Learning to Sail Further, Cruise Longer, and Breathe Deeper
Smooth seas don’t make you a better sailor. But an on-the-water experience that leads you outside your comfort zone into unfamiliar water certainly might.
For crews aboard the Naos Yachts Channel Islands Flotilla charter, our June 18–23 voyage was that and so much more. Over five days, seven boats covered nearly 200 nautical miles exploring three of Southern California’s Channel Islands: Santa Cruz, Santa Barbara, and always-magical Catalina.
It was a sailing-forward adventure packed with jaw-dropping island vistas and marine wildlife. But, it was also a hands-on learning experience where skippers and crew left the inner waters of Santa Monica Bay to practice planning, provisioning, navigation, and passage-making; sailing upwind and downwind, anchoring overnight, and becoming more self-sufficient and confident sailors.
Naos Channel Islands Flotilla Yacht Charter: Fleet Snapshot
Seven boats joined our Channel Islands Flotilla yacht charter, offering a unique mix of onboard cruising amenities and sailing capabilities:
- Catalina Breeze – Lagoon 42 (Lead Boat, and the only multihull)
- Tequila – Beneteau Oceanis 40.1
- Aviation– Beneteau Oceanis 46.1
- Sasha Marie– Dufour 47
- Claire Elise – Beneteau Oceanis 37.1
- Sensei – Beneteau Oceanis 46.1
- Citadelle – Beneteau Oceanis 37.1
From larger boats with lots of space, to nimbler hulls with responsive light wind performance, the Naos fleet’s variety added depth to the flotilla charter, allowing sailors to observe and learn from different boat configurations and sailing styles.
Day 0: Pre-Departure Preparations
The original plan was straightforward: Depart early from Marina del Rey, motor northwest in calm seas, and spend most of the trip anchoring on Santa Cruz Island. Think short day sails and casual nights at anchor in idyllic coves. But, as the saying goes, sailing plans are written in sand at low tide.
It turned out a Gale Watch was issued by NOAA for the weekend with predicted winds approaching 30 knots around the Channel Islands. So we pivoted, and a new itinerary was set that would take us farther and wider:
- Day 1: Motor sail from Marina del Rey to Scorpion Anchorage, Santa Cruz Island
- Day 2: Downwind sail to Santa Barbara Island
- Day 3: Sail to Cat Harbor, Catalina Island
- Day 4: Explore Catalina, then sail to Avalon
- Day 5: Return sail to Marina del Rey
Day 1: Marina del Rey to Santa Cruz Island ≈ 60 NM
We left Marina del Rey in calm conditions, motoring northwest past the sand beaches of Malibu and the cliffs of Point Dume; and, by afternoon, we were powering into building conditions: 15 knots of true wind and 3 to 6-foot swells on the bow.
As we made our way, boats and crew came together and began to gel. Some were students seeking additional training, others were seasoned sailors on a chartered adventure, and a few were relatively new to sailing. Taking turns at the helm, trimming sails, monitoring our progress, or standing on the bow, we swapped stories about our sailing backgrounds and shared love of the water. Bonds formed quickly, and they would serve us well.
Our lead boat, a Lagoon 42 catamaran named Catalina Breeze, was captained by James Lee, our flotilla charter leader. With 25 years of experience in the U.S. Navy, and countless miles of cruising, racing, and chartering, he could already recognize the value and importance of a trip like this for new and developing sailors.
On this trip, every crew will be paying attention to navigation, batteries, and water management,
he said as we passed Anacapa Island to port.
Being aware of your environment—physical and material—matters.
Night one, we made an epic sunset arrival into Scorpion Anchorage. VHF radios crackled as excited crews coordinated anchoring in 35 feet of clear blue-green water. For some, it was their first time anchoring outside a practice setting—and they nailed it! By dusk, the boats looked like a watercolor against the island backdrop.
Day 2: Santa Cruz to Santa Barbara Island ≈ 40 NM
Santa Cruz Island is a dramatic sight when seen from the water. As the morning marine layer burned off, a wild and remote coastline came into view. Crews dinghied ashore and paddled kayaks along the island’s cavernous edge. Santa Cruz is the largest Channel Island, known for its massive sea caves. Paddles in hand, we explored deep caverns, drifted through kelp forests, and spotted garibaldi, seals, sea lions, and brown pelicans.
The plan was to depart by 1 p.m., but cruising timelines are always flexible. One of our Beneteau monohulls, Aviation, had challenges weighing anchor, so the crew ingeniously improvised, rigging a line to the winch and hauling the anchor chain up manually. Time-consuming? Yes. But it built grit, teamwork, and confidence.
Once underway, the roughly 40-nautical-mile leg to Santa Barbara Island offered Citadelle a sweet reward: sunshine, downwind sailing, and spectacular conditions: breeze in the teens, swell on the stern quarter, and a sunset passage through the channel between picturesque Santa Cruz and Anacapa Islands.
On arrival, Santa Barbara Island offered a welcome sense of calm. As one sailor said,
One minute you're out in the wind and swell, and the next, you're in a completely calm pocket between Arch Point and Landing Cove. Amazing!
At Santa Barbara Anchorage, boats lowered anchors in 30 feet water with a sandy bottom on 80 to 100 feet of chain. A couple of boats rafted up. Others dragged briefly before finding a solid hold. Along the way, everyone stayed cool, worked together over VHF, and made it happen.
