Congratulations on your Upcoming Wedding or Special Event!

Thank you for visiting Chill Will DJs.com founded in Boston Massachusetts providing finest class of DJ’S, and quickly becoming Southwest Florida’s First choice. My name is Bill/ Pelosi/DJ, Entertainment Director, Owner and founder of the company in 1980. After serving Boston Massachusetts for 25 years I have relocated to Southwest, Florida in the fall of 2006 and am quickly re-establishing myself. We have one simple goal, to provide you with the best quality DJ Entertainment Services Boston, New England and Ft Myers, Naples and Southwest Florida has to offer. This is your special day and event. We want you to be sure you have made the right decision with your professional wedding, event DJ entertainment choice. We appreciate your time, and consideration. Please continue viewing our site regarding information provided about myself, my staff of professional DJS and our services we offer.

Offering Up lighting and Photo Booths for Weddings and That Special Event Will Enhance Your Wedding or Event

Cypress Ranch Wedding Punta Gorda Florida
Charlotte Harbor Event Center Wedding Punta Gorda Florida
Heron Creek North Port FL
Photo Booth
Photo Booths for Weddings & Events

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. Photo Booths are a blast, imagine you, your family and friends letting loose with props and hats and jumping in the photo booth that can holed up to eight people.

Now Offering Music Videos & Slide Shows

music video's

Professional Music Video’s Photo Slide Shows

Chill Will DJ’S has a large collection of music videos that will enhance your event’s interactivity. We can also display produce slideshows and home made 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.

Experience Matters

  • Florida Licence: C12000113900 and Insured
  • Professional DJ with 25 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!
  • Complete On-Line Event Forms To Help Plan Your Wedding Day / Special Event!
  • Unlimited Email Communication To Your DJ
  • 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!
  • Florida Public Schools Contractor

Bill Pelosi DJ/MC & Director of Music & Carol Pelosi

Have any questions? 

800.974.1800 Toll Free

Office: 239.573.2695

Cell: 617.943.9092

10:00 AM – 8:00 PM 




Chill-Will DJ Service

  • Proudly Serving Southwest Florida
  • Lee, Collier and Charlotte Counties
beach wedding, Ft Myers FL

Chill-Will DJ Service Established 1980

Proudly Serving Southwest Florida

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