The Magic of Gasparilla Island |
The Magic of Gasparilla Island |

The Magic of Gasparilla Island

Gasparilla Island, Florida
filed under:

At the end of April, Edwin and I flew south and spent 4 nights on Gasparilla Island at The Gasparilla Inn & Club. It was everything and more. The magic of Gasparilla Island is apparent from the first breath of salty air you take. This was the first real trip the two of us have taken together without the kids since we had Henry a year ago. It might just be me, but I have felt that when I have a baby, I kind of miss the season the baby is in that year. Right after having Henry in April 2021, I was feeling all the joys of a new baby but also feeling like I was missing spring.

So, a year out, I booked our trip to Gasparilla Island so that Edwin and I could have a few days of dedicated springtime time together. Everything about Gasparilla is perfection – it is delightfully relaxed yet full of things to do and manages to feel both fresh and historic at the same time. Here’s a recap of our trip to Gasparilla Island and what to do when there.

The Magic of Gasparilla Island |
The Magic of Gasparilla Island |

Dress / Shoes / Purse (old – similar)

Reward Style Loads
Where to stay, eat, drink, and explore on Gasparilla Island
Jillian Eversole wearing a yellow Fanm Mon dress at The Gasparilla Inn

The Magic of Gasparilla Island

Where to Stay on Gasparilla Island

Gasparilla Island is such a spectacularly beautiful little strip of land but part of what makes the island so magical is The Inn. The Gasparilla Inn & Club is one of those places that has that special touch I am always looking for in a hotel. It is so gorgeously decorated yet completely comfortable, it is so well appointed yet wonderfully salty and old school at the same time. The historic inn (over 100 years old!) really is Old Florida as it was meant to be. Everything about The Inn is inviting and makes you want to stay awhile a long while. It is so understandable why so many people make it an annual pilgrimage for their families.

The Inn is open seasonally from October to July every year and has something for everyone – tennis, golf, beach, pool, spa, a fitness center, and lots of activities. Guests can either stay in the main inn building or in one of the cottages. The beach front cottages are extra dreamy and fantastic for families but you really can’t go wrong. The Inn is an absolute gem within the Sunshine State and absolutely responsible for the magic of Gasparilla Island.

Where to Eat and Drink on Gasparilla Island


Now this is a perfect bar. The decor is reminiscent of old world Florida. The whole bar is so perfectly appointed for the atmosphere with backgammon boards aplenty. I love the comfortable vibe of the inside but also gravitated toward the outdoor terrace for that warm rich Florida air. We spent some part of every evening at BZ’s before heading off to dinner. Truly my kind of watering hole.

The Beach Club:

I couldn’t get enough of the menu at The Beach Club – so many fresh, delicious items. The inside of the restaurant is beautiful yet completely relaxed but it was hard for me to want to sit inside because the ocean views outside were too good to pass up. The Beach Club and its accompanying bar serve drinks poolside and beachside too, so delightful.

The Dining Room at The Inn:

The Inn’s dining room serves breakfast and dinner every single day. It is one of those rooms that is both gorgeous and so inviting at the same time. I loved how bright and light it was for breakfast, making it the perfect place to start our days. At dinnertime, I loved the traditional menu and the nod to old Florida with the dress code.

Temptation Restaurant (The Temp):

What a spot. The Temp is so old school in all the best ways. It is dark, salty, and no unnecessary frills with great food. The temp will also cook your own fish here if you go fishing and want to eat what you catch. We brought in pompano that we caught and they prepared it expertly for us. The best way to dine!

The Pink Elephant (The Pink):

The Pink is a short little walk down from The Inn and a great option for lunch or dinner either in the downstairs pub, on the outdoor patio (where we sat), or in the upstairs dining room. Expect fantastic cocktails and lots of local fish on the menu.

The Picnic Basket:

Right across the street from The Inn, you’ll find the cutest food truck called The Picnic Basket. In the morning, they serve up coffee and pastries etc. and at lunchtime it is the perfect place to grab quick and yummy sandwiches.

The Pink Pony:

Would it be a beautiful idyllic seaside town without a beloved ice cream shop? I think not so thank goodness for The Pink Pony. This family-owned spot is the place to head when your mid-afternoon sweet tooth strikes.

The Gasparilla Inn, Florida as it was meant to be
A travel guide for Florida's best historic gem: Gasparilla Island

What to Do on Gasparilla Island

The Beach Club Pool:

If you are staying at The Gasparilla Inn, then you get access to their pool at The Beach Club and you’ll be happier for it. The pool is simple but great but it’s everything else that really makes it wonderful – the Beach Club restaurant is really delicious, the pool/beachside bar is amazing (the piña colada is out of this world… you can trust me, I’m a piña colada connoisseur), the service is great (they set you up with towels, umbrellas, drinks, everything one could need!), and finally the view! From your chaise lounge, by the pool you look out over the turquoise waters of the Gulf of Mexico. We loved nestling in at the Beach Club pool all afternoon long and swimming in the pool after taking a tip in the ocean.


