I‘m a bit over due for an update so here is a long one

I‘m a bit over due for an update so here is a long one…….

As I last shared, we made it back to the states and made landfall in West Palm Beach! They have a huge free dock for visitors, it was a wonderful spot. We stayed for one week while visiting friends and getting ready for the next chapter.

Now, I always said my relationship with this boat was transitory… She’s a GREAT boat and has served me very well on all of my adventures, but, for full time cruising she’s a bit on the small side. She was a great platform for me and the dogs to cruise, but if we add in another human, it gets cramped fast..

While we were in West Palm I got some wonderful news in regards to Rambler Rallies that I can announce now that the contracts are signed. I’m thrilled to welcome Hemmings.com as the title sponsor for my remaining three events, and to welcome them as our Vehicle Martketplace partner. This sponsorship means we will be expanding these three events beyond what I had initially planned, it also means next year we are going to be expanding to 3 more markets, and are flirting with a possible euro event. But all this great news means I need to be home to focus on the business, not being a beach bum in paradise.

So with that news, and my preference for a larger boat, I made the decision to list her for sale. In just a few days we had lots of interest, and a couple offers. I ended up accepting an offer from a expat living in Costa Rica, he flew up and we closed on Tuesday. He got a great boat for a great price, and I got a great deal as well. I actually ended up making enough on the sale that I covered my purchase of the boat, upgrades, and my cruising costs for the season. Who doesn’t love a free 7 month vacation?! Gypsy was a great boat. We did a lot together; Won our section in the 2022 Solo Mac Race, comepeted with the Bandit crew in the race to Chicago Yacht Club Race To Mackinac, trips to Saugatuck with friends, and plenty of beautiful sunsets. She never once let me down.

It was a bit bittersweet, but, it felt like a great ending to this amazing chapter of my life. This was a trip I had dreamed about for years, and I finally pulled it off. I would have loved to cruise longer, and further south, but we will have plenty of time to do that in the future, let’s make some money first 😎.

While it only lasted 7 months, we sure did jam a LOT of adventure into it. We covered 4,700nm, met tons of new life long friends (hey Explore With Perseverance and Sailing Sommer Wind), explored remote islands, swam with turtles, rays, and even sharks… it was a perfect way to skip a Chicago winter, and celebrate my 30TH trip around the sun.

Wednesday we loaded up a friends car (luckily he had a car in Florida he needed moved to Chicago) and the dogs and I headed north. We stopped in Asheville and spent the night, so the next day I could scout some routes for Circle The Smokies Rally Presented By Hemmings.

Making the turn onto Lake Shore Drive at McCormick Place, felt like Christmas morning as a kid. I was SO EXCITED to be back. I’ve never been so happy to sit in traffic on Lake Shore Dr. I rented a place from a friend in Lakeview, the boys are adjusting to land life well. They sure are adaptable….

So here we are. Back in Chicago, with new roommates (both human and dog, which Bosun loves), and getting back into the swing of city life. I didn’t realize how much I missed this place till I was back. After all my years on the road touring around the world, and the miles under my keel sailings warmer climates, there’s a lot of great places on this blue marble, but there is only one Chicago. That’s where I always want to call home.

I’d love to catch up with all of you! So if you see me at the club, or in Belmont, or on the water say hi! A highlight of this trip for me was sharing it with all of you, I hope you all had fun following along as we sailed to paradise and back…

Cheers GS