightings of humpback whales—nothing Captain Steve can’t handle! After a quick trip...
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