Sailing Clewless Crew
Midlife sailing adventure | Retired couple living on a catamaran | Full-time liveaboard sailing We’re John & Sha, a retired couple in our mid-50s preparing to move aboard our catamaran this April. After retiring from full-time careers, we’re transitioning to full-time liveaboard sailing and documenting the entire journey. Right now, we’re sailing the Ionian in Greece. Stunning anchorages, pretty fishing villages and gusty winds are all on the agenda here. In the near future we will head off to Albania and Montenegro. From catamaran living and liveaboard life to sailing adventures, slow travel, and going where the wind takes us — this is our next chapter. If you’re interested in sailing in your 50s, retirement adventures, boat life preparation, or leaving the 9–5 for freedom and travel, subscribe and join us.
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Sailing Clewless Crew Latest Episode
Midlife sailing adventure | Retired couple living on a catamaran | Full-time liveaboard sailing
We’re John & Sha, a retired couple in our mid-50s preparing to move aboard our catamaran this April. After retiring from full-time careers, we’re transitioning to full-time liveaboard sailing and documenting the entire journey.
Right now, we’re sailing the Ionian in Greece. Stunning anchorages, pretty fishing villages and gusty winds are all on the agenda here. In the near future we will head off to Albania and Montenegro.
From catamaran living and liveaboard life to sailing adventures, slow travel, and going where the wind takes us — this is our next chapter.
If you’re interested in sailing in your 50s, retirement adventures, boat life preparation, or leaving the 9–5 for freedom and travel, subscribe and join us.
Sailing Clewless Crew Journey and Videos Locations
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Watch Sailing Clewless Crew's Latest Videos
Catch up on the most recent updates. Browse the complete video archive and Follow the journey.
Showing 1-24 of 61 results
Our FIRST Overnight Sail! Montenegro to Italy 🇮🇹 Crossing the Adriatic.
It’s time to prepare for our Montenegro-to-Italy crossing! With engine checks, sail repairs and homemade bread sorted, we fuel up and clear out at Porto Montenegro before heading across the Adriatic. Light-wind sailing, fishing for tuna and mahi-mahi, sunset at sea and first-night-passage nerves all...
Tuna fishing
Tuna fishing in the Adriatic. Had a few of these of these today, watch tomorrows Longform video for more Tuna action. Hi and welcome, we are John and Sharon a mid 50's retired couple who brought a boat to live on and are currently sailing in the mediterranean. Follow in real time: Watch her...
Alberobella Italy
Step into Alberobello, Puglia—Italy’s fairytale town of whitewashed trulli: unique cone-roofed limestone homes built using traditional dry-stone techniques. This magical corner of southern Italy has been a UNESCO World Heritage Site since 1996, with more than 1,500 of these remarkable dwellings stil...
40 Knot Bora Hits Kotor Bay! We Escape the Marina + DIY Dyneema Upgrade
We arrive in Porto Montenegro only to find our berth is more bus stop than marina, then welcome Sharon's brother Sam and his friend Rich aboard 23 Pioneer for a chaotic long weekend in the stunning Bay of Kotor. From a dinghy mishap and a failed hike towards the Kotor castle to gusts of 40 knot...
Dyneema spliced low friction ring
Short video of splicing a low friction ring onto dyneema rope loop. ideal for rigging improvements et al. Hi and welcome, we are John and Sharon a mid 50's retired couple who brought a boat to live on and are currently sailing in the mediterranean. Follow in real time: Watch here to see the...
Light WIND SAILING in Montenegro… Then the Dinghy Fuel Problem RETURNED! The reality of cruising.
Sailing Clewless Crew navigates the fjord-like waters of the Bay of Kotor in Montenegro, practicing light-air sail handling before tackling persistent dinghy outboard fuel starvation.
Cooking on a monohull. It’s a test of nerve! #sailing #yacht #boat
This was the main reason for us purchasing a catamaran, where whilst life can be off balance. It’s certainly more normal than a monohull to undertake simple daily tasks.
This yacht crashed straight into theirs #catamaranlife #sailing #yacht
This is one of our main worries as we liveaboard. As they always say, it’s not normally you that’s the issue, it’s those around you. Ouch!
Things that make sense on a sail boat #sailing #liveaboard #yachting
Some useful information for living comfortably on a yacht.
Epic Mountain Views & Thrills Falcon Fly Adventure Awaits!
Hi and welcome, we are John and Sharon a mid 50's retired couple who brought a boat to live on and are currently sailing in the mediterranean. Would love of you to join our journey, so subscribe to stay connected. Follow in real time: Watch here to see the how we got the boat ready for this...
