California Classic Sail LLC


Give as a Gift

In a Nutshell

A vintage-style yacht, designed according to a 1938 blueprint, skims Monterey Bay on cruise with optional hands-on sailing instruction

The Fine Print

Promotional value expires May 16, 2013. Amount paid never expires. Limit 1 per person, may buy 2 additional as gifts. Limit 1 per visit. Valid only for option purchased. Reservation required; subject to weather and availability. 24hr cancellation notice or $58 or $66 fee may apply, depending upon option purchased. Must sign waiver. Not valid on weekends or for Wednesday Night Sailboat Races. Merchant is solely responsible to purchasers for the care and quality of the advertised goods and services.

Bodies of water are frequent metaphors in poetry due to their unfathomable depths, unknowable sprawl, and unattainable porpoises. Set sail into the enigma with today’s Groupon.

Choose Between Two Options

  • $129 for a two-hour sailing charter for up to four (a $290 value)
  • $149 for a two-hour private sailing charter for up to six (a $330 value)

A vintage-style wooden yacht helmed by a professional captain ferries passengers from Santa Cruz during charters that hold up to six passengers. The captain also offers optional, hands-on sailing instruction for those aboard.

California Classic Sail

When Forest Roberts was 9 years old, he built a boat in his backyard with money saved from his paper route. Since 1989, Roberts has participated more officially in the maritime industry, working water-related jobs from commercial diving to boat building—and often living aboard boats—before opening his sailing-charter company in 2006. Today, California Classic Sail operates from Santa Cruz on the shores of Monterey Bay, earning praises from previous passengers and a Santa Cruz Sentinel feature story.

Roberts’s background in the building industry helped him recognize the superb craftsmanship in his current yacht, Sarah. The builder, William Garvie—who named the vessel after his granddaughter—constructed the 52-foot-long boat based on a line drawing published in an early 20th-century yachting-magazine spread. Made of wood instead of the fiberglass many modern boats are made of, its vintage style and wood hull set it apart from other Santa Cruz charter vessels. Dubbed a “Sharpie” for its long, narrow shape, rather than an ability to leave permanent wakes, the graceful yacht zips through the bay waters on chartered trips for groups of up to six. Passengers can relax onboard as Roberts steers, or choose to learn basic sailing maneuvers through hands-on instruction. Roberts can also tailor trips to special occasions such as engagements and birthdays, and can sail during many times of day, including more-scenic mornings and sunsets.

Customer Reviews

We had such a great time with Captain Forest Roberts! Sara is a beautifully crafted boat; Forest was even kind enough as to let us take part with the actual sailing! I have been thinking about making time to go again very soon! :)
Adrienne S. · August 9, 2016
Captain Forest is great! My husband and son got to practice their sailing skills and we all had a delightful afternoon onboard Sarah.
Cynthia R. · September 22, 2014
We had a wonderful time! I would never have thought to do a private sailboat charter without the Groupon, but I'm so glad we did it!
Kerina M. · August 29, 2014

By purchasing this deal you'll unlock points which can be spent on discounts and rewards. Every 5,000 points can be redeemed for $5 Off your next purchase.