Monday Never

We are Cat, Will and Maddie sailing SV Paradox II, a Contest 46 and documenting our adventures. We're Cat and Will.

In 2015 we quit our jobs in San Francisco to move aboard a 1989 CS 36 Merlin. We spent a year cruising the Caribbean and Bahamas before selling her in Florida and buying a sidecar motorcycle rig and driving around Europe trying to avoid calamity at the hands of Italian drivers. We sailed back across the Atlantic on a delivery trip with friends, before setting up shop in Chicago and going back to w

ork, saving for the next adventure. We had a baby along the way and we’re now in St Pete, FL fixing up our new to us 1995 Contest 46 and slowly getting ready for the Big Trip, timeline undefined.

02/26/2026

BIG NEWS INCOMING! We've been pretty quiet recently about what's been cookin' over here in South Carolina since we moved off of Paradox. Since swallowing the anchor, we've been putting all the pieces in place to start our new business and today's the day we're sharing it with the world. We've partnered with our dear sailing friends Brandon and Amber Morse from everyday saturday and we're launching The Cruisers Company, a cruising yacht brokerage & boat life training company!

We are putting our many years and tens of thousands of miles of cruising and hard-won experience to work to make the process of transitioning into and out of cruising easier. We're arming soon-to-be-cruisers with the knowledge required to find a boat that meets all of their needs and goals and avoid the pitfalls. On the other side of the equation, we are helping current cruisers transition to land by representing their beloved boats for sale with the absolute best, most visually stunning, highly-informative listings and marketing.

It's been a long time coming. We've felt called in this direction for nearly a decade, when we were a few signatures away from purchasing a brokerage in the BVI as we were wrapping our time on our first boat. Unrelated life events prevented that from happening, but not this time! We're stoked about what we're doing and really proud of what we've already accomplished. We built our website ourselves from the ground up and it's gorgeous, particularly the listing pages for our first two catamarans! It would mean the world if you'd go check it out and give us any feedback you've got. Link in the comments.

That's it for now, but lots more to come!

10/27/2025

Great days out at the beach with friends make for long sleepy boat rides home

09/29/2025

A brief reflection on nearly 4 years cruising:

This was our second time cruising long term as a couple, first time as a family of three. Since we sailed out of St. Pete in late 2021 we've covered 10,000 or so nautical miles and had the time and space to grow as a family. We've watched Maddie go from barely walking, barely talking when we moved on to the boat, to being a bold little sea critter that only stops chattering and singing when she's diving down deep under the sea. There has been no greater gift than that.

The other tremendous gift that we were granted during cruising 2.0 was a wonderful community. On our 1st cruise, we were rushing everywhere we went and were decades younger than nearly everyone we met. We made some great friends, but they were few and far between. This time around, we were amazed to see how many of our peers were out sailing. Every anchorage had families on boats. Maybe we're just older now and that's why everyone seems closer to our age, but I think COVID, youtube, Starlink, and remote work has fundamentally changed the accessibility of cruising for folks younger than retirement age.

This time we went slowly and let our plans evolve with the friends we made. It was the most social period of our adult lives, matching even college life, where rarely a day went by without a beach hang, sundowners, a pot luck, or commiserating over fixing some marine system. We have so many friendships that will forever be what defines our memories of these years.

The sailing itself was just as delightful this time around. Maybe more so, even if it isn't as new and exciting. We understood our boat and our abilities intimately. Bad weather and breakages no longer bring anxiousness. We could (usually) just focus on enjoying every day in paradise.

So why did we stop? It simply felt like we'd reached the end of this phase. There was no negativity, just excitement for the next period of geographic stability, a community without so many see-ya-laters, and the opportunity for Maddie to go to school. There's no doubt that we'll go cruising again in the not too distant future. Med? Pacific? Canals? We'll see!

09/19/2025

We're long overdue for a life update! After a wonderful 3.5 years cruising, we've landed in Beaufort, South Carolina!

Going from the idyllic scenery and slow rhythms of cruising life to land life is a tricky transition. The last time we did this in 2017, we went straight from a life-changing Atlantic crossing to an apartment in the heart of downtown Chicago and fast paced-, dressed-up workdays in high rise office buildings. It was brutal. This time around, we were determined to bring the cruising lifestyle with us to land. We have found exactly what we were looking for here in the Low Country!

