Pineapple Cup Log – “Stardate” 2015

Liz compiled a great blog along the course of the Pineapple Cup. Read on for a “flying fish” look at what life was like offshore en route to Jamaica.

flying fishPineapple Cup Log – Oakcliff Racing/Bodacious Dream
Class 40 – Double-handed 
Co-Skippers Elizabeth Shaw & Jeff MacFarlane
-Latitude 27: start off Fort Lauderdale at latitude 27 on port tack. Heavy air, heavy seas in Gulf Stream. Course due east. Our first victim, little Sammy Sledgehammer, the tiniest flying fish the crew has ever seen. The first of many, I’m sure.
-Latitude 26: course more southerly than easterly one, yet still on port tack. Colder than you would think and very, very wet. 
-Latitude 25: Still on the port tack. Still wet and cold. When do we see the pineapples?
-Latitude 24: Passing through Bahamas cold, in heavy seas and on port tack. Yes, that was port. And did I mention that EVERYTHING is wet, everything.
-Latitude 23: Full southerly course now… Still on port.
-Latitude 22: Long Island, an island that is long. Just one of the many thoughts that I’ve had as we pass it on a port tack.
-Latitude 21: Course more southerwesterly as we beat along on A PORT TACK (!) toward Cuba. Is this real life?
-Latitude 20: Nighttime encounter with the Cuban military. They had two boats floating close to our inshore course; better not get too close or they’ll shoot. Good thing I speak Spanish and good thing I’m Canadian, I’ll waive my passport! As day breaks, the sunlight reveals two small buildings on the coastline. Crisis averted, no need to pull out the passport. Situation with Cuban military fabricated by a mind that knows only the port tack.
-Latitude 19: Best. Day. Ever. Starboard tack! Oh, but so short-lived. Back onto port. In other news I saw a shark, long and skinny. Approximately 7 feet long. Have no idea what type. He was Cuban. Oh wait: squalls, squalls and more squalls the whole way down the rhumb line. Little nasty breezeless rain squalls and big dirty 40 knot rain cutting your skin can’t see squalls. Oh and on the port tack. 
-Latitude 18: As we approach the finish line, my co-skipper and I reminisce about what a race it has been. Mostly upwind on the port tack, and much of it beating into heavy seas. We plan to find the nice gentleman who exclaimed at the Competitors Meeting in Fort Lauderdale “…a guaranteed sleigh-ride once your round Cuba!” and have a chat with him about his so-called guarantees.


You’ll notice that we sailed through 10 latitudes on courses due east, due south and then west and did so almost exclusively on one tack upwind. How is this possible, you say? My only response is: it happened.
Thanks to the amazing Race Committee and Dockmaster for their help under very difficult conditions by getting us into the dock without damage (other than an injured left wing on this  little sailor) after us loosing our engine on the way in from the finish line. Absolutely pro job by the MBYC bunch, so thank you, thank you, thank you.
Also, I’m not sure a beer has ever tasted so good as that Red Stripe that was handed to me on the dock by a small crowd offering one of the warmest welcomes we’ve ever had anywhere.


zebra chairFun Facts About Our Race; it’s all in the numbers:
- 24: the number of freeze dried meals carried aboard for the race
- 4: the number of freeze dried meals consumed during the race (most popular flavor was the “breakfast skillet” which had eggs, potato, peppers and sausage
- 35: the number of minutes it took me to comb the tangles out of my long hair (only offshore sailors with long hair will appreciate this, it was BAD)
- 120: the number of seconds it took us to consume our first Red Stripe after making the dock
- #1 spot to sleep, the long bean bag purchased the morning of the race. #2 spot to sleep, the zebra print bean bag chair from the nav station.

“Dream” Continues to be a Reality for Oakcliff

2015 mobay dock sparklersMontego Bay, Jamaica (February 12, 2015)- The Oakcliff Racing Team crossed the finish line of the 2015 Montego Bay Race for the Pineapple Cup at 23:28:21 February 10th. After jostling with another class 40, Amhas 2, for most of the race. Oakcliff’s Elizabeth Shaw and Jeff McFarlane finished strongly with a 2nd in class and 4th overall result and a total elapsed time of 4:10:23:21. The only major hitch came after the finish when the motor decided to quit and they began drifting toward a reef. Once safely at the dock, sparklers, Red Stripe and a celebration followed.

Liz described the race as a “challenging experience through 10 latitudes, 8 of which were sailed on the same port tack, in heavy air and seas.” She added that it was an experience the left side of her body would never forget and she was never more grateful for the trainers at Hammer Human Performance who put her through the paces because, “without that, [she] would have been damaged goods!”

As for her thoughts on the team, she shared: “Jeff is known for his single-handed sailing and a serious demeanor while I am the opposite but on the boat, that switched. Jeff is a lot funnier than people think and I, more serious. That is one reason we were a great team. Our personalities met in the middle”.

