Monday Never

We are Will, Cat and Maddie – a family of three sailing and documenting our misadventures along the way. We are now sailing Paradox II, a Contest 46, all over the Bahamas and beyond.

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Monday Never Latest videos

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Watch Monday Never from the Beginning!

Showing 1-36 of 131 results
Leaving San Francisco – a quick look at our apartment & Cole Valley
Monday Never
Leaving San Francisco – a quick look at our apartment & Cole Valley
Before our journey begins, here is a quick look at our packing mess and the neighborhood we are leaving behind
We left San Francisco, no turning back now (EP 1 – Monday Never Sailing)
Monday Never
We left San Francisco, no turning back now (EP 1 – Monday Never Sailing)
Our journey officially begins. The car's packed. The apartment empty. Away we go roadtripping across the country and headed to the Caribbean. Guess we can't back out now.
Well… it’s a sailboat (EP 2 – Monday Never Sailing)
Monday Never
Well… it’s a sailboat (EP 2 – Monday Never Sailing)
The first few days as sailboat owners. And let's just say, not everything went quite as planned.
Sweating and Sailing (EP 3 – Monday Never Sailing)
Monday Never
Sweating and Sailing (EP 3 – Monday Never Sailing)
After a grueling week of work in Nanny Cay, we finally get her off the docks and under sail. Check out our blog: http://www.mondaynever.com or our FB page: http://www.facebook.com/mondaynever to follow us on our misadventures
Virgin Islands Shakedown Cruise (EP 4 – Monday Never Sailing)
Monday Never
Virgin Islands Shakedown Cruise (EP 4 – Monday Never Sailing)
We thought we were leaving Nanny Cay for a day. That day turned into 2 weeks of snorkeling, sailing and avoiding doing boat projects. Check out our blog: http://www.mondaynever.com or our FB page: http://www.facebook.com/mondaynever to follow us on our m...
Playing Tourist with the Parents (EP 5 – Monday Never Sailing)
Monday Never
Playing Tourist with the Parents (EP 5 – Monday Never Sailing)
We get our first visitors! Cat's parents come down to spend a week bopping around the BVIs. They make sure we are safe and well-fed. Once they leave, then it's back to the grind at Nanny Cay as we make out dingy outboard cover look rad and prepare to leave...
First Overnight Passage – BVI to St Martin (EP 6 – Monday Never Sailing)
Monday Never
First Overnight Passage – BVI to St Martin (EP 6 – Monday Never Sailing)
At long last, we leave the Virgin Islands and tackle the Anegada passage. Now, we are in St. Martin drinking our fill of Ti Punch, exploring the sites and must have "tourist" clearly written all over us. For more information about our passage or our boat ...
St Barths, Ile Fourchue and our visitor catches lunch (EP 7 – Monday Never Sailing)
Monday Never
St Barths, Ile Fourchue and our visitor catches lunch (EP 7 – Monday Never Sailing)
We get our first visitor brave enough to stay on the boat with us as we continue to explore the Leeward islands. We travel to Ilet Pinel, Ile Fourchue and St. Barths. Along the way, we finally catch a fish and celebrate Cat's birthday.
S/V Paradox – Quick Boat Tour
Monday Never
S/V Paradox – Quick Boat Tour
Here is a short tour of our floating home for anyone interested in taking a peak inside. We are aboard Paradox, a 36-foot 1989 CS Merlin. Compared to the average sailing vessel in the Caribbean, she's tiny - but she's all the boat we need. Hope you enjoy! ...
So long St. Martin, off to St. Kitts (EP 8 – Monday Never Sailing)
Monday Never
So long St. Martin, off to St. Kitts (EP 8 – Monday Never Sailing)
We unintentionally stayed in St. Martin too long - long enough for birds to mistake our sail for a logical place to build a nest. But with the New Year finally came a weather window to leave. After a quick stop in St. Barths to see the mega yachts, we head...
Volcanos, Nosebleeds, and Baguettes – sailing through the Leewards (EP 9 – Monday Never Sailing)
Monday Never
Volcanos, Nosebleeds, and Baguettes – sailing through the Leewards (EP 9 – Monday Never Sailing)
In this episode, we continue to make our way south through the Leeward islands. We visit Montserrat, which was partially destroyed by a volcano in 1997. From there, we head to Guadeloupe where we stop in Deshaies, Pigeon Island and Les Saints. We do a lot ...
Getting lost in Dominica (EP 10 – Monday Never Sailing)
Monday Never
Getting lost in Dominica (EP 10 – Monday Never Sailing)
We spend four days getting ourselves very lost in Dominica under the misconception that we could navigate an island with no roadsigns by ourselves. Along the way, we tour the Indian River, visit Emerald Lake, and hike to the Boiling Lake. Not a lot of sail...
