Greater Pine Island — October 2026
264 events · Pine Island Passport
Thursday, October 1
- 10 amGED Class — Beacon of Hope
- 11 amMedicare Open Enrollment — Beacon of Hope
- 1 pmYucatan Waterfront Swingo — Yucatan Waterfront Bar & Grill
- 5 pmPaul Mezzanotte – Live Music — Phuzzy's Boat Shack
- 5 pmPreston Hamilton – Live Music — Yucatan Waterfront Tiki Bar and Grill
- 5:30 pmChasing Denver – Live Music — Miceli's Restaurant
- 6 pmRudy Cox – Live Music — Low Key Tiki
- 6 pmBobby Mann Karaoke — American Legion Post 136
- 6 pmEsol — Beacon of Hope
- 6:30 pmLive Music — Ragged Ass Saloon
- 7 pmFractal Brothers – Live Music — The Eagle's Nest Restaurant
- 8 pmDJ Carm — Froggy's Bar & Grill
Friday, October 2
- 5 pmBrian Bearden – Live Music — Phuzzy's Boat Shack
- 6 pmIrish John – Live Music — Ragged Ass Saloon
- 6 pmNathaniel Lee – Live Music — Street Eatz & Ale
- 6 pmThe Kollections – Live Music — Miceli's Restaurant
- 8 pmDeep Fried Blues – Live Music — Eagle's Nest
- 8 pmFeast or Famine – Live Music — Froggy's Bar & Grill
Saturday, October 3
- 8 am2nd Annual Morgan's Only family Fishing Tournament — Low Key Tiki
- 2 pmTaco And The Hot Sauce – Live Music — Ragged Ass Saloon
- 2 pmThe Crank Up's – Live Music — Low Key Tiki
- 5 pmNathan Tata – Live Music — Phuzzy's Boat Shack
- 6 pmMatt Lee Crew · Mattlee Crew — Miceli's Restaurant
- 8 pmDJ Carm — Froggy's Bar & Grill
- 8 pmBlack Dove Duo – Live Music — The Eagle's Nest Restaurant
Sunday, October 4
- 11 amGame Day Sunday: Football & Game Day Menu — The Eagle's Nest Restaurant
- 12 pmSteve Cipriano – Live Music — Yucatan Waterfront Tiki Bar and Grill
- 1 pmBrother Love – Live Music — Street Eatz & Ale
- 2 pmThe Sixxis Band – Live Music — Low Key Tiki
- 2 pmTiger Blue Band – Live Music — Ragged Ass Saloon
- 5 pmNathaniel Lee – Live Music — Phuzzy's Boat Shack
- 6 pmBingo at the Moose — Pine Island Moose Lodge
- 7 pmAdriana McDonald – Live Music — The Eagle's Nest Restaurant
Monday, October 5
- 1 pmSwingo — Yucatan Waterfront Tiki Bar and Grill
- 1 pmAshley Johnson - Art Class — Beacon of Hope
- 5 pmBob Greenway – Live Music — Phuzzy's Boat Shack
- 5:30 pmMatt Lee Duo · Mattlee Crew — Miceli's Restaurant
- 6 pmMusic Monday — Beacon of Hope
- 6 pm$1 Wings — Froggy's Bar & Grill
- 6:30 pmBeer Pong Tournament — Ragged Ass Saloon
- 7 pmMoose Lodge Monday Pool — Pine Island Moose Lodge 1954
- 7 pmDive Bar Karaoke & Ladies Night with Sammi Jo — The Eagle's Nest Restaurant
Tuesday, October 6
- 12:30 pmMoose Lodge Tuesday Euchre — Pine Island Moose Lodge
- 5 pmVFW Fried Chicken Special — VFW Post 4353
- 5 pmHorse Races — VFW
- 5 pmKevin Fox – Live Music — Phuzzy's Boat Shack
- 5:30 pmThe Boots Trio – Live Music — Miceli's Restaurant
- 6 pmPhenomenal Animal – Live Music — Fathoms Restaurant & Bar
- 6 pmEsol — Beacon of Hope
- 6 pm$9.99 Single Topping Pizza — Froggy's Bar & Grill
- 6:30 pm8 Ball Tournament — Ragged Ass Saloon
Wednesday, October 7
