Monterey Bay Sailing: Scenic Cruises, Lessons & Rentals

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.

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.

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.

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.

Set sail on Monterey Bay with a serene 75-minute catamaran cruise. Enjoy wildlife sightings and breathtaking ocean views while sipping complimentary drinks.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.