WorldSailors. World Wines. World Travel.

In less than a couple hours we landed in Santiago. I thought about the miracle of flight given that I’d last been in Santiago in January and it took my almost two months to ride from here to Buenos Aires going the “long way around” the tip of South America and then up the Atlantic Coast. I never made it to Valparaiso or Vina del Mar in January. So this was my chances, sans moto, to see a few of the other Chilean sites I’d missed – notwithstanding the wine regions both north and south of the capital city.

Through a couple mishaps with the car rental agency we were upgraded to a Toyota 4Runner, or at least the South American equivalent. Tim and I wasted no time as within an hour outside of Santiago we climbed a small mountain range and descended into Valle de Casablanca not only does this valley take us to the Pacific Coast, but it’s also home to Chile’s best white wines. Tim and I wasted no time and committed to stopping at 2 or 3 wineries before making our way to Vina del Mar where we hoped to connect with Tim’s coworker Melissa who had flown to Chile a few days earlier to meet up with the captain of the sloop “Tom Bowling” and begin preparations for the 6-9 month journey across the Pacific Ocean.

Vines across the valley floor and crawling up the hillsides.

Tasting Casablanca Valley’s fruity whites.

Ruta del Vinos in Casablanca Valley, Chile.

By the time we navigated through the busy streets of the coast towns north of Valparaiso and armed with more definitive directions to the yacht club from the tourist information office in Vina del Mar we soon found ourselves in passing the guard gates at the new marina – Club de Yates Higuerillas – in the sleepy community of Concon. Walking through this small marina Tim spotted a young woman who seemingly was practicing yoga on the docks. “I’ll bet you that’s her,” quipped Tim. “That’d be just like Melissa.” Sure enough that was Melissa. She eagerly but with a sense of doubt in her voice showed us the way to the 37′ sloop, “Tom Bowling” that’d be her home for most of the year remaining. Ralph, the soft spoken curly haired skipper and owner of “Tom Bowling” granted us permission to board. The quarters were modest and the boat seemed to be in various states of maintenance and preparation. But the casual host he was he grabbed a cardboard box of red wine and poured us all a little wine in paper cups. Tim and I looked at each other and then toasted the skipper and his crew – which at this point numbered two – Melissa and Jeff. The third crew member had decided to return home after many month traveling in South America. This left Ralph and the others in a scramble. They needed to find the fourth crew member. Melissa had no real sailing experience. She’d be there to support as an extra hand, help in the kitchen and provide moral, mental and whimsical support.

The Club de Yates Higuerillas in Concon, Chile just north of Valparaiso.

Melissa with skipper Ralph and his Tom Bowling in the background while sunsets on Concon.

Captain Ralph aboard the Tom Bowlling.

Bowling crew first mate, Jeff.

New crew member Melissa ready for adventure and the open sea.

Tim scoping out the Tom Bowling and inspecting its seaworthiness. “Yes. It floats!”

The first two weeks of their journey to Australia would likely be the toughest as they’d be tackling the largest and longest open water crossing of the entire journey. From Concon to Robinson Crusoe Island and then from Robinson Crusoe to Easter Island (Rapa Nui). The first leg to Robinson Crusoe Island should take them a few days. Then they’ll make the nearly 2,000 mile open water crossing to Easter Island. The journey has got to be harrowing. And much more mentally challenging than riding Ruta 40 or the Cross Siberian Highway. It’s the middle of the ocean. This journey takes weeks. There’s no stopping for gas. You won’t see land or another ship for weeks. And the ocean, in its whimsical madness, could turn on you. At least on the Tom Bowling they’ll be comfort in numbers. Four insane adventurers cooped up in a tiny cabin under sail through 2,000 miles of open Ocean. From Easter Island the sailing gets easier. At least pockets of land (islands) are more frequent. Their route will be Easter Island – Pitcairn – Gambiers – Marquesas – French Polynesia – Fiji – New Caledonia – and finally Australia.

Sounds like a challenge. They asked Tim and I if we’d like to join them. But the thought of missing Mendoza the second time around wasn’t appealing. And Tim has a project for which he needs to be back in New York later this month. Though the concept fills me with ideas and dreams. One day.

So instead, we ask Melissa and Ralph if they’d like to join us on our journey to Santa Cruz for the Vendimia Festival. We casually suggest to Ralph we’ll find some wine with different characteristics, more body and complexity than his boxed friend. He agrees. Melissa agrees. They’ve still got provisioning to do, customs paperwork and recruit another crew member, but they reason it’s the weekend.

We leave first thing tomorrow morning.