An Ultimate Sailing Experience for Romance, Excitement or Plain Relaxation.

Whether planning the perfect date or introducing the family to the joy of sailing in Santa Cruz, the 2-hour Private Sail on Monterey bay is the ultimate classic wooden yacht experience. Captain Forest Roberts creates an amazing atmosphere while maintaining the charm of sailing a classic yacht. (Private sails are family friendly too – there is no age limit on private charters) 

For up to 4 Passengers 

2  Hours any time  

For up to 6 Passengers 

2  Hours any time  

Classic yacht deck at senset
Santa Cruz Lighthouse at sunset
CaliforniaClassicSail Classic yacht at Sunset
Sailing-with-friends on californiaclassicsail wood yacht

Let’s Go Sailing and Have Some Fun!

Need more info? Call us directly at 831.706.8574 or send us a note. 

“GREAT EXPERIENCE” – boat was perfect size for me, my wife and 19 year old daughter. Captain Forest was great! Couldnt have asked for more. GREAT VALUE
Reviewed July 31, 2016
“BEST BIRTHDAY SURPRISE FOR A SAILOR” – Forest and his fiance were awesome! I booked this event for a birthday surprise and it was great. They were also so kind to pick up the pizza and the cake that I ordered 🙂 They also took some pictures of us and emailed it back to us. I would highly recommend it.

About Sarah, she is a beauty! It was y first time sailing with a tiller instead of a wheel and omg, what a difference. I would feel the water.”

Reviewed March 8th 2015
“WE HAD A GREAT DAY SAILING OVER LABOR DAY WEEKEND” – Had a 2pm charter for the wife and I over our anniversary weekend. Forrest was a very competent sailor that knows how to sail this classic sail boat. Highly recommend this one of a kind activity.
Reviewed on 9/4/2016
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Category:     Product #: Operating a beautiful classic sailing charter boat on the Monterey Bay from the picturesque Santa Cruz Harbor. California Classic Sail offers two-hour public and private sailing charters.
Regular price:,
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Private Sailing Charter by California Classic Sail