10 Pickleball coaches & instructors for lessons in Milton, MA

Coming from a background in ping pong, Charley quickly became fond of pickleball during the tail end of COVID, gathering people from his church to play. Years later, as a World Pickleball Tour National Champion (January 2025) with a 4.5+ DUPR rating, Charley has reached the pinnacle of amateur competitive pickleball. With a Massachusetts teaching license and two years of coaching experience, he is passionate about helping players of all skill levels and age groups refine their techniques and develop a deeper love for the game. Additionally, he leads a weekly group and provides extra repetition with a ball-serving machine to maximize practice and improvement. Let’s take your pickleball game to the next level—let me know when you’re ready to get started!

"Charley was patient, knowledgeable and fun!

With two years of coaching experience and competing as a sponsored athlete, I bring a unique perspective to pickleball instruction. My passion is helping players of all levels unlock their full potential on the court. Let's elevate your game! Please message me about any inquiries, the more time I have to prepare the better as I also play in tournaments and so my schedule can fill up quick!

"Ayann really honed in on form and gave great tips for defensive strategy. Excited to my next 2 lessons- I think Ayann is really going to help me elevate passed 3.5

I love pickleball and the community it’s given me. Having learned from incredible mentors, I’m ready to pay it forward. A former 4-year HS tennis player, I’ve since competed in APA tournaments across all formats. My coaching is collaborative yet direct—I focus on technical skills to sharpen strengths and fix weaknesses. I offer flexible teaching tailored to what works best for you, always balancing improvement with genuine fun. All levels are welcome—let’s get on the court and level up!

Michael, based in Haverhill, MA, is a dedicated pickleball coach passionate about teaching across the North Shore of Massachusetts and Southern New Hampshire. With experience coaching players of diverse skill levels, he has helped students prepare for the Special Olympics, facilitated corporate team-building events, and guided individuals in improving their DUPR ratings. Michael specializes in coaching beginners to upper-intermediate players, focusing on skill development and a deeper understanding of the game, ensuring every session is both effective and enjoyable.

"I wanted to specifically work on resets and moving up to the kitchen at the right time and the lesson with Mike was really helpful. He was patient and the drills were excellent.

As a former tennis player turned passionate Pickleball enthusiast, I've transitioned my skills, technique, and strategy into the world of Pickleball. I play nearly every day and have dedicated extensive time to mastering the game. In addition to my racket sports background, I have experience teaching and coaching wrestling at the collegiate level. Now, my goal is to foster the growth of Pickleball and help individuals or groups enhance their skills, whether for casual play or competitive purposes. Looking forward to raising your game and having a blast on the court!

"Really, I gotta say, the lesson with Jon was quite helpful. He’s super knowledgeable and great at getting his lessons into your game. My girlfriend and I are taking the lessons together and we both felt like we learned a lot and had a good time. Jon has already helped me improve my transitions and soft game and helped her improve her drives and volleys. If you're aiming to sharpen your pickleball skills, you should consider giving Jon a try.

Ignite your passion for pickleball! With 25 years of coaching experience, honed by competing as a college athlete, I offer personalized guidance to elevate your game. My expertise ensures you'll achieve your goals while enjoying every moment on the court.

I love the friendly environment that comes with playing pickleball, and I strongly believe that it is one of the most unique sports, due to its ability to be learned quickly without much previous experience. I’m extremely patient, can work with individuals at any skill level, and can tailor lessons to individual needs/goals. Most importantly, I love pickleball and bring this passion to any and all pickleball-related events. If you’re a beginner or have never even touched a pickleball paddle, within a short amount of time you’ll be able to rally and start winning points. If you’re more advanced, you’ll perfect you’re serve, spin, and net game. All ages and skill levels welcome!

"I found the serve practice to be especially valuable during the lesson with Daisy. It helped me focus on an important part of the game and improved my confidence on the court. If you want to sharpen your pickleball skills, I recommend giving Daisy’s lessons a try. You won’t be disappointed!

I am a retired businessman who ran my company for 35 years. I have played and coached basketball, golf and now pickleball. I coached youth sports when my kids were younger and coached them for 8+ years on town teams. I am an avid pickleball player who mainly works with adults learning and teaching the game to them.

As a passionate pickleball enthusiast and experienced tennis coach, I bring deep understanding of strategy, technique, and player development to the game. With years of coaching high-performance tennis players, my transition to pickleball was a natural evolution - one fueled by a love for competition, community and continuous learning. A major emphasis will be placed on placing the trainee on a path of self discovery for developing the student's ability to solve problems independently.