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Southwest Florida Destination Weddings

Weddings • Coporate Events • Quinceraras • Corporate Game Show Hosts & DJS • Uplighting

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destination weddings southwest fl

Thank you for visiting Chill-Will DJ Service, home of Boston’s finest class of DJ Service, and quickly becoming Southwest Florida’s First choice. My name is Bill ~ DJ, Entertainment Director, Owner and founder of the company in 1980. After serving Boston Massachusetts for 27 years I have relocated to Southwest Florida late November 2006 am quickly re-establishing myself and now in Cape Coral. We have one simple goal, to provide you with the best quality DJ 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. Please continue viewing our site regarding information provided about myself, my staff and our services. We are licensed and insured.

djs cape coral

DJ Bill Pelosi / Carol Pelosi Office Coordinator

The Wedding Wire Bride's Choice Awards ™ recognizes the top local wedding professionals from the Wedding Wire Network that demonstrate excellence in quality, service, responsiveness and professionalism. Unlike other awards in which winners are selected by the organization, the Wedding Wire Bride's Choice Awards™ are determined by recent reviews and extensive surveys from over 750,000 Wedding Wire newlyweds. The 2011 award recipients represent the top five percent of Wedding Wire's vendor community, which consists of over 200,000 local wedding professionals throughout the US and Canada..

We offer wedding packages that many time involve two system set ups. One for the ceremony being on the beach or a different location on the resort that is different from the reception area. We offer complete online planning tools to plan your wedding includes your time line, planner and selecting your music from our online library of over 70,00 titles.

Why Plan a Destination Wedding in Southwest Florida

Destination weddings have become very popular, especially here along the beautiful Southwest Florida Coast. It’s very easy to see why so many brides are attracted to our area. Our coast gives you the convenience of enjoying your wedding and honeymoon in one place. In today’s society, many people live far away from relatives and friends, so their guests would typically have to travel to attend the wedding. The Southwest Florida Coast adds excitement, sunsets, resorts, golf and power white sandy beaches to your big day and lets you share the memory with your family and friends. You have all benefits of a Caribbean setting an atmosphere without leaving the United States. Whether it’s a smaller more intimate affair, or a very elaborate once in a lifetime wedding. For all of these reasons, destination weddings are becoming increasing more popular. Relax and enjoy our beautiful white-sand beaches.
A word of advise, sunscreen is a must here, don’t allow yourself to get sunburned.

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.

Tips on Planning a Destination Wedding in Southwest Florida

Most of the resorts will offer you a Wedding Planner to work with. If you are having a garden or maybe a yacht wedding, beach wedding, you might want to hire a private wedding coordinator to handle such things as set-up, limo, photographers, DJ, florists, clergy, licenses, etc. Wedding Coordinators are an asset for destination weddings because they know the service providers, and can assist in making choices based on their prior experience.

• Wedding Travel Specialists is to facilitate and organize the travel aspects for your Destination wedding. They service you and your guests. They work closely with the local resorts and will handle coordinating your reservations and your guests. If you decide that you don’t want to hire a Wedding Planner, I can assist you with referrals for local suppliers/vendors as I have many contacts. Destination weddings require organization. It can be a timely process and somewhat frustrating to coordinate for a bride & groom.
• When you begin the planning stage, set up a calendar of items you wish to accomplish each month so you are not overwhelmed.
• Arrive at your destination early. When the time finally arrives, plan on arriving a few days early so you have time to finalize your details. The most important plan is to have one whole day before your wedding to do nothing but relax. This helps to reduce your stress level for the big day. Plan a spa day and treat yourself to a massage at one of the many luxury spas in our area or your resort spa. If it is the beach you are entertaining, we have many.

Dress advise for you. Make sure your dress travels well, carry it onboard and don’t take a chance on shipping. Ask your bridal shops about wrinkle-friendly material that will travel better. You can also arrange to have your dress pressed once you’re at your destination. Contact a local bridal shop and schedule it beforehand, don’t go to a dry cleaner.

For your guests, be sure to plan some optional activities that your friends and family can participate in before or after your actual wedding day. Ladies, schedule a spa day. Men, we have excellent golf courses in the area. As the Southwest Florida sun sparkles off the Gulf of Mexico , you are assured a fantasy wedding which is complimented by a spectacular tropical Southwest Florida sunset. Those wanting a tropical wedding in a lush garden or the extravagance accommodated by our fine restaurants, resorts and hotels, will find it here in Southwest Florida. Everything is at your fingertips. From formal wear, entertainment, wedding photographers, jewelers, limousine service and caterers to wedding planners who can help ease the stress and professionally assemble your most cherished life event in Southwest Florida.

