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Inside the epic voyage of 45m Dorothea III

14 October 2021 • Written by Sophia Wilson

The owner of superyacht Dorothea III has never been keen on following the milk run, but his latest 20-month cruise pushed the boundaries of tandem yachting further than ever before. Ambassador Steven Green and Captain John Crupi, a panelist at year's Explorer Yachts Summit, talk us through the epic journey that won the 2020 Voyager's Award.

‘One yacht good, two yachts better,’ was the mantra that Ambassador Green and his long-serving captain John Crupi adopted when planning their latest two-year adventure, which incorporated two Atlantic crossings, circumnavigating South America and crossing the Pacific.

In the Marquesas.

Not content with just setting forth with the faithful 45 metre Cheoy Lee Dorothea III, who has cruised more than 170,000 miles during the Green’s ownership, they decided that GT63 Hatteras Post One, should also join for the adventure. A feat that as far as the duo are aware has never previously been attempted.

The route – which saw the Green family spend time in Central America, The Azores, Portugal, Cape Verde, Brazil, Patagonia, French Polynesia, Tonga and Australia – was dictated by several criteria. “We try and orientate ourselves around land activities for the family and fishing for me,” explains Ambassador Green, who served as the US ambassador to Singapore under President Clinton.“I also said once I turned 65, which was ten years ago, I didn’t want to ever live in a place where the temperature [in Fahrenheit] was below my age. So, we were trying to find places that were in the warmth and sunshine.”

Sports fishing vessel Post One joined Dorothea III on her round-the-world trip. All imagery courtesy of yacht Dorothea III.

With all this in mind Post One seemed like the obvious addition to the trip. “My grandson and my son in law like to fish but my daughters and my wife don’t, so they spent more time on Dorothea,” he explains.

Having both boats may have been the dream for family dynamics but for Crupi it presented the monumental technical challenge of how to allow the sportsfish vessel to “run on her own bottom” during a global voyage, with three ocean crossings. “The logistics surrounding it were intense because the cruising schedule was pretty aggressive,” says Crupi.

Post One is thought to be the first ever sportsfish vessel of her size to complete the Atlantic crossing.

Post One underwent modifications during her build – including more robust pumps, additional fuel transferring systems, and state of the art electronics – but Crupi still had to work out how to refuel underway. “It is not something you can Google or ring somebody else and get advice on,” he says. “We tried a variety of methods of positioning both boats in different sea states and in different winds and currents until eventually we found a recipe that worked. It’s definitely not for the faint of heart. For a total refuel you have got both boats sitting at roughly ten metres apart, for upwards of an hour and twenty minutes, in any sort of seaway.” 

Crupi also hired a captain and deckhand specifically for Port One. “They had to be on board 100% because at the end of the day we are sort of living in luxury and they are pounding their way across the ocean. It has got to be something that you want to do it’s not something you can pay somebody to do,” he adds.

The voyage started in Central America.

The voyage started close to home in February 2018, visiting Mexico, Costa Rica, Panama and Bermuda before embarking on the first Atlantic crossing in July. With four refuels completed on route, Post One is thought to be the first ever sportsfish vessel of her size to complete the crossing. The duo successfully arrived in the Azores ten days later. 

Crupi had scheduled in time to visit six of the nine Atlantic islands, which proved to be one of the biggest surprises of the entire trip. “We loved the Azores, we thought they were one of the most beautiful places we had been,” enthuses Ambassador Green. “The people are great, the food is wonderful and we would definitely go back. It’s basically a fuel stop, which is just so strange because the cruising is absolutely wonderful.” Crupi was also taken aback by what the Azores had to offer. “The thing that really surprised me is that 80 percent of the boats coming from the States to the Med every year stop there but nobody does any trips,” he agrees. “We were only the second or third boat that our agent had put together some kind of cruising itinerary for and he deals with practically every yacht that comes through Horta.”

The journey featured plenty of opportunities for wildlife spotting,

After the Azores the Greens enjoyed two more trips on the other side of the Atlantic, taking in Portugal’s southern coast and the rich fishing grounds of Cape Verde, before Dorothea and Post One embarked on the South Atlantic crossing to Brazil, via Ascension Island. “You might have said you were in the middle of nowhere before but unless you were on Ascension you were lying,” jokes Crupi. 

The 91 km2 volcanic island – which is 860 nautical miles from the coast of Africa and 1,200 nautical miles from Brazil – nearly put the entire voyage in jeopardy. “The communication with the island is horrible, basically an email every other week, but we had managed to pre-order about 25,000 litres of fuel,” says Crupi. “Then one day away from Ascension I gave the harbour master a call and he said that because the ship that normally comes from the UK three times a year was only going to be able to make it twice they wouldn’t be able to give us the fuel, but they were happy to give us back the money. It wasn’t much comfort when I was basically two thirds of the way to Brazil with two boats and the fuel that we were reliant upon was now in question.” Thankfully, Crupi was able to negotiate getting a portion of the fuel and, after the 18-day crossing, both yachts arrived in Brazil at the end of November.