Trying to catch fish without drowning (EP 11 – Monday Never Sailing)
Monday Never
Trying to catch fish without drowning (EP 11 – Monday Never Sailing)
In this episode we adventure through Martinique, St. Lucia and St. Vincent. We find ourselves in a bit of a daunting situation spear fishing with a local and drifting too far from our dinghy. We attempt slightly safer fishing techniques by catching and fil...
Picture Perfect Paradise, Bequia and the Tobago Cays (EP 12 – Monday Never Sailing)
Monday Never
Picture Perfect Paradise, Bequia and the Tobago Cays (EP 12 – Monday Never Sailing)
In this episode, we continue our journey south to Grenada with our friend Tim. We spend time in beautiful Bequia and the picturesque Tobago Cays where the color of the water was something out of a dream. We celebrate super bowl 2016 with a big night out an...
Fixing the boat in Grenada (EP 13 – Monday Never Sailing)
Monday Never
Fixing the boat in Grenada (EP 13 – Monday Never Sailing)
For all of you who are interested in boat projects, this is your episode! We take time in Grenada to fix (and break) a whole lot on SV Paradox. We replace a sink drain, solve our coolant leak, and almost lose Will down the lazarette as he fixes the autopil...
Storms and Sushi (EP 14 – Monday Never Sailing)
Monday Never
Storms and Sushi (EP 14 – Monday Never Sailing)
In this episode, we start our run north back to St. Martin. As we race up the island chain, we get stuck in Dominica when the weather turns sooner than expected. Once we start sailing again, we make it to Antigua and check out Falmouth Harbour and English ...
Chasing the Story in Anguilla (EP 15 – Monday Never Sailing)
Monday Never
Chasing the Story in Anguilla (EP 15 – Monday Never Sailing)
This is what happens when you get too many people who live on boats together and put them on an island during the biggest fish festival of the year. In this episode, we get to hang out with some of our favorite cruiser friends Ryan and Tasha and their amaz...
Fun with friends in the Virgins (EP 16 – Monday Never Sailing)
Monday Never
Fun with friends in the Virgins (EP 16 – Monday Never Sailing)
After sailing for more than six months, we are back to where we started - the Virgin Islands. And boy, does it feel good to be back! Beautiful sailing weather, gorgeous islands, and good times with better friends. The Virgin Islands are our favorite place ...
Gone Fishin’ (EP 17 – Monday Never Sailing)
Monday Never
Gone Fishin’ (EP 17 – Monday Never Sailing)
The winds stopped blowing. So instead of trying to sail around the BVI, we took the boat up to the North Drop and spent the day fishing with our friends. One big eye tuna and a HUGE mahi later, we have fish for days. Our fishing game has definitely come a ...
Carnival, Beach Fires and Mast Boots – USVI (EP 18 – Monday Never Sailing)
Monday Never
Carnival, Beach Fires and Mast Boots – USVI (EP 18 – Monday Never Sailing)
After just missing Carnival everywhere else we traveled, we finally get to experience it in St. Thomas. What starts off as a slow and rainy start to the day ends up being well worth the weather. After the crowds of Carnival, we head over to St. John to exp...
Zika RUINS fun (EP 19 – Monday Never Sailing)
Monday Never
Zika RUINS fun (EP 19 – Monday Never Sailing)
Those of you who follow us on Facebook may have been wondering what our plans are. One day we're posting that we are staying in the Caribbean for another season, the next we are posting pictures from the Bahamas. What gives? In this episode, we finally rev...
Highway to the Danger Zone (EP 20 – Monday Never Sailing)
Monday Never
Highway to the Danger Zone (EP 20 – Monday Never Sailing)
In our last episode, we shared that we were heading back to the US. And we are, but not without seeing some more of the Caribbean first! In this episode, we sail the 250 miles to Luperon in the Dominican Republic. While we heard that the island may have so...
Catching Marlin Under Sail (short fishing clip)
Monday Never
Catching Marlin Under Sail (short fishing clip)
Last week, we had the best experience of the trip. We CAUGHT A MARLIN! We're working on the episode now, but thought you all might want to see this. Special thanks to Skabenga Lures (http://www.skabengalures.com) for teaching us how to fish! To find out m...
Bahamas: Sharky and Underwhelming (EP 21 – Monday Never Sailing)
Monday Never
Bahamas: Sharky and Underwhelming (EP 21 – Monday Never Sailing)
After 9 months sailing the West Indies, we FINALLY make it to the Bahamas. We'd been dreaming about this portion of the trip since before we left. Pristine water. Deserted beaches. Spear fishing. What more could you want? But, it turns out that after seein...
Bacon in the Bahamas (EP 22 – Monday Never Sailing)
Monday Never
