Surfing 🏄 lessons with
Jaycob Milstein
Get a free trial lesson
Pay $0 today$213per lesson after trial
Surfing 🏄 lessons with
Jaycob Milstein
Get a free trial lesson
Get a free trial lesson
Pay $0 today$213per lesson after trial80
Happy Student ScoreFair
Jaycob is dependable, though reschedules are more frequent. Best if your schedule is flexible.
Coach Rating
5.0
2 ratingsNo reviews
80
Happy Student ScoreFair
Jaycob is dependable, though reschedules are more frequent. Best if your schedule is flexible.
Coach Rating
5.0
2 ratingsNo reviews
About your surfing coach
Born in San Francisco and raised in Marin County, I've spent the last 11 years mastering the waves along the Northern California coastline and around the world. From the beginner-friendly breaks of Bolinas to the challenging waves of Advanced Ocean Beach, I've navigated it all with skill and expertise. With a deep understanding of tides, weather patterns, rip currents, and ocean conditions, I provide a comprehensive surfing experience that prioritizes safety and progression. Whether you're just starting out or looking to take your skills to the next level, I'm here to guide you on your surfing journey. Book a lesson with me today and let's hit the waves together. Whether you're a beginner or a seasoned surfer, there's always something new to learn and discover in the exhilarating world of surfing.
👋
Teaches: Kids, Teenagers, Adults, Seniors
🌱
Levels: Beginners, Intermediates, Experts
📍
Lives in: Sausalito, California
🎓
Years Playing: 11 years
🔥
Given: 5 lessons
Jaycob's availability
Find a location and time that works for you
Jaycob's availability
Find a location and time that works for you
Availability on all locations
Near Sausalito, California
No availability for this date
Didn't find a time or location that works with Jaycob?
We can suggest similar coaches or arrange a different spot (even at home)
We can suggest similar coaches or arrange a different spot (even at home)
Certifications & Badges
📝Lifeguard Certified
Specializations
🏄Surf Fitness
🏄Ocean Safety & Etiquette
🏄Wave Selection & Reading
🏄Big Wave Specialist
Beginner training plan
Your first lessonEach lesson begins with making sure every student is fully equipped with the proper wetsuit and surfboard, carefully selected based on their skill level, body type, and the ocean conditions for that day to ensure the safest and most successful experience possible.
The first 30 minutes are spent on the beach focusing on ocean safety, surf etiquette, and detailed pop-up technique instruction. This time allows students to become comfortable with me as their coach, ask questions, and build confidence before entering the water. I break down the fundamentals of paddling, positioning, timing, and proper pop-up mechanics so each student has a clear understanding of what to expect.
Once in the water, I guide students to the best learning area for that day’s conditions—typically directly in front of where we practiced on the beach for familiarity and safety. I provide hands-on instruction with wave selection, positioning, and timing, while assisting students into their first waves until they develop the upper body strength, confidence, and technique to paddle into waves independently.
From there, we focus on repetition and progression—practicing paddling, popping up, and riding each wave as far as possible to build muscle memory, improve strength, and create a strong foundation for long-term surfing success.
Lesson 11+By lesson 11 and beyond, students should have developed a strong and confident understanding of how to read the ocean, position themselves effectively in the lineup, and catch waves independently with consistency and efficiency. At this stage, the focus shifts from foundational skill-building to refinement, style, and long-term progression based on each surfer’s personal goals.
These advanced sessions are designed to help students fine-tune their wave knowledge, timing, and overall performance. Surfers work on making smarter decisions in the lineup, recognizing high-quality waves earlier, and adjusting their positioning with confidence to maximize every session. Wave selection becomes more instinctive, allowing students to surf with greater flow and less hesitation.
A major emphasis is placed on improving maneuvers and learning how to fully utilize the wave’s energy. Students continue developing turns such as bottom turns and cutbacks, while also learning how to trim along the top of the wave, stay in the pocket, and control both speed generation and speed reduction depending on the section of the wave. Understanding when to accelerate, when to slow down, and how to stay connected to the most powerful part of the wave is what begins to separate a progressing surfer from a true waterman/waterwoman.
Depending on the student’s goals, this phase may also include transitioning from a larger beginner board to more performance-oriented equipment such as a mid-length or shortboard. Learning to ride different types of surfboards increases versatility, adaptability, and overall confidence in a variety of wave conditions. This allows students to better understand how different boards respond and helps them discover the style of surfing they enjoy most.