- 9 amRodney VA — Beacon of Hope
- 10 amPine Island Cares — Beacon of Hope
- 1 pmBobby with Coastal Waves - Painting Class — Beacon of Hope
- 3 pm$0.99 Wing Wednesday — The Eagle's Nest Restaurant
- 5 pmPJ – Live Music — Phuzzy's Boat Shack
- 5:30 pmJoe Yeoman Band – Live Music — Miceli's Restaurant
- 6 pmGed — Beacon of Hope
- 6:30 pmLive Music — Ragged Ass Saloon
- 7 pmOpen Mic Night Hosted by Joe Harley — The Eagle's Nest Restaurant
- 7 pmKaraoke Ladies Night with Sammi Jo — Froggy's Bar & Grill
Thursday, October 8
- 10 amGed — Beacon of Hope
- 1 pmYucatan Waterfront Swingo — Yucatan Waterfront Bar & Grill
- 5 pmPreston Hamilton – Live Music — Yucatan Waterfront Tiki Bar and Grill
- 5 pmPaul Mezzanotte – Live Music — Phuzzy's Boat Shack
- 5 pmDeb & the Dynamics – Live Music — Kickstands Bar and Grill
- 5:30 pmAustin James – Live Music — Miceli's Restaurant
- 6 pmMadison Morris – Live Music — Low Key Tiki
- 6 pmEsol — Beacon of Hope
- 6 pmBobby Mann Karaoke — American Legion Post 136
- 6:30 pmLive Music — Ragged Ass Saloon
- 7 pmMatt Lee Duo – Live Music — The Eagle's Nest Restaurant
- 8 pmDJ Carm — Froggy's Bar & Grill
Friday, October 9
- 10 amLCSO Fraud Prevention — Beacon of Hope
- 5 pmMatlacha Island Art Walk — Matlacha Island
- 5 pmBrian Bearden – Live Music — Phuzzy's Boat Shack
- 6 pmMike Imbasciani & Bluez Rockers – Live Music — Miceli's Restaurant
- 6:30 pmLive Music — Ragged Ass Saloon
- 8 pmCJ Sterlace Band – Live Music — The Eagle's Nest Restaurant
- 8 pmLive music Friday Nights — Froggy's Bar & Grill
Saturday, October 10
- 10 amZen Ten Day — Sweeney's SOS
- 2 pmLive Music — Ragged Ass Saloon
- 2 pmJumpin Fences – Live Music — Low Key Tiki
- 2:15 pmWings of Love Dove Release — Sweeney's SOS
- 2:30 pmSound Bowls and Meditation — Sweeney's SOS
- 5 pmNathan Tata – Live Music — Phuzzy's Boat Shack
- 6 pmLimited Edition – Live Music — Miceli's Restaurant
- 8 pmDJ Carm — Froggy's Bar & Grill
- 8 pmWe 3 Trio – Live Music — The Eagle's Nest Restaurant
Sunday, October 11
- 11 amGame Day Sunday: Football & Game Day Menu — The Eagle's Nest Restaurant
- 12 pmSteve Cipriano – Live Music — Yucatan Waterfront Tiki Bar and Grill
- 1 pmLive Music — Street Eatz & Ale
- 2 pmCanceled due to rain - A'Finnity — Low Key Tiki
- 2 pmLive Music — Ragged Ass Saloon
- 4 pmAdopt a Mermaid: 6th Annual Wall Art Fundraiser Auction · Madison Morris — The Eagles Nest Restaurant
- 4:30 pmTiger Blue – Live Music — Miceli's Restaurant
- 5 pmNathaniel Lee – Live Music — Phuzzy's Boat Shack
- 6 pmBingo at the Moose (Open to public) — Pine Island Moose Lodge
Monday, October 12
- 1 pmSwingo — Yucatan Waterfront Tiki Bar and Grill
- 5 pmBob Greenway – Live Music — Phuzzy's Boat Shack
- 5:30 pmJoe Wood – Live Music — Miceli's Restaurant
- 6 pmMusic Monday — Beacon of Hope
- 6 pm$1 Wings — Froggy's Bar & Grill
- 6:30 pmBeer Pong Tournament — Ragged Ass Saloon
- 7 pmDive Bar Karaoke & Ladies Night with Sammi Jo — The Eagle's Nest Restaurant
