2004 Hunter 356 | $540/2 Hours | $900/All Day
Experience the thrill of Monterey Bay’s coastline aboard Calypso, a roomy 35-foot Hunter sailboat perfect for family and friends. Discover why this rental is a top choice for hands-on sailing adventure in California’s iconic marine sanctuary.
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Difficulty
moderate
Duration
2–6 hours
Fitness Level
Moderate physical fitness recommended to manage lines and move around the boat safely.
Wildlife
History
Monterey Bay was declared a National Marine Sanctuary in 1992, protecting its rich marine ecosystems.
Conservation
Visitors are encouraged to follow responsible wildlife viewing practices to minimize disturbance to the sanctuary's diverse animals.
Sail Monterey
2004 Hunter 356 | $540/2 Hours | $900/All Day
Sail Monterey is a Monterey Bay sailing company offering guided cruises, sailing lessons, and sailboat rentals.
With a fleet that includes a classic 24-foot wooden sloop (Jeannette), a Hunter 30 (Willow), a Hunter 34 (Euca) and a spacious catamaran for daytime and sunset cruises, Sail Monterey provides options for families, learners, and experienced sailors. The company runs wildlife-focused daytime catamaran cruises and romantic sunset sails that include complimentary drinks and snacks, making wildlife watching and scenic views accessible to all ages.
Sail Monterey teaches sailing with an ASA 101 Basic Keelboat Sailing Course and a 2-hour Introduction to Sailing. The ASA 101 course is a multi-day, hands-on program that covers sail handling, knots, navigation basics, and safety; students complete the course with a certification. The 2-hour class offers a practical, friendly introduction to steering, sail trim and onboard safety for newcomers.
Boat rentals include self-skippered options and checkout procedures for Jeannette, Euca, and Willow, all equipped for comfort and ease. For adventurous groups, Sail Monterey runs a voyage from Monterey to Santa Cruz with overnight opportunities, plus local sailing races for competitive sailors.
Safety, experienced instruction, and a focus on low-impact wildlife viewing guide every offering. Sail Monterey emphasizes small groups, hands-on learning, and clear rental checkouts so guests leave confident, informed, and inspired.
Certain charters, like Euca, host small groups of up to six and include beverages and snacks on daytime and sunset options. Booking is available online with clear pricing and rental checkout details. Accessible to all ages.
Fleet
24', 30', 34' & catamaran
Choose the right boat
Certification
ASA 101 Course
Basic keelboat certification available
Cruise Types
Daytime & Sunset
75–90 minute catamaran tours
Destinations
Monterey Bay & Santa Cruz
Bay cruises and overnight voyage
Reserve a daytime cruise, sunset sail, lesson, or private rental — spots fill quickly during peak season.
Book Your Checkout Sail Early
If you're new to qualifying for the Calypso, schedule your one-hour checkout sail with an instructor at least a few weeks in advance to ensure availability.
Bring Layers for Changing Weather
Monterey Bay weather can shift quickly; pack a windbreaker or fleece to stay comfortable on the water.
Check the Local Tide and Wind
Understanding tide schedules and wind conditions before your sail will help optimize your trip and safety.
Keep a Marine Wildlife Watch
Monterey Bay is a marine sanctuary; use binoculars and keep a respectful distance from wildlife.
Windbreaker Jacket
Protects against cool bay winds during spring sailing trips.
spring
Non-Slip Deck Shoes
Provides grip and safety on wet boat surfaces.
Sunglasses with UV Protection
Essential to reduce glare reflected from the water.
summer
Sunscreen SPF 30+
Protects skin from prolonged sun exposure out on the water.
summer