We mainly beached in front of the Beach Club but there are lots of stretches of beach to explore all over Gasparilla Island. The water and the sand are beautiful so it’s just such a delight to spend as much time on the beach as possible.


I was really looking forward to shelling and it did not disappoint. We asked a women who worked at The Inn for her recommendation for where to go shelling on the island and followed suit. Edwin and I went out one morning and came home with so many gorgeous shells. I took them all home with me to add to my jars of shells. It was peaceful, beautiful, relaxing, and so enjoyable. For me, the shelling contributed to the magic of Gasparilla Island, I just really enjoyed it.

Boating and Fishing:

We took a boat out for a day and went with Sweet Water Excursions per a recommendation from my girlfriend Jackie who goes to Gasparilla every year. And we had the most fun day! We spent part of the day fishing, part of it island hopping, and part of it lunching out at a local spot.

Shop at Grande Stitches:

If you are a fellow needlepointer, then you can’t go to Gasparilla Island without paying a visit to Grande Stitches. It is a wonderful needlepoint shop with a great selection of canvases including some special Gasparilla canvases and some canvases painted by the shop owner’s daughter.

Play Games:

The Gasparilla Inn is a bit of a playground for adults when it comes to games. The inn has backgammon boards nestled throughout it as well as chess boards, a ping pong table, and great tables for card games. We spent cocktail hour every single day of our trip in our favorite way – with a cocktail in hand while playing backgammon or gin rummy. It was sublime.

Pickleball and Tennis:

The Inn has tennis and pickle ball courts along with a cute little tennis pro shop. Edwin and I played pickleball throughout our trip and had a blast together. It was one of our favorite parts of the trip.

Exploring the Island:

You can really easily explore Gasparilla Island on bikes or golf carts that you can rent in town or through The Inn. It was so delightful biking and carting along the paths to see the gorgeous beaches, beautiful homes, stunning banyan trees, and historic lighthouses.


If I’m being honest, I’d say the spa is the only part of The Inn that leaves a little to be desired. I had a massage and my treatment was wonderful but the facilities aren’t state of the art. It didn’t bother me because I wasn’t mentally hoping for a full spa day (rather I intended to go in for my massage and then leave, which is exactly what I did) but it is something to note and be aware of.

Jillian Eversole wearing a yellow Fanm Mon dress at The Gasparilla Inn
Stuart Weitzman raffia bow block-heel sandals
Jillian Eversole wearing a yellow Fanm Mon dress at The Gasparilla Inn

Frequently Asked Questions About Gasparilla Island

How Do You Get A Reservation?

The amount of people who have asked me about Gasparilla is astounding… apparently everyone wants to go here! The question I’ve gotten the most is “how’d you get in?” because Gasparilla is notorious for booking far in advance and because they honor past guests bookings first. We were open to going any days of the week (not just weekends) so I think that helped. Also, we booked the trip through my sister, who is a travel advisor, so perhaps that helped too! Either way, we booked in April 2021 for April 2022 and were so pleased! When you stay at The Inn, you can chat with their booking team about booking for the following year before you even check out!

Is Gasparilla Great for Kids?

I’ve also been asked countless times about going with or without kids. My answer: you simply can’t go wrong. Edwin and I both agreed that it is a place we’d like to return to again with our children and without our children. It was incredible to spend the days exactly how we wanted them without working around early morning wake-ups, nap schedules, bedtimes, and possibly trying to find a local babysitter. We spent an entire day on a boat, which just wouldn’t have happened if we’d had our boys. We played pickle ball in the middle of the afternoon one day, which wouldn’t have happened due to afternoon naps. On the other hand, it is a dream destination for children because the beach and pool are wonderful and there are activities to keep kids engaged and entertained all day long. It was honestly paradise for every age.

How Do you Get to Gasparilla?

It was super easy. The two closest airports are Sarasota and Fort Myers, which are both about equidistant from the island (approximately an hour and 20 minutes). The Tampa airport is larger and about 2 hours away, so it also makes sense to fly into Tampa. We reserved a golf cart for our time on Gasparilla so we knew we wouldn’t need a car while there other than going to and from the airport. My sister compared the cost of a rental car with the cost of a driver and the driver ended up being more affordable (and so much easier + quicker). So, we flew into Sarasota and then had a driver pick us up and take us to The Inn. Easy peasy.

Reward Style Loads
Share post:

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.

powered by chloédigital