Join Sail Monterey’s local sailing races to test your skills on the vibrant waters of Monterey Bay. Experience thrilling competition, spectacular marine life, and a rich sailing culture.
More ways to explore the area's outdoor wonders
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Difficulty
moderate
Duration
2–5 hours per race
Fitness Level
Good physical condition needed for handling sail adjustments and balance during dynamic conditions
Wildlife
History
Monterey’s Old Fisherman’s Wharf has been a hub for commercial and sport fishing since 1900, grounding these races in a rich maritime tradition.
Conservation
Sail Monterey supports clean water initiatives and encourages minimal environmental impact during events to preserve the bay’s ecosystem.
Sail Monterey
Join Sail Monterey’s local sailing races to test your skills on the vibrant waters of Monterey Bay. Experience thrilling competition, spectacular marine life, and a rich sailing culture.
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.
Check Weather and Wind Conditions
Monterey Bay winds can shift quickly; always confirm forecasts before heading out.
Wear a Personal Flotation Device
Safety first—ensure your PFD fits properly and complies with regulations.
Arrive Early for Pre-Race Briefing
Get the latest race instructions and tide updates to stay informed.
Protect Against Sun Exposure
Even on cool days, UV rays reflect strongly off the water; use sunscreen and wear a hat.
Sailing gloves
Protects hands from rope burns and improves grip.
summer
Waterproof sailing jacket
Keeps you dry and warm during chilly, spray-heavy conditions.
spring
Non-slip footwear
Ensures steady footing on wet decks.
Polarized sunglasses
Reduces glare and helps spot changes on the water surface.
summer