Watch Sailing & Boating Adventures Around the World tagged “Sailboat shopping”

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.

Showing 1-24 of 53 results
The WORST Listings I’ve Ever Seen (15 MASSIVE Sailboat Red Flags)
Sailing Zingaro

The WORST Listings I’ve Ever Seen (15 MASSIVE Sailboat Red Flags)

I’m breaking down HUGE red flags I’ve seen in real boat listings—stuff that should make you think twice (or run for the hills). From hurricane damage to sketchy new paint jobs, I'll show you how to read between the lines of listings and photos so you...
Top 5 things you must know, Used Sailboat Buying 2025
Chasing Latitudes

Top 5 things you must know, Used Sailboat Buying 2025

Patreon really helps me keep the channel going, for only 10 per month you get full access to my private members area with thousands of other members just like you looking to get on the water sooner than later in the most cost effective manner possible. htt...
Sailboat Shopping: What’s the Most IMPORTANT Thing to Look For?
The Foster Journey

Sailboat Shopping: What’s the Most IMPORTANT Thing to Look For?

When shopping for a sailboat, what's the most important thing to look for?
Boat TOUR! Jeanneau Gin Fizz Same Boat Model Laura Dekker Circumnavigated In  EP 8
Sailing Pachamama

Boat TOUR! Jeanneau Gin Fizz Same Boat Model Laura Dekker Circumnavigated In EP 8

We continue the drive from Annapolis down to Georgia to look at a Jeanneau Gin Fizz. The Same boat model Laura dekker circumnavigated in when she was 16! Though her sailboat was in much better condition when she made her epic voyage.. We have been wanti...
EXPLORING TOP TRAVEL DESTINATIONS | Tobago Cays Slow Travel Vlog
Living Hakuna

EXPLORING TOP TRAVEL DESTINATIONS | Tobago Cays Slow Travel Vlog

This weekly vlog is all about taking a beach walk, slow travel and exploring top travel destinations, an island nearby tobago cays and the beautiful beaches of the grenadines and Union island. ► SUBSCRIBE for a new video every Sunday ☺ https://www.you...
Never buy a boat before seeing it in person.  We learn the hard way the boat is rotted out!  EP. 2
Sailing Pachamama

Never buy a boat before seeing it in person. We learn the hard way the boat is rotted out! EP. 2

In episode two, Andrea and Logan get a taste of some of the challenges of the boat buying process. BUT, they are also reminded that life doesn't start when you buy a boat, so it's time to enjoy what you have where you are now. A gentle warning to never s...
Talking About Our Next Cruising Sailboat | Sailboat Story 147
Sailboat Story

Talking About Our Next Cruising Sailboat | Sailboat Story 147

The time is upon us to find our next cruising sailboat. We've got about 6 months until the next cruising season kicks off, so we need to track down the boat, buy it, and get it set up for cruising ASAP. We've got our work cut out for us and not a lot of ti...
Could This Be Our Next Cruising Sailboat? | Sailboat Story 146
Sailboat Story

Could This Be Our Next Cruising Sailboat? | Sailboat Story 146

To begin the search for our next cruising sailboat we self survey an Endeavour 40. The good news is that it's received nearly 100k worth of upgrades, but the bad news is that it still needs a tremendous amount of work. Could this be our next cruising sailb...
Exploring, Wind over Water, Episode #54
Wind over Water

Exploring, Wind over Water, Episode #54

Windover's crew leave the boat to check out the sights around Calabash Creek North Carolina, we fly the spinnaker up the ICW and we take a close look at a boat that has been on our short list for a while. Could this be the one we have been looking for? #wi...
Maine Cat 41 Catamaran Tour – Performance & Functionality
The O'Kelly's

Maine Cat 41 Catamaran Tour – Performance & Functionality

Modern production catamarans have been getting bigger and taller, and with extraordinary levels of accommodation. While having all the conveniences of home is awesome, with some newer builds comfort has come at the cost of performance and seakindliness. Th...
Costly first-time buyer mistakes (we made)
The O'Kelly's

Costly first-time buyer mistakes (we made)

Don't be fooled by the BLING! Also, sellers, if you want top dollar, we have some tips! When we started out 17 years ago, we didn't know what we didn't know, and it cost us! As sailing noobs it's easy to be taken advantage of. Pop some corn, pour a cold d...
Ep 71 More Drama – Dragging and Drifting Into Other Boats (Sailing Talisman)
Sailing Talisman

Ep 71 More Drama – Dragging and Drifting Into Other Boats (Sailing Talisman)