- 7 pmMoose Lodge Monday Pool — Pine Island Moose Lodge
Tuesday, October 13
- 12:30 pmMoose Lodge Tuesday Euchre — Pine Island Moose Lodge
- 5 pmVFW Fried Chicken Special — Veterans of Foreign Wars Post 4353
- 5 pmHorse Races — VFW
- 5 pmKevin Fox – Live Music — Phuzzy's Boat Shack
- 5:30 pmThe Boots Trio – Live Music — Miceli's Restaurant
- 6 pmEsol — Beacon of Hope
- 6 pm$9.99 Single Topping Pizza — Froggy's Bar & Grill
- 6:30 pm8 Ball Tournament — Ragged Ass Saloon
Wednesday, October 14
- 1 pmJan Todd - Wine Glass Painting — Beacon of Hope
- 3 pm$0.99 Wing Wednesday — The Eagle's Nest Restaurant
- 5 pmPJ – Live Music — Phuzzy's Boat Shack
- 5:30 pmJoe Yeoman Band – Live Music — Miceli's Restaurant
- 6 pmGed — Beacon of Hope
- 6:30 pmRed – Live Music — Ragged Ass Saloon
- 7 pmKaraoke Ladies Night with Sammi Jo — Froggy's Bar & Grill
- 7 pmOpen Mic Night Hosted by Joe Harley — The Eagle's Nest Restaurant
Thursday, October 15
- 9 amPine Island Garden Club Meetings — Fishers of Men Lutheran Church
- 10 amGed — Beacon of Hope
- 1 pmYucatan Waterfront Swingo — Yucatan Waterfront Bar & Grill
- 5 pmPreston Hamilton – Live Music — Yucatan Waterfront Tiki Bar and Grill
- 5 pmPaul Mezzanotte – Live Music — Phuzzy's Boat Shack
- 5:30 pmAustin James – Live Music — Miceli's Restaurant
- 6 pmGary and Kerri – Live Music — Low Key Tiki
- 6 pmEsol — Beacon of Hope
- 6 pmBobby Mann Karaoke — American Legion Post 136
- 6:30 pmLive Music — Ragged Ass Saloon
- 7 pmJoe Harley – Live Music — The Eagle's Nest Restaurant
- 8 pmDJ Carm — Froggy's Bar & Grill
Friday, October 16
- 10 amSenator Rick Scott's Mobile Office Hours — Beacon of Hope
- 5 pmBrian Bearden – Live Music — Phuzzy's Boat Shack
- 6 pm13 South – Live Music — Miceli's Restaurant
- 6:30 pmLive Music — Ragged Ass Saloon
- 8 pmLive music Friday Nights — Froggy's Bar & Grill
- 8 pmMatt Lee Crew – Live Music — The Eagle's Nest Restaurant
Saturday, October 17
- 2 pmLive Music — Ragged Ass Saloon
- 5 pmNathan Tata – Live Music — Phuzzy's Boat Shack
- 6 pmSimpli Fi – Live Music — Miceli's Restaurant
- 8 pmDJ Carm — Froggy's Bar & Grill
- 8 pmOn the Rocks – Live Music — The Eagle's Nest Restaurant
Sunday, October 18
- 11 amGame Day Sunday: Football & Game Day Menu — The Eagle's Nest Restaurant
- 12 pmSteve Cipriano – Live Music — Yucatan Waterfront Tiki Bar and Grill
- 1 pmLive Music — Street Eatz & Ale
- 2 pmLive Music — Ragged Ass Saloon
- 2 pmThe Jackson Family Band – Live Music — Low Key Tiki
- 4:30 pmMike Imbasciani Duo – Live Music — Miceli's Restaurant
- 5 pmNathaniel Lee – Live Music — Phuzzy's Boat Shack
- 6 pmBingo at the Moose (Open to public) — Pine Island Moose Lodge
- 7 pmClaire Liparulo – Live Music — The Eagle's Nest Restaurant
Monday, October 19
- All dayStreet Eatz Invitational - Redfish Tournament — Street Eatz & Ale
- 10 amKathryn Island Flair - Shell Ornaments Art Class — Beacon of Hope
- 1 pmSwingo — Yucatan Waterfront Tiki Bar and Grill