Boat Engine Repair Fixing Cross Threading Like a Pro!
Hi and welcome, we are John and Sharon a mid 50's retired couple who brought a boat to live on and are currently sailing in the mediterranean. Follow in real time: Watch here to see the how we got the boat ready for this adventure: Here you will be able to see how we navigated Greece: We...
Is This Montenegro’s BEST View? Kotor Cable Car & Friends Aboard 23 Pioneer
Hi and welcome, we are John and Sharon a mid 50's retired couple who brought a boat to live on and are currently sailing in the mediterranean. This week a tour of the Bay of Kotor with old friends, a hike up the mountain, and a few boat jobs on 23 Pioneer. We cruise past Our Lady of the Rocks ...
Dog Watches Storm! Boat Wash & Danger at Sea!
Hi and welcome, we are John and Sharon a mid 50's retired couple who brought a boat to live on and are currently sailing in the mediterranean. Follow in real time: Watch here to see the how we got the boat ready for this adventure: Here you will be able to see how we navigated Greece: We...
Sailing Nightmare Anchor Chains, Storms, Then Paradise Found!
Hi and welcome, we are John and Sharon a mid 50's retired couple who brought a boat to live on and are currently sailing in the mediterranean. Follow in real time: Watch here to see the how we got the boat ready for this adventure: Here you will be able to see how we navigated Greece: We...
We Dragged, Got Tangled & Had to Jump In! | Bay of Kotor Catamaran Life
#CatamaranLife #SailingMontenegro #BayOfKotor #AnchorLife #SailingLife Hi and welcome, we are John and Sharon a mid 50's retired couple who brought a boat to live on and are currently sailing in the mediterranean. This week on 23 Pioneer, we kick things off exploring the stunning luxury marin...
We Didn’t Expect This… Bad Weather AND an Electrical Fire!
A tropical-style storm hits Kotor Bay without warning, flooding the saloon, soaking Sharon and Cleo, and causing a power outage across the town — and that’s just day one! Then, while moving anchorage, we open the engine bay to find two Mastervolt shunts have melted due to corrosion, knocking out our...
Cleaning boat hulls Satisfying underwater task revealed!
#hullcleaning #sailing #montenegro Hi and welcome, we are John and Sharon a mid 50's retired couple who brought a boat to live on and are currently sailing in the mediterranean. Follow in real time: Watch here to see the how we got the boat ready for this adventure: Here you will be able...
Venetian Fortress Defence 16th Century Bay Battles & Towers
#perast #kotor #montenegro Hi and welcome, we are John and Sharon a mid 50's retired couple who brought a boat to live on and are currently sailing in the mediterranean. Follow in real time: Watch here to see the how we got the boat ready for this adventure: Here you will be able to see ...
We Found Montenegro’s Hidden Watermill Restaurant! | Catamaran Life, Perast & Boat Lasagne
We discover one of Montenegro’s most beautiful hidden spots—by fully sending the dinghy! From our catamaran in Risan Bay, we head through a narrow bridge entrance to an incredible old watermill restaurant surrounded by streams, stone bridges and lush greenery in the Bay of Kotor. Hi and welcome, we...
Boat Water Maker FAIL Pressure Drops During Operation!
Hi and welcome, we are John and Sharon a mid 50's retired couple who brought a boat to live on and are currently sailing in the mediterranean. Follow in real time: Watch here to see the how we got the boat ready for this adventure: Here you will be able to see how we navigated Greece: We...
Hidden Crystal Clear Beaches You WON’T BELIEVE Exist!
Hi and welcome, we are John and Sharon a mid 50's retired couple who brought a boat to live on and are currently sailing in the mediterranean. Follow in real time: Watch here to see the how we got the boat ready for this adventure: Here you will be able to see how we navigated Greece: We...
Exploring Herceg Novi, Montenegro | Catamaran Boat Servicing & Cruising Life
Hi and welcome, we are John and Sharon a mid 50's retired couple who brought a boat to live on and are currently sailing in the mediterranean. Follow in real time: Watch here to see the how we got the boat ready for this adventure: Here you will be able to see how we navigated Greece: We...
Authentic Beach BBQ Cooking Local Fish on Driftwood!
We found a little gem in the south of Albania, only reachable by boat. A little bar called #tongobar. If you get the chance please visit, simply outstanding. Fresh fish cooked over fire burnt wood. yummy! #albania, #fish, #catamaran