Pine Island is spoiled for choice with restaurants and several of them are in the St. James City area minutes from the door. Local restaurants within three miles include: Woody’s Waterside, The Low Key Tiki, The Ragged Ass Saloon and The Waterfront (known locally as JD’s after the owner) all offer waterside dining and have docks available if you go by boat. There is also Froggy's Bar for late-night entertainment.

If you feel like travelling further afield (which on Pine Island never means more than twelve miles) there’s The Lazy Flamingo, Miceli's Italian Restaurant, Saltwater Smokehouse, Blue Dog Bar & Grill, Sandy Hook Fish & Rib House and Bert's Bar & Grill. For fine dining, there’s TheTarpon Lodge and for something quick there’s a Subway, A Dairy Queen and numerous other choices for sandwiches,pizza, etc. The choices are too numerous to mention here.

Groceries & Supplies

Pine Island has a Winn Dixie supermarket close to the centre of the Island and a General Store just around the corner from the property. Gas is available at the Circle K station at the centre of the island, where you’ll also find an ACE hardware. For fishing supplies, the Old Pine Island Marina and the Monroe Canal Marina are about a mile from the house and have everything from bait and fishing shirts to rods, reels and tackle.

There’s also a Publix supermarket just off-island, about ten miles from the house.

Nightlife

Pine island has bars and restaurants that are full of life until just after the sun sets. The Ragged Ass Saloon and Woody’s are both a big draw for day trippers and their car parks are regularly full of shiny Harleys, Indians and classic cars driven out for a day of sun and live music. Once the sun sets, you can head to Froggy’s in St James or Bert’s Bar and Grill in Matlacha.

If you want nightclubs, dance clubs or sports bars, you’re going to have to leave the island and head for Cape Coral, Fort Myers or Fort Myers Beach. Pine Island is fun, but it is never going to be a party capital. Which is a big part of why so many people like it.