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TORI O'CONNELL
Tori O'Connell
Hey Mama Darling

I'm Tori and a proud wife to my college sweetheart & mama of two beautiful girls. We live in the Midwest with our pup, Charlotte. I created Hey Mama Darling to journal the journey of motherhood with its rewarding highs and challenging lows. I'm equally passionate about all things home decor and fashion. My hope is that Hey Mama Darling sparks joy in your life in some way today!

sincerely, tori

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Boca Grande, Florida

Exploring one of the richest cities in Florida located on Gasparilla Island.

Gasparilla Island made history when the Dupont family pioneered a quiet residential island community called Boca Grande in 1909 first constructing The Gasparilla Inn for employees and stockholders in 1911.


The simple Frame Vernacular style hotel quickly grew to a world-class resort allowing for characteristics of the Queen Anne style of architecture and, by 1915, was already a huge success with great demand.


Expansions in 1920's included 18-hole golf course & The Beach Club which was rebuild in '28 due to a hurricane and again in '86. The building of residential homes did not really happen until after the Florida Land Boom of the 20's.


By the 1970s and 1980s, the Gasparilla Island Conservation and Improvement Association (GICIA) worked hard to preserve the "old way of life" on the island, preventing excessive development.


Today, when you step foot on the island, you are instantly consumed by the peaceful, natural beauty. And like many places on the island, The Gasparilla Inn is preserved perfectly as if you are stepping back in time to luxury 1930's.


The Gasparilla Inn & Club


I'm going to say it again because it was one of my favorite parts of the Boca Grande experience: you step back in time to the early 1900's when walking into the Inn. Not only was the luxury decor and architecture beautifully preserved, the staff and service was exceptional as to the early 1900's standards. Perfectly minted staff opened the door for you as you walked in, a friendly face greeted you eager to assist, the bartenders in suit and tie crafted incredibly challenging cocktails perfectly at BZ's, and don't get me started on the life-changing 5-star dining in The Inn's Dining Room!



The Gasparilla Inn is known for hosting a good representation of the Social Register, financial tycoons, and politicians over the years. But what I found to be the most profound element of all, was wrapping my mind around the sheer amount of history of this place. As they say, "if walls could talk." The hallway littered with historical pictures of life on the Island over years.


The private membership clubs do have dress code requirements. Here were some of the pieces I packed along for the trip to meet dress code at various restaurants. Some were casual:



The Beach Club



Clean and calm. Crisp white walls and flooring matched the white sandy beaches. The infinity pool over looked the Gulf. Pick any spot on the club side of beach and staff will drill in an umbrella and provide lounge chairs. Shelling along the beach is a common pass time.


Of all the swimsuits worn on this trip, this was my favorite! The visor is absolutely perfect for travel; it rolls up, air drys quickly and UV protectant.

All the suits brought on this trip were from Summersault. I'll be honest, I was a bit shocked at the price at first but let me tell you how freakin' worth it they are! I will never be going back to another one piece suit because the material and how they are constructed are incomparable to any knock off on amazon. I usually am a SheCup lover, but for one pieces, this is the way to go. They are thick and even when wearing white, you could not see the breast pads. The ruffles are so cute!





Shopping & Entertainment

Although bustling during the day, Boca Grande is pretty quiet once the sun goes down. You do not come here to party, but here are a few placed that stay open past 8:30pm that we found:

  • The Pink Elephant - part of the club, it will stay open longer than 9:00pm if people are there.

  • The Temptation Bar


Top Places to Dine in Boca Grande

Please keep in mind some of these selections are a part of private membership clubs.


Final Thoughts

Although Shane and I traveled as a couples only trip, Gasparilla Island, particularly Boca Grande, would definitely be a great family vacation spot. The key to gain access to The Beach Club and dining would to be a guest at The Gasparilla Inn or be a guest of a member. There are things to do and access without, but for a short time (1-2 days). The island is under developed with tourist attractions (and rightly so) as parts of the island remain beautifully untouched. Take a boat cruise from a local. Make friends! The social part is equally as dreamy as the beach.


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sincerely, Tori

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