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Sailing Sitka
April 13, 2025
Sailing Sitka

Sailing Sitka

Hi Everyone! We are two crazy Coconuts by the name of Jay and Kenna! For years we have prepared our 1976 Cheoylee Offshore 41 for her big offshore passage…finally we have hit the high seas and are heading south from Victoria, BC, Canada! Follow our journey as we slowly attempt to sail around the world. First stop, Mexico!🥥⛵️

Sailing Sitka Journey and Videos Locations

Sailing Sitka Latest Episode

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Sailing Sitka Lastest Videos

San Blas at Last: A Sailors Dream Years in the Making | Sailing Sitka Ep 163
San Blas at Last: A Sailors Dream Years in the Making | Sailing Sitka Ep 163
Jay and Kenna depart from Shelter Bay marina after a week straight of boat work and diagnosing problems. Finally, after stopping in Linton bay for one night, they sail to the desolate and world renowned San Blas islands. A dream come true. They've worked h...
“50 years of history GONE in a second…” | Sailing Sitka Ep 162
“50 years of history GONE in a second…” | Sailing Sitka Ep 162
Jay and Kenna are in Shelter Bay Marina, fixing some minor and major problems they've encountered while transiting the Panama Canal, on top of that they do some routine and periodic maintenance to make sure their 50 year old sailboat is ready to sail her w...
Why our engine FAILED while transiting the Panama Canal | Sailing Sitka Ep 161
Why our engine FAILED while transiting the Panama Canal | Sailing Sitka Ep 161
Jay and Kenna are now tied along a dock in Shelter Bay marina after undergoing two of the most stressful days of their lives. While transiting the Panama Canal, their Yammer 56 engine failed several times in the worst possible scenarios. Surprised they eve...
Engine Nightmare, Breakages & Bad Luck Continues… Panama Canal Day 2 | Sailing Sitka Ep 160
Engine Nightmare, Breakages & Bad Luck Continues… Panama Canal Day 2 | Sailing Sitka Ep 160
Panama Canal Day 2: Engine nightmare & bad luck continues, Atlantic awaits... In this episode jay and Kenna (along with @SailingSVBully ) continue their unexpected adventure through the Panama Canal with their unreliable engine. Their troubles aren't d...
Panama Canal Nightmare: Engine Failure, No Sails, Will we make it through? | Sailing Sitka Ep 159
Panama Canal Nightmare: Engine Failure, No Sails, Will we make it through? | Sailing Sitka Ep 159
Engine Failure in the Panama Canal: Will we make it or get Fined? In the very exciting episode of Sailing Sitka, Jay and Kenna ( along with their pals @SailingSVBully ) embark on their most stressful journey yet. The Panama Canal is an emotional strain alr...
Final prep & nerves before our Panama Canal transit (real talk and costs $) | Sailing Sitka Ep 158
Final prep & nerves before our Panama Canal transit (real talk and costs $) | Sailing Sitka Ep 158
Jay and Kenna share some real thoughts and info as they prepare to transit the Panama Canal from the pacific to the Atlantic. But not before they enjoy some time enjoying the city life in Casco Viejo. Thanks for watching and subscribe if you enjoy. Stay tu...

Watch Sailing Sitka From The Beginning!

