Bill Tripp, Jr.


William (“Bill”) H. Tripp, Jr. had a knack for building beautiful boats that were faster than their ratings.  Classic lines, simple beauty and efficiency of design were Bill Tripp’s key criteria in building the perfect boat.  As one of America’s most successful yacht designers in the 1950’s and 60’s, drawing custom ocean racers for a distinguished clientele and smaller boats for production builders like Seafarer and Columbia Yachts, Tripp’s talents were highly sought-after and well-renowned.  We are honored at SailLibra to be able to share the experience of offshore blue water sailing on a vessel, s/v Libra, Bill Tripp, Jr. himself put so much thought and time into.


Sadly, Tripp died suddenly, in a car crash at just 51 years of age. He was included in Bill Robinson’s The Great American Yacht Designers (1974) and the more recent collection (2005) by Lucia del Sol Knight and Daniel MacNaughton, The Encyclopedia of Yacht Designers and will be forever remembered as an innovative, elegant yacht designer.


Some more articles about Bill Tripp Jr.:

Good Old Boat:


Sea to Summit:

1,001 Boats:

First Inaugural “Pensacola a la Habana Race” success!

Adventure found sailing to Havana!

On the last Friday in October 2015, eleven guys–a few friends, a few acquaintances, a few total strangers–loaded onto the sailing vessel Libra for an adventure they’ll never forget.  Video for you here from the Morro Castle Race in Havana!

Sailing Vessel Libra had circumnavigated the globe at least twice before retiring to Orange Beach, Alabama a decade or so ago. Captain Ryan Rayfield bought Libra a few years ago with the hopes of fixing up the custom 1969 Bill Tripp design and turning her into a blue water sailing school.

What better shake down cruise than the inaugural “Pensacola a la Habana Race”?

When the Pensacola Yacht Club announced their plans to hold such an event, Ryan poured everything he had into getting the boat ready, while Co-Captain Randy Smith climbed the mountain of paperwork.

By the time the eleven of us moved on board, Ryan and Randy were exhausted. And the trip was only beginning.

A Sam’s Club provisioning run filled 4 shopping carts to be loaded into a van already full of West Marine bags.


The skipper’s meeting, held at the Pensacola Yacht Club Friday night, promised rough seas and sailing conditions with 15-20 knot SE winds coming directly from Cuba, our destination.

The course from Pensacola Bay to Cuba was just over 500 miles. With the tacking back and forth required to get to the finish line, we would cover over 700.

The Starting Line

The race began at 8am with 22 boats, 5 in our “Classic Cruiser” class.

We jockeyed for the starting line and had a good clean start, then managed to wrap a mizzen staysail around the main sheet trying to show off. We looked pretty ridiculous for a few minutes trying to untangle everything, but then we justified it by comparing ourselves to pool sharks who throw the first game.


The first 5 miles of the course through Pensacola Bay and out into the Gulf were brutal. The south winds along with an outgoing tide created a gnarly tidal rage that was throwing steep 6-10′ waves at us as we were trying to tack back and forth towards clear water.


It quickly became clear that none of the crew thought to properly prepare the cabin down below because the pot of coffee flew off the stove and crashed across the galley, spewing coffee and grounds onto everything else that had already made its way to the floor from the nearby bunks and counters.

Wet Ride

It also didn’t take long to learn that Libra was a wet boat. The 50 year old gaskets on the v-berth hatch, perfectly positioned above 4 of our bunks, created an impressive waterfall each time we buried the bow in a wave.

This is supposed to be fun, right?

Once we cleared the last buoy to starboard, we aimed for Texas to try and get as far southwest as possible before the winds clocked around further south. We had a full suit of sails up with 15-18kts of wind, heeled over at 20 degrees with the rail nearly in the water for the better part of 36 hours.

