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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.
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.
Book with Sail Monterey
Verified experiences and guided adventures in the surrounding area.
Operated by Sail Monterey · Monterey, California
Located along California's rugged Central Coast, Monterey Bay delivers some of the West Coast's most stunning coastal scenery and marine life encounters. Taking to the water aboard Calypso, a 35-foot Hunter monohull sailboat, offers a unique way to experience this iconic bay. This rental appeals to both seasoned sailors and adventurous families eager to explore Monterey’s shimmering waters.
Calypso stands out as the largest monohull in the Sail Monterey fleet, designed to comfortably host up to eight passengers. Equipped with a furling mainsail and jib, plus an autopilot system, it blends classic sailing with modern ease, allowing more focus on the views and less on manual trimming. Bluetooth stereo functionality adds an extra layer of enjoyment whether you’re cruising past the colorful waterfront or anchored near scenic coves.
This boat rental is perfect for those who want a private, hands-on sailing adventure. While less experienced sailors need to schedule a one-hour checkout sail with an instructor ($285) and provide a sailing resume prior to booking, experienced captains can helm Calypso themselves, making it both accessible and empowering. Whether you’re looking to drift beneath Monterey’s clear skies or race the winds with friends, this rental makes an exceptional platform to do so.
Monterey Bay is famed for its marine sanctuary, a protected area rich with sea otters, harbor seals, migrating whales, and diverse birdlife. Exploring on the water reveals perspectives unreachable from shore—for example, spotting sea lions lounging on rocky islands or catching sight of gray whales migrating offshore.
The rental location at 78 Old Fisherman’s Wharf puts you steps away from Monterey’s historic waterfront, with restaurants, shops, and the famous Cannery Row nearby. This adds to the convenience if you’re visiting the city for a weekend escape or longer. The region’s mild climate, typically cool and breezy, provides optimal sailing conditions through spring, summer, and fall.
What makes Calypso exceptional is its balance between size, comfort, and ease of handling. Large enough for groups and family outings, yet equipped with features to make sailing approachable, it offers a memorable, customizable experience on one of California’s premier sailing grounds. For travelers seeking a quintessential maritime adventure with stunning coastal views, this Hunter 35ft rental is a standout.
Nearby City: Monterey, California
moderate.
2–6 hours.
Moderate physical fitness recommended to manage lines and move around the boat safely.
Calypso can only be rented by qualified sailors who have completed a one-hour checkout sail and submitted a sailing resume.
The rental includes the boat, sails, autopilot, and stereo system; fuel and other amenities are typically provided but confirm with the operator.
Beginners must complete a paid checkout sail with an instructor to demonstrate competency before renting Calypso independently.
Calypso accommodates up to 8 sailors comfortably.
The meeting point is at 78 Old Fisherman’s Wharf in Monterey, California.
Bring layered clothing, sunscreen, sunglasses, and non-slip shoes to stay comfortable and safe.
Monterey Bay was declared a National Marine Sanctuary in 1992, protecting its rich marine ecosystems.
Visitors are encouraged to follow responsible wildlife viewing practices to minimize disturbance to the sanctuary's diverse animals.
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.
Book with Sail Monterey