New Beginnings Onboard SITKA. Ep 1
New Beginnings Onboard SITKA. Ep 1
This video is the story of how we met along with the adventures and projects that come along with the live-aboard lifestyle. Join us!
Boat Cabin BEFORE and AFTER Remodel Ep 2
Boat Cabin BEFORE and AFTER Remodel Ep 2
In this video we show the step-by-step process on how we insulated and remodelled our quarter berth.
Young Couple Living ABOARD a 41 foot SAILBOAT! Ep 3
Young Couple Living ABOARD a 41 foot SAILBOAT! Ep 3
This video shows you what it is like to live aboard a sailboat and what our day-to-day routines consist of.
30 CENT FIX to a $5000 System! Ep 4
30 CENT FIX to a $5000 System! Ep 4
In this weeks episode, Jay surprises Kenna with a more efficient and organized idea for the clothing locker. More importantly, we fix an expensive problem with a cheap solution!!
Installing an Outboard Lift on SITKA Ep 5
Installing an Outboard Lift on SITKA Ep 5
In this episode we install an outboard lift so we can now raise and lower the outboard motor on and off our dinghy.
Are WE Ready to Sail OFFSHORE?! Ep 6
Are WE Ready to Sail OFFSHORE?! Ep 6
In this weeks episode we have an honest chat about our fears, concerns and excitments about our upcoming offshore sailing plans.
NEW CREW ONBOARD!? / Cockpit Refit Pt 1 Ep 7
NEW CREW ONBOARD!? / Cockpit Refit Pt 1 Ep 7
In this episode we introduce to you our newest crew member who will be sailing offshore with us. In addition to that, we remodel our cockpit to better suit our needs.
Monkey-ing Around in Our NEW COCKPIT (Refit Pt 2) Ep 8
Monkey-ing Around in Our NEW COCKPIT (Refit Pt 2) Ep 8
In this week's episode we continue working away at upgrading our cockpit.
Getting the Boat READY for OFFSHORE SAILING (Refit Pt 3) Ep 9
Getting the Boat READY for OFFSHORE SAILING (Refit Pt 3) Ep 9
In this episode we made progress on the cockpit refit project by installing the winches on our new custom cockpit coaming.
How NOT to SINK Your Boat! (High Water Bilge Alarm/Pump Install Pt 1) Ep 10
How NOT to SINK Your Boat! (High Water Bilge Alarm/Pump Install Pt 1) Ep 10
In this episode we install our bilge pump and alarm set up for offshore sailing. Jay takes his previous experience sailing offshore and applies it to this boat.
WILL WE FLOOD THE BOAT!? Ep 11
WILL WE FLOOD THE BOAT!? Ep 11
In this episode we put our high alarm/bilge pump to the test by filling the boat up with water...
23 Year Old Uses a 1969 Sewing Machine POWERED by the SUN! Ep 12
23 Year Old Uses a 1969 Sewing Machine POWERED by the SUN! Ep 12
In this episode, Kenna sews cockpit cushions (with zero experience) using a 1969 Sewing Machine powered by our solar panels!
Wilfred is ALIVE! (HYDROVANE Install Gone WRONG) Ep 13
Wilfred is ALIVE! (HYDROVANE Install Gone WRONG) Ep 13
In this video, we attempt to install our new hydrovane named Wilfred in some unfavourable conditions...
FINALLY SAILING! Ep 14
FINALLY SAILING! Ep 14
After months of boat projects trying to get Sitka ready for offshore, we set her sails in effort to find our first anchorage of the season!
FULL BOAT TOUR (Young Couple Living Aboard a 41ft Sailboat) Ep 15
FULL BOAT TOUR (Young Couple Living Aboard a 41ft Sailboat) Ep 15
In this episode we give you guys a full tour of Sitka, our 1976 Offshore 41 built by Cheoy Lee in Hong Kong. She was designed by Raymond Richards and here are a few stats on her: Length: 40.92ft/12.47m LWL:32.5Oft/9.91m Beam: 12.75ft/3.89m Draft: 6ft/1.83m...
Getting Our WOODEN MASTS Offshore READY Ep 16
Getting Our WOODEN MASTS Offshore READY Ep 16
In this video, we varnish our main mast and the bottom portion of our mizzen. We also get around to putting Sitka's name on after 6 years, as well as her port of call.
Sailing, Sunsets and SHARKS! Ep 17
Sailing, Sunsets and SHARKS! Ep 17
In this episode we sail to a near by anchorage to fish and have some fun!
BROKEN SPREADER?! (Could’ve lost the Rig) Ep 18
BROKEN SPREADER?! (Could’ve lost the Rig) Ep 18
Big Daddy Safari takes the reins this episode by building 2 new spreaders from scratch. He also introduces you to a good friend named Henry Ford and services an old winch.
Rain or Shine, WE SAIL! Ep 19
Rain or Shine, WE SAIL! Ep 19
In this episode, Kenna's mom is here for a visit and gets to experience sailing for the first time! We sail to Pender Island, eat some good food and experience a drastic change in weather (but that doesn't slow us down.)
Finally LEAK FREE! Ep 20
Finally LEAK FREE! Ep 20
In this episode Jay takes care of some leaky portholes that were driving us insane! We also get a surprise visit from an old buddy who brought a life changing piece of equipment on board Sitka.
Beaches, BABES and Boat Work! Ep 21
Beaches, BABES and Boat Work! Ep 21
