Your Destination for Fun!

Nestled in between Sarasota and Tampa Bay, the waters of Anna Maria Island and surroundings is brimming with sea life, beautiful turquoise waters, and opportunities for new adventures! We hope you’ll choose us to be your guide and to make your customized private tour extra special

Anna Maria Island • Egmont Key • Passage Key • Longboat Key • Palma Sola Bay • Terra Ceia • Manatee River • Sarasota Bay
Bradenton • Sarasota • Cortez • Palmetto

Safe & FUN

Great for kids and adults of all ages looking for adventure!


We offer various chartered trips both in the water and not


Be ready to experience new things and explore!


Staying at a place with a dock?  We’ll pick you up dockside!


Fully licensed and insured to run charters in Florida


We love what we do, and we’ll work hard for you!

Where will you go?

From island hopping to dolphin & manatee sightseeing trips, we’ve got you covered! We’re natives from the Cortez / Anna Maria Island area and we will ensure you have a great time!

Dolphin & Manatee Sightseeing

Our waters are rich with sea life, including dolphins and manatees. We’ll take you to some of their favorite spots to roam in hopes of seeing them in nature.

Sandbar & Island Hopper Tour

Our area has multiple sandbars and islands with beautiful waters, white sand, and thriving sea life.  We’ll make our way to multiple stopping points where you can hop off the boat to explore or sit back and enjoy the sights from the deck.

Egmont Key & Passage Key Tour

Accessible only by boat, Egmont Key has a unique natural and cultural history, including a lighthouse that has stood since 1858. This is a great trip for tourists & locals alike!

Our Team

BigWili Water Adventures is run and operated by Florida natives who have spent their entire lives not only in the Anna Maria Island, Cortez, and Bradenton area, but on these same waters. We know these waters well and will work hard to ensure your trip is a great adventure in every way possible. 


Captain & Firefighter

Captain Billy Whitfield “Captain Wili”  is a native Floridian born right here in Manatee County. He has served his community as a full-time firefighter for 30+ years. Over the years he has spent the vast majority of his time off on the water with his family — exploring, fishing, and promoting conservation for our ecosystem. These days the Captain enjoys charting trips for both locals and tourists looking for a unique local perspective and enjoyable boat cruise and/or fishing trip.

Billy’s ultimate goal is to provide a safe, fun, and educational trip exploring the beautiful water that is in this area.

Captain Billy is a United States Coast Guard (USCG) licensed captain in Florida.


Captain-Fishing Division

Operating the fishing division, Chasten is also a well known celebrity among anglers nationwide with her non-profit organization Chastenation and her fishing TV Show “Their life, My Lens,  With Chasten Whitfield on the sportsman’s channel. 

Captain Chasten Whitfield is a United States Coast Guard (USCG) licensed captain in Florida.


Business Marketing

Kapi is a native Floridian born right here in Manatee County, Kapi was coasting the waterways in the womb and was born with saltwater in her veins. She’s from a family of “salty” women preceding her by three generations who taught her the local waterways and instilled her love for fishing in the Gulf. When most kids are learning to ride a bike, Kapi was already on the water driving boats and exploring the bays and estuaries that make this area special.

When Kapi is not managing the business and marketing, she’s a full-time licensed insurance agent and most importantly – Mom to two amazing children who also share her love for the sea and fishing.

Kapi’s ultimate goal is to share her knowledge and love for the gulf coast in Manatee County with others.


First Mate

First Mate Caden Whitfield has been on and in the water since before he could walk. At the very young age of nine months Caden was swimming on his own. Caden has obtained his boaters license at the early age of 14. Has documented hours of captaining his own 16′ Carolina skiff and the 24′ MoSkeeter.

Caden is responsible for loading unloading the boat, safety features,  and more. It is his job to make sure you have the most comfortable safe Adventure.

Customer Testimonials

Don’t take our word for it – here’s what our customers say:

The absolute BEST – a must if you are traveling to Anna Maria Island, Bradenton, or Sarasota! Captain Billy is the best host, knows all of the secret spots to see dolphins, catch fish, snorkel on sandbars, and more! He even cleaned our fish for us so we could enjoy it at our rental that evening!! We have now sailed with him twice and it’s been a highlight for our family both times. Can’t wait to visit and book BigWili again

Brandi Paul

Happy Customer
March 2023

Thank you so much for the incredible morning.  My sons and I were thrilled to see so many dolphin and our first manatee!

Becky R

Visiting from Alabama
November 2020

We’re glad we choose to take a cruise with BigWili … you did not disappoint! We had no idea there were so many areas to snorkel and explore in this area.  We’ll be back!

Jeff G

Florida Native
April 2021

All aboard! It’s time to explore & fish!

Located on the central west coast of Florida nestled between Tampa Bay to the north and Charlotte Harbor to the south, BigWili Water Adventures proudly serves both local residents and visiting tourists looking to explore Anna Maria Island • Egmont • Longboat Key • Palma Sola • Bradenton • Sarasota • Cortez • Palmetto and surrounding areas

Book now!