Sailing With Zest

rupert holmes yachting world

Kass and Rupert enjoy a relaxing daysail on Zest in Ponta Delgada

Kass Schmitt

I am an American-born Londoner. Raised in Rochester, NY on the shores of the mighty Lake Ontario, I waited until I was a Computer Science student at the University of Wisconsin-Madison to take up sailing on a puddle called Lake Mendota. Go figure.

After university I moved to Chicago, and there I got into racing on Lake Michigan. A couple of years later I moved to London and mostly forgot about boats for a decade or so (I was preoccupied with the Web, art, programming and punk rock). While working at the BBC I took up dinghy sailing at a club based in Brighton. In 2007 I ran away to sea for the first time, crewing on 40 foot classic yawl from the Canaries to Brazil via Senegal and Cape Verde. Shortly after my return I met my partner Rupert . Together we have cruised and raced over 15,000 miles on my boat Zest and Rupert’s Discovery 3000 based near the Sporades in Greece. We also put many fun miles under the keel of Minestrone, our quarter tonner, which we sold in late 2015. In the winter we both race in the Illusion fleet at Bembridge Sailing Club, and in the Summer, if I’m not off racing Zest, then I enjoy crewing on Etchells and Dragons in Cowes.

I originally bought Zest in early 2013 with the intention of taking part in OSTAR 2013 (The Original Single-handed Trans-Atlantic Race). I didn’t make it to that start line, but remain committed to being there in 2017. In the meantime I have been racing Zest extensively, both solo and double-handed.

Rupert and Kass head out to start the 2015 Rolex Fastnet Race

Rupert and Kass head out to start the 2015 Rolex Fastnet Race

Rupert Holmes

Rupert is a prolific freelance yachting journalist with more than 75,000 miles of offshore cruising and racing experience in waters ranging from the North Sea to the Southern Ocean. As well as extensive cruising he has raced a wide variety of yachts, from the smallest of keelboats to Farr 45s and TP52s, but now prefers the challenge of long-distance short-handed sailing.

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Great to see Minestrone is still going. She looks great. My father, Ken Wyllie, commissioned her to be built for the 1975 quarter ton cup in Deauville. Many happy memories!

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Hello!!!! I just saw your indie Gogo campaign and am so excited for you!! I donated what I could. I am preparing to do my 2nd singlehanded transpac and am working on a documentary about he history of women in that race (as you can imagine there are sadly way fewer women than men). I want to also interview other women who do solo offshore sailing. Would you be willing to let me interview you for my project? It seems we have the same drive to inspire more women and girls to get out on the water and seek adventure!!! Either way I am rooting for you and can’t wait to track your progress!! Warmly,Margie Woods.

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Wow! Thanks Margie for your very generous contribution. I would be honored and thrilled to be interviewed for you project. Good luck with your second transpac, I would love to do that race someday. Keep an eye out for my friend, Richard Lett, who is also intending to enter the next one.

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Yachting World

Yachting World

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rupert holmes yachting world

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Round the Island Race: tips for a safe, enjoyable and fast...

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Short-handed Playbook: Downwind (Part 3)

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The Rolex Fastnet Race – what makes it such a thriller?

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Short-handed Playbook: Doubling Up (Part 2)

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J/99 Boat Test

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Short-handed Playbook: Set-up essentials (Part 1)

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Video series: Sportsboat playbook

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Onboard Maserati

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Grand Soleil 34 Boat Test

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Jim Beviglia

There was a bit of mystery and sleight of hand at play when Bobby Caldwell hit it big with his single “What You Won’t Do for Love” in 1978. But that has long since faded, and the charms of the smooth song that fits so comfortably into so many genres, including yacht rock, have endured.

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What is the song about? How did Caldwell write it on demand? And why did Caldwell’s record company tried to hide his identity to an extent when the song was released? Here are the details behind “What You Won’t Do for Love,” Caldwell’s first and most successful single.

A Multifaceted Background

When you hear “What You Won’t Do for Love,” you’ll probably notice it’s somewhat uncategorizable, in large part because it seems to draw from a deep well of influences. That starts to make sense when you understand how Bobby Caldwell came to that point in his career.

Born in Manhattan, raised in Miami, Caldwell was turned on by his parents to big-band singing heroes like Ella Fitzgerald and Frank Sinatra. A multi-instrumentalist, he worked for a while in Little Richard’s touring band, while also spending time as a member of the Miami outfit Kathmandu. He was good friends with Bob Marley.

