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

95% of 38 Groupon Customers Recommend

Give as a Gift
Over 30 bought
Limited quantity available

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

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.


Tips from Groupon Customers

  • “Great captain; nice wooden boat Would recommend to others”

  • “Great time, Comfortable boat in the water. ”

  • “Good for anyone wanting a gentle, leisurely sail or first time sailing experience.”


  1. 1

    Santa Cruz Harbor - West Side

    Santa Cruz Harbor Dock F

    790 Mariner Park Way

    Santa Cruz, California 95062

    831-706-8574

    Get Directions

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

Expires Oct 15th, 2014. 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. Merchant is solely responsible to purchasers for the care and quality of the advertised goods and services.

Gear and getaways for outdoor adventures, from hiking to ski vacations