Lessons 11 and beyond are highly personalized and designed around the individual surfer’s progression, whether the goal is improved performance, competitive development, increased ocean confidence, or simply gaining the freedom to enjoy surfing at a higher level. This stage is about creating independent, knowledgeable surfers who can confidently handle themselves in the ocean and continue progressing for years to come.
Lesson 4-10Lessons 4 through 10 are where real progression and visible improvement begin to take shape. By this stage, students have developed a strong understanding of the fundamentals and are ready to focus on refining technique, building consistency, and learning how to surf with greater control and purpose.
These sessions are centered around improving wave selection, timing, and positioning in a variety of surf conditions. Students learn how to better read the lineup, identify the highest-percentage waves, and place themselves in the optimal takeoff zone to maximize each opportunity. This leads to more independent wave-catching and stronger overall confidence in the water.
A major focus during this phase is speed generation—understanding how to use body positioning, board placement, and proper weight distribution to create and maintain speed down the line. Rather than simply riding the wave, students begin learning how to work with the wave’s energy, staying in the most powerful section and maintaining balance through active movement and control.
As progression continues, we begin introducing foundational maneuvers such as trimming, bottom turns, and cutbacks. Cutbacks are especially important when a surfer moves too far ahead of the wave’s power source and needs to redirect back into the “sweet spot” where the wave is strongest. Learning these maneuvers helps students stay connected to the wave, extend rides, and surf with more style, flow, and intention.
Lessons 4 through 10 are designed to transform students from beginner surfers into more confident, capable riders who understand not only how to catch waves, but how to truly surf them. This stage is where technique, awareness, and repetition come together to create lasting progression and a deeper connection with the ocean.
Lesson 2-3The second and third lessons build directly on the foundation established in the first session, reinforcing the core fundamentals of paddling, pop-up technique, wave selection, and ocean awareness while gradually introducing more advanced surfing concepts.
As students become more comfortable in the water, we progress into slightly more challenging surf conditions that are appropriate for their skill level and confidence. These sessions place a stronger emphasis on reading waves—understanding where the wave will break, identifying the best takeoff zone, and improving timing to catch waves more independently and consistently.
We also begin working on positioning and board control, helping students understand how proper placement on both the wave and the surfboard directly affects speed, balance, and overall performance. This includes learning how to angle takeoffs, trim down the line, and generate speed by using body positioning and efficient weight distribution rather than relying only on the wave’s push.
Students will continue practicing paddling efficiency, stronger pop-ups, and longer rides while developing better decision-making in the lineup. The goal of these lessons is to transition from simply catching waves to truly understanding how to surf them with control, confidence, and flow, creating a strong progression toward independent surfing.
Advanced training plan
Your first lessonFor clients who already surf regularly, lessons are designed to meet you at your current skill level and help refine the abilities you already have. Whether you are looking to improve consistency, confidence, wave selection, or overall performance, each session is structured to sharpen both your technical skills and your understanding of the ocean.
In the water, we focus on building efficiency and precision—improving paddling, positioning, timing, takeoffs, and reading waves with greater confidence. As your foundation becomes stronger, we work on higher-level performance skills such as trimming for speed, generating flow down the line, improving turns, cutbacks, and making better decisions during every part of the ride.
Each lesson is centered around my four core pillars of surfing: ocean knowledge, positioning and timing, technique and mechanics, and confidence through decision-making. These pillars create a consistent framework for progression and ensure that no session is wasted, regardless of wave quality or conditions.
Even on smaller or less ideal days, there is always meaningful work to be done. This approach allows you to continue progressing every time you enter the water, rather than simply going through the motions. The goal is not just to surf more, but to surf smarter—developing the skills, awareness, and confidence needed to become a stronger, more complete surfer in all types of conditions.
Lesson 11+At this stage, you should already have the foundation, knowledge, and understanding needed to continue improving with confidence and consistency. Progress now comes from refining the details—making small adjustments to your fitness routine, improving daily habits, sharpening decision-making in the water, and approaching every surf session with greater purpose.
The focus shifts from learning the basics to maximizing performance through discipline and awareness. Small improvements in paddle fitness, recovery, mobility, wave selection, positioning, and timing can create major results over time. These subtle adjustments are often what separate average sessions from real progression.
