We’ve made it! It’s finally time to leave the dock and set sail on the adventure of a lifetime.
After one last family goodbye—to Cole’s mom and stepdad—we spent the evening before our departure on final chores. With a few more goodbyes at Regatta Point Marina (check out what our neighbors Tom and Cheryl gave us!) and a last meal at the marina’s awesome restaurant, we headed back to the dock and straight to bed, gearing up for the big day.
The next morning before the sun even rose, we untied from the dock and set sail.
Goodbye, dry land
The moment was…surreal. It’s been more than two years since we got this crazy idea to buy a boat and travel the world together. What started as, “One day I’d love to travel,” eventually turned into, “How do we make this happen?” There have been so many surreal moments leading up to this one, but actually leaving the dock hit us harder than all the others.
Honestly? We were scared. There are so many unknowns and what-ifs. But what we find even scarier is settling for society’s norms and waiting around for retirement. Some might say buying a boat and quitting jobs is risky (and trust us, we’ve heard it all). But isn’t it even riskier to wait to live your life? To wait for the right time is to waste time. Life is short, and tomorrow isn’t promised.
That moment as we sailed out of Regatta Point, we teared up a little. We’d done it. And we’ll tell you again, probably not for the last time: if you have a dream, make a plan and figure out how to do it.
More hurricane aftermath
Our first stop: Cayo Costa State Park. We knew Hurricane Ian had hit hard there, and we wanted to see how bad the damage was. Sixty-five miles later, we got a good look. Broken docks, downed trees—we couldn’t even find a place to tie up the boat. We eventually found out the park was closed (and it will stay closed until at least July 2023!).
Although we weren’t able to explore the state park by land, that didn’t stop us from exploring by water. We took our dinghy into the Manatee Hole, a small lagoon where manatees can be found almost every day of the year.
After a few mini adventures including dragging our dinghy across a sandbar and navigating a partly-damaged “Tunnel of Love”, we headed to Cabbage Key, a nearby charming island with a long history.
Delights of Cabbage Key
To step onto Cabbage Key is to step back in time to old Florida. No cars, no paved roads—just 100 acres of undeveloped paradise only accessible by boat. Talk about quiet.
This small island has had many inhabitants over the years: the Calusa Indians, Cuban fishermen, and then a string of private owners and researchers. Today, one of Cabbage Key’s most popular spots is the Dollar Bill Bar, a little restaurant papered with more than $70,000 in dollar bills signed by patrons, including the famous musician Jimmy Buffet.
As this bar is known for its cheeseburgers, it’s rumored that Jimmy Buffet’s inspiration for the song “Cheeseburger in Paradise” came from his time here. He even played music here! We added our signed dollar bill to the wall, and later we got to talk with the restaurant manager, Scott. Check out our conversation with him in the video.
If anyone is interested in visiting Cabbage Key, this is your friendly reminder that they’re open for business. Although this picturesque island is only accessible by personal boat or water taxi (or helicopter, if you’ve got one), it’s definitely a must-see on Florida’s west coast. You’ll find it at channel marker 60, intercoastal west.
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Exploring Cabbage Key was a great start to our journey. Next week, we sail to Key West, and it’s anything but smooth sailing. You won’t want to miss the next episode.
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