Watch Sailing & Boating Adventures Around the World – Page 3 of 3

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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Pirate Wench Explores St Augustine – | Sailboat Story 28
Sailboat Story

Pirate Wench Explores St Augustine – | Sailboat Story 28

We've anchored the Sandflea at the Bridge Of Lions in St Augustine. The current is strong, but our anchor is holding strong. Aside from an absolutely ripping current running through the anchorage, our St Augustine stop was just great! What a wonderful city. It's so well managed, so clean...
Searching For Wild Horses On Cumberland Island | Sailboat Story 27
Sailboat Story

Searching For Wild Horses On Cumberland Island | Sailboat Story 27

We've cruised our sailboat along the ICW all the way to Cumberland Island, the Southernmost barrier island of Georgia. It's time to explore Cumberland Island - land of the wild horses - and to see if the cousins of the Carrot Island herd are as bloodthirsty as their kin. No joking now......
A Short Break From The Cruising Life GRIND | Sailboat Story 26
Sailboat Story

A Short Break From The Cruising Life GRIND | Sailboat Story 26

In this video, we take a break from cruising life to visit our family that has come to meet us at St Simons Island. The good news - we'll get to visit our family one last time before we head to the Bahamas for a while. The bad news - now we have to say goodbye all over again! In this video, ...
Cruising To Tybee Island + Interview With Molly | Sailboat Story 25
Sailboat Story

Cruising To Tybee Island + Interview With Molly | Sailboat Story 25

Thus far, we've sailed from Maryland to Tybee Island, GA. I hate to say it, I really do, but our home state of Georgia has been the least fun section of the ICW for us. We've grounded 3 times, and had to be SUPER on top of our navigational skills to make it through this tricky GA stretch....
Liveaboard Family Explores Beaufort SC | Sailboat Story 24
Sailboat Story

Liveaboard Family Explores Beaufort SC | Sailboat Story 24

We've anchored our sailboat in Beaufort. That's Byew-Fert. Now, to further clarify... Boh-Fort is a completely different place, and is in fact, in a completely different state... NC to be exact. Moving on... BEAUFORT, SC! Great little town. One great thing is that the marina offers FREE...
Intracoastal Waterway Cruising To Charleston | Sailboat Story 23
Sailboat Story

Intracoastal Waterway Cruising To Charleston | Sailboat Story 23

Our leisurely ICW cruise aboard our sailboat has brought us to the historic coastal town of Charleston, SC. Probably the nicest city we've stopped at so far, and absolutely the WORST anchorage. Good grief! Ripping current, trashy bottom, & dragging anchors make for a pretty sketchy anchori...
Anchoring in Georgetown, SC | Sailboat Story 22
Sailboat Story

Anchoring in Georgetown, SC | Sailboat Story 22

Our Endeavour sailboat, the might S/V Sandflea has brought us to a lovely anchorage in Georgetown, SC. We drop anchor and go exploring. Speaking strictly of the anchorage itself, its probably my favorite anchorage thus far. It takes a bit of tight maneuvering to get your boat tucked in, but once yo...
Pals, Pigs, & Poltergeist In Wrightsville Beach | Sailboat Story 21
Sailboat Story

Pals, Pigs, & Poltergeist In Wrightsville Beach | Sailboat Story 21

After cruising our sailboat down the ICW for a days, we finally drop anchor at the ICW coastal town of Wrightsville beach. This coastal town is certainly ranks as one of our favorite stops along the Intercoastal Waterway. Nice anchorage, wonderful sunsets, and loads of dolphins. We make new frien...
Bikini Babe Bucket Bathing & Carnivorous Ponies | Sailboat Story 20
Sailboat Story

Bikini Babe Bucket Bathing & Carnivorous Ponies | Sailboat Story 20

There's nothing quite like watching a bikini babe bathing herself in a bucket. Oh - the rare treats we experience when living on a sailboat. Morning breaks, and we breathe a collective sigh of relief... we've survived the night-long onslaught of a billion unidentifiable, nocturnal flying ...
Cruising The ICW By Boat | Sailboat Story 19
Sailboat Story

Cruising The ICW By Boat | Sailboat Story 19

After sailing the Chesapeake, and we begin cruising south down the intracoastal waterway, which is called the ditch, or the ICW. From here, there are 1000 miles of "The Ditch" for us to navigate before we reach Miami. Still, there are so many great sights to see along the way that we are ...
Solo Sailboat Mast Climbing With Acrophobia | Sailboat Story 18
Sailboat Story

Solo Sailboat Mast Climbing With Acrophobia | Sailboat Story 18

Solo climbing a sailboat mast is scary, especially for someone like me who suffers from acute acrophobia. We've officially started making progress South! So many things to learn along the way. It's amazing all of the little skills that need to be acquired in order to become competent and...
First Days Living Aboard A Small Boat | Sailboat Story 17
Sailboat Story

First Days Living Aboard A Small Boat | Sailboat Story 17

The first days living aboard a sailboat allowed us to get accustomed to our new routine. Also, we say goodbye to convenient transportation, we wait out what's left of hurricane Matthew, we go sailing for the first time all by ourselves, and we check out the Annapolis Boat Show. Thanks for wat...
Moving Aboard Our Endeavour 32 Sailboat | Sailboat Story 16
Sailboat Story

