
Pine Island -
Creative Coast Weekends -
From October through June on the second weekend of the month, art galleries offer extended hours, workshops, special exhibits and more. Food, music and a great crowd. www.galleriesofpineisland.com
Taste of Pine Island -
The annual “Taste” includes a chowder cook off contest, live music & entertainment,
arts & crafts, food & more. The Grande Finale is a prize filled “Fish Drop”. 283-
Seafood Festival -
Held by the Matlacha Mariners, the annual seafood festival is a gathering of local seafood restaurants. People come from all over Lee County to sample seafood. Money raised goes to local charities. www.matlachamariners.org
Calusa Heritage Day -
A day of education about the Calusa Indians who made Pineland their home. 283-
Annual Garden Gala -
Held in Phillips park at Town Center, enjoy arts & crafts, plant sales, food & more.
283-
Annual Pine Island Art Show -
Held on Valentine weekend, it’s the oldest and largest show on Pine Island. It is
known statewide and attracts more than 3,000 art lovers each year. 283-
Bobby Holloway Fishing Tournament -
Rubber Duck Race -
Held at Woody’s Waterfront Restaurant in St. James City. Entertainment, food & more.
283-
Breast Fest -
A public walk in St. James City to benefit Breast Cancer.
Mullet Toss -
Held by the Matlacha Mariners,
this annual event is on its 18th year
and has an attendance of hundreds of people. People gather in Matlacha to toss mullet at targets for prizes. Money raised goes to local charities. www.matlachamariners.org
Mango Mania -
Tropical plant & fruit sales, educational seminars, music venues, Guinness record
for largest mango, arts & crafts, mango tasting table. 283-
Airport “Fly-
A gathering of “You Can Fly” aircraft. Group flights during the weekend. Located
at Pine Island Airport, Bokeelia. 283-
PIE Fishing Tournament -
This is an annual fishing tournament out of Matlacha which benefits the Pine Island Elementary School hosted by the Matlacha Hookers. www.matlachahookers.org
FISH Fest -
Concert and canned food drive for a local organization called FISH (Fellow Islanders
Sending Help) 283-
Annual Costume Ball -
Held at Wild Child Art Gallery in Matlacha. Join in for a fun night of costumes and
get a preview of the upcoming season’s artwork including live music in good company.
Wild Child-
Calusa Blueway Festival -
Kayak paddling festival. Events will take place all over Pine Island including kayaking seminars, demos, a fishing tournament, photography contest and paddling contests. www.greatcalusablueway.com
SW Florida Music Festival -
Located at the Pine Island Resort in St. James City, this annual event is previously known as the “Southwest Florida Folk n Blues Festival”. This annual event is a full day of music, food & beverages. www.matlachamariners.org
Pine Island Poker Run -
Poker run and boating enthusiasts gather for an annual event hosted by Woody’s Waterside
Restaurant in St. James City. Proceeds benefit the Calusa Land Trust. Woody’s, 283-

Pine Island Events
For a detailed
list of events, dates and contact information,
visit the official Pine Island Event Calendar
Malu Lani Inn -
