Most folks, even many yachtsmen, don’t even know where Guadalupe Island is.  This fascinating island is about 150 nautical miles west of Scammons Lagoon where the California grey whales spend the winter, and it is 300 miles south of Marina del Rey.  The rhumb line from MdR to the island just nips the west end of Catalina, lies a little west of the west end of San Clemente island, and passes a little east of Bishop Rock on Cortes Bank.  After that it is just 200 miles of open Pacific Ocean to Guadalupe Island.

The island is just slightly smaller than Catalina being about 25 miles long and 5 miles wide.  But, unlike Catalina, Guadalupe is high and steep sided, rising over 4000 feet from the surrounding ocean.  There are no facilities or services of any kind on the island.  On the southern tip of the island there is a weather station manned and maintained by the Mexican Navy. There are also several families that live permanently on the island and make a living fishing the reportedly bountiful local waters.  The fishermen, offering huge lobsters to trade for almost anything you have, beer, magazines, canned food, and clothes being the most popular in that order, approach boats anchoring or transiting the area.  The west side of the island is steep and rocky with many charted and uncharted rocks.  This is a lee shore and there are no anchorages on this side of the island.  On the east side there are several anchorages but they are all exposed to the south and southeast and should be considered open roadsteads.  The island is often shrouded in low hanging clouds that give it a forbidding and ominous appearance.

Pacific Singlehanded Sailing Association held the first Guadalupe Island race in 1981.  The previous year the new club had held the MdR 300 race, which wove its way around and through the Channel Islands and served as a qualifying race for those wishing to participate in the Singlehanded TransPac from San Francisco to Hawaii.  The MdR 300 was a good, tactical race but since you were never more than about 50 miles from some kind of land you didn’t get the feeling that you had been ’out there’ and exposed to conditions in the open ocean.  Guadalupe Island had been used as a racing mark for crewed boats since the 1950s so it was a natural for the PSSA founding fathers to institute the first Singlehanded Guadalupe Island race in 1981.  The race was held every year until 1985 when a doublehanded class was added and it was changed to a bi-annual event.  In 1988 it was changed from the odd numbered years to the even numbered years in order to better accommodate those racers going on to the Singlehanded TransPac which is also run in even numbered years.  The first winner was David Lay whose time has not been recorded but David went on to win again in 1982 in a corrected time of 5 days, 20 hours, 30 minutes and 28 seconds. The record for the fastest corrected time belongs to Jeff Winkelhake at 3 days, 7 hours, 43 minutes and 43 seconds.  The slowest time belongs to M. and K. Anderson who took 9 days, 4 hours and change to complete the 630 NM course.

Is the Guadalupe Island race for you?  Well, that depends.  It is by far the most demanding and challenging event on the PSSA calendar.  Sea Tow won’t be able to help you and neither will the Mexican Navy.  For most of the race you will be out of easy reach of the U.S. Coast Guard.  You will be in the open ocean for 4 or 5 days and must be prepared to deal with whatever problems or weather you encounter.  There is no easy harbor to duck into if you decide you don’t want to race anymore.  All that being said, finishing a Guadalupe Island race is bound to be the high point of anyone’s single or double handed career.

Preparing for a Guadalupe Island race is neither easy nor cheap.  First, you will need to do a qualifying race or cruise of at least 100 miles.  PSSA’s Bishop Rock race is an ideal opportunity to see if you like offshore racing and if your boat is adequate for the purpose.  If you have done a Bishop Rock (or two) and had a ball then you are probably ready to step up to Guadalupe Island.  Second, you will need to up grade the safety systems on your boat above those required by the other PSSA races.  You will need a life raft and about $400 worth of SOLAS grade flares in addition to the safety gear you normally carry on PSSA races.  PSSA will want to inspect your boat to make sure that the equipment complies with the requirements outlined in the sailing instructions.  This seems like a lot of trouble and expense but you have to remember that there isn’t one single West Marine store between here and the island.

Once the qualifying race and safety requirements have been met you can start thinking about the race its self.  The start, in MdR is usually in light air.  Most folks decide to leave Catalina Island to port because there is usually more wind west of Catalina and San Clemente than there is to the east of them.  Once you get a little past San Clemente Island the wind picks up to 15 to 20 and hauls around to the stern.  There is usually a 4 to 6 foot swell running so this is the time to get the spinnaker up and start surfing the long Pacific swells.  These conditions usually prevail, night and day, all the way to the island.  The island its self may be hard to spot right away, even from less than 2 miles out.  Approaching from the north you will be looking at the island’s narrow side and heavy clouds usually surround it.  This is where you will get the most benefit from your GPS.  Since the west side of the island is a rocky lee shore it is best to give it a wide berth.  There is one navigation light about half way down the west coast and another at the southern tip of the island.  You may also see the lights of the weather station and the fish camp if you happen to be there after dark.  At the south end of the island are two large rocks that must be left to port per the sailing instructions.  Both are well charted and present no particular navigational problems.  Rounding these rocks does not necessarily mean that the race is half over.  The finish line and home are 300 miles away and dead to weather.

Going up the east side of Guadalupe Island is much like going up the east side of Catalina Island.  You are in the lee of the island and sometimes it pays to stand off a little to get more wind and sometimes it’s best to hug the coast and hope for some down drafts from the mountains.  Whichever route you choose, you will get a big lift and quite a bit more wind at the north end of the island.  From there you will find that there is usually more wind on the left side of the rhumb line. The conventional wisdom suggests that you stick pretty close to the rhumb line as you beat north to the finish.  If you get too far to the left you get more wind and chop than you want and if you get too far to the right you get into light air and the south bound current.  The finish for the 2014 edition of the race is at the East-End Light of Catalina Island.

The Guadalupe Island race is a challenge that should not be taken lightly.  However it is within the capability of any dedicated offshore sailor.  The sense of satisfaction and accomplishment you get when you finish is indescribable.  You will always look back on the race as one of the tougher and better races you have ever done.  Mark Twain said “ Twenty years from now you will look back with more regret about the things you didn’t do than the things you did do”.  The time is now short for the ‘14 Guadalupe Island race but you can still make it.  If you need a qualifier there is the Bishop Rock race in February.  As this piece is written there are several boats already planning on going.  There is always room for more.  There are several members at PSSA that would love to answer your questions and help you out.