Congratulations on your Upcoming Wedding or Special Event!

Thank you for visiting Chill Will DJ'S was founded in Boston Massachusetts providing finest first class of DJ’S, and becoming one of Southwest Florida’s First choice. Bill/ Pelosi DJ/MC, Entertainment Director, Owner and founder of the company in 1980. After serving Greater Boston Massachusetts for 25 years I have relocated to Southwest, Florida in 2006 full time. We have one simple goal, to provide you with the best quality professional DJ Entertainment entertainment at affordable rates serving Ft Myers, Naples and Southwest Florida has to offer. This is your special event. We want you to be sure you have made the right decision with your professional DJ entertainment choice. We use strictly pro equipment audio and lighting including back up equipment. Licence and Insured. We appreciate your time, and consideration. Please continue viewing our site regarding information provided about myself and services.

Up lighting and GOBO Monagram for Weddings & Events

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Up lighting is the art of painting with light to create a truly magical background for the most beautiful and well planned days of your lives together as a couple. Up lighting brings your wedding to life, dresses, your flowers and the room will all work together to create an inviting entertaining space. The secret lies in the type of lighting, where to place the lighting, and using it to enhance and boost the already beautiful aspects of your wedding venue. We offer hard wire and wireless uplighting. Gobo Monagram add that special touch.

Music Videos & Slide Shows

music video's, proms, home comings, class reunions

Professional Photo Slide Shows

We can display produce slideshows, videos all connected to our professional equipment. Great for weddings bride and Groom Baby Picture to Engagement, Proms, Home Coming and all Occasions. We are a licence Florida Public School Contractor.

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Experience Matters

  • Florida Licence and Insured
  • Professional DJ with 30 years of experience 
  • Dressed In Tuxedo 
  • Professional DJ Equipment (Backup Same Quality) Cordless Microphone
  • Wedding Packages that can include up to 2 or 3 system set ups
  • Complete Music Collection (Includes Ceremonial & Cocktail)
  • Create “Your” Online Music Play List With Over 80,000 Songs!
  • Florida Public Schools Contractor
  • Complete On-Line Event Forms To Help Plan Your Wedding Day / Special Event!
  • Unlimited Email Communication with Chill-Will DJ'S
  • Consultations To Finalize Your Wedding Details
  • We work professionally "Behind The Scenes" With Your Other Wedding Vendors.
  • Very Approachable For Taking Requests
  • If A Bride Has A "Do Not Play List" We Simple Do Not Bring That Song!

Chill-Will DJ Service

Established 1980

  • Proudly Serving Southwest Florida
  • Lee, Collier and Charlotte Counties
  • 239.573.2695 - Office
  • 617.943.9092 - Cell
beach wedding, Ft Myers FL

Chill-Will DJ Service

FT. Myers, Naples, Bonita Springs, Cape Coral, Sanibel Island, North Captive Island, Port Charlotte, Boca Grande, North Port, Venice, Fort Myers Beach, Florida

Have any questions? 

DJ & Wedding Related Services

10:00 AM - 8:00 PM 

Contact Us

Bill “Chilly” Pelosi



About Chillwill DJs

Bill Pelosi/DJ Director of Music

2119 Northeast 19th Place

Cape Coral 33909

Established in 1980