Sunsail Series to be Sailed at Oakcliff


Wednesday sailing at Oakcliff will now be known as the Sunsail Series. Beginning May 6 every Oakcliff Supporter who races at least 5 Wednesdays will receive a 5% discount on a Sunsail charter over the winter. If they form and sail as a team 5 times they receive an additional 5% when they charter as a group. Oakcliff is also a US Sailing Team Sperry Training Center and if supporters are members of US Sailing they can pile up an additional 5% discount.

Brittany Weatherby, Marketing Manager for Sunsail says “We are looking forward to working together with Oakcliff to grow their already successful summer racing program. It is great to see so many adults working to improve their skills in this strong program. Seeing their hard work paying off while sailing through the Caribbean will be a great pleasure. This partnership embodies what Sunsail believes in for the future of sailing: people living their dreams and embracing new adventures at any age.”

The Sunsail series is sailed in Oakcliff’s Match 40s and Shields and run by Sagamore Yacht Club. Oakcliff provides real-time coaching during the fleet racing with prebriefs and debriefs at their America’s Cup style campus in Oyster Bay New York. Supporter can race their own boat in this fleet and qualify as well.   More information and registration is available at

“Racing, learning and cruising are not mutually exclusive and we are excited that Sunsail is supporting our efforts to continue to strengthen American Sailing,” explained Oakcliff’s Executive Director Dawn Riley.   She added, “what a bonus that while staff is servicing our 83 boats each winter our supporters can still be sailing… in the warmth!”

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For 40 years Sunsail has led the way in sailing adventures. From the first pioneering flotillas in Greece to today’s choice of the best and most exotic yachting destinations; beginners can now enjoy the world’s best cruising grounds by hiring a skipper from any Sunsail base. Sunsail strives to provide our customers with the most exciting experience at the greatest possible value. Sunsail brands include Sailing Vacations by Independent Charter and Flotillas, Sailing Schools, Events and Yacht Ownership. Sunsail operates in 26 exotic and diverse destinations throughout the globe on a fleet of over 800 yachts and catamarans.

Dave Perry Wins Ultra-Competitive Qualifier


April 14, 2015, Dave Perry with a team comprised of local sailor Jon Singsen, New York Times Correspondent Chris Museler, and Californians Doug McLean and Steve Natvig went undefeated in the first qualifier of the year: A difficult feat given the level of competition in this qualifier with half of the top 10 in the country competing.

In addition, several of the teams had top 25 skippers sailing as part of the crew this week and Peter Wickwire was previously ranked 30th in the world, before taking a short hiatus to be with his young family. Team Perry earned a spot at the U.S. Match Racing Championships that will be held at Oakcliff October 10-12, 2015.

Saturday saw heavy air racing with steady winds in the low twenties and gusts into the high twenties in the middle of the day requiring the RC to fly the no spinnaker flag for 5 flights. Sunday was the antithesis with light fluky winds. PRO Todd Field and a very talented team was able to get as much sailing as possible out of the conditions to complete the format.

OA Bill Simon, Dave Perry, Steve Natvig, Jon Singsen, Doug McLean, Chris Museler and PRO Todd Field

OA Bill Simon, Dave Perry, Steve Natvig, Jon Singsen, Doug McLean, Chris Museler and PRO Todd Field

Second place went to Canadian sailor Peter Wickwire sailing with regular crew Hamish and Ali Mathews, Jim Barnash and the oldest foredeck crew of the regatta Terry Shannon. Other than their losses to Dave Perry’s team their only other loss was to Doug Shannon.

The winner of the petit finals was David Storrs sailing with USone (2013 World Match Racing Champions) team members Rod Dawson tactician, Hayden Goodrick, Mal Parker and Ricky McGarvie.

New this year, the qualifier system has removed the geographical areas so any match racer can request an invitation to any of the 6 qualifiers still to be held at St. Francis YC (May 23-24) and (Sept. 5-6), CMRC (May 30-31), San Diego YC ( June 13-14), Annapolis YC (June 20-21) and Bayview YC (June 27-28). Female skippers can qualify for the USWMRC at most of these qualifiers. Details can be found at

Final Results
1. Dave Perry
2. Peter Wickwire
3. David Storrs
4. Chris Poole
5. David Niemann
6. Peter Holz
7. Doug Shannon
8. Steven Lopez

Oakcliff Leading a Trend in Marblehead to Halifax Race

great pic! Farr 40 hikingLiz spoke with Fletcher Boland of the Marblehead to Halifax Race (MHOR) about Oakcliff’s entry in the race and the trend towards a dominant youth presence in the event. The result: a great write-up for Oakcliff. We are thrilled to be playing our part in the push of strong, young, talented teams in events such as this. The momentum continues to grow, folks! Read the full article here.

Breaking News: Ice to Melt – Regatta Registrations Open

Oakcliff International

Racing at Oakcliff  begins exactly one month from today with a qualifier for both the US Women’s and US Open Match Racing Championships on  April 10. This regatta already has 5 of the top 20 match racers in the United States entered.  Oakcliff’s 12 Match 4os will also be used at the Open Championship which will be at Oakcliff October 10 – 12.

“I am excited we have removed the geographical limitations for the qualifier. Now any sailor in the country can apply to any of the eight qualifiers”, explained Bill Simon, Race Program Director and US Match Race Championship committee member. “Even with the busiest of schedules everyone should find a qualifier they can attend. I expect the changes we are making to strengthen the Championships”

Registration is open for the entire 2015 season including 21 match race regattas, equating to 38% of all match racing in the United States. Each event has a clinic attached.

Additionally, supporters can sign up to train and compete in 11 inshore regattas and 9 offshore providing just over 2000 miles of intense offshore sailing.   Once again the 49er, 49erFX and Nacra 17 Nationals will be at Oakcliff August 27-30. The full calendar is available at

New this year and combining multiple disciplines is the Oakcliff Challenge. This event is open to any community sailing organization or yacht club that wants to field a team to sail on the 12 Match 40s. Day one will see a clinic hosted by Dave Perry. Day two will be fleet racing and will serve to seed the teams into the final day’s match racing. There will be prizes for both genres of racing as well as an overall prize. All teams will be invited to stay together in the Oakcliff Bunkhouse ensuring three full days of learning, competing and fraternizing.

While visiting competitors and supporters are at Oakcliff for set periods of time, the signature training program participants dubbed Acorns and Saplings train 7 days a week for a minimum of 2 weeks in very diverse racing disciplines. The full time Sapling program is at capacity but the shorter and more focused Acorn programs still have room.

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 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.


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: