Watch Sailing & Boating Adventures Around the World tagged “Upwind sailing”

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 26 results
This is why we Cruise! Ep.21
A Life Awry Sailing

This is why we Cruise! Ep.21

Join Leanne, Kieran, and little Jack in this incredible sailing adventure, where they leave the Kles with a three-day weather window to reach their next destination at Harvey Bay. Experience the highs and lows of their journey and learn about life aboard t...
SPORTY & SPICY SAILING SARDINIA! EP-116
Leading the Escapade

SPORTY & SPICY SAILING SARDINIA! EP-116

SUP exploring the beauty of Sardinia, sailing La Maddalena National Park, swimming in crystal clear waters, anchoring in our shallowest water yet and sporty sailing to Olbia!! LOVE OUR CONTENT?? Here are the many ways you can support us! ❤️️ Suppo...
We’ve sprung a leak! Ep.21
A Life Awry Sailing

We’ve sprung a leak! Ep.21

Hi everyone, This we officially leave the Whitsundays and do the jump from Shaw Island to Scawfell Island. It's much more pleasant sailing thankfully. However, we do need to spend a few days at Scawfell to hide away from 30+ knots before making our next ...
The CHALLENGES we face sailing the east coast on a STRICT timeframe! RAW with minimal edits Ep.20
A Life Awry Sailing

The CHALLENGES we face sailing the east coast on a STRICT timeframe! RAW with minimal edits Ep.20

Hi everyone, It's time to sail south again but unfortunately the winds are not favourable. We have no choice but to make ground as we have only 4 weeks to get to Brisbane to catch a flight to Dublin, Ireland. Let's just say it's far from smooth sailing o...
Upwind sailing in 28 knots and finally some clear water!
Sailing Adventure Can't Wait

Upwind sailing in 28 knots and finally some clear water!

We bash north sailing upwind in 28 knots. The sea state becomes uncomfortable as we remember why "gentleman don't sail to weather." Most cruisers heed that advice, and we quickly remember why! Sailing upwind in a strong breeze while also fighting a curre...
Goodbye Civilization! Taking Off For The Patagonian Fjords In Our Sailboat [Ep. 115]
Sailing Sweet Ruca

Goodbye Civilization! Taking Off For The Patagonian Fjords In Our Sailboat [Ep. 115]

You haven't seen YouTube sailing HERE! It's time to take off for the Patagonian fjords - some of the most remote sailing, but surrounded by majestic mountains that can sometimes cause treacherous williwaws and challenging sailing. Our first day in the fj...
A Smooth Sea never made a Skilled Sailor- Sailing SV Bohemian- episode 48
Sailing SV Bohemian

A Smooth Sea never made a Skilled Sailor- Sailing SV Bohemian- episode 48

A smooth sea never made a skilled sailor. We went on a 10 trip in the Chesapeake. Sailing from the C7D canal to Solomon Island and back. We encountered gale force winds and 3-6 ft seas. We learned alot and enjoyed the freedom of being on the hook. Can't wa...
How to sail – Sailing Ep 275
followtheboat

How to sail – Sailing Ep 275

This is how we sail SY Esper, our Oyster 435 cutter-rigged ketch. The principles apply equally to most sail plans... 🥂 PATREON | FTBMates | Rum Fund - https://followtheboat.com/pub/ 🍻 00:00 Sailing basics 00:43 Stowing, planning, weighing 02:0...
Life On The Lean: Sailing From Sardinia to Menorca | Ep. 20
Navika Sailing

Life On The Lean: Sailing From Sardinia to Menorca | Ep. 20

Hello! Join us as we leave Sardinia in this video and embark on our 2 day passage across to Menorca, the first of the Balearic Islands coming from the East. We have a hard time getting comfortable as we're close-hauled or close-reached the whole way, so we...
We FINALLY made it to George Town! | SAILING THE BAHAMAS
Holly and Ray

We FINALLY made it to George Town! | SAILING THE BAHAMAS

Join us on our sail south! We started off the week sailing upwind from Sampson Cay to Black Point, where we waited a few days for the wind to clock back around before starting our trip down to George Town. We caught our first tuna in the Bahamas on the way...
WE Sail Into the Wind | Sailing to the Sea of Cortez | Episode 75
WEsail

WE Sail Into the Wind | Sailing to the Sea of Cortez | Episode 75

On this episode of WE|Sail, we are back out at sea only after just a few days on land again from our 18 day passage. We set sail from Zihuatenejo to our new final destination for the summer to San Carlos, Mexico in the Sea of Cortez. We have another week...
Boat 1, Nicole Zero…
Adventures of Two Afloat

Boat 1, Nicole Zero…

Yes we are the upwind boat, at least that is what it feels like. But we do get this little jib under control finally after I (Nicole) have an all out battle with it. We are also outta here for a while. We're off to the Tuamotus and beyond for cyclone se...
Lively Sailing in South America  [Adventure #197]
Adventure Adrift

Lively Sailing in South America [Adventure #197]

