Sailing during the day with OYC blends tranquility and scenic elegance with luxury and comfort. Glide over shimmering waters against the stunning backdrop of the California coast, where you might see seals, dolphins, sea otters, and whales. Experience a seamless blend of natural beauty and adventure, powered by the gentle ocean breeze and warm sunlight.

Sunset sails in Monterey Bay capture the magic of evening's glow, as the sky turns into a canvas of vibrant colors and the sun sets, bathing the bay in golden light. Amidst the serene waves and cool breeze, time pauses, enveloping you in a tranquil, romantic ambiance. This picturesque scene creates an unforgettable backdrop for any occasion, turning a simple sail into a captivating journey through nature's artistry.

Experience the thrilling Wednesday Regatta, offering a spectacular view of the competitive action amongst local sailors! These sails typically offer a wonderful sunset and are often paired with our Local Wine Tasting Sails or our Local Beer Sampling Sails.

Raise a toast to our Local Wine Tasting Sails, where the allure of popular local wineries meets the wonder of sailing! Picture yourself savoring the finest wines from Santa Cruz's renowned local names, all while gliding smoothly along the coastline. Whether you choose the vibrant ambiance of the daytime or the serene beauty of the sunset hour, each sail is a perfect blend of leisure and excitement. It's more than just a tasting; it's an adventure that tantalizes all the senses!

Fill your glass with tasty brews and relax as you enjoy the wonders of Monterey Bay! These sails feature some of Santa Cruz County’s beloved breweries, old & new, and are paired with a selection of daytime, sunset, and regatta sails throughout the season! Gourmet pizza is also provided and complimentary with your reservation.