Join the Sail Monterey Crew
At Sail Monterey, we don’t just sail—we create unforgettable experiences for locals and visitors alike. We like to work hard, have fun, laugh, and share advenutre. We’re looking for passionate, skilled, and enthusiastic team members to help us bring the joy of sailing to our community.
Sailing Instructor/Captain
The Captain & Sailing Instructor is at the heart of the Sail Monterey experience. This role combines hands-on sailing instruction with leading public and private cruises, ensuring every guest leaves with lasting memories. Captains & Instructors are responsible for teaching, guiding, and inspiring, while also supporting the smooth operation of our office and fleet.
Requirements:
- USCG MMC OUPV Near Coastal (Minimum)
- ASA certification 201 minimum (202, 203, 204, 205, & 206 most usefull)
- 3+ years of sailing experience
- Strong communication and teaching skills
- Passion for sharing the joy of sailing with others
Responsibilities:
- Teach introduction to sailing classes
- Teach American Sailing Classes 101 & up
- Take paying passengers on public and private sailing cruises
- Share information about sailing, local history, and wildlife with guests
- Help run office operations (answer phone calls and emails)
- Help maintain the Sail Monterey fleet
Perks:
- Competitive hourly pay ($25/hr min) + tips + bonuses
- Opportunities to grow within a passionate sailing team
- Access to a well maintained fleet of boats and waterfront activities
Experience Coordinator
The Experience Coordinator is responsible for coordinating sailing cruises and lessons, managing client and captain schedules, and ensuring a positive and seamless experience for all Sail Monterey guests. This role serves as the primary point of contact for customer inquiries, supports the daily administrative and operational needs of the office, and assists with marketing initiatives to grow Sail Monterey’s Club and Community.
Requirements:
- Kind, joyful & cooperative disposition
- Proficient computer skills
- Professional communication skills (Phone, text, and email)
Responsibilities:
- Answer phone calls and emails to:
- Answer prospective customer questions
- Make reservations
- Take payments
- Plan and execute routine email marketing campaigns
- Create and post social media posts
- schedule captains and instructors to respective activities
- Use sales techniques to increase customer and member LTV
Perks:
- Competitive hourly pay ($25/hr min) + tips + bonuses
- Opportunities to grow within a passionate sailing team
- Playing a central role to grow and run a small business
Sail Monterey Vision, Mission, and Values
The Vision – We are creating…
A thriving sailing community that inspires adventure, connection, and growth—for locals, visitors, and our crew alike.
The Daily Mission – Everyday…
We work as a crew to build connection and community through sailing—creating meaningful experiences and bringing lasting value to our members, joy to our guests, and prosperity to our business and crew.
Sail Monterey Core Values
Community First
We believe experiences on the ocean and sailing should be shared with EVERYONE. We nurture a supportive, inclusive community—for locals, visitors, and our crew.
Respect for the Ocean
The sea commands respect. We approach it with humility, skill, and vigilance—and practice good stewardship to ensure it remains a source of life and adventure for generations to come.
Teamwork with Purpose
We operate as a crew—united, dependable, and mission-driven. Success is a shared effort, from the office on the pier to sailing on the bay.
Excellence in Experience
Every cruise, class, and conversation is an opportunity to deliver something memorable, meaningful, and joyful.
Growth with Integrity
We grow our business to support our team, our members, and our community—never at the expense of our values.
Joy and Adventure
We bring the spirit of fun, freedom, and discovery to everything we do, sharing the magic of sailing with everyone we meet.
Meaningful Work
We believe our work should enrich not just our guests, but ourselves. We’re here to do something that matters.
Interested?
Send your resume and a brief cover letter to Paul@sailmonterey.com with the subject line:
“Sailing Instructor Application”
“Experience Coordinator Application”
We can’t wait to meet you and welcome you aboard!