Two-Hour Private Sailing Tour for up to Five from California Classic Sail (Up to 42% Off). Two Options Available.

Santa Cruz Harbor - West Side

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In a Nutshell

A vintage-style yacht, designed according to a 1890's blueprint, skims Monterey Bay on cruise with optional hands-on sailing instruction

The Fine Print

Promotional value expires Oct 16, 2014. Amount paid never expires. Must sign waiver. Subject to weather. Reservation required. Charters available Mondays at 1 pm and 3 pm, Tuesdays and Wednesdays at 3 pm, Sundays at 3 pm, and select Saturdays at 3 pm. Subject to availability; please allow 3 options to choose from when submitting a date. Merchant's standard cancellation policy applies (any fees not to exceed Groupon price). Limit 1 per person, may buy 1 additional as a gift. Valid only for option purchased. Only available for select weekday and weekend dates. Merchant is solely responsible to purchasers for the care and quality of the advertised goods and services.

Choose Between Two Options

  • $139 for a two-hour private sailing charter for up to five, valid Monday–Wednesday ($240 value)
  • $152 for a two-hour private sailing charter for up to five, valid Saturday or Sunday ($240 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

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
It was really fun and relaxing. The weather and the views were stunning and Captain Forrest was delightful and welcoming.
Michael D. · August 29, 2014
Merchant Location Map
  1. 1

    Santa Cruz Harbor - West Side

    Santa Cruz Harbor Dock F

    790 Mariner Park Way

    Santa Cruz, CA 95062


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