Ronnie Simpson is a passionate sailor and has experience as a racing sailor, live aboard cruiser, delivery captain and USCG licensed charter captain who has accumulated about 130,000 offshore miles. He has experience ranging from sailing small cruising boats solo to racing and delivering Grand Prix racing yachts to driving 65′ catamarans full of tourists. He has also worked as a professional yacht rigger, racing yacht preparateur, yacht racing journalist and sailing media professional. He has taught sailing in San Francisco and New Zealand, and has co-founded a small non-profit that introduces wounded veterans to sailing.
Ronnie began sailing in 2008 and ultimately abandoned his first boat at sea, while attempting to sail solo from San Diego to Hawaii. Before abandoning the boat, he lost his rudder in heavy weather on the outskirts of the Category 4 hurricane Norbert in October 2008. A fully-crewed 46′ foot cruiser also abandoned nearby the night before. Arriving in China on a freight ship having lost every possession he owned, Ronnie stayed in Hong Kong for a few months and did a lot of sailing and racing. He eventually bought a bicycle to ride back home. In 2009, he spent seven months in the saddle of a bicycle pedaling about 9,000 miles through 20 countries to get home. During this time, he became passionate about the Vendée Globe sailing race, and pursued every sailing opportunity that he could while traveling. He began to develop a deep dream of sailing in the Vendée Globe and decided to pursue solo ocean racing.
Returning to California in late Summer 2009, he parked the bike and purchased a $1,000 Cal 25 and began preparing it to race solo to Hawaii in the 2010 Singlehanded Transpac. A Vietnam veteran Marine from the east coast learned of Ronnie’s story and donated the Mount Gay 30 ‘Warrior’s Wish’ to Ronnie to race in the 2010 Singlehanded Transpac. Working on the boat extensively in North Carolina and then trailering it to San Francisco, Ronnie lived on the boat and scraped together enough money and support to race it to Hawaii in June of 2010, reaching Kauai after 15 days and 6 hours and finishing second in division. On the doublehanded delivery home, the boat sustained a complete keel failure and lost it’s entire keel while 760 miles offshore of San Francisco. Determined to not go 0 for 2 on losing boats, Ronnie and co-skipper Ed picked up diesel fuel from a nearby freighter and motor sailed all the way in to San Francisco using the 1 cylinder 9 hp motor, arriving just hours before it started blowing a NW gale.
In 2011, Ronnie raced in the Transpac on a 1D35, and then delivered a very fast 45-footer home, ‘Criminal Mischief’. In October, he purchased a Moore 24 to campaign in the Singlehanded Transpac. He managed to find a significant amount of sponsorship and put together a race winning campaign for the 2012 Singlehanded Transpac, though he was still scraping together money to get to the starting line. He sold his 28-foot live aboard sailboat just days before the race start to pay for expenses, and was effectively all-in on his Moore 24 for that summer of sailing. Arriving to Kauai after 14.5 days at sea, Ronnie won his division by just an hour and a half after a very difficult and challenging, but rewarding two weeks. Weeks later, he would deliver a competitor’s boat back to Seattle, where he would step off of the delivery and purchase a Cal 2-27, to live on, with the delivery proceeds.
On that Cal 2-27, he slowly cruised it down the coast in the wrong season, arriving to San Francisco in January 2013. During this trip, Ronnie was fueling his passion for the Vendée Globe. Making headlines as an American solo sailor over the past two years, he managed to get himself to the Vendée Globe start in November 2012 and also to an IMOCA event in Switzerland in May 2013. During 2013, he was also sailing racing boats extensively and was with the Criminal Mischief program full time, where he did a full season of high-level offshore racing, shore work and delivering which culminated in a 2013 Transpac division win. After delivering the boat home from Transpac, Ronnie sold his Moore 24 and then left San Francisco, headed south, on MONGO in September of 2013.
