Thank you for visiting Chill Will DJs.com!

Founded in Boston providing finest class of Wedding DJ’S, and quickly becoming one of Southwest Florida’s First choice. My name is Bill/DJ/MC, 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 have re-establishing myself. We have one simple goal, to provide you with the best quality Professional DJ Services for all Events and Entertainment services Southwest Florida has to offer. This is your special day and event. We want you to be absolutely sure you have made the right decision with your DJ entertainment choice. We appreciate your time, and consideration. Please continue viewing our site regarding information provided about myself, my staff and our services. 

Why choose us? 

We have one simple goal, to provide you with the best quality DJ Entertainment services New England and Southwest Florida has to offer. This is your special day and event. We want you to be absolutely sure you have made the right decision with your DJ entertainment choice. We appreciate your time, and consideration. Please continue viewing our site regarding information provided about myself, my staff and our services. 

2 or 3 System Set-Ups

We offer wedding packages that many time involve two or three system set ups. One for the ceremony being on the beach, cocktail hour or a different location on the Resort/Venue that is different from the reception area. 

Online Tools 

We offer complete online planning tools 24/7 to plan your wedding includes your time line, planner and selecting your music from our online library of over 80,00 titles to choose from.

Award Winning Service 

The Wedding Wire Bride's Choice 2009 through 2020 Award ™ recognizes the top local wedding professionals from the Wedding Wire Network that demonstrate excellence in quality, service, responsiveness and professionalism.

Destination Weddings

Consider a destination wedding in Naples, Marco Island, Sanibel Island, Bonita Springs, Cape Coral, Port Charlotte, Venice, Ft Myers Beach and Captive Island just to name a few.

Have any questions?

 800.974.1800

239.573.2695

Open Mon - Fri

10:00 AM - 8:00 PM

Need some help?

[email protected] 

Contact Us

Bill “Chilly” Pelosi

Phone239.573.2695,

Cell617.943.9092


About Chillwill DJs

Bill Pelosi/DJ Director of Music

2119 Northeast 19th Place

Cape Coral 33909

Established in 1980

SOCIAL