All those various experiences and influences eventually earned him a record deal with TK Records. That label did big business in the disco-heavy late ’70s, most notably with KC & the Sunshine Band. Caldwell earned the opportunity to release his debut album as a singer/songwriter on the label in 1978.

“Love” Story

Caldwell wrote and recorded several songs he thought were prime candidates for a release as a single. But the record label pushed him to keep trying, as they weren’t blown away with his choices. He quickly came back with “What You Won’t Do for Love,” which was co-written by Alfons Kettner.

The song boasted an outstanding horn arrangement provided by Mike Lewis. This was exactly what the label had been seeking. But they made the interesting decision to restrain from publicizing Caldwell’s picture, as they correctly surmised that many audience members wouldn’t realize, based on his soulful voice and the smoothly funky arrangement, that he was white.

They needn’t have worried. Caldwell eventually had to go out and promote the record, and it didn’t stop the momentum of “What You Won’t Do for Love.” The song hit the Top 10, and endured not just through its inclusion on yacht rock stations and playlists, but also from being sampled often, most notably by Tupac Shakur on his 1998 song “Do for Love.”

What is the Meaning of “What You Won’t Do for Love”?

Caldwell’s lyrics on “What You Don’t For Love” touch on many aspects surrounding the search for that all-too elusive connection. His narrator begins by explaining it took some work on himself before he was ready to open up to someone else: I guess you wonder where I’ve been / I searched to find the love within .

The self-discovery led him to an inescapable conclusion: Got a thing for you and I can’t let go . And he laments there are those who don’t ever experience what he has discovered: Some people go around the world for love / But they never find what they dream of . The title refers to the hangups that ultimately hold you back from a special relationship, which need to be overcome: In my world, only you / Makes me do for love what I would not do.

It’s a clever and novel way to say what’s been said in song many times before. “What You Won’t Do for Love” propelled Bobby Caldwell into a long, varied career in music. He passed away in 2023, leaving behind an impressive legacy and a signature song that, contrary to initial worries, has enthralled all races and creeds over the years.

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COMMENTS

  1. Rupert Holmes, Author at Yachting World

    Rupert Holmes has some 85,000 miles of offshore cruising and racing experience in waters ranging from the Norwegian fjords to the Southern Ocean, plus the Caribbean and Mediterranean. As well as ...

  2. What does it take to sail two-handed around the world?

    Rupert Holmes discovers what cruisers can learn from their tough circumnavigation TAGS: Double handed sailing Top stories Long-distance offshore racing nurtures extraordinary levels of self ...

  3. Hit by a rogue wave and dismasted

    36ft Zest is hit by a '14m' rogue wave and dismasted off Spain. Skipper's story. Yachting World. July 7, 2016. 0 shares. En route to the Canary Islands Rupert Holmes's yacht Zest was ...

  4. Yachting World

    Rupert Holmes steps onboard 11th Hour Racing's new IMOCA 60 - the first to be built with fully crewed racing in mind Yachting World ... Yachting World ...

  5. Rupert Holmes « YachtWorld UK

    For a long time yachts appeared to be immune to depreciation - at least in cash terms - which is another factor that may lead some experienced and long-standing owners to over value their craft. For many decades depreciation in real terms was masked by high inflation, such that boats would maintain their cash price, but this is no longer ...

  6. IT TAKES TWO

    rupert holmes discovers what cruisers can learn from their tough circumnavigation. read this exciting story from yachting world july 2023. the double-handed globe 40 teams powered around the world over eight legs in just nine months. rupert holmes discovers what cruisers can learn from their tough circumnavigation

  7. SHAKING UP THE INDUSTRY

    read this exciting story from yachting world august 2023. the biggest transformation of boatbuilding - and the wider marine industry in our lifetime is under way, with the drive to eliminate carbon emissions and use composites th that can be recycled into a new boat. rupert holmes visits those yards spearheading the change

  8. The Team

    Rupert Holmes I've been messing around in boats all my life and started sailing full time as a yachtmaster instructor at Southern Sailing, instead of getting a proper job after university. ... Yachting World and Yachts and Yachting - as well as a number of other titles around the world. In all I've sailed some 85,000 miles - much of it ...

