Hands-on keelboat courses, family-friendly catamaran cruises, and private sailboat rentals for every skill level.
From quick introductions to overnight voyages — choose a curated Monterey Bay sailing adventure.
boat-charters · Monterey
Discover the beauty of Monterey's coast with a private keelboat cruise. Perfect for relaxing, learning, and wildlife watching, this experience offers a unique perspective on California’s stunning shoreline.
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.
“Every outing is organized with local river knowledge, basic safety instruction, and equipment checks before departure.”
Choose the right boat
Basic keelboat certification available
75–90 minute catamaran tours
Bay cruises and overnight voyage
Open the individual experience guide to confirm current availability, pricing, policies, conditions, and inclusions before booking.
The operator provides clear meeting points, departure times, and destination coordinates for all outings.
Personal flotation devices, emergency protocols, equipment checks, and paddling orientations are provided before departure.
Recommended layering, water shoes, sunscreen, and dry bags are detailed in each experience guide.
Guides share rich knowledge of regional flora, fauna, scenic landmarks, and river navigation.
A glimpse into the experiences, natural landscapes, and adventures waiting on your next trip.
Images supplied on the current Sail Monterey listing.
Sail Monterey offers a variety of guided outdoor excursions, scenic routes, rentals, and custom itineraries tailored for families, couples, and adventure enthusiasts.
Yes. Most trips feature comprehensive safety orientations, equipment fittings, and calm routes suited for first-time adventurers. Check the details on individual experience guides for specific age and skill requirements.
Standard safety equipment (such as certified life vests and essential gear) is supplied for each booking. Detailed checklists regarding weather-appropriate attire and personal items are provided prior to departure.
Reserve a daytime cruise, sunset sail, lesson, or private rental — spots fill quickly during peak season.
boat-charters · Monterey
Master sailing basics aboard a 30-foot keelboat in beautiful Monterey Bay. Join a small group for hands-on lessons and earn your ASA certification in just a few days.
water-activities · Monterey
Ready to try sailing? Join this private 2-hour class in Monterey to learn all the basics, enjoy beautiful coastal views, and get hands-on practice with expert instructors guiding you every step.
boat-charters · Monterey
Set sail on a classic Carol 24ft wooden catamaran in Monterey Bay. Perfect for families and wood boat lovers looking for a private, memorable day on the water.
boat-charters · Monterey
Set sail on Monterey Bay with a serene 75-minute catamaran cruise. Enjoy wildlife sightings and breathtaking ocean views while sipping complimentary drinks.
boat-charters · Monterey
Enjoy a romantic 1.5-hour catamaran cruise at sunset on Monterey Bay with complimentary drinks and wildlife spotting. Discover stunning coastal views and local marine life on this private sailing adventure.
water-activities · Monterey
Explore Monterey Bay aboard the spacious 34' Hunter 340 with Sail Monterey. A perfect boat rental for family outings or sailing with friends, enhanced by modern features and stunning coastal views.
water-activities · Monterey
Enjoy a private sailing experience on Monterey Bay with the Hunter 30ft rental catamaran, Willow. Perfect for all skill levels, this trip offers modern comforts and stunning coastal views.
boat-charters · Monterey
Embark on a two-day sailing adventure from Monterey to Santa Cruz that combines active water time with beach relaxation and local culture. Experience sleeping aboard your vessel and savor unforgettable Pacific coast views.
water-activities · 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.
water-activities · Monterey
Master your maritime navigation skills on the stunning Monterey Bay with the ASA 105 course—a hands-on day of chart plotting, electronics, and practical testing.
boat-charters · Monterey
Sail Monterey offers a three-day hands-on course teaching key bareboat cruising skills on California’s stunning central coast. Learn navigation, docking, and sail handling aboard a Hunter 340 while traveling between Monterey, Moss Landing, and Santa Cruz.
water-activities · Monterey
Join Sail Monterey’s Starboard Club and unlock exclusive benefits for sailors of all levels on the stunning Monterey Bay. Gain priority access, skill clinics, and special discounts that deepen your connection to the water.
boat-charters · Monterey
Gain hands-on sailing skills during a three-day ASA 103 Basic Coastal Cruising course aboard a Hunter 30T with Sail Monterey. Learn coastal navigation, anchoring, and sail trim in Monterey Bay’s dynamic waters.
others · Monterey
Push your sailing expertise beyond the basics with Sail Monterey’s focused Skill Session clinics. Master advanced techniques on Monterey Bay’s challenging waters in tailored, hands-on sessions.
boat-charters · Monterey
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.
otherwater-activities · Monterey
Set sail from Monterey Bay for a private 3–4 hour whale watching cruise offering intimate encounters with whales, dolphins, and sea lions. Discover California’s rich marine life framed by the historic Cannery Row backdrop.
otherwater-activities · Monterey
Sail quietly across Monterey Bay on a spacious catamaran, watching sea lions, otters, dolphins, and whales glide alongside. This 75-minute eco-cruise blends wildlife encounters with peaceful ocean breezes for a refreshing marine adventure.
Click into any experience card above to view current dates, live availability, transparent pricing, cancellation policies, and booking details.