All Signs Point To GO

Sand Snowman

With any luck, Claire will be making these this time next year! (Photo: Konrad Mostert, Getty Images/iStockphoto)

Out of all of our material things, I think I will miss our bathtub the most.

Slowly but surely, we are working toward our goal of cruising south to the Caribbean! Decisions have been made and plans put in motion the past few months that mean there’s no turning back. Together, Aaron and I seem to have conquered the biggest challenge for living the dream: forward momentum.

As you know, we put the boat on the market in October. We have had three serious interested parties, which is a great sign! No offers yet, though. All I want for Christmas is the boat to sell, the boat to sell, the boat to sell…

We will also be putting our condo on the market right after the holidays. Our dream is already starting to feel real, but with this step checked off, it will feel really real.

While we’re not sure how the plan will play out and are trying to stay flexible (limbo is HARD!!), here are the potential paths to adventure:

Option 1: The boat and condo sell right after the holidays
What a wonderful problem this would be! In this case, we would find a short-term rental contract here in Oak Park and ramp up our boat search on the East Coast. Once we find the right fit, we’d pack up the loose ends and make the move.

Option 2: The boat sells, but the condo doesn’t
One out of two ain’t bad, right? Especially in this market. We’d ramp up the boat search, but shift gears on the condo to trying to find renters. We’ve already had one interested party inquire about renting, so there’s promise there.

Option 3: The condo sells, but the boat doesn’t
We’d again find a short-term rental contract here in Oak Park, but we’d shift gears to outfitting Clarity for ocean travel. This would mean Aaron (with my help when I can) would take on refitting the boat in the late-winter and spring, with the hopes that she’d be ready to go in late spring/early summer. But then how would we get her out to the East Coast? There are a few ways. More on that in a later post :).

Option 4: The condo and the boat don’t sell
Well, shoot. Dreams are hard! But we’ll take the less-than-ideal hand and raise you some determination! We’d find renters for the condo and outfit Clarity as in Option 3. Our adventures are happening, friends! No matter what.

We are still thinking through what the magic “deadline” would be for selling either before we’d resort to the less-favorable options, but in general, we’d need to know about the boat by mid-winter or so, so there’s still enough time in the yard to work on Clarity before setting sail.

And in the meantime, there’s plenty to do here. Aaron is in the process of defining his work situation for when we’re cruising – both what exactly he’ll be doing and how much he’ll be doing it. I’ve also lined up a new contract that allows me to continue to work remotely to the extent that I want or need. We are both very blessed to have these options.

I’m doing as much research and fact-finding as I can on figuring out healthcare during our travels. While we’re still here in the states, we’ll need a plan recognized by ACA (the Affordable Care Act), but once we leave the states, quality routine healthcare is ridiculously affordable out of pocket, so we have to find the balance of what makes the most financial sense while making sure we’ll be taken care of when necessary. More on this, too, in a later post, as I continue to sort through more of the details.

And we’re both de-cluttering and simplifying as much as possible in the meantime. This means selling or donating what we don’t need and identifying what things we want to pack away for “the next chapter” after the cruising chapter. Aaron has also taken on the epic task of scanning all of our important documents, including our entire filing cabinet plus boxes of other files, so they are all easily accessible from wherever we are, not to mention ripping our CDs and DVDs. He’s likely already shredded and/or recycled at least one full dumpster’s worth of paper. It’s unbelievable how much we accumulate in papers, even in this digital age.

In addition to a rental storage unit for our furniture and other big stuff, we’re unbelievably grateful that our family has offered to store remaining bins and boxes of stuff, and also offered to take our beloved cat, Tink, who I will miss dreadfully, but who would be in the company of two sweeter-than-pie golden retrievers.

Exciting things are happening here, with so many more to come. In a way, it feels like we threw our entire lives in a bag, turned it upside down and shook it all out. But for the first time, the unknown seems necessary. And in a way, comforting.

We’re cherishing our last (hopefully!) holiday season here on land for awhile. Thank you for taking this journey with us! And the happiest of holidays to you and yours.


This will be Aaron and me next year. I have no idea where Claire is. I imagine she’s just out of the shot, making a sand snowman… (Photo care of