Quitting MLB to go Sailing

Ahoy, Welcome to I’dRatherBeSailing! We tried to buy a new sailing hat yesterday, but just couldn’t - we were too worried about cap sizing. Anyways, it’s been a busy week, and we’ve got some exciting news for you, let’s get into it.

In today’s email:

• From Fastballs to Squalls: Quitting MLB to chase sunsets.

• Race Updates: The GGR & TOR.

• I’dRatherBe…Chartering? An exclusive subscriber announcement.

• Slice of Pi: The Pizza Boat goes for sale, and other sailing news.

The First Baseman and the Sea

For the past few years, John Jaso had been sneaking off during breaks at his day job to do something we’re all guilty of: look at sailboats. His day job was slightly unusual though. He was first baseman for the Pittsburgh Pirates.

A few months after the season ended, a couple reporters wandered over to John Jaso’s locker to ask him what his plans were.

“I have a sailboat,” he said, “so I just want to sail away.”

Whenever the team played near a body of water, he heard the siren call of the marina. On a muggy Maryland June day, before the sunset first pitch, he drove up to Annapolis, where he found his retirement plan. A beautiful Jeanneau 44, which he named Roaming Rose. Now all he had to do was learn to sail.

He found a captain on Craigslist, and set to learning the art of messing about in boats. “It was like learning to hit a fastball and lay off a slider,” he told The New York Times. “You can hear coaches talk about it all day, but you’ll only learn how to do it if you face it in a game.”

Before chasing sunsets, Jaso had started to become disillusioned with the day-to-day life of the MLB. “Baseball set me up for life,” he said. “I love it, and I respect it. But it was part of this culture of consumerism and overconsumption that began to weigh really heavily on me. Why do we always have to have more, more, more?”

After learning the lines, and getting into the greasy nitty-gritty of diesel engine maintenance, Jaso was ready to cast off aboard Roaming Rose. He started with day trips into the Gulf, and made his first big passage down to Key West. From the keys, he headed to The Abacos, gunkholing in shallow bays of the Out Islands for months. A storm brewing in the Atlantic chased them back home, where John and Roaming Rose got their first taste of white knuckled storm sailing.

“In the moment, you’re terrified, and you want to be as far away from danger as possible,” he said. “But once it’s over, you appreciate where you’re at more. There’s this euphoria that comes over you when the storm clouds part. It’s like holding your breath underwater and then coming back up to the surface and taking that first gulp of air.”

Before the pandemic, Roaming Rose made it to Turks and Caicos, where she remained stuck for a couple years with travel restrictions. Jaso tries to spend six months a year on Roaming Rose, the rest of the time heeding the cries of land-lubber-life, as we all must sometimes do. But, come spring, he’ll be back out on the water.

“When you’re sailing, you’re going back to something primitive,” he said. “You’re removing yourself from the material world — this concrete, electronic world. And you’re returning to this sense of wonder. It’s the same sense you get when you’re holding a newborn baby, looking into their eyes, and feeling the world disappear around you.

“Sometimes it’s easy to forget that we all come from the same place. When you’re out there on the water, you remember.”

Race Updates

Catching up with racing news from the past week. After a brutal month at sea, the 3rd leg of The Ocean Race came to a close this week with a dramatic win. All accolades aside, Sailing Anarchy called the race ‘a bit of a wank’ with only four boats in the race, and the boat names lacking the nautical nomenclature of yore. Ah well, can’t win ‘em all.

• Team Malizia wins Leg 3 of The Ocean Race after 35 days and 14,714 nm at sea, battling a broken mast, head injury, a lost sail, and 50 knot screaming winds while racing neck and neck with Team Holcim PRB. The official race report is here.

• They’re calling it “The Golden Globe Doldrum Conundrum.” The leading three sailors are wafting in the doldrums of the Northern Hemisphere, unaware of each other’s positions in the race. Kristen still leads the pack, with Abhilash clinging on to second place, behind her since the middle of the Pacific. Read the full GGR update here.

Special Subscriber Announcement

As we already know, the secret to the universe is 42. So it only seems appropriate that the secret to chartering is… 24! That’s right, you old salts are the first to learn the secret of the chartering-universe. If you didn’t spit out your coffee in shock, let me explain. If you did spit out your coffee, please clean it up and come back.

We’ve been trying to crack the chartering nut for awhile, and oh buoy is it a very expensive, over-complicated nut to crack. The boats, the features, the prices, and did we mention the prices. The view may be priceless, but getting there sure isn’t. Well, the nut is finally cracked.

In an unmarked vessel far out into international waters, Capn’ I’dRatherrrBeSailin’ slammed down grog with Capn’ DreamYachtWorldWide, the most fearsom’ pirate to roam a mooring field. The leaky bilge soaked their boots and the rusty hull creaked as negotiations waged late into the dying night, tryn’ to strike a deal…

Actually, it was just a phone call to our friends, but…

We are ridiculously excited to announce that I’dRatherBeSailing is now offering exclusive discounts to our readers on DYW Charters, anywhere in the world, up to 24% off. So there you have it, 24, that’s the secret to the chartering world.

These discounts aren’t available anywhere else on the internet, the world, or the galaxy. (Actually, some of our subscriber discounts are better than 24%, but for the sake of the Hitchhiker’s Guide to the Galaxy reference, we went with that.) The newsletter discounts lets our readers stack exclusive discounts on top of existing discounts. For instance, if DYW is running an existing discount of 14% off, I’dRatherBeSailing readers will be able to stack exclusive discounts of 5%-15% on top, for a total discount of… a lot. Arrr, we’re sailors, not mathmatists.

But Why? Because we love you, dear readers. And we really love sailing, especially when it’s awesome places for great prices.

But How? What happns’ offshore stays offshore…

If you’re planning a charter this year, we’d love to help! Our team just booked a charter for an eye-wateringly good price, and in upcoming newsletters we’re going to find and cover incredible deals. Our goal is to spot week-long charter deals that work out to be less than $100 per person, per day. More boat for your buck, more sailing for your savings.

For more details, hail Ben at [email protected]

Sailing ‘Round the Web

$425,000 Slice: Pizza Pi, the USVI Pizza Boat, is for sale. Any cruiser that’s visited St. Thomas has seen the iconic boat. Now, they’re selling the business with the boat, the mooring ball, and delivery boats. Just for fun here’s the listing. If any of you buy it, invite us for dinner next time we’re in your neck of the woods, we’ll help with dishes!

47m Royal Huisman sailing yacht Nilaya christened in Amsterdam, the first superyacht to use the new Featherlight™ design and production. See the pictures of the beautiful cruiser sloop.

A Sailor’s Life for Me: One Sailboat, Three Children, and Thirteen Years at Sea. Florida sailing instructor Rose Ann Points passes on the lessons she and her family learned on the water, by Beth Graham. First appeared in Garden & Gun.

Superyacht Rescue: Captain and Crew of 121ft superyacht rescue migrants from capsized fishing vessel in tragic accident. 

That’s it for today you Salty Dogs, safe winds. Ketch you later!