Our whirlwind adventure in Santa Cruz lasted just 14 hours, but it was enough time to soak in the city’s charm, enjoy a stunning sunset, and take a peaceful morning stroll along the Arana Gulch trail, which is home to one of the last remaining habitats in the county for the endangered Santa Cruz tarplant. The trail led us to the boatyard, where we explored in search of a replacement outboard motor for the dinghy which has been a bit temperamental since our time in San Francisco. We meandered back along tranquil residential streets adorned with unique homes and vibrant lemon trees in the yards. Returning to the lively wharf, we carefully descended the somewhat sketchy ladder to the public dock, paddled back to the boat while bidding farewell to the beautiful backdrop of the boardwalk as we set our course for Pebble Beach.

We departed early on September 20, leaving behind the chilly cove waters and the serene beauty of the golf course as we set our course for Port San Luis, marking our first overnight sail since our six-day journey down the Oregon coast. As with previous days, we were greeted by a vibrant display of sea life, including humpback whales, playful dolphins, and curious otters, all lending their cheers as we passed iconic landmarks like the Big Sur lighthouse. The winds were gentle, allowing us to sail smoothly with just the head sail until around 1500, when the breeze strengthened. We raised the main sail, but halfway up, the winch began to jump and sputter, leaving the sail stuck in position. We faced a crucial decision: push on or turn back, and we chose to trust that the winds would be favorable throughout the night. By 2000, we were making progress at 4 knots on a broad reach, despite the main sail being only partially raised. As the winds eased around 2300, we secured the head sail, while the main sail remained precariously stuck halfway up, banging against the mast. We hoped we weren’t causing additional damage to the sail as we navigated through the thick fog toward Port San Luis. After a drama-free night, we anchored off Avila Beach around 0830 on September 21, where Alex ascended the 59-foot mast to inspect the situation. Unfortunately, the halyard issue prevented us from using the electric winch for his ascent. After a sleepless morning, we discovered a burnt pulley needed replacement, and true to Alex’s resourcefulness, we had the necessary spare parts on hand. We then took the opportunity to explore the charming artisan town of Avila Beach and the Harford Pier before departing the following afternoon for San Miguel Island.