Watch Sailing & Boating Adventures Around the World – Page 2 of 3

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Showing 25-48 of 66 results
Is Sydney Harbour worth sailing half way around the world for? – Sailing Australia Ep.48
Sailing Yacht Florence

Is Sydney Harbour worth sailing half way around the world for? – Sailing Australia Ep.48

Sailing our own boat under the Sydney Harbour Bridge has been a bucket list item for us since we set off from England 2.5 years ago at the start of our circumnavigation. Having sailed across two oceans to get here it was a real highlight for us to finally tick it off the list. We spent some time exp...
Bienvenido a Culebra! (Calico Skies Sailing Ep. 13)
Calico Skies Sailing

Bienvenido a Culebra! (Calico Skies Sailing Ep. 13)

The tiny island of Culebra packs a big punch - From the incredibly clear and beautiful greeny-blue water full of sea life to the numerous chill bars with easy dinghy access, we couldn't have asked for more from our very first Puerto Rican experience. While there, we also paid a visit to the fab...
Sailing South Africa to USA.  We arrived in Namibia.  Voyage update video.
Cruising Off Duty

Sailing South Africa to USA. We arrived in Namibia. Voyage update video.

This is an update video on the sailing voyage so far. Each time I arrive in a new harbor and I can find decent wifi, I will try and post a quick update video so the viewers learn about our progress and get a synopsis of what has happened and get a glimpse of what they will see in the full detailed ...
Neighbor Island’s: Same Caribbean, Different Worlds (Calico Skies Sailing Ep. 12)
Calico Skies Sailing

Neighbor Island’s: Same Caribbean, Different Worlds (Calico Skies Sailing Ep. 12)

It's hard to top the enchanting Indian River we explored in last week's episode but our discovery of an incredible waterfall just inland from our anchorage here in Dominica might be the islands best surprise yet. It's our last bit of tropical jungle exploration before setting off on a...
Stormy Sailing South to Sydney – Sailing Australia Ep.47
Sailing Yacht Florence

Stormy Sailing South to Sydney – Sailing Australia Ep.47

The weather gave us some challenges making our way down the coast of Australia towards Sydney. After spending a lot of time creeping through the inshore channels, heading out to sea was a bit of a shock to our systems, especially when we were caught in an un-forecasted storm. Along the way we went i...
Welcome to the Jungle (Calico Skies Sailing Ep. 11)
Calico Skies Sailing

Welcome to the Jungle (Calico Skies Sailing Ep. 11)

It's all fun and games in the exotic Caribbean island of Dominica. In this episode we make the 36 hour sail from Grenada and arrive into a mountainous island covered in rain forest and dense, tropical jungle. The first thing we do is take a trip via rowboat up the enchanting Indian River where ...
We are a Sailboat Again! (Calico Skies Sailing Ep. 10)
Calico Skies Sailing

We are a Sailboat Again! (Calico Skies Sailing Ep. 10)

This week we FINALLY finish boat repairs: Calico Skies has never been in better shape, and we've never been more excited! We still need to prepare for departure though, which means provisioning (aka buying lots of chocolate), cleaning the boats anchor chain and bottom to remove growth, and sque...
South Atlantic Sailing Crossing.  What gear am a bringing to film it.
Cruising Off Duty

South Atlantic Sailing Crossing. What gear am a bringing to film it.

What camera gear am I bringing to film the 8 week, 10,000 mile South Atlantic Sailing Voyage from Cape Town, South Africa to the USA? Can I fit it all in my camera backpack? Want to know what gear I use. You can click this link to go to my website for a list of all my gear. There will be a Li...
Boat Tour: Our live aboard bluewater cruiser Florence – Ep.46
Sailing Yacht Florence

Boat Tour: Our live aboard bluewater cruiser Florence – Ep.46

What does a live-aboard blue water cruiser look like? We have had lots of requests to see more of our yacht 'Florence', so come aboard and have a look around. We have lived aboard her for 3 years now, sailing double handed across 2 Oceans on our around the world sailing adventure. Florence...
When Opportunity Knocks we Top Up the Cruising Kitty (Calico Skies Sailing Ep. 9)
Calico Skies Sailing

When Opportunity Knocks we Top Up the Cruising Kitty (Calico Skies Sailing Ep. 9)

This week we take on a couple of odd jobs to help offset the cost of transatlantic boat repairs. We also make time to explore Grenada's north shore and make a trip to a stunning deserted island off the coast. As per usual, there's also more boat repairs made to Calico Skies who's in ...
Chocolate, Rum and Our Golden Ticket (Calico Skies Sailing Ep. 8)
Calico Skies Sailing

Chocolate, Rum and Our Golden Ticket (Calico Skies Sailing Ep. 8)

This week we learn how rum is made, tour a chocolate factory and find our very own golden ticket when our Amazon order arrives and it's everything we've ever dreamed of and more! We also continue repairing breakages from the transatlantic and move one step closer to becoming a sailing vess...
Sailing 10,000 Miles from South Africa to the USA.  Plans, Hopes and Fears.
Cruising Off Duty

Sailing 10,000 Miles from South Africa to the USA. Plans, Hopes and Fears.