Moving Aboard Our Endeavour 32 Sailboat | Sailboat Story 16

We move aboard our Endeavour 32 sailboat. She's a 1979 32 foot sloop with solar panels, composting toilet, dinghy davits, and a Yanmar 3YM20 diesel engine. This is it. The time is now. Time to load up our things, leave town for the final time, and move aboard our new home - a 1979 Endeavour 3...
Probably Buying An Endeavour 32 Sailboat – Family Sailing Vlog 13
Sailboat Story

Probably Buying An Endeavour 32 Sailboat – Family Sailing Vlog 13

We travel head to Mayo, MD to check out an Endeavour 32 sailboat that's outfitting for extended cruising. We really like this sailboat, and it seems to have really been taken care of and maintained. Negotiations will ensue, contracts will be signed, and money will change hands. Things are get...
The “Rock Solid” Pearson 35 Sailboat With A SOFT Deck | Sailboat Story 12
Sailboat Story

The “Rock Solid” Pearson 35 Sailboat With A SOFT Deck | Sailboat Story 12

This Pearson 35 sailboat has a very soft deck. MAN, if only we had known that before making this trip! We travel to Washington, NC, to check out a Pearson 35 sloop. It's been described to us as being 100% ROCK-SOLID, no soft spots, completely refit, newer rigging, good sails, and it even come ...
She Really Likes The Hunter 30 | Sailboat Story 11
Sailboat Story

She Really Likes The Hunter 30 | Sailboat Story 11

The Hunter 30 sailboat is a great coastal cruiser... and Tambi likes it. In this video we make another trip to Florida in an attempt to find our perfect sailboat. While we're there, we end up seeing a Watkins 33, a Endeavour 37, a Hunter 30, and a Rival 34. Out of that bunch, guess which one ...
Inspecting An Endeavour 33 | Sailboat Story 10
Sailboat Story

Inspecting An Endeavour 33 | Sailboat Story 10

We travel to Savannah, GA to check out an Endeavor 33 sailboat that we found online. Sounds like it could be a real bargain, so we load up for a long drive to see what this sailboat can offer us. Along the way we have fun as a family, meet some cool and experienced sailors, go sailing on a Morgan O...
Sailboat Shopping In St Petersburg | Sailboat Story 9
Sailboat Story

Sailboat Shopping In St Petersburg | Sailboat Story 9

We go searching for a sailboat to buy in St Petersburg. If you recall the last video... we struck out on the S2 9.2c. Great boat, but it was just too stinkin' small for the 3 of us to live on comfortably. Being the unstoppable dynamic trio that we are, we decided to make the most of our trip ...
Sea Trial On A S2 9.2C | Sailboat Story 8
Sailboat Story

Sea Trial On A S2 9.2C | Sailboat Story 8

Taking a S2 9.6C sailboat for a test sail in Crystal River, FL. Thanks for watching!! Ben, Tambi, & Molly | S/V Sandflea | "SAILBOATSTORY" ******* BECOME A PATRON ************************************ ||| Pledge anything from $1 to $50 per video we create. This is th...
Is this S2 9.2c Sailboat… The One? | Sailboat Story 7
Sailboat Story

Is this S2 9.2c Sailboat… The One? | Sailboat Story 7

We travel to Crystal River, Florida to inspect a S2 9.2c sailboat. Who knows - this could be the sailboat we've been looking for! Thanks for watching!! Ben, Tambi, & Molly | S/V Sandflea | "SAILBOATSTORY" ******* BECOME A PATRON ************************************ ...
Working Hard To Fill Our Cruising Kitty | Sailboat Story 6
Sailboat Story

Working Hard To Fill Our Cruising Kitty | Sailboat Story 6

It takes money to live travel while living on a sailboat. We're working hard to fill our cruising kitty. We'll share everything from how we are maximizing our remaining time that we are "landlocked" by working hard to earn as much money as possible, to how we are planning to fun...
Sailboat Shopping & Basement Dwelling | Sailboat Story 5
Sailboat Story

Sailboat Shopping & Basement Dwelling | Sailboat Story 5

We are now officially shopping for our sailboat. Our house is rented out at this point, so we're living in our Inlaw's basement - AKA "The Dungeon". Tambi and I are both working hard to save up as much money as we can while we have the opportunity to do so. It's going to b...
Ericson 32 Sailboat Tour | Sailboat Story 4
Sailboat Story

Ericson 32 Sailboat Tour | Sailboat Story 4

Here's a walkthrough tour of an Ericson 32 sailboat. Since we're currently on the hunt for our own sailboat, we thought it would be helpful to compare & contrast our friend's Ericson 32 against our own liveaboard sailboat requirements. This particular Ericson is pretty close to ...
Selling It All To Buy A Boat | Sailboat Story 1
Sailboat Story

Selling It All To Buy A Boat | Sailboat Story 1

Before we can move onto a sailboat, we have to pack up our things and move out of our house. We've got to somehow escape the life that we've built around ourselves over the last 10 years or so. Amazing how much stuff you accumulate from everyday life! We do own a house, so our plan is t...
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