After delivering a boat from Mexico to San Diego, Ronnie got an invite to sail in the 2013 Sydney – Hobart, and so he did that and then decided to sail MONGO to Australia. In March 2014, Ronnie sailed MONGO to Hawaii and then dismasted on April Fool’s Day in Maui. By the end of May, Ronnie miraculously had a new rig in the boat and was sailing again thanks to amazing people in Maui. By August, MONGO was in Fiji and by November 2014, Ronnie and MONGO had ended up in New Zealand. Ronnie sold MONGO in New Zealand in returned to San Francisco where he purchased the Cal 2-29 ‘Loophole’ in March 2015.
Ronnie desired to return to academia and finish a degree with his GI Bill, so he solo sailed his Cal 2-29 Loophole to Hawaii in December 2015 and then began university classes in January 2016. During this time, he sold Loophole and bought the Peterson 34 that he renamed QUIVER. Planning for a circumnavigation, Ronnie re-fit and sailed the boat extensively and then departed Hawaii right after his graduation. In January 2019, he sailed solo from Honolulu to the Marshall Islands, where he stayed for about six weeks. In late March, he sailed south to Kiribati and then Tuvalu, before sailing to Fiji. Once in Fiji for the second time, he fell in love with Fiji and decided to stay there and build a company around sailing.
Starting a company in Fiji the day before COVID ended up being really bad timing, so Ronnie was forced to bail out of Fiji in May of 2021 and sail solo back to Hawaii, 29 days up wind and against the current on the Peterson 34. It was the most horrible sailing trip of all time, but absolutely nothing went wrong with the boat and Ronnie smoothly sailed back into Waikiki and sold the boat in a matter of days. After doing the second leg of a powerboat delivery from Fiji to Hawaii to Seattle, Ronnie traveled back to Maui to begin a new job with a charter company called Sail Maui in August 2021.
Ronnie achieved his first USCG Captain’s License in December 2021, and currently holds a 50-ton near-shore master’s license with a sailing endorsement. In March of 2022, Ronnie purchased the 43 foot Doug Peterson designed Serendipity 43 ‘MatuaMai’, and has plans to do the Baja Haha ’22 and then most likely deliver to Hawaii before making plans to head back to Fiji.
Career Racing Highlights Include:
- 3x Transpac participation (2011, 2013, 2017), including division victory on the R/P 45 ‘Criminal Mischief’ in 2013.
- 2x Singlehanded Transpac participation (2010 and 2012), including division victory on the Moore 24 ‘US 101/ Hope for the Warriors’
- 1x Pacific Cup participation (2016)
- 1x Rolex Sydney-Hobart participation (2013)
- 1x Newport – Cabo Race participation (2013)
- 1x overall win in Coastal Cup race (2015)
- 1x overall win in Doublehanded Farallones race (2012)
Career Cruising Highlights Include:
- Sailing the engineless Cal 2-27 ‘MONGO’ mostly solo from Tacoma, Washington to Opua, New Zealand between 2012 and 2014.
- Sailing the Peterson 34 ‘QUIVER’ around the Hawaiian Islands and then solo to Fiji and back 2016-2021.
- Sailing the Cal 2-29 ‘Loophole’ from San Francisco Bay to Hawaii in 2015, solo.
- Baja Haha and return to San Francisco in 2011 on a friend’s 47-foot monohull.
Delivery Highlights Include:
- 2x return skipper from Transpac for the Rogers 46 ‘Varuna’
- 1x return skipper from Transpac for the Santa Cruz 52 ‘Prevail’
- 2x Transpac return delivery for R/P 45 ‘Criminal Mischief’
- 1x Transpac return delivery on the Bakewell-White 100 ‘Rio 100’
- 1x Sydney – Hobart return delivery on the Juan K 100 ‘InfoTrack’
- Captain of 52′ powerboat Fiji – Hawaii – Washington during COVID
- Island Packet 38 delivery captain Hawaii – Seattle, Acapulco to San Diego
- 1x Bermuda to Rhode Island doublehanded race boat delivery
- 1x delivery skipper Fiji to New Zealand on Elliott 10.5m ‘Squealer’
- Multiple ‘Baja Bash’ as captain and crew