Join us as we embark on some boisterous sailing through Patagonia, bashing our way South through the Chiloe archipelago and across the Gulf of Corcovado. We do a man overboard drill to retrieve lost shore lines, refill our fuel tanks with jerry cans and s...
Gentlemen Really Shouldn’t Sail to Weather – Ep 109
Out Chasing Stars

Gentlemen Really Shouldn’t Sail to Weather – Ep 109

A word of advice. It's perhaps not the best idea to take two ladies on a sailing passage that turns into a tough upwind bash. Especially when it's the first time one of them has ever sailed overnight! Our friend Sara had a flight to catch on the island ...
Who needs a Gearbox anyway… (Sailing Nandji) Ep 112
Sailing Nandji - Frothlyfe

Who needs a Gearbox anyway… (Sailing Nandji) Ep 112

The wind disappears and drifting in the current we are heading towards the busy shipping lane... This engine will be the death of us! https://www.sailingnandji.com This week on Sailing Nandji, we return to the islands of Karimunjawa to fix our headsail ha...
It’s upwind to paradise – Sailing Tarka Ep. 24
The Adventures of Tarka

It’s upwind to paradise – Sailing Tarka Ep. 24

Proceeds from this video will go to the Coral Reef Alliance, but you can also support me directly (and specifically the production of these videos) by becoming a Patron: https://www.patreon.com/theadventuresoftarka Tarka is a 1973 Albin Vega 27 (8.2m) tha...
Ships, Currents, Upwind and a Scooter? Exploring Rote Island (Sailing Nandji) Ep 107
Sailing Nandji - Frothlyfe

Ships, Currents, Upwind and a Scooter? Exploring Rote Island (Sailing Nandji) Ep 107

Another Upwind passage competing with Currents and Ships, then a Scooter? https://www.sailingnandji.com This week on Sailing Nandji, After successfully clearing back into Indonesia, we head to sea on a upwind passage South to the island of Rote in search ...
Upwind Sailing to Indonesia (Sailing Nandji) Ep 106
Sailing Nandji - Frothlyfe

Upwind Sailing to Indonesia (Sailing Nandji) Ep 106

Bonita is back on Nandji, I have overstayed my visa... Must be time to sail! Of course something goes wrong... https://www.sailingnandji.com This week on Sailing Nandji, Bonita returns back to Dili, after a 3 week trip to Australia for medical and family ...
The Lows of Sailing around the World (Sailing Nandji) Ep 104
Sailing Nandji - Frothlyfe

The Lows of Sailing around the World (Sailing Nandji) Ep 104

Sailing around the World is not always easy... https://www.sailingnandji.com This week on Sailing Nandji, Bonita is faced with some difficult times. After receiving bad news from home, she had a health scare. The hard part about being away from friends an...
ep47 – Sailing Chesapeake – Betterton to Edgewater – Hallberg-Rassy 54 Cloudy Bay – Oct 2018
Sail Cloudy Bay

ep47 – Sailing Chesapeake – Betterton to Edgewater – Hallberg-Rassy 54 Cloudy Bay – Oct 2018

s/v Cloudy Bay (Hallberg-Rassy 54) left the quiet overnight anchorage of Betterton in the northern end of the Chesapeake and had a wonderful sailing trip to Edgewater on South River, just south of Annapolis. At first light wind and current against us, but ...
Rough Seas, Strong Winds! Hang onto your knickers! (Sailing Nandji) Ep 102
Sailing Nandji - Frothlyfe

Rough Seas, Strong Winds! Hang onto your knickers! (Sailing Nandji) Ep 102

Huge Rough Seas, Strong 30 knot winds on the nose, all makes a difficult up wind Offshore 400nm passage! https://www.sailingnandji.com This video is a in depth view of what life at sea is really like and the problems faced at all hours of the night. This...
ep39 – Sailing Bristol – Sailing Rhode Island – Hallberg-Rassy 54 Cloudy Bay – Sep 2018
Sail Cloudy Bay

ep39 – Sailing Bristol – Sailing Rhode Island – Hallberg-Rassy 54 Cloudy Bay – Sep 2018

After 4 days in Newport, s/v Cloudy Bay (Hallberg-Rassy 54) sailing adventure in Rhode Island continues to Bristol. Sailing from Newport to Bristol turned out to be mostly motoring, but on the return trip it was a totally different sailing experience! To b...
Why is it so hard to turn around? (Sailing Nandji) Ep 82
Sailing Nandji - Frothlyfe

Why is it so hard to turn around? (Sailing Nandji) Ep 82

Without a weather forecast, we attempt to sail upwind to Noro being smashed by squalls. https://www.sailingnandji.com In this episode of Sailing Nandji, the question is asked. Why is it so hard to turn around? We attempt to sail 80nm to Noro without a wea...
BAJA BASH: THE EASY WAY [Adventure #102]
Adventure Adrift

BAJA BASH: THE EASY WAY [Adventure #102]

Sailing on our own terms, we go against the normal cruising route and continue our sailing passage north, heading up the Baja California peninsula. We sail close hauled and try to keep the actual bashing to the minimum, tacking our way up the coast. We a...
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