This episode of Cruising Off Duty, I am going to explain the plans for the upcoming sailing voyage from South Africa to the USA. This will be a 10,000-mile transatlantic crossing on a 50' Xquisite X5 Catamaran. The journey will take us across the South Atlantic, the equator and then into the ...
Sailing Moreton Bay – Sailing Australia Ep.45
Sailing Yacht Florence

Sailing Moreton Bay – Sailing Australia Ep.45

Florence plowed through a smack of jellyfish we entered Moreton bay but with poor weather forecast we went and hid in a marina. This allowed us to meet up with a couple who follow our channel and they very kindly lent us their car so we could make the most of the time by exploring inland and the gla...
How To Follow My TransAtlantic Sailing Voyage Live. Channel Origin Story & I cross 20K subscribers!
Cruising Off Duty

How To Follow My TransAtlantic Sailing Voyage Live. Channel Origin Story & I cross 20K subscribers!

In this episode of Cruising Off Duty, I bring my good friend Terry Billingsly back on the channel. He helped me in the planning when I started this channel and he is the one that Created the Cruising Off Duty App that will help you stay connected to me while I do the 10,000 Mile TransAtlantic Saili...
The Cruising Life: Fixing the Boat in Exotic Places (Calico Skies Sailing Ep. 7)
Calico Skies Sailing

The Cruising Life: Fixing the Boat in Exotic Places (Calico Skies Sailing Ep. 7)

It's time to get moving on boat repairs after our big transatlantic passage. But like anything in life, its all about balance. In this episode we tackle sail repairs and a solar panel installation but also make our way deep into Grenada's lush, tropical jungle for a hike to one of the isla...
Minisode 1: Island Hopping: Sailing the Caribbean Sea
Calico Skies Sailing

Minisode 1: Island Hopping: Sailing the Caribbean Sea

We had a beautiful 300 mile, 45 hour sail from Guadeloupe to Puerto Rico in ideal Caribbean sea conditions. Check out the highlights in this 'Mini-sode' and get a glimpse of our sailing journey as a crew of two in this real time clip. More to come when we put together the full Episode! -~...
Anchors down! Welcome to the Caribbean (Calico Skies Sailing Ep. 6)
Calico Skies Sailing

Anchors down! Welcome to the Caribbean (Calico Skies Sailing Ep. 6)

A celebration is in order after arriving to the Caribbean after almost 27 days at sea! In this episode excitement is at an all time high and it takes us some time to ease back into the good ole regular cruiser life. -~-~~-~~~-~~-~- Thanks to our Patrons! Enjoying our channel? Consider joining the...
Engine failure in the Great Sandy Straits, Australia – Sailing Australia Ep.44
Sailing Yacht Florence

Engine failure in the Great Sandy Straits, Australia – Sailing Australia Ep.44

Experiencing engine failure twice and coming face to face with a wild Dingo on Fraser Island. The life of a cruising sailor can be very varied, having to fix an engine issue in the middle of a massive thunder and lightning storm is not our favourite occupation, and coming face to face with a Dingo a...
Trans-Atlantic Arrival: Land Ho!! (Calico Skies Sailing Ep. 5)
Calico Skies Sailing

Trans-Atlantic Arrival: Land Ho!! (Calico Skies Sailing Ep. 5)

We're on the home stretch of this mammoth journey and time seems to stand still until all at once and in an instant we experience what it feels to see land after nearly a month at sea. -~-~~-~~~-~~-~- Thanks to our Patrons! Enjoying our channel? Consider joining the Calico Skies Patreon fami...
Trans-Atlantic: Tough Stuff (Calico Skies Sailing Ep. 4)
Calico Skies Sailing

Trans-Atlantic: Tough Stuff (Calico Skies Sailing Ep. 4)

We're at the mercy of Mother Nature when rough weather brings breakages, leaks, and a whole lot of discomfort. -~-~~-~~~-~~-~- Thanks to our Patrons! Enjoying our channel? Consider joining the Calico Skies Patreon family for as little as $2 a month to get lots of extra goodies :) -~-~~-~~~...
Trans-Atlantic: In for the Long Haul (Calico Skies Sailing Ep. 3)
Calico Skies Sailing

Trans-Atlantic: In for the Long Haul (Calico Skies Sailing Ep. 3)

After being at sea for a week we are in the groove of our passage. We decide to skip a stop in the Canary Islands and take our chances continuing non-stop to the Caribbean! -~-~~-~~~-~~-~- Thanks to our Patrons! Enjoying our channel? Consider joining the Calico Skies Patreon family for as little ...
Completing our voyage across the Worlds Largest Ocean – Sailing the Pacific Ep.43
Sailing Yacht Florence

Completing our voyage across the Worlds Largest Ocean – Sailing the Pacific Ep.43

This 6 day offshore passage from New Caledonia to Australia completed our 12000 mile journey across the south pacific, the worlds largest ocean. Despite ripping our mainsail and having to come up with an alternative sail plan, we finally reach Australia, the end of the south pacific journey for us. ...
Trans-Atlantic Crossroads (Calico Skies Sailing Ep. 2)
Calico Skies Sailing

Trans-Atlantic Crossroads (Calico Skies Sailing Ep. 2)

It's around the 5 or 6 day mark of our Trans-Atlantic and we're just starting to get into the groove when we're forced to make a choice which becomes a defining moment in our passage. We're facing the first big challenge on this journey but its all just part of the adventure! -~...
Place your bets! (Calico Skies Sailing Ep. 1)
Calico Skies Sailing

Place your bets! (Calico Skies Sailing Ep. 1)

As temperatures drop in Gibralter this fall we decide to make a beeline back to the Caribbean and have big money riding on our plan to complete the 3400 mile trip in just 25 days - no crew - just us, our 36 foot sailboat, and a whole lot of ocean. -~-~~-~~~-~~-~- Thanks to our Patrons! Enjoying o...
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