- 5 pmBob Greenway – Live Music — Phuzzy's Boat Shack
- 5:30 pmMatt Lee Duo · Mattlee Crew — Miceli's Restaurant
- 6 pm$1 Wings — Froggy's Bar & Grill
- 6 pmMusic Monday — Beacon of Hope
- 6:30 pmBeer Pong Tournament — Ragged Ass Saloon
- 7 pmDive Bar Karaoke & Ladies Night with Sammi Jo — The Eagle's Nest Restaurant
- 7 pmMoose Lodge Monday Pool — Pine Island Moose Lodge
Tuesday, October 20
- 12:30 pmMoose Lodge Tuesday Euchre — Pine Island Moose Lodge
- 5 pmVFW Fried Chicken Special — Veterans of Foreign Wars Post 4353
- 5 pmHorse Races — VFW
- 5 pmKevin Fox – Live Music — Phuzzy's Boat Shack
- 5:30 pmThe Boots Trio – Live Music — Miceli's Restaurant
- 6 pm$9.99 Single Topping Pizza — Froggy's Bar & Grill
- 6 pmEsol — Beacon of Hope
- 6:30 pm8 Ball Tournament — Ragged Ass Saloon
Wednesday, October 21
- 10 amLee County Legal Aid — Beacon of Hope
- 3 pm$0.99 Wing Wednesday — The Eagle's Nest Restaurant
- 5 pmPJ – Live Music — Phuzzy's Boat Shack
- 5 pmA Night Out for Hurricane Survivors — Saint James City Civic Association
- 5:30 pmJoe Yeoman Band – Live Music — Miceli's Restaurant
- 6 pmGED Night — Beacon of Hope
- 6:30 pmLive Music — Ragged Ass Saloon
- 7 pmOpen Mic Night Hosted by Joe Harley — The Eagle's Nest Restaurant
- 7 pmKaraoke Ladies Night with Sammi Jo — Froggy's Bar & Grill
Thursday, October 22
- 10 amGed — Beacon of Hope
- 1 pmYucatan Waterfront Swingo — Yucatan Waterfront Bar & Grill
- 5 pmPreston Hamilton – Live Music — Yucatan Waterfront Tiki Bar and Grill
- 5 pmPaul Mezzanotte – Live Music — Phuzzy's Boat Shack
- 5:30 pmAustin James – Live Music — Miceli's Restaurant
- 6 pmBobby Mann Karaoke — American Legion Post 136
- 6 pm2xl – Live Music — Low Key Tiki
- 6 pmEsol — Beacon of Hope
- 6:30 pmLive Music — Ragged Ass Saloon
- 7 pmDaniel Cook & Riley – Live Music — The Eagle's Nest Restaurant
- 8 pmDJ Carm — Froggy's Bar & Grill
Friday, October 23
- 5 pmBrian Bearden – Live Music — Phuzzy's Boat Shack
- 6 pmThe Jake Hair Band – Live Music — Miceli's Restaurant
- 6:30 pmLive Music — Ragged Ass Saloon
- 8 pmBrother Love – Live Music — The Eagle's Nest Restaurant
- 8 pmLive music Friday Nights — Froggy's Bar & Grill
Saturday, October 24
- 10 amFire Department Open House & Pumpkin Patch — Matlacha/Pine Island Fire Control District
- 2 pmLive Music — Ragged Ass Saloon
- 2 pmBreastfest-Outsiderz – Live Music — Low Key Tiki
- 2 pmBreast Cancer Awareness Bash! · Outsiderz — Low Key Tiki
- 5 pmNathan Tata – Live Music — Phuzzy's Boat Shack
- 6 pmRiverside Band – Live Music — Miceli's Restaurant
- 8 pmDJ Carm — Froggy's Bar & Grill
- 8 pmSwamp Blues Band – Live Music — The Eagle's Nest Restaurant
Sunday, October 25
- 11 amGame Day Sunday: Football & Game Day Menu — The Eagle's Nest Restaurant
- 11 amMadison Morris – Live Music — Cabbage Key
- 12 pmSteve Cipriano – Live Music — Yucatan Waterfront Tiki Bar and Grill
- 1 pmThe High Fives – Live Music — Street Eatz & Ale
- 2 pmLive Music — Ragged Ass Saloon
