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1 Boat and 4 Islands in 8 Hours: Part Two – Boca Grande to Little Gasparilla

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Photos by Premier Photographic Events

In my last blog post, you read about the start of my island hopping adventure with the Freedom Boat Club. We began our day at the Cape Haze Marina and voyaged to a very enchanting Useppa Island. Now, we continue the journey on to two nearby barrier islands.

Beloved Boca Grande
Within fifteen minutes of our departure from Useppa, we were floating through the captivating canals of Boca Grande, the charming community on Gasparilla Island.


DSC_2563_BocaGrande_PremierWe floated by the breathtaking 18-hole championship golf course – part of the  The Gasparilla Inn & Club.

DSC_2594_BocaGrande_PremierSeven miles long and only one mile at its widest, in Boca Grande you’ll find exquisite homes combined with idyllic streetscapes, tropical vistas, an old Florida character, and a quaint village central to the island.


DSC_2585_SouthernIslands123We had lunch at a diner-style joint, a local favorite called The Innlet. Docking our boat right outside, we entered through the patio.

DSC_2586_BocaGrande_PremierJim Cull pulling our boat into slip #12!

From left to right: Steve Lineberry, Jim Cull, me, Carol Stewart, Kevin Hyde, Captain Marti

From left to right: Steve Lineberry, Jim Cull, me, Carol Stewart, Kevin Hyde, Captain Marti

Joining us for sandwiches (and some darn good coffee) were Michael Saunders & Company agents, Carol Stewart and Kevin Hyde. As we ate, Kevin tried to sum up what makes Boca Grande so special.

“It’s not really the luxury element,” he explained. “It’s the down-to-earth people you run into every day. It’s the local store owner who is a successful business man but enjoys spending his afternoon helping to bag your groceries.”

Furthering this simple truth, once lunch was over Kevin confided in me that an Egyptian princess (!!!) had just sat at the table next to us. I am not joking. Royalty dined beside us while were munching on our French fries.DSC_2599_BocaGrande_Premier

SouthernIslands150After lunch (and our brush with monarchy) Captain Marti got us back underway for our next stop.

DSC_2600_BocaGrande_PremierPelicans have made themselves at home on the old bridge to Boca.

Castaway on Little Gasparilla Island
Perhaps the most surprising (and therefore most treasured) part of my day was our tour through Little Gasparilla Island, a community only accessible by boat with no cars or commercial development.

DSC_2657_LGI_PremierSituated ten minutes from the mainland, its seven miles of pristine beaches are only part of its allure.

DSC_2605_LGI_PremierCone Darnell, a third generation island resident and agent with Michael Saunders & Company, met us at her dock.

DSC_2628_LGI_PremierOn sturdy golf carts we trekked from the south to north end along dirt roads with lush canopies.DSC_2637_LGI_PremierIts atmosphere of off-the-grid meets Caribbean Island provided something of a true castaway-like experience.

This beachfront residence for sale is listed at $799,999.

This beachfront home for sale is listed at $799,999.

Most of the island offers tropical-style single-family-homes. Several multi-family complexes exist but zoning regulations no longer allow them as new construction. Residents want to preserve their way of life, which has gone mostly unchanged for generations.

DSC_2611_LGI_PremierCommunity events bring people together at the island’s unofficial hub – The Hideaway, where the beach and bay are only moments apart. According to Cone, “This area is party central; everything ends at this point.”

She also explained that numerous renters visit the island for long weekends or many months.DSC_2615_LGI_PremierThe south end has homes along canals (there are only two canals on the island).


DSC_2633_LGI_PremierVarious street names and signs provide a glimpse into the laid-back community character.

DSC_2625_LGI_PremierA firetruck.

DSC_2634_LGI_PremierConch shells adorn properties like “nautical gnomes”. (I can’t take credit for that awesome alliteration…thanks Lucy!)

DSC_2640_LGI_PremierA classic chapel offers non-denominational services. Cone explained that with no overhead lights inside, Christmas is never more magical as it is in the chapel amidst glowing candles and holiday lights.DSC_2643_LGI_Premier

DSC_2666_LGI_PremierRoad maintenance.


DSC_2651_LGI_PremierBecause every island should have it’s own lending library.

DSC_2660_LGI_PremierThere were plenty of people enjoying their day at the beach.

IMG_1456As we made it back to our boat for the last leg of our daytrip, it occurred to me that Little Gasparilla Island is someplace truly memorable. It’s hard to explain, but the island’s determined character mixed with its appreciation for simplicity made me excited to have stumbled upon it. I consider myself a city-girl, but my brief view of this rustic, distinctive island left me positively giddy. Nowadays, with so many cities and streets looking like the other, I suppose I can appreciate a piece of paradise that can’t be found anywhere else.

Come back for my final blog post of this series where we finish out the day on Palm Island! Read Here.


Read more about Boca Grande from this blog: 9 Reasons Why There’s No Place Like Boca Grande

Browse Boca Grande homes for sale or Little Gasparilla Island homes for sale on the Michael Saunders & Company website.



1 Boat and 4 Islands in 8 Hours: Part Two – Boca Grande to Little Gasparilla was last modified: March 26th, 2015 by Kathryn Parks