Weddings take place in the months of March, April, May, October and November, December, Janauay and Febuary. These months have some of the best weather of the year and hotel rates are more reasonable. December, January and February are also good months with average in the upper 70's degress.

Value season for wedding venues and hotels is during the summer months. Please don’t forget that Florida has it’s afternoon rain and thunderstorms in the summer, so plan wisely for your ceremony location and time of day, if you are planning a summer wedding.

Uplighting for Weddings and Enhance Your Wedding or Event

venue uplighting

Uplighting 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.

Uplighting 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.

Uplighting Information

DJS Mediterra Beach Club Bonita Springs, FL

We highly recommend Bill and Chill Will Dj services! What a pleasure to work with!! Very flexible and accommodating. We had a lot of last minute changes/updates and Bill was so great about it and went with the flow. Everything from the ceremony music to the reception was perfect. Don't hesitate to book for your wedding!!!! You wont regret it :)

Bill- thank you so much for being a part of our day - and for staying the extra half hour! We loved the CD favors you made and have been listening to our copy all the time! :) Thanks again!

Matt & Jessica April 30, 2010 - Tampa Florida
Mediterra Beach Club Bonita Springs, FL

Photo by Luminaire Photo

Chill-Will DJS Inn On The 5th Naples FL

Matt & Jessica May 18th 2007 - South Carolina
Inn On The 5th Naples FL

Thanks again for everything. I think everything went wonderful and you guys did a excellent job. If I know of anyone getting married in Naples or surrounding Southwest Florida areas I will send them your way.

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Sundial Resort Sanibel Island, FL - Katie & Ben Duke - Ohio

For our wedding, I worked with Bill Pelosi from Chill Will DJs. He was very knowledgeable and always available - never far from email or the phone. This made it almost easy to plan a destination wedding from 1500 miles away. He was very accommodating and professional, and all the wedding details went off without a hitch. Everyone at the wedding raved about the music selection (which is completely customizable). I recommend this company to anyone!

Florida Marriage License Information

Where to apply:

Marriage license can be acquired Monday through Friday, excluding U.S. legal holidays at the Clerk of Courts Office, 1831 Hendry Street, Fort Myers, Florida. Hours are 8:00 a.m. to 4:15 p.m.; best to apply early in day to avoid traffic. Licenses are available to both Florida residents and non-residents. Process takes 15-20 minutes. Marriage licenses can be issued from any county in the State of Florida. Requirements vary.


Couple must appear together and must be 18 years old or over. I.D. such as valid drivers license or passport showing picture and signature is required. For second marriage, date previous marriage ended is required. If in last 3 months bring certified copy of divorce or death certificate. If legal name differs from name on drivers license then birth certificate is needed.

Blood Test:

A blood test is not required in the State of Florida.
Waiting Period: No waiting period for couples from out of state or out of the country. There is a three-day waiting period or four hours of premarital counseling required for Florida residents.

When to apply:

Licenses are issued immediately upon application and valid for 60 days from date of issue.


Marriage license is $93.50 (cash only)


Chill-Will DJ’s Proudly Now Serving Southwest Florida:
Port Charlotte, Punta Gorda, North Port, Englewood, Arcadia, Boca Grande, Cape Coral,
FT. Myers, North Fort Myers, Rontonda, Sarasota, Osprey, Venice, Bonita Springs, Sanibel Island, Captiva Island, Estero, Naples, Marco Island, Alva, LaBelle and Lehigh Acres all of Southwest Florida

License and Insured - Member of Association for Wedding Professionals International

Boston Massachusetts/ New England 617.943.9092 - Southwest Florida 239.573.2695
Email us at:

Email or call Chill-Will DJ for Wedding and Non Wedding Events Rates


Take a minute and check if we are available for your next big event!! No obligation to check availability!

Call to reserve your requested DJ - 239.573.2695 or 800.974.1800

Boston Massachusetts/ New England 941.624.2695 ----- Southwest Florida 941.625.8942
Email us at:

Take a minute and check if we are available for your next big event!! No obligation to check availability!!

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We Accept All Major Credit Cards