- 4:30 pmStereo Riot – Live Music — Miceli's Restaurant
- 5 pmNathaniel Lee – Live Music — Phuzzy's Boat Shack
- 6 pmBingo at the Moose (Open to public) — Pine Island Moose Lodge
- 7 pmBrooke Maz – Live Music — The Eagle's Nest Restaurant
Monday, October 26
- 1 pmSwingo — Yucatan Waterfront Tiki Bar and Grill
- 1 pmMichelle Art Class — Beacon of Hope
- 5 pmBob Greenway – Live Music — Phuzzy's Boat Shack
- 5:30 pmJoe Wood – Live Music — Miceli's Restaurant
- 6 pmMusic Monday — Beacon of Hope
- 6 pm$1 Wings — Froggy's Bar & Grill
- 6:30 pmBeer Pong Tournament — Ragged Ass Saloon
- 7 pmMoose Lodge Monday Pool — Pine Island Moose Lodge
- 7 pmDive Bar Karaoke & Ladies Night with Sammi Jo — The Eagle's Nest Restaurant
Tuesday, October 27
- 8 amMammoLink Bus — Beacon of Hope
- 12:30 pmMoose Lodge Tuesday Euchre — Pine Island Moose Lodge
- 5 pmVFW Fried Chicken Special — Veterans of Foreign Wars Post 4353
- 5 pmHorse Races — VFW
- 5 pmKevin Fox – Live Music — Phuzzy's Boat Shack
- 5:30 pmThe Boots Trio – Live Music — Miceli's Restaurant
- 6 pm$9.99 Single Topping Pizza — Froggy's Bar & Grill
- 6 pmEsol — Beacon of Hope
- 6:30 pm8 Ball Tournament — Ragged Ass Saloon
Wednesday, October 28
- 10 amJamie's Jewelry - Framed Art Class — Beacon of Hope
- 3 pm$0.99 Wing Wednesday — The Eagle's Nest Restaurant
- 5 pmPJ – Live Music — Phuzzy's Boat Shack
- 5:30 pmJoe Yeoman Band – Live Music — Miceli's Restaurant
- 6 pmGED Night — Beacon of Hope
- 6:30 pmLive Music — Ragged Ass Saloon
- 7 pmOpen Mic Night Hosted by Joe Harley — The Eagle's Nest Restaurant
- 7 pmKaraoke Ladies Night with Sammi Jo — Froggy's Bar & Grill
Thursday, October 29
- 10 amGed — Beacon of Hope
- 1 pmYucatan Waterfront Swingo — Yucatan Waterfront Bar & Grill
- 1 pmKat One on One - Caregiver Support — Beacon of Hope
- 5 pmPreston Hamilton – Live Music — Yucatan Waterfront Tiki Bar and Grill
- 5 pmPaul Mezzanotte – Live Music — Phuzzy's Boat Shack
- 5:30 pmChasing Denver – Live Music — Miceli's Restaurant
- 6 pmBobby Mann Karaoke — American Legion Post 136
- 6 pmEsol — Beacon of Hope
- 6 pmRaiford Stark – Live Music — Low Key Tiki
- 6:30 pmLive Music — Ragged Ass Saloon
- 7 pmBanjo Steve – Live Music — The Eagle's Nest Restaurant
- 8 pmDJ Carm — Froggy's Bar & Grill
Friday, October 30
- 5 pmBrian Bearden – Live Music — Phuzzy's Boat Shack
- 6 pmMike Imbasciani – Live Music — Miceli's Restaurant
- 6:30 pmLive Music — Ragged Ass Saloon
- 8 pmLive music Friday Nights — Froggy's Bar & Grill
- 8 pmDeep Fried Blues – Live Music — The Eagle's Nest Restaurant
Saturday, October 31
- 2 pmLive Music — Ragged Ass Saloon
- 5 pmNathan Tata – Live Music — Phuzzy's Boat Shack
- 5:30 pmTrick or Treat the Fish Streets — The Fish Streets (Cubles to Marina)
- 6 pmOtr Band – Live Music — Miceli's Restaurant
- 6 pmRemedy – Live Music — Low Key Tiki
- 8 pmHalloween Party with Dirty Work — The Eagle's Nest Restaurant
- 8 pmDJ Carm — Froggy's Bar & Grill