Just before leaving cell range, we were all getting texts because on the race website it appeared we were in first place by a significant distance. Our joy was short-lived when we realized it was because our satellite tracker updated every 2 minutes, as opposed to everyone else’s 30. It looked like we were 3 miles ahead of everyone, until their tracker updated and showed their actual position, just in front of us.


By dark on Day 1, Saturday, we were able to tack back to the southeast towards Tampa. As the boat found her groove, we had some autopilot issues & discovered the boat would steer herself even better than we could. The crew settled into our watches–3 hours on, 6 hours off–and proceeded to dodge storms with the radar all night.


Day 3

Day 3 started out rough and the crew was feeling it. Several guys were feeling less than stellar. Going down below to make coffee or use the head was a chore. Life jackets with tethers were worn almost nonstop above deck.

Luckily, there were a couple of the Louisiana boys, Doc and Jon, who were just hungry enough to brave the galley when everyone else was just trying to hang on.


Fish on!

I personally was on the provisioning run, so I knew what we’d put in the pantry. But for the life of me, I couldn’t reconcile the ingredients on board with the dishes that were coming from the galley. A black fin tuna Doc wrangled in while still sailing at 7 knots provided fresh civiche, fish tacos (with slivers of apple!), and seared tuna alfredo.


The alfredo sauce was concocted from a handful of mini-moo coffee creamers and a green jar of parmesan cheese. Creative, much? Considering we were heeled over enough to walk on the walls and the oven was swinging wildly on its gimbal, it was gourmet.


It finally calmed down as we neared Tampa late afternoon of Day 3. We reached shore enough to download weather and call home. Everybody thought we were quitting the race because we tacked so far over…a lot of other boats have been tacking up & down the rhumb line, apparently.


With the Sunshine Skyway Bridge in sight, our wind died. The strategy was to get close to shore in hopes of picking up some land-effect easterly breeze. It didn’t exactly work as planned, so after an hour of bobbing around near the shipping channel, we took a vote and cranked up the motor.

This is a sailboat race, so motoring isn’t exactly a good thing. However, the race committee didn’t want to disqualify anyone for using their “Iron Genny”, so they implemented a penalty system. Basically, for every 1 hour you motor, they added 3 hours to your finish time.


We knew our time in Cuba was limited, and we suspected the other boats in our class were also motoring, so we went full throttle towards the Dry Tortugas.

Dolphins at the Bow

I awoke on Day 4 and we were still motoring on calm seas. I finally felt good enough to get the cameras out and do some creative videoing. At one point we had a GoPro on the end of a 20′ boat pole just as a pod of dolphins found our bow wave. I can’t wait to show you the video soon…it was incredible.


Leaving the US

As the sun set, Fort Jefferson was looming on the horizon, marking roughly 100 miles to go before the lights of Havana. Tuesday night was a bit tense as we played frogger, crossing south along the east-west gulf stream. At one point on the AIS screen we had 4 800′ ships headed directly for us.

All was forgotten as the sun rose over the Havana skyline and we heard the horn sound as we passed alongside the race committee boat. We raised our quarentine flag an Cuban courtesy flag, and were escorted to the customs dock where our passports were stamped with an official Cuba visa.



Once all the papers were in order, we were handed their signature drink as a welcoming present. A special moment that was not lost on this Libra crew.


The few days spent exploring Marina Hemingway and Old Town Habana went way too quickly, and we all left hoping to visit again someday.


We won!

We didn’t leave, however, before the awards banquet where we were handed a first place trophy and a few more of those Cuba Libre’s.



If I may, I would like to quickly thank Capt. Ryan for restoring an incredible boat and making her sail again; Capt. Randy Smith for keeping us legal and putting together such a perfectly matched crew; Doc for keeping our sail up, plus he & Jon for being galley wizards; Don for the cajun groceries; Dave for finding the coffee spot; Mr. Wayne for the jokes; Rick for washing the boat so we didn’t have to; Harley for the tuna and cigars; and last, but not least, Dean, for telling stories that no one will ever believe, and even occasionally sharing a bean bag chair.

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