β΅ New Website, New Career, Dinghy Driving 101, Meet Skipper Cliff πβ¨
Before we dive into sailing, thereβs a little life update! ππ Iβm excited to share news about the next chapter of my aviation career as I step into the Type I helicopter world as a Director of Training. Itβs a big change, but donβt worryβ¦ Gnomad Sailing Adventures is still full steam ahead! β΅π
Then itβs on to the fun stuff! Iβll give you a tour of the brand-new Gnomad Sailing website π, share a few tips (and laughs π) about mastering the mighty dinghy π€, and introduce you to one of our legendary skippersβ¦ the one, the only, the infamous Cliff! ππ» If youβve ever wondered who keeps our flotillas on course while keeping everyone entertained, this is your chance to meet him! β΅π
πβ΅ She's Finally Launched! Welcome to the New Gnomad Sailing Website! π
Your home port for unforgettable flotillas, sailing inspiration, destination guides, and finding your TRIBE. πβ
After many cups of coffee β, a few late nights π, and only the occasional muttering at my computer π», I'm excited to announce that the new Gnomad Sailing Adventures website is live! πAlong with a new logo:

The new site is designed to be your home port for everything Gnomad. You'll find information about our flotillas π΄, upcoming adventures π, destination inspiration πΊοΈ, photos from past trips πΈ, our philosophy, and plenty of reasons to start planning your next escape. β
Whether you're dreaming of sailing the Greek Islands, exploring Thailand, discovering the Sea of Cortez, or joining us in the British Virgin Islands ποΈ, you'll find it all in one place.
This is just the beginning! I'll continue adding new destinations, articles, photos, videos, and helpful sailing resources as we grow our amazing TRIBE. π€
So grab your favorite beverage πΉ, have a wander around GnomadSailing.com, and let me know what you think. I'd genuinely love your feedback! π¬
Fair warning... browsing may result in an irresistible urge to book your next sailing adventure. πβ΅π
πβ΅ She's Finally Launched! Welcome to the New Gnomad Sailing Website! π
πβ Check it out here! I'd love to hear what you think. Feedback is always welcome... just remember, I'm a sailor, not a web designer! πβ΅ Be kind, have a browse, and let me know your favorite part! π
The Times They Are A Changing
Some know, others do not, The G~Manβs life has been in turmoil for the past 6-8 weeks, and is finally coming together.
As of tomorrow, Friday, my 20-year chapter with Redding Air Service will come to a close. π Although it isn't how I expected this chapter to end, I'm deeply grateful for the opportunities, friendships, and experiences I've had along the way. I'm incredibly proud of everything we, (myself & Philβ those that know...know), accomplished together.
I'm not disappearing just yet! I'll continue assisting Redding Air Service during the transition to help ensure a smooth handover. After two decades, it only seems right to help pass the baton. π€
As one chapter closes, another begins. I'm thrilled to share that I've accepted a new role as Director of Training with a prominent utility helicopter company. πβ¨
As I enter the shoulder season of my career, this feels like the perfect opportunity to leave a lasting legacy by mentoring pilots, strengthening training programs, and helping shape the next generation of utility helicopter professionals.
More will be revealed in the next newsletter, but needless to say, I'll be stepping into the Type I helicopter world, get to keep flying for a tad longer, and take on exciting new challenges, earning new type ratings, and continuing to learn every step of the way. ππ₯
And for my sailing friends... don't worry! β΅π Gnomad Sailing Adventures isn't going anywhere. In fact, my new company is incredibly supportive of my sailing ventures, so our flotillas will continue full steam ahead, with plenty more adventures on the horizon! πβAnd some new tribe members joining us.
Here's to new horizons, fresh challenges, and the adventures still to come. π»