We can't catch a break. Winds pick up in Kioni Harbor, and suddenly Talisman seems to have no holding. We find ourselves being blown back onto the quay, and alarmingly also into the adjacent boats.
Ep 69 Cruising Destinations III – Porto Spilia, Greece
Sailing Talisman

Ep 69 Cruising Destinations III – Porto Spilia, Greece

Sailing in Greece is so much fun. The bareboat and charter operations take up a lot of room, but we like having people around and the mood is universally festive. For this portion, in the middle of a week of dead wind we actually find an afternoon of 20 kn...
Ep 68 Cruising Destinations II – Kioni and Sivota, Greece
Sailing Talisman

Ep 68 Cruising Destinations II – Kioni and Sivota, Greece

As we enter the early summer of 2018 in Greece, we find some real gems. We're still learning the habits of Talisman, our Oyster 485 sloop, but she's a rugged and spirited boat. She doesn't steer in reverse very well, but with practice things start to come ...
Ep 66 Crossing the Ionian Sea aboard Oyster 485 Talisman
Sailing Talisman

Ep 66 Crossing the Ionian Sea aboard Oyster 485 Talisman

As the title says, it's time for a big hop and the 3-on-3-off watchkeeping rotation that we all love so much. Our trip begins with the dreaded currents of the Strait of Mesina, where we dodge ferry and fishing boat traffic. Then it's out into the wild blue...
Ep 63 Cruising the Amalfi Coast (Sailing Talisman)
Sailing Talisman

Ep 63 Cruising the Amalfi Coast (Sailing Talisman)

Talisman continues east, reaching Capri and the famed Amalfi coast. Life is good. Having lived aboard the boat for almost a year, and covering over 4000 nautical miles, the daily groove of sailing from place to place is starting to seem normal. The small ...
Ep 62 Anchoring Italian Style (s/v Talisman)
Sailing Talisman

Ep 62 Anchoring Italian Style (s/v Talisman)

We arrive at Procida, just off Naples, to find ourselves in the midst of a huge party.
How much does it cost to buy a sailboat?
Wildly Intrepid Sailing

How much does it cost to buy a sailboat?

Have you ever wondered how much does it cost to buy a sailboat? There's more involved than straight up purchasing the sailboat of your dream. In this episode we cover some of the other related costs such as the survey, registration and more. And if you are...
7 Things to avoid when buying a sailboat to live on
Wildly Intrepid Sailing

7 Things to avoid when buying a sailboat to live on

Here are 7 things to avoid when buying a sailboat to live on plus a bonus at the end. All those bits of advice are from our own experience so that you do not repeat our mistakes. The boat we almost bought, a Bayfield 32c ▶http://www.youtube.com/watch?v=...
Ep 59 Docking and Undocking in Rugged Southern Sardinia
Sailing Talisman

Ep 59 Docking and Undocking in Rugged Southern Sardinia

It's hop skip and jump up the southeastern coast of Sardinia.
MISTAKES… We’ve Made a Few [Adventure #134]
Adventure Adrift

MISTAKES… We’ve Made a Few [Adventure #134]

We’re not perfect, and sometimes we don’t make the best decisions…. What did we get ourselves into? How do we keep going? Trying something new doesn’t always go according to plan, but the important things is to learn from it, and figure out how t...
Ep 57 Who Needs A Working Bilge Pump Anyway?
Sailing Talisman

Ep 57 Who Needs A Working Bilge Pump Anyway?

Talisman's wonky bilge pump wiring is finally addressed.
Buying our first sailboat & exploring Niagara Falls Canada [Ep 7]
Wildly Intrepid Sailing

Buying our first sailboat & exploring Niagara Falls Canada [Ep 7]

Have you ever been to the famous Niagara Falls in Ontario, Canada? The falls are stunning and Clifton Hill is quite the sight. And guess what!? We're buying our first sailboat. #wildlyintrepid #niagarafalls #buyingfirstsailboat Want to know how we did it...
Ep 55 New Electronics for Talisman
Sailing Talisman

Ep 55 New Electronics for Talisman

We add some new Raymarine i50 and i60 (wind, speed, depth) instruments to our system. These plug directly into the new SeaTalkNg backbone and eliminate the last vestiges of the legacy ST1 system. Here's how we did it.
Epic water experiences, one click away.

Something AWESOME is coming!
Be the FIRST to know⛵

Sign up for exclusive updates and be the first to hear when we go live!
Get sneak peeks, exciting announcement, and special content straight to your inbox!

We don’t spam! Read our privacy policy for more info.


WeBoating
Logo
Shopping cart