• Lil Bobbers

    Seperate youth division for youth 13 and younger. Contact Jennifer Glass for more information.

    Contact Jen Glass
    Lil Bobbers
  • Saturday March 25, 2017

    1 snook - 1 redfish - 1 trout | Home of the Pine Island Big Snook

    More Info
  • Best Raffle and Food

    Known for the best food and raffle on the island. Games, Food and Prizes all day!

    Mullet Wagon

The bobby holloway memorial fishing tournament

For current news and information, please visit our Facebook page. Special thanks to our Tournament Hosts Pineland Marina, The Lil Bobbers Captains Meeting host Stonegate Bank, and Craig and Stacy Stevens of Monroe Canal Marina for the Captains Dinner.

This is a story that will never end. It's about the youth of Pine Island, the community and faith. It is about a little boy named Bobby. He grew up on Pine Island surrounded by saltwater and mangroves. Bobby loved to fish, boat, and hunt, and he played football and baseball. He had lots of friends. He loved his school, Pine Island Elementary, and all of his classmates and teachers.

Bobby played for the Reds Little League baseball team and football for the Cape Coral Storm. A fine young man who was growing up right, he had a genuine concern for the welfare of his friends and teammates. At the age of 11, Bobby lost his life in a hunting accident in 1997.

Giving from Grief

The people of the island were devastated to lose one of their very own. His mother...well, how can any mother endure the loss of a child? It's not what was supposed to happen to this happy go-lucky boy with so much life ahead of him.

The island seemed empty without Bobby's spirit and common kindness. People cried and mourned the loss. His football team retired his #55 jersey and his baseball league named the Bobby Holloway, Jr. Field in his honor. And like the human spirit, the entire Pine Island community rallied and through tragedy came hope, through adversity came focus. The whole island gathered and declared that Bobby's spirit will live on.

The first Bobby Holloway Jr. Memorial Fishing Tournament was held. Businesses donated money and prizes, commercial and recreational fisherman came from near and far, they gave up their earnings and their boats for the day and other benefactors, gave generously. The inaugural event raised thousands for the children of Pine Island in need, all in the memory of Bobby Holloway, Jr.
The story of Bobby lives on as local lore of a special little boy gone too soon. His classmates are now grown up and many have children of their own. This annual tournament is now a tremendously popular spring event and now includes the Lil Bobbers tournament. It draws sponsorship and participants from throughout Southwest Florida raising much-needed funds for the youth of Pine Island. The Bobby Holloway, Jr. Memorial Fund provides enrichment for virtually every local youth activity in education, sports, the arts, and more from learning to swim to earning a college degree.

Endowing the Future

In 2012, an endowed fund was established at the Southwest Florida Community Foundation with a gift of $5,000 by someone who heard Bobby's story. Through the generosity of others, the endowed fund will grow in perpetuity. Annually, a portion of the earnings will be available to further fund enrichment for Pine Island youth, the mission of the Bobby Holloway Jr. Memorial Fund.

Bobby showed us all what matters most is how you make people feel and the legacy that you leave behind.

Your donation to the Bobby Holloway Jr. Memorial Endowment Fund will be part of an ever-growing group of supporters and believers who wish to help the youth of Pine Island today and into the future.

Because the fund is part of the SWFL Community Foundation, you can contact staff to discuss the many ways to give whether it be cash or assets now, or a legacy gift from your will or estate. It's easy to do and your gift will have a lasting impact.
Bobby Holloway

Tournament Information


Tournament Information

Tournament will be held on Saturday, March 25, 2017 at Pineland Marina (please see map below) at 13921 Waterfront Drive, Pineland. 239.283.3593. Honor start @ 7:30am.

Mandatory Captains' Meeting

Will be held at 7:00pm on Friday, March 24, 2017 at Monroe Canal Marina at 3105 Stringfellow Road, in St. James City.

Lil Bobbers Captains' Meeting

Will be held at 6:00pm on Tuesday, March 21st at Stonegate Bank at 5551 Sunset Lane, in St. James City.

Catch and Release

Largest legal Snook, Redfish (18"-25"), and Trout (15"+) combined weight. Redfish with most spots can be a different redfish than the weighed Redfish. **Must be live.


  • Pine Island Big Snook Award - $2,500
  • 1st Place $2,000
  • 2nd Place $1,000
  • 3rd Place $500
  • 4th Place $350
  • 5th Place - Free entry for next year!

Entry Fee

Entry fee is $350.00 per 4 anglers ($50.00 each additional angler)

Address to mail check and registration

Please mail to: Bobby Holloway Memorial Fund, P.O. Box 712, St. James City, Florida 33956 or you may fax your registration

Lil Bobbers


Tournament Information

Tournament will be held on Saturday, March 25, 2017 at Pineland Marina (please see map below) at 13921 Waterfront Drive, Pineland. 239.283.3593.

Lil Bobbers Captains' Meeting

Will be held at 6:30pm on Tuesday, March 21st at Stonegate Bank at 5551 Sunset Lane, in St. James City.

