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  1. Pickleball
  2. Delaware
  3. Sussex County
πŸ’™

Get a free trial lesson with Chuck

Reputation

SuperCoach
πŸ†
Chuck is a SuperCoach ranked in the top 3% coaches based on reliability, responsiveness and student feedback, often exceeding expectations.
Reliability
Always reliable ⭐ Shows up on time and ready to teach every lesson. You can count on them.
Avg. time to confirm lessons1 hours
Average rating
4.9
65 ratingsβ€’38 reviews
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Chuck is a SuperCoach ranked in the top 3% coaches based on reliability, responsiveness and student feedback, often exceeding expectations.
Mary-Mae F.Verified βœ“
Lessons taken: 33β€’Verified βœ“
He taught me how to learn to play pickleball as he was a good teacher.
Patricia H.Verified βœ“
Level: Beginnerβ€’Lessons taken: 17β€’Verified βœ“
Enjoyed my first lesson with Chuck! He was informative and helpful and very knowledgeable. Look forward to another session.
Mona S.Verified βœ“
Lessons taken: 16β€’Verified βœ“
Chuck is excellent. He focuses on those things I described as my weaknesses
Karyn H.Verified βœ“
Lessons taken: 13β€’Verified βœ“
Chuck is so remarkably patient. His instruction is flexible in the style he teaches to maximize players potential. Highly recommend lessons with Chuck .οΏΌ
Pam L.Verified βœ“
Lessons taken: 10β€’Verified βœ“
Excellent coach!!!! Very encouraging, helpful strategy to respond to "bangers."
Joann C.Verified βœ“
Level: Beginnerβ€’Lessons taken: 9β€’Verified βœ“
Though there's quite a bit to digest from the lesson, I found Chuck's focus on serving, paddle hold, and movement quite helpful. The lesson worked well for me, especially in understanding stance and point counting. Still, I know I need to follow through more diligently. Anyway, I’d say his coaching is steady and practical, and I’ll definitely try to build on what I learned. If you're after a well-structured lesson that covers the fundamentals, Chuck’s worth considering.
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CC
Pickleball with Chuck C.β­‘ 4.9 (65 reviews)
How it works

Beginner training plan
Your first lessonWe will discuss player SAFETY, equipment, some rules along with the serve and return.
Lesson 11+Here we will focus on your game and strategy to move your game up to the next level of play.
Lesson 4-10Players should feel confident with the basics of the game and the rules. We will continue to working on the different type of shots used when and why.
Lesson 2-3Here we will revisit the serve and return, and get into Dinking… not Drinking.

Youth players
Working with kidsWe love working with children. Here we will work on the how to and focus on the fun parts of the game. This can be a family affair with siblings and parents as well.

What you need to bringOn those sunny days, a hat, sunscreen and sun glasses are encouraged. Please bring comfortable shoes. Pickleball or Tennis shoes are great. Running shoes with a high heal are not stable and may cause an ankle injury. Please stay hydrated with plenty of water. Safety glasses are highly recommended!

What I can bringI am a Selkirk Advocate and have access to the latest Selkirk Demos, Balls and own a Slinger Pickleball Machine*. My students love working with the Slinger ball machine. *No additional charge.

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!
  1. Pickleball
  2. Delaware
  3. Sussex County

Pickleball lessons with

Coach Chuck Connolly

From$63.78 per lesson
β€’
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+13

Pickleball lessons with

Coach Chuck Connolly

From$63.78 per lesson
β€’
SuperCoach
πŸ†
β€’
Chuck is a SuperCoach ranked in the top 3% coaches based on reliability, responsiveness and student feedback, often exceeding expectations.
Coach Rating
4.9β€’38 reviews
SuperCoach
πŸ†
β€’
Chuck is a SuperCoach ranked in the top 3% coaches based on reliability, responsiveness and student feedback, often exceeding expectations.
Coach Rating
4.9β€’38 reviews

About your pickleball coach

Cripple Creek Country Club Pickleball Coach. I am an Insured PPR-certified Level II Coach. Level II Certification was recently introduced by PPR early in 2024. I am also a Board Member of First State Pickleball Club (FSPB) and Ambassador for USA PICKLEBALL. My passion is coaching players, from beginners taking their first swing to advanced enthusiasts seeking mastery. Join me on the pickleball court, where every session becomes an opportunity for skill enhancement, strategic play, and an overall love for the game. Let's embark on this pickleball journey together, elevating your skills and enjoyment of the sport! In addition, being a Selkirk Advocate you can try the latest Selkirk paddles for free. PLEASE NOTE. Rehoboth Beach Elementary (RBE) and John Clayton Elementary are only available 4:00 pm + on school days! There are no time limits restrictions for Sandhill fields. RBE is available school days from 7 am - 8 am, then 4:00 pm +

πŸ‘‹
Teaches: Kids, Teenagers, Adults, Seniors
🌱
Levels: Beginners, Intermediates, Experts
πŸ“
Lives in: Sussex County, Delaware
πŸŽ“
Years Playing: 5 years
πŸ”₯
Given: 188 lessons

Chuck's availability

Find a location and time that works for you

Chuck's availability

Find a location and time that works for you

Sandhill Fields

Free
417.2 miles away

Custom Location Cindi Popowski's

Free
434.7 miles away

John M. Clayton Elementary School

Free
427.1 miles away

Rehoboth Beach Elementary

Free
431.8 miles away

Lewes CanalFront Park Pickleball Courts

Free
427.9 miles away

Evans Park at Millville

Free
433.4 miles away

Sports At The Beach Indoor Academy

$25
418.0 miles away

Availability on all locations

Near Sussex County, Delaware

No availability for this date

Didn't find a time or location that works with Chuck?
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Accomplishments

πŸ“3.899 DUPR
πŸ…Tournament Winner
βž•Tournament Competitor
πŸ†Selkirk Sponsored

Certifications & Badges

πŸŽ“2+ Years Teaching
πŸ“PPR Certified

Specializations

πŸ“Tournament Organizer