After the lightning fast sale of Paradox II (3 weeks from hitting 'post' on the listing to waving goodbye - more on that in another post), we scrambled to figure out where to settle. A quick weekend trip to Beaufort/Port Royal made it instantly apparent that we could build a life here. Slow pace of life, warm and open people, tons of young families, surrounded by water and marshes and natural beauty, live oaks dripping with Spanish moss. It checked all the boxes for us. So in typical fashion, we struck while the iron was hot, moved down that week, made an offer on a house within the following week, and settled in quick.

In barely two months we've already made lots of new friends, Maddie is thriving in her kindergarten class, and we are continually in awe at how lucky we are to have had such an easy and rewarding transition from cruising to land life.

And if you're wondering how we can stand to be surrounded by water without a boat, we solved that problem within a week of arrival as well. A little 21' bay boat has us cruising the marshes and pulling up to the sandbars every weekend.

So if you're in the area or passing through, holler at us and let's head out on the motor boat. If you're a cruiser that's starting to think about where you'll land, let us sell you on the charms of the Low Country.

06/09/2025

Paradox II, our 1995 Contest 46/48, is officially FOR SALE! $165k.

Beaufort, NC (current) - Annapolis, MD (late June onwards).

Paradox has been a rock solid cruising machine and wonderful home for the last 4 years and 10,000 nautical miles in the Caribbean and Bahamas, but all good things must end, and it's time for our family to start a new phase on land and refocus on our careers and giving Maddie some new and different opportunities. It's bittersweet, because the cruising lifestyle and Paradox has been so incredibly good to our family and we still love every moment of it, but we know we'll be back on the water again in another 5 years.

Paradox is seriously well equipped and has been majorly refit ($150k+) through our 5 years of ownership. Almost every system has been replaced or fully serviced. She is truly ready to turn around and head offshore and back to the islands with nothing more than groceries.

If you are in the market for a powerful bluewater cruiser in great condition that is fully rigged for off-grid living (new solar, lithium batteries, watermaker, etc etc), this is the one. I do not believe you can find a boat in this class, size and condition anywhere in the USA for even close to this price.

Why are we pricing her so low? We want to drive a quick, private, no-haggle sale. We all know that time is money, and if we also factor in spending months and months on marina fees, insurance, maintenance, trips back and forth to the boat, paying a broker, etc just to squeeze out an extra $30k or whatever, we would rather accept this low price ASAP so that both parties win. Another sailor once said that he "prices his boats like he actually wants to sell them" and that lesson has stuck with us.

There's a link in our bio to a website with more pictures and a complete description of equipment and upgrades. Get in touch!

05/21/2025

West Palm Beach in a nutshell. We got FANCY for a wedding, Maddie lost her 4th tooth, and then there was this cute pic of Maddie and Will. More happened of course, but to share would have required us to take a photo 😂

Back in the US has been great so far. Enjoying all that “land” has to offer, but missing the beautiful waters of the Bahamas, especially as temperatures rise above 90 this week!

04/25/2025

With a mask and fins on, there is nothing this girl won’t do in the water.

04/02/2025

Maddie in the wild.

03/14/2025

Bahamas bliss. We had friends on board and now have beautiful pictures to share! The Bahamas are all that we remember. Neon blue water, fish, sharks, kid boats, and serene peaceful days perfect for painting, reading, hiking, swimming, fishing, and for being still.

02/24/2025

Proof of life.

Enjoying immensely living quietly here in our little slice of the world and not even thinking about posting. But we are alive and very well! We just got to the Bahamas where we’ll be through April.

The past months have been great. We went from the BVI to the USVI. Then to PR and then DR. Now, after a 3 day passage, we are in the Bahamas and currently soaking in everything Georgetown has to offer. Beach yoga, sand castle competitions, all the kids, cruiser music shows. It's great.

This first photo I love so much. Maddie took it. She somehow made it black and white. And I didn't even know it existed until I found it on my phone.

12/17/2024

Happy birthday to our fearless firecracker, who is now 5!!!

10/31/2024

Happy Halloween 🎃

Address

Port Royal, SC
29935

Website

http://www.contest46.com/

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