Oakcliff congratulates Amhas 2 for a well-sailed race!

Oakcliff Sailing, Oyster Bay, New York is the only complete training and coaching center in the world. Oakcliff’s America’s Cup style campus, with a new 40-person dormitory, creates complete sailors who are capable of sailing in any position, fixing every aspect of a boat and managing a small marine business.  Oakcliff trains sailors in match and fleet racing, inshore and offshore, fully crewed and short handed as well as providing access to historically significant classic yachts. Each sailor leaves Oakcliff a leader with comprehensive skills and the benefits of an organization that boasts an 87% industry job placement. Graduates go on to compete in events including The Volvo Ocean Race, America’s Cup and the Olympics. Applications for Oakcliff’s 2015 programs are being accepted here

Oakcliff Sailing is a 501(c)(3) non-profit organization which graciously accepts donations monetarily or in-kind. All donations are tax deductible to the fullest extent of the law and Oakcliff supporters benefit from sailing on our extensive fleet.

Oakcliff is proudly partnered with

Gill, Oyster Bay Marine Center, Awlgrip, Harken, Marlow, Spinlock, Hammer Human Performance, B&G, Expedition Marine, North U, Katadyn and PSA Inc.


For more information:


BYM Pineapple Cup – Montego Bay Race

pineapple cup


Oakcliff’s Training Program Director Liz Shaw along with Oakcliff grad Jeff MacFarlane will race Bodacious Dream in the 800+nm Pineapple Cup Montego Bay Race starting Feb 6th.

The coverage starts now, however, as Liz shares her thoughts with BYM News and Scuttlebutt Sailing is also quick to the mark covering the race. Check out both articles below and standby for more updates!



Mardi Gras Comes Early at Oakcliff

2015 joe prosser awardL-R: US Sailing President Tom Hubbell, US Sailing Training Committee Vice Chair & Nominator Charlie Arms, Oakcliff’s Elizabeth Shaw, award presenter and Chairman of the US Sailing Training Committee Richard Jepsen

New Orleans, LA (January 22, 2015)- Mardi Gras may not be for another month but US Sailing’s National Sailing Programs Symposium (NSPS) kicked it off early for Oakcliff Sailing this year. This evening, Oakcliff received The Captain Joe Prosser Award, given to an organization that has made an exemplary contribution toward improving the quality and safety in the training or instruction of sailors. This is the top award a training facility can receive from US sailing and embodies everything that Oakcliff stands for.

Elizabeth Shaw, Oakcliff’s Training Program Director, got her beads, dancing shoes and taste buds packed and flew down to accept the award on behalf of Oakcliff Sailing. Liz said of the evening “It was truly an honor to be recognized by so many inspirational peers in the sailing community. The knowledge that we are filling a void in American sailing is an integral part of what keeps us moving ahead with our goals and ambitions at Oakcliff.”

This recognition is also a celebration of the award coming full circle. In 1994 Dave Perry, who is a board member at Oakcliff, was the first recipient of the award. He congratulated Oakcliff on its award stating, “Education is the cornerstone of growing and advancing the sport. Oakcliff Sailing is at the forefront of doing just that through its many educational programs and opportunities.” In 2015, Oakcliff expands its Acorn program with 5 options designed to introduce sailors to the fundamentals of different aspects of competitive yacht racing. The Tune Up is a 2-day intensive program on 40’-50’ keel boats with on-board coaching. The Offshore program, designed by Dawn Riley, focuses on logging miles, safety at sea and career training. The Skiff and Cat program utilizes 24 Olympic Class skiffs (49er and 49erFX) and multihulls (Nacra 17) with a focus on problem solving and campaign management. The Inshore immersive program boasts private coaching, instruction on various common repairs, racing rules and tactics, and intense match racing. Finally, the Intensive is an all-around program focusing on the foundations of a successful program (maintenance, provisioning, scheduling and logistics). More information can be seen in Oakcliff’s 2015 brochure.

 The Sapling program is a summer-long dive into professional sailing through a structured apprenticeship at Oakcliff’s America’s Cup style campus. The sailor leaves this program a leader with comprehensive skills ranging from marine electronics to successful campaign management. The program boasts an 87% industry job placement.

 Applications for Oakcliff’s 2015 programs are now being accepted here

 Oakcliff Sailing is a 501(c)(3) non-profit organization which graciously accepts donations monetarily or in-kind. All donations are tax deductible to the fullest extent of the law and Oakcliff supporters benefit from regularly scheduled training on our extensive fleet.

 For more information:


Oakcliff Ocean Racing Team Wins RORC Transatlantic Race

Andrew O'Donnell, Dan Flanigan, Chris Kennedy, Hobie Ponting winning jump

Andrew O’Donnell, Dan Flanigan, Chris Kennedy, Hobie Ponting winning jump

First in IRC One Second Overall

Grenada – Oakcliff Ocean Racing Team has finished 1st in class and 2nd overall in the RORC Transatlantic Race marking 3,100 miles raced in their epic 7,000 mile ‘delivery’ of Oakcliff’s new Class 40.