β΅ Dinghy Driving 101πβ¨
The biggest boat in the flotilla gets all the attention. The smallest boat causes most of the stories. π
Whether we're sailing in Greece, Thailand, the Amalfi Coast, or the Sea of Cortez π΅, the humble dinghy becomes our taxi, grocery getter, beach shuttle, exploration vehicle, and occasionally our excuse for getting unexpectedly wet. π¦
Many first-time flotilla guests assume driving a dinghy is easy. How hard can it be? It's just a tiny boat with a tiny motor. Famous last words. π
The first lesson is simple: weight matters. Put four adults in the back of a dinghy and the bow points toward the moon π while the motor works overtime trying to push a floating wheelie across the harbor. Spread people out and suddenly everything works much better.
The second lesson is that dinghies have reverse gear, but not always the kind you're expecting. Many small outboards require rotating the entire motor around to back up. The first time you try this near a crowded dock full of expensive yachts, things can get exciting in a hurry. π¬β
Then there are beach landings. ποΈ Done correctly, everyone steps gracefully ashore looking like seasoned sailors.
Done incorrectly, someone ends up knee-deep in water holding a backpack over their head while the rest of the crew laughs uncontrollably. Ask me how I know. π
One of my favorite parts of flotilla life is the nighttime dinghy ride back to the boat. πβ¨ Dinner is finished. The harbor lights are reflecting on the water. The conversation is flowing. Everyone piles into the dinghy for the ride back to the catamaran. Those little trips often become some of the most memorable moments of the entire week.
Of course, they also remind us why a flashlight π¦, life jacket, and a healthy respect for the water are always good ideas.
The most important thing to remember is that the dinghy isn't a toy. It's an essential piece of cruising equipment. Treat it with respect, pay attention to weather and waves, keep your hands and feet inside when docking, and always attach the engine kill-switch lanyard when underway. π
The good news?
Most people become surprisingly competent dinghy captains after just a few trips. By the end of a flotilla, guests who were nervous on Day One are confidently running ashore for ice, groceries, or a forgotten bottle of wine. π·π
Like so many things in sailing β΅, dinghy handling looks ridiculously easy... right up until it's your turn! π One minute you're confidently casting off, the next you're wondering why the dock seems determined to chase you. π€£ Don't worry... we've all been there!
This article may give you some of the fundamentals, some practical tips, and a few hard-earned tricks I've collected over the years. But here's the secret: reading about dinghy handling is a bit like reading about riding a bicycle. It'll point you in the right direction, but the real learning happens when you're on the water with one hand on the tiller, the other on the throttle, and a big grin on your face. π€π
Every landing β, every gust of wind π¨, every current, every "creative docking maneuver," and yes... the occasional audience at the marina ππ, teaches you something new. Before long you'll instinctively know how the dinghy will react, and those little corrections become second nature.

The best dinghy drivers aren't the ones who've read the most articles. They're the ones who've spent time behind the tiller π―, made a few spectacularly average landings π , accidentally selected reverse instead of forward π, laughed it off π», and headed back out for another lap.
So grab your life jacket π¦Ί, untie the painter, and go play! Explore that hidden beach ποΈ, make a coffee run β, discover a waterfront tavern πΉ, or simply spend half an hour practicing coming alongside your boat. Every trip builds confidence, every mistake becomes a story π, and every smile reminds you why we love life on the water. Before you know it, you'll be the one everyone trusts to ferry the crew ashore... and somehow you'll also become the designated grocery transporter! ππβ
And if you happen to get a little wet while learning? Congratulations.π
You're doing flotilla life correctly. π€ππ»
Live β’ Learn β’ Share β’ Give β’ Protect β’ Grow β’ TRIBE β΅π
Meet Skipper Cliff
π From English Shores to World Voyages, Sharing Adventure Every Nautical Mileβ΅

As a young boy growing up on the beaches of Englandβs south coast π¬π§, Iβd stare out at the yachts on the horizon and imagine the adventures waiting beyond the sea. Every sailboat seemed to carry a thousand possibilities, and I dreamed of one day being at the helm of my own. β¨β΅
Those dreams started becoming reality when I met my wife, Mary, in Michigan β€οΈ. Fortunately, we shared the same passion for sailing, and with friends who owned boats on the Great Lakes, we quickly found ourselves spending as much time on the water as possible. After completing the RYA Day Skipper course in both the UK and Antigua, we embarked on our first charter adventure along Greeceβs beautiful Ionian coast, with our two young children proudly crewing alongside us. π¨βπ©βπ§βπ¦β
When we later moved to Southern California βοΈπ΄, we dove headfirst into the sailing lifestyle. We earned our ASA 101 and 103 certifications, purchased our own Beneteau 41 π₯οΈ, and continued building experience with ASA 104/114 certifications and eventually a USCG Captainβs License. πβ
The next chapter took us even farther afield to the turquoise waters of French Polynesia ποΈπΊ, where we first met Gordy and his crew. We hit it off immediately at a legendary Pirate Party β οΈπ. Somewhere between sea stories and laughter, someone said, βNext time youβre on our boatβ¦β and we happily accepted the invitation!
That friendship has since carried us across some incredible sailing destinations, including Croatia, the Bahamas, Greece, Thailand, and most recently Italy. Along the way, Iβve explored the Aegean, the Balearic Islands, the Florida Keys, and sailed alongside Gordy in Mexico, taking on adventures like the famous Baja Ha-Ha and the Newport-to-Ensenada Race. πβ΅π
One of the things I enjoy most about skippering is helping others discover their own confidence at sea. Whether you're taking the helm for the first time or sharpening existing skills, I encourage everyone to participate as much as theyβd like. Thereβs nothing better than watching people grow, learn, and realize theyβre capable of more than they imagined. ππ
Iβm looking forward to many more adventures, fair winds, unforgettable sunsets, and reconnecting with friends old and new along the way. π β΅πΉ
Fair winds and following seas,
Cheers, Cliff βππ»
Some useful Freebies
These are the tools I actually use out here, and if you sign up using my links below youβll usually get a little bonus or discount, while also supporting Gnomad Sailing at no extra cost
- Morning: LMNT Hydration π
- Route planning/Navigation: Savvy Navvy + Orca π¬οΈ
- Teaching: NauticEd modules π
- Crew online: Saily + Surfshark π
- Journaling the madness: reMarkable βοΈ
- Training, books, and newsletter: The Boat Galley
- Starlink