Smooth seas don’t make you a better sailor,
James, our lead captain and flotilla charter leader, later said, enjoying a toast of white wine with the crew on Aviation, and congratulating them for their ingenuity raising anchor.
These are the experiences you carry with you.
Day 3: Santa Barbara Island to Catalina ≈ 28 NM
Waking up in a remote cove is an incredible gift. As the sun rose over the mainland, the cliffs and volcanic features of Santa Barbara Island came into relief. Going ashore here is difficult-at-best; instead, with coffee in hand, crews ran dinghies along the shoreline where sea lions had somehow scrambled to high ledges to perch above the cove.
At brunch, the flotilla rafted up with dinghies around Catalina Breeze to share highlights from the previous day, discuss the coming leg, and, of course, to caffeinate.
By mid-morning, we were Catalina-bound. Pointed southeast toward Cat Harbor, wind was near perfect—12 to 15 knots—and boats found their groove. Crew on Sacha Marie, our Dufour 47 took turns at the helm, napped, or laid out on the foredeck to take in a couple of hours of sunny skies and following seas. Then, flanked by other boats, they flew deep downwind to enter Cat Harbor’s protective cove.
Day 4: Cat Harbor to Avalon ≈ 10 NM
From Cat Harbor, crews each chose their own adventure. Some boats sailed the rugged backside of the island, others rounded the western tip to cruise the southern shore. Hidden coves, snorkeling stops, and secret anchorages dotted the day.
Friends chartering Tequila, our Beneteau Oceanis 40.1, stopped off and enjoyed a “lunch hook” in Emerald Bay to spend time in the water, practice diving and spear fishing.
The best part of this trip is the nature element,
TJ said, after hauling up the anchor.
I’ve done outdoor adventuring in the San Juan Islands, the British Virgin Islands, even Martha’s Vineyard, but there was crystal clear water and a lot of fish this weekend in the Channel Islands. Today, Emerald Bay looked like a fish tank.
Others emphasized the value of the flotilla’s community and on-site support.
I probably wouldn’t have run up to Santa Cruz Island with the forecast we had,
one crew remarked.
But with a group of boats and experienced leadership, I did. That made a huge difference. You don’t get that sort of support chartering other places.
By late afternoon, boats rendezvoused in Avalon where mooring was easy, and dinghies were soon zipping to shore. Gathering for a night out, crews celebrated and shared stories, raising glasses, and reliving highlights of the trip under the glowing lights of lovely Avalon. It was a picture-perfect finish, but the trip wasn’t over yet. After a night of sleep, crews reassembled, readied the boats, and cast off of moorings to undertake one last leg – 60 nautical miles from Avalon to Marina Del Rey.
Day 5: Reflections on the Sail Home
Final days at sea are always bittersweet. Under blue skies, a light wind eventually built and, as it did, a clear sense of satisfaction and accomplishment was shared between sailors and reported over VHF communication between boats.The takeaway? The Naos Yachts Channel Islands Flotilla yacht charter wasn’t just a sail-vacation. It was a sailing-intensive, skill-building, confidence-growing adventure. For some, the highlight was experiencing the wild nature and remote anchorages right here in Los Angeles’ backyard. For others, the trip’s top value was the learning – taking on challenges of navigation, passage planning, itinerary changes, and anchoring in unfamiliar places. Either way, the trip offered something most charter experiences don’t: a mix of autonomy and support.
Instead of just handing over a sailboat with emergency contact info, the Naos Yachts Channel Islands Flotilla yacht charter provided on-the-ground expert guidance when needed—plus space to sail, practical problems to solve, and situations to stretch and expand skills. Having a seasoned lead boat ready to answer questions or offer encouragement was empowering, not intrusive.
In short, this trip gave captains and crew the chance to sail harder, cruise further, and breathe deeper—and return home better sailors than when we left.
Crew Testimonials & Trip Reflections
The best part of this trip was the nature element. I’ve done outdoor adventuring in the San Juans, the BVI—even Martha’s Vineyard—but there were a lot of fish here. Crystal-clear water. Emerald Bay looked like a fish tank.
— TJ, Charter Captain Tequila
I probably wouldn’t have run up to Santa Cruz Island with that forecast. But with a group and support, I did. In other places, like chartering in the Caribbean, that support just isn’t there. Having experienced leadership nearby made all the difference.
— Crew, Tequila
That moment felt like a turning point—for confidence, teamwork, and learning on the fly. The crew of Claire Elise arrived at Santa Barbara Island just before dusk and helped a nearby boat that was dragging anchor. It was a high-stakes lesson in anchoring—and a bonding moment.
— James, Flotilla Charter Lead Captain, Catalina Breeze
We got good at working together. Each day, we got more efficient as a crew. For me, the west end of Santa Barbara Island was unforgettable. Smooth rock, dramatic cliffs, turquoise water—you could feel the beauty and remoteness. It was amazing.
— Sean, Crew, Claire Elise
For us, the highlight was doing boat life. Eating together, preparing food, and cooking aboard—it brought us closer and made the whole trip more memorable.
— Chris, Captain, Claire Elise
Watching how Captain James led by example was really valuable. His calm, clear communication, and knowledge helped everyone enjoy the entire trip—even the challenges that come with cruising—and become more capable and self-sufficient.
— David, Crew, Catalina Breeze