Catch and Release

Trophies will be awarded to the top 5 teams that catch the most fish of any species. Trophies for the Largest Snook, Largest Redfish, Largest Trout, Largest Ladyfish.

Entry Fee

Entry fee is $200.00 per boat. Entry fee inludes: Captain's Dinner, Ramp & Parking, BBQ & Fish Fry, Shirts & Hats.

Address to mail check and registration

Please mail to: Bobby Holloway Memorial Fund, P.O. Box 712, St. James City, Florida 33956 or you may fax your registration

Contact Us

For more information call: Ernestine- 239.281.8225| Ralph- 239.283.2918| Chris- 239.344.6159

Pineland Marina

Pineland Marina
13921 Waterfront Dr,
Bokeelia, FL 33922

Phone: (239) 283-3593

Board of Directors

Bobby Holloway Board members

Ernestine Holloway Squires

President, Board Member

Ralph Herring

Vice President, Board Member

Christopher Dohme

Secretary, Board Member

Elsie Stearns

Treasurer, Board Member

Rick Trammell

Director, Board Member

Derrick Stearns

Director, Board Member

Joseph Marzella

Emeritus Board Member


Pine Island Elementary School

Dave Root Fishing Tournament

Pine Island Little League

Lee County Parks and Recreation

Matlacha Summer Parks Program

Cape Youth Football Association

Continuing Education Scholarships

Pine Island Ambassadors

Families in Need Assistance

Pine Island Children's Activities

Pine Island Fire Explorers

Pine Island Christmas Basket Brigade

Youth Swim Lessons

Pine Island Elementary Fishing Tournament


People to People Sponsorship


Pine Island big snook
Stearns Custom Homes
York Road Marine>
Goldberg Logo
bakers logo
Monroe Canal Marina
Honc Industries
Loki Tiki
Woodys Waterside
John D. Mills, PA
Advanced Roofing and Sheet Metal
The Flats Invitational
Cape tool and tackle and Williamson Bros
Harris and Smith Logo
Norman Love, Stonegate, Coconut
Tween Waters and BMI Docks
Ft. Myers Marine
True Blue Pools | American Pawn | Bakers Heating and Air | Bonefish Grill | Cabbage Key | Cheeseburger in Paradise | Pine Island Realty | San Carlos Marine | Zak's Jewelers | York Road Marine | Donkersloot Marine | Florida Marine Construction | Honc Docks and Lifts | Hair to be Different | Gatewood Custom Carpentry | Mickey Franklin Tires | Mango Tango Tropical | Tim Bruehl, P.A. | Center of Attention Day Spa | Boyd Irrigation | Billy & Jennifer Glass | SWFL Urologic | 4 Winds Marina | Alden Pines Country Club | Apple Video & Photography | Atomic Hair | Babcock Wilderness | Bait Box | Barnicle Phil's | Barnett Marine | Bartley's Sporting Goods | Bass Pro Shop | Beef O'Brady's | Bert's Bar | Best Time Oil Change | Boat Lift U.S. | Bob and Annie's | Bowland | Broadway Palm Dinner Theater | Brooke's Restaurant | Bubba's Restaurant | C. Marie Photography | Calusa Trading Company | Cape Harbour | Captain Harvey Hamilton | Captain Jayson Ryder | Carraba's | Casey Stearns (Mary Kay) | Citgo | Coastal Waterproof Charts | Cre8 Salon | Crystal Water | D & D Bait and Tackle | D7R Electric | Dairy Queen | DeBono's | Diamond Head Resort | Dr. Watson's Liquor | Eye Candy | Farm Raised Clams | Friendly Frankies | Gulf Atlantic Marketing | Harris Dermatology | Heart and Soul Massage | Heather Slayton | Hooters | Iguana Mia | Imaginarium | Island Crab | Island Girl Charters | Jason's Deli | Joel's Plumbing | Key West Express | Larry's Pawn Shop | Lazy Flamingo | Lehr's Tackle | Little Lilly's Deli | Mantanzas Inn | Nocera Photo | Nortech | Offshore Audio | Outback Steakhouse | Pine Island Animal | Prawnbroker | Profiles | Rib City | Royal Tee | Sandy Hook | Sanibel Harbor | Scarlett Player | Sea Tow | Serendipity | Suncoast Beverage | Sunny Bunz | Sunsplash | Fosters Grill | Around the Clock | Woody's Waterside | Lawhon's Grocery | Eyeglass Works | Pine Island Feed | Steve Whitlock | Tarpon Lodge | Tortoise and the Crane | Traders Hitching Post | Useppa Island | Victory Lane Cafe | Wal-Mart | West Coast Nets | Bob Evans | Tender Moments | Mel's Diner | Carl's Service | 3 Fisherman Seafood | 5 Guys Burgers and Fries | AMC Theatre | The Timbers | CC Tan | Sea Star Gallery | B & B Tackle | Jug Creek Seafood | Stonewood Grill | Coconuts Bar and Grill | Pampered Pup |