Daysailer or Weekender Rental in South San Francisco

27 ft
8 Guests

About This Boat

Perfect for day sailing -- head into the city to check out the Bay Bridge from below or cruise past ATT Park while the Giants are at bat, find seals near Alcatraz, and get some great views of San Francisco's iconic Golden Gate Bridge from the water. Anchor and overnight at Angel Island, Treasure Island and more for a truly unique San Francisco experience. She can accommodate 8 but is ideal for groups of 4-6.

She has few frills, but is rigged for single handed sailing. There's also a pump head and a pump freshwater sinks. The boat has a unique charm and offers more than 6 feet of standing headroom, a real head, and cozy accommodations -- all in a little 27-footer. The head comfortably sleeps 2 and the in-cabin seats convert to 2 additional single sleeping spaces to accommodate a total of 4 guests for in boat overnights.

Our lady comes with a small fridge, alcohol stove, oven, tea kettle, sink, flat screen TV, and bathroom sink. There is tiller steering and a manual furling. You must be hooked up to dock power to use the electronics like the TV / tea kettle / fridge. 

We enjoy our boat because it's overbuilt by today's standards which amounts to a reliable ride wherever we go.


We ask that you treat our boat like your own. Be safe and cautious at all times. Smoking is not allowed inside or outside the boat. The captain must be sober at all times.

***If you are looking to rent without a skipper/captain, someone in your group must be familiar with sailing in the Bay area waters as tides, winds, and water traffic can quickly change. Please note experience when inquiring. If you do not know how to sail or do not have experience on the Bay, please make a request to have a captained charter.

**Most non-captained chartered bookings need to be made in advance as we need to coordinate with you to get you onto the dock and show you the nuances of the boat.


  • Type: Daysailer
  • Capacity: 8 People
  • Make Model: Cal 2-27
  • Year: 1975
  • Rental Minimum: 1 day
  • Length: 27 ft
  • Cancellation: Full Refund 14 Days Prior

Rental Requirements

Day rentals are based on bookings up to 8 hours, over-night rentals are based on bookings up to 24 hours.

Qualified-Certified sailors with SF Bay or similar area experience can charter a boat without a skipper/captain. Due to strong winds, currents and heavy marine traffic, these are the only conditions for non-skipper/non-captain charters. Please include certifications / list experience when inquiring.

✓ All sailors must have a good familiarity with their intended sailing venue, including prevailing conditions and dominant weather patterns.


  • Life jackets/required safety gear
  • Cabin
  • Outboard Engine
  • Fuel type: Gas
  • Berth

More Images

More Cal 2-27 images

Meet Jennifer


Member Since Jan 2017

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