  9. Yachting World

    Rupert Holmes takes a first look at a new collaboration between Brooklin Boat Yard and designer, Jim Taylor.

  10. Rupert Holmes, Author at Yachting World

    December 2, 2022. After winning the Sevenstar Round Britain and Ireland Race aboard JPK 1010 Jangada Rupert Homes provides this full offshore sailing clothes review. Rupert Holmes has some 85,000 ...

  11. About us

    Rupert Holmes Rupert is a prolific freelance yachting journalist with more than 75,000 miles of offshore cruising and racing experience in waters ranging from the North Sea to the Southern Ocean. As well as extensive cruising he has raced a wide variety of yachts, from the smallest of keelboats to Farr 45s and TP52s, but now prefers the ...

  12. NEW GEAR

    Read this exciting story from Yachting World December 2020. RUPERT HOLMES INVESTIGATES A CLEAN ELECTRICAL POWER SOURCE FOR YACHTS. ... This story is from the December 2020 edition of Yachting World. Start your 7-day Magzter GOLD free trial to access thousands of curated premium stories, and 9,000+ magazines and newspapers. ...

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    Browse, borrow, and enjoy titles from the Missouri Libraries 2Go digital collection.

  14. Rupert Holmes, Author at Yachts and Yachting

    Rupert Holmes-May 17, 2023. 0. Short-handed Playbook: Downwind (Part 3) ... Yachts & Yachting is the leading performance sailing magazine, covering every aspect of the racing scene, from dinghies to keelboats. ... Our insightful features and stunning photography bring you the inside track on the world's most exciting regattas together with ...

  15. Epic Round Britain and Ireland Race decided by minutes

    Among them were Richard Palmer, sailing with Yachting World regular contributor and boat tester Rupert Holmes on the JPK1010 Jangada, who are currently leading as 1st IRC overall, having finished ...

  16. 15th CIC Normandy Channel Race Day 2

    Sail World - The world's largest sailing news network; sail and sailing, cruising, boating news. ... However, Jangada's skippers Richard Palmer and Rupert Holmes are still in good spirits, determined to give their all to make up their deficit and complete the 1,000-mile race.

  17. Rupert Holmes, Author at Yachting World

    Yachting World. Search for: Search. Subscribe. ... Rupert Holmes. The future of boatbuilding: a greener approach ... When enjoying a glorious day on the water it's easy to assume sailing must be ...

  18. Rupert Holmes « YachtWorld UK

    Posts Tagged 'Rupert Holmes' ... In the UK and main European boating markets the average time to achieve a sale of all but the smallest sailing and motor yachts is more than a year. Many vessels stick on the market for several years, often deteriorating while they wait for a buyer, before selling for a fraction of the initial asking price. ...

  19. HIGH TECH WOOD

    HIGH TECH WOOD Yachting World | May 2023 RUPERT HOLMES REPORTS ON LATEST DEVELOPMENTS IN WOODEN CONSTRUCTION, AND WHY THIS ANCIENT MATERIAL IS BEING USED FOR HI-TECH CONTEMPORARY DESIGN- . RUPERT HOLMES. Why would a naval architect and structural engineer used to working with cutting edge materials for America's Cup teams, including INEOS Britannia, and companies like Airbus, be excited about ...

  20. Rupert Holmes, Author at Yachting World

    Yachting World. Subscribe; Digital Edition ... Rupert Holmes. First Look: Arcona 50 - a different philosophy ... It's not long since 60ft yachts were the preserve of custom or semi-custom ...

  21. Yacht Rock Essentials: "What You Won't Do for ...

    Yacht Rock Essentials: "Him" by Rupert Holmes, a Savvy Follow-Up to a Monster Hit Read More Yacht Rock Essentials: "Time Passages," the Smash Hit Al Stewart Wrote and Performed but Never ...

  22. NEW YACHTS

    NEW YACHTS Yachting World | June 2022 RUPERT HOLMES REPORTS ON A CROP OF ATTRACTIVE FAST CRUISERS- . RUPERT HOLMES. Arcona 50 . Hull length 14.99m 49ft 2in Beam 4.60m 15ft lin Draught 2.95m, 2.5m or 2.2m 9ft 8in, 8ft 2in or 7ft 3in Displacement (deep keel) 13,900kg 30,650lb Ballast (deep keel) 4,600kg 10,140lb Price TBA arconayachts.se. This Swedish yard's new flagship represents more than ...