In this episode, Kenna's best friend visits Vancouver Island and experiences sailing for the first time! We love sharing our growing passion for sailing with others. Thanks for coming out Justice!
Building a NEW Door for our HOME on the OCEAN! Ep 22
Building a NEW Door for our HOME on the OCEAN! Ep 22
In this week's episode, Jay builds a new door for our companionway from scratch! Follow along to see his process!
From NO Sailing Experience to SAILING THE WORLD! (Jay’s Story) Ep 23
From NO Sailing Experience to SAILING THE WORLD! (Jay’s Story) Ep 23
In this week's episode Jay shares with us how he got into sailing and how he went from knowing nothing to activley pursuing his dream to sail around the world.
PRAIRIE GIRL turned SAILOR! (+ DOOR REFIT pt 2) Ep 24
PRAIRIE GIRL turned SAILOR! (+ DOOR REFIT pt 2) Ep 24
In this video, Jay adds some finishing touches on the door to get it closer to completion. We also pack our bags and drive east to visit Kenna's family in Alberta, home of the Canadian Prairies (and dinosaurs.)
Boys Trip & BOAT WORK Ep 25
Boys Trip & BOAT WORK Ep 25
In this episode, Jay and Mikey go sailing for the weekend... but the boat work doesn't stop there!!
Final PREP Before SAILING to MEXICO! Ep 26
Final PREP Before SAILING to MEXICO! Ep 26
In this episode we show you the projects we have been wanting to get done in preparation for offshore. We also go over our list for what else needs to be done before we take the big left turn!
The OFFSHORE PREP Continues… Ep 27
The OFFSHORE PREP Continues… Ep 27
In this episode we continue working to prep Sitka for her big offshore passage coming up quicker than we think...
Saying Bye to Family & Continuous BOAT PREP Ep 28
Saying Bye to Family & Continuous BOAT PREP Ep 28
In this episode, Jay does some much needed boat work in preparation for our offshore passage. We then fly to Jays hometown Quebec City to experience some incredible culture!
SEWING a STACK PACK from SCRATCH! Ep 29
SEWING a STACK PACK from SCRATCH! Ep 29
In this episode we got a crispy new mizzen sail which meant some more sewing! Jays friend Ryan dives under boat and Jay receives an awesome gift from a local sailor. To follow our journey on a more personal level, become a Patreon! https://patreon.com/sa...
Provisioning in Preparation for our OFFSHORE Passage! Ep 30
Provisioning in Preparation for our OFFSHORE Passage! Ep 30
In this video, you meet our third crew member HARRY HALL! We go provisioning as well as finish up some last minute boat projects. Thank you for watching! If you want to support us further, check out our Patreon page! https://patreon.com/sailingsitka?utm_...
All Things WOODEN! Ep 31
All Things WOODEN! Ep 31
In this episode, Big Daddy Safari does some woodworking himself and afterwards we go and take a visit to the Victoria Classic Boat Festival where we see some old wooden beauties. Love what you're watching and want more? Support us on Patreon! https://pat...
Engine PROBLEMS Days BEFORE Leaving OFFSHORE Ep 32
Engine PROBLEMS Days BEFORE Leaving OFFSHORE Ep 32
In this episode the boys are trying to diagnose a problem with our outboard engine. Before that, Jay does some more boat projects and then stops to see a good friend who happens to be a world renowned artist and sailor! Love our content and want to suppor...
A SH*TTY Start to our OFFSHORE Passage! (Literally💩) Ep 33
A SH*TTY Start to our OFFSHORE Passage! (Literally💩) Ep 33
Hours before leaving the dock, we find an unpleasant surprise... We then sail to Port Renfrew BC to make our way towards the BIG LEFT! Offshore sailing here we come!!! Love what you see? Become a Patreon! We would love to have you aboard! www.patreon.com/...
RIG FAILURE OFFSHORE | Sailing Sitka Ep 34
RIG FAILURE OFFSHORE | Sailing Sitka Ep 34
RIG FAILURE OFFSHORE. In this episode we enjoy the best qualities of sailing offshore. Dolphins, tuna, watching movies and warm weather...suddenly interrupted by a drastic emergency with the rig within seconds. Sailing offshore will be the best times of yo...
OFFSHORE EMERGENCY diverts us to LAND Ep 35
OFFSHORE EMERGENCY diverts us to LAND Ep 35
In this weeks episode we make our way towards Eureka California to make emergency repairs to our rig. Before getting there safely, we sail though some tough weather all while making spicy tuna rolls. Love what you see? Become a Patreon! We would love to h...
Back OFFSHORE After EMERGENCY Repairs! (Pt 1) Ep 36
Back OFFSHORE After EMERGENCY Repairs! (Pt 1) Ep 36
In this episode, we sail offshore towards San Diego after fixing our broken spreader from our main mast! Kenna conquers her sea sickness while we get many visits from nature along the way! . Love what you see? Become a Patreon!! We would love to have you ...