Sailing through French Polynesia.

The Greens flew to meet Dorothea there, spending time in Rio, Buzios for the New Year celebrations and Ilha Grande. One of only a handful of yachts to visit the country, it came with a unique set of challenges “Brazil is a beautiful country with wonderful people. We enjoyed interacting with the Brazilians and we loved visiting some of the more scenic places, but it is a place where you have to be careful,” says Ambassador Green. “It was one of the few places in the world where you had to have security 24 hours a day on the boat.”

As the captain, Crupi also felt the pressure. “Being there with two boats and a high profile obviously put us on high alert,” he says. “It was my first experience of dealing with armed security on the boat and all of the precautions that you have to put in place become fatiguing for a boat crew.” Despite this Crupi doesn’t think yachts should be put off visiting. “Brazil is beautiful and could and should be done by a lot of boats,” he says. “We were the first boat to cruise southern Brazil in three years and you are talking about a country that has got 6,000 miles of coastline.”

From Polynesia to Patagonia, Dorothea III has cruised more than 170,000 miles during the Green’s ownership.

Dorothea III is no stranger to visiting less economically developed countries and has an established philanthropic programme, including delivering supplies after hurricanes and supplying educational materials and water filtration systems on previous trips. “Philanthropy is very important and what I love is that my crew also think it is important,” says Ambassador Green. “It’s important that if people in these communities see a big yacht pull up, they feel that they are interested in the community or the tribe.”

During this trip the crew decided to develop the programme further with the launch of the Marlin Mission, which invited people to pledge a donation for each fish they caught and released. The campaign saw them raise nearly $30,000 dollars, which they used to purchase school supplies for under privileged children in Cape Verde and Brazil. “It gave us the ability to really do some stuff,” says Crupi. “In Cape Verde for example we took twenty-five children to the optometrist. Some of them were nearly blind and they put glasses on them and for the first time they suddenly realised that a tree wasn’t a green blob.”

A seal stops by for a visit on board Dorothea III in the Galapagos.

After their time in Brazil the two boats temporarily parted company, as Post One was shipped to Panama and Dorothea headed south to explore Chilean Patagonia. Once there Crupi was relieved that he only had one yacht to take care of. “From a navigation standpoint Southern Chile was a disaster because their charts are not corrected to WGS84, which is what we use for digital cartography,” he explains. “Anything that you plot on paper and correspond to anything digital is just way off. As a result the paper charts are more like treasure maps and digital doesn’t really work.” Despite the navigational challenges Crupi was blown away by the destination. “Patagonia was unbelievable,” he says. “Having spent a lot of time in Alaska I am used to colder destinations, but Patagonia has a completely different feeling.”

The two yachts were reunited in the Galapagos before both heading into the more familiar territory of the South Pacific. “We have made multiple trips to the South Pacific because we love it there,” says Ambassador Green. Highlights of this voyage’s trips included swimming with whales off Tonga, visiting an active volcano in Vanuatu and spending time with local communities. “The grandkids really enjoyed interacting with some of the small islands in Tonga. says Ambassador Green. “On one island they visited a school and set up a volleyball net. It is a great lesson for my grandchildren.”

Docking in Fiji.

In October in 2019 Dorothea III and Post One arrived in Cairns Australia, marking the end of the voyage. “It’s pretty crazy that we were able to do it,” reflects Crupi. “When you think of all the things that could have gone wrong, from a mechanical standpoint, from a weather standpoint, from just a you are in a 60ft [18.2m} boat in the middle of the Pacific Ocean standpoint. It’s pretty extreme, looking back at it.”

Having spent more than twenty years together, Ambassor Green credits his captain as the reason things didn’t go wrong. “When you do a trip like that, taking a fishing boat across the Pacific, it takes meticulous planning,” says Ambassador Green. “John is a great planner and a great executor of the plans he makes. It’s a very interesting thing to do but you want to have a competent captain.”

The well travelled Dorothea III is now for sale with Merle Wood & Associates and Camper & Nicholsons International.

With long haul flights becoming an increasingly unattractive option for the Ambassador and his wife, he is realistic that this might be his last great adventure with Dorothea III, who is now for sale. “Most people say that the two happiest days of their life are when they buy and when they sell a boat,” he says. “For me it will be a very unhappy day when I sell. We have enjoyed every minute of it, there is just no way to rewrite these memories.”

Captain John Crupi will be speaking on a panel at this year's Explorer Yachts Summit, unpacking owners' obsession with cruising high latitudes and predicting where we all might be adventuring next. 


More about this yacht

Cheoy Lee   45 m •  2007

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