Bacon in the Bahamas (EP 22 – Monday Never Sailing)
After an underwhelming start to our Bahamas adventure in the last episode, we make it to the Exhumas chain. This portion of the world was EVERYTHING we hoped the Bahamas would be. Postcard perfect deserted islands. Not another boat in sight. And, of cours...
Fish Fight – final days in the Bahamas (EP 23 – Monday Never Sailing)
Monday Never
Fish Fight – final days in the Bahamas (EP 23 – Monday Never Sailing)
It has finally arrived, our last few days in the Bahamas. But before we head back to the US, we have some serious fishing to do. The Bahamas have some of the best deep-sea fishing around -- and for us that meant hooking on to a Marlin! Yes, we admit, this ...
Selling our Sailboat – Season 1 Finale (EP 24 – Monday Never Sailing)
Monday Never
Selling our Sailboat – Season 1 Finale (EP 24 – Monday Never Sailing)
This is it. Our last episode of season 1. In this episode, we sell Paradox - our home for the greatest adventure we have yet to go on. While it was an emotional day for us, selling our sailboat means that we now have the funds to keep on traveling and maki...
Traveling by Sidecar – Monday Never Season 2 Trailer
Monday Never
Traveling by Sidecar – Monday Never Season 2 Trailer
Here it is, the BIG UNVEIL for Monday Never season 2. Last season, we bought a sailboat sight unseen and traveled the Caribbean for 10 months. Now, we are about to start our second season - and we are going to go traveling in a sidecar motorcycle. Where ...
We bought a sidecar! (EP 25 – Monday Never Sidecar)
Monday Never
We bought a sidecar! (EP 25 – Monday Never Sidecar)
On little more than a whim, we decide to buy a sidecar motorcycle and go traveling on a second season. Our plan is to head to Europe and travel for a few months until it gets too cold. In this episode, Will flies to North Dakota to pick up our new rig whil...
This may be our WORST idea yet (Ep 26 – Monday Never Sidecar)
Monday Never
This may be our WORST idea yet (Ep 26 – Monday Never Sidecar)
We typically keep our episodes light hearted and focused on our fun time traveling. But in order to appreciate the good, sometimes, you need to go through some of the realities of pushing outside of your comfort zone. So for all of you who wonder what goes...
Who knew…you can FLY a motorcycle to England (EP 27 – Monday Never Sidecar)
Monday Never
Who knew…you can FLY a motorcycle to England (EP 27 – Monday Never Sidecar)
After serious doubts as to the sanity of this second adventure, we persevere on and decide to fly to bike (and ourselves) over to England to continue on with this journey. But first, we meet up with new friends in Toronto for some sailing during the last ...
Cheers to Amsterdam, our new Favorite City (EP 28 – Monday Never Sidecar)
Monday Never
Cheers to Amsterdam, our new Favorite City (EP 28 – Monday Never Sidecar)
When we started this trip – we had only two firm plans. First, fly to England. And second, visit friends in Amsterdam. In this episode, we get ourselves to the Netherlands by way of a potentially risky ferry ride into France. And then spend a couple of g...
Crossing the Alps in a Ural (EP 29 – Monday Never Sidecar)
Monday Never
Crossing the Alps in a Ural (EP 29 – Monday Never Sidecar)
Winter is coming, so they say. And we are definitely NOT into that. So it is now time to cross the Alps and get into the warm weather of the Mediterranean ASAP. We cover a lot of ground in this episode, almost 1,000 miles and find some very, very nice wea...
Nothing beats being on a boat (EP 30 – Monday Never Sidecar)
Monday Never
Nothing beats being on a boat (EP 30 – Monday Never Sidecar)
After a bit of a break, we finally have a new video! In this episode, we make it to the Mediterranean and back onto a sailboat. But first, we stop in Verona for a night out at the "opera" and have a few glorious days in Piran, Slovenia. If you ever have a ...
Hidden Gems: Montenegro & Albania (EP 31 – Monday Never Sidecar)
Monday Never
Hidden Gems: Montenegro & Albania (EP 31 – Monday Never Sidecar)
As Americans, when we think of traveling to Europe, it's typically France, Italy, Spain, etc. Not too many of us know about Montenegro and Albania (at least we didn't). And as it turns out, these countries are GREAT! Nice people, beautiful coast line, chea...
Driving lessons: Athens & Santorini (EP 32 – Monday Never Sidecar)
Monday Never
Driving lessons: Athens & Santorini (EP 32 – Monday Never Sidecar)
Will is the driver of our sidecar rig, but in this episode I (Cat) get a lesson. Let's just say, it's probably a good thing we only need one driver on this trip... We also pick up our friend Matt and tour Athens, take the world's longest ferry ride, and re...

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