Immediately after the finish Hobie Ponting exuded “That was epic, we have crossed an ocean the first time any of us have done it and it feels fantastic. The last 24 hours was the hardest of all. We had very little wind and it was frustrating having spent days charging along at 20 knots. We have all worked so well together and we have finished this race better friends than we started.” He added ‘we don’t know what day it is right now and a shower, some good food and a bed with sheets is top priority.”

Less than 2 months ago Oakcliff received a call that the Bodacious Racing Team in Chicago wanted to donate their Class 40 sailboat to Oakcliff. The detail that the boat was in Hamble, England was quickly remedied when the core of the Oakcliff Ocean Racing Team motivated to create and execute a plan that had them flying to the UK with coach, top short-handed sailor, and also Oakcliff graduate Jeffrey MacFarlane. In the UK they would take possession and deliver the boat to the Canary Islands off of the West coast of Africa to start the RORC Transatlantic Race.

It was a wild trip across the brutal Bay of Biscay but they made it to the start line. Coach Jeff left them here as they headed off to race from Lanzarote, Gran Canaria to Granada, which is surprisingly close to Venezuela – only 230 miles. After some much deserved R&R and a little spiced rum they will hop back onboard and deliver the boat to Charleston, SC. It is arguable that they couldn’t possibly have sailed any more distance in transporting the boat from England to the US but what an opportunity. To put it in perspective: they will have sailed well over 7,000 miles – longer than any one leg of the Volvo Ocean Race and almost a third of the way around the world!

“This is just one of the exciting and life-changing opportunities that Oakcliff is providing to young hungry athletes who come to Oyster Bay to test themselves in the extreme world of Ocean Racing, the uber-competitive match racing world or to aim for the Olympics” explained Executive Director Dawn Riley. Applications for Oakcliff’s 2015 training programs are open and can be accessed through

The team of Dan Flannigan, 23 (Rhode Island), Hobie Ponting, 23 and Chris Kennedy, 26 (Wisconsin) and Andrew “OD” O’Donnell, 27 (New York) are all keen to get home to America to see their families and friends and, if they can make it on time, they will have many stories to share around the Christmas Tree!

Oakcliff is proud to have the following partners:  Heron Financial, The Better Chip, Gill, Spinlock, Expedition Navigation and yacht racing solutions , Katadyn Watermakers , Sea Logic a B&G Dealer, Power Specialist Associates.

Wet & Wild Win for Young Team at Halloween Invitational


The conditions were as fierce as the competition this weekend at Oakcliff Sailing’s Halloween Invitational.

Ten teams from the United States, Canada and Bermuda battled 30 knot plus winds, heavy rain and biting cold to see who would take top honors at Oakcliff’s final match racing event of the 2014 season. With Sunday’s even more aggressive forecast looming the race committee ran eight hours of punishing races on Saturday to complete a full round robin. The uber-close competition left the organizers with the hefty task of breaking multiple ties to see who the hero would be. And here is where the real story begins…

Young-gun Christophe Killian from the Balboa Yacht Club in southern California got the win by coming out on top of a three-way tie with Canadian Nicholas Kroeger and Bermudian Lance Fraser. Killian’s match racing resume is impressive, including a win at this year’s Rose Cup, the US Youth Match Racing Championship, and that earned him an invitation to this event.

Even more impressive was Killian’s command on the water competing in the Swedish Match 40s, the largest boat used on the circuit in extreme conditions. “It’s my first time ever driving a boat with a wheel,” admitted the College of Charleston freshman as he stood accepting his prize with his young co-ed team in front of the experienced field that included six skippers ranked in top 100 of ISAF’s Match Racing Rankings.

The prize giving was held Sunday morning after racing was cancelled due to extreme winds with 50kt gusts howling down the harbor: Oakcliff Sailing events are about joining together to compete and learn. With all teams staying in the newly renovated bunkhouse fun is definitely a factor

Executive Director Dawn Riley stated that while “…three days of partying and one day of racing,” is not the ideal ratio, all competitors at the 2014 edition of the Halloween Invitational were offered top-of the line racing in competitive boats “and that’s a success for everyone involved.”

2014 Oakcliff Halloween Invitational Results:

1. Christophe Killian, USA – 78%
2. Lance Fraser, BER – 78%
3. Nicholas Kroeger, CAN – 78%
4. Peter Holz, USA – 56%
5. Chris Johannessen, USA – 56%
6. Chris Poole, USA – 56%
7. Jon Hammond, USA – 56%
8. Landon Gardner, CAN – 33%
9. Chris Foley, USA – 11%
10. Derek Webster, USA – 0%

Full Results:

This is what 50 knots looks like at the dock