A perfect introduction to sailing on Monterey Bay, this two-hour experience offers just the right amount of time to get out on the water, feel the motion of the boat, and take in the coastline. Depending on your interest, you can be as involved as you’d like—taking the helm, helping trim sails, or simply enjoying the ride. It’s a flexible, approachable option that delivers a true sailing experience while leaving you wanting more.

Set out for golden hour as the light softens over the Monterey Bay and the coastline comes alive. This is a relaxed, scenic sail designed to help you unwind—whether you’re celebrating a special occasion or just need some time to take in the beauty of coastal Santa Cruz. Sit back or take a turn at the helm as the sun dips below the horizon.

on this four-hour experience, we’ll set a course under sail into the bay and run through sailing maneuvers before dropping anchor in Cowell's Cove. After setting anchor, the crew can relax, enjoy a meal, and jump in the water conditions-permitting. Ask about meal catering options when you reach out.

Enjoy a catered meal from a local chef, served at anchor as the sun sets over the Santa Cruz coastline. Choose from custom menu options, local freshly caught fish, and thoughtful pairings—all prepared locally and served by the crew aboard Songline. Options include fresh seafood from H&H, grilled burgers on the stern deck, Spanish paella, or other made-to-order meals designed to be enjoyed on the water.

Come aboard Songline for a hands-on introduction to how sailing actually works. Before we leave the dock, we’ll walk through the fundamentals—boat systems, points of sail, and essential safety—so you step out with confidence and clarity. Once underway, you’ll take an active role at the helm and on the sails, learning steering, sail trim, wind awareness, and the basics of navigation in real time. It’s an engaging, confidence-building experience designed to turn curiosity into real skill on the water. This is a great option for new sailors interested in digging deeper into what it takes to manage a sailboat on the water.

Experience the incredible marine life of Monterey Bay from the quiet vantage point of Songline under sail. This region is one of the richest marine ecosystems in the world, with frequent encounters with dolphins, sea lions, harbor seals, and a variety of seabirds. Depending on the season, you may also spot migrating humpback and gray whales feeding in the bay. Sailing allows us to move through their habitat with minimal disturbance, creating a more natural and intimate wildlife experience along the coastline. Migrating Humpbacks, as well as the massive flocks pf Sooty shearwater, can usually be spotted between April and November.