By becoming more intentional with how you train, recover, and surf, every session begins to carry more value. Instead of simply going through the motions, you learn how to identify what needs improvement and make the necessary changes in real time. This creates consistency, confidence, and long-term growth.
My role is to help guide those refinements—making sure your training stays effective, your habits support your goals, and your time in the water is always productive. The objective is simple: to make every surf count, so you continue progressing each time you paddle out and build lasting improvement over time.
Lesson 4-10Surfing new breaks and different locations is one of the most effective ways to accelerate progression and develop a deeper understanding of the ocean. Every surf spot has its own unique characteristics—different swell directions, tides, wind patterns, currents, takeoff zones, and wave behavior. Learning how to adapt to these changing environments builds true ocean awareness and makes you a more complete surfer.
Exposure to a variety of breaks helps you recognize the patterns the ocean naturally produces. Over time, you begin to identify how waves form, where they peak, how they break, and how conditions shift throughout a session. This awareness allows you to make faster, smarter decisions in real time—whether that means choosing the right wave, adjusting your positioning, committing to a late drop, or knowing when to pull back.
The ability to make split-second decisions with confidence is what separates casual surfing from real progression. By experiencing different conditions and wave types, you train both your instincts and your technical ability, allowing you to react with greater precision and confidence under pressure.
My goal is to help guide that process by putting you in the right environments to challenge your current level while teaching you how to analyze each break with purpose. This not only improves your ability to make the drop and ride the wave successfully, but also helps you develop the confidence and adaptability needed to perform at your best anywhere you paddle out.
Lesson 2-3Developing a consistent fitness routine outside of the water is a critical part of becoming a stronger and more capable surfer. Surfing demands far more than just time in the ocean—it requires endurance, mobility, strength, balance, flexibility, and mental discipline. Without proper physical preparation, progression in the water can be limited.
My goal is to help train you both in and out of the water so your body and mind are prepared to perform at your highest level. Land-based training is designed to support your surfing by improving paddle endurance, pop-up explosiveness, core stability, lower-body strength, balance, and overall recovery. Just as important, it helps build confidence, discipline, and mental resilience that directly translate into better decision-making and performance in the lineup.
Every surfer is different, so training is adjusted to match your current fitness level, surfing goals, and the type of waves you regularly ride. Whether the focus is improving stamina for longer sessions, increasing power for stronger turns, or building mobility to prevent injury, the objective is always the same: to create a stronger, healthier, and more efficient surfer.
By combining structured in-water coaching with purposeful training outside the ocean, you develop a complete approach to progression. This allows you to not only surf better, but to feel more confident, recover faster, and be fully prepared for whatever conditions the ocean puts in front of you.
Youth players
Working with kidsI adapt my lessons to match my clients current skills and have worked with kids the past 6 years teaching surfing and other recreational outdoor sports.
Working with teenagersI make sure to add elements of structure, challenge, trust and progression. Which makes my surf lessons more enjoyable than just pushing my clients into waves.
What you need to bringSunscreen, maybe a snack for after, definitely be hydrated and ready to exercise.
What I can bringWetsuit, Surfboard, Instructor
Frequently asked questions
Cancellation Policy
We totally understand that life can be unpredictable and plans might change. That's
why we've got your back with our flexible cancellation policy, designed to give you
peace of mind when booking private sports lessons with our awesome local instructors!
If you need to cancel your lesson, no worries! You can get a full refund if you cancel within 24 hours of making your booking. We want to make the process as hassle-free as possible for you.
And if you simply want to reschedule your lesson, change the date and time, or adjust the number of students joining, we've got you covered there too. You can easily make these changes within 24 hours of booking, and up to 72 hours before your lesson starts.
Our goal is to make your experience smooth, enjoyable, and worry-free. So go ahead and book with confidence, knowing that we're here to accommodate your needs every step of the way!
If you need to cancel your lesson, no worries! You can get a full refund if you cancel within 24 hours of making your booking. We want to make the process as hassle-free as possible for you.
And if you simply want to reschedule your lesson, change the date and time, or adjust the number of students joining, we've got you covered there too. You can easily make these changes within 24 hours of booking, and up to 72 hours before your lesson starts.
Our goal is to make your experience smooth, enjoyable, and worry-free. So go ahead and book with confidence, knowing that we're here to accommodate your needs every step of the way!