The Gasparilla Inn

I have to do a little recap of our stay at The Gasparilla Inn last week. It is such a happy place for me and I wish everyone can experience it at some point. My family went there together for the first time a couple of years ago and I have been dreaming about going back ever since. (80% of the dreams involve the pancakes, seriously.) My sister has been to Boca Grande a bunch, but as a family, we hadn’t gone. We mostly went to The Keys as kids, Seaside a few years in a row when I was a teenager, and Long Boat Key a bit too. Why hadn’t we considered Boca Grande?! It’s under two hours away from Tampa and it feels like time slows down a bit when you get there.

At the end of last year, the hotel contacted me about coming back for a second visit. With my move, it was kind of hard for me to think about travel. But then my trip to Tampa materialized and I figured I could easily make the trip work. Even better? Originally, just Carter was going to meet me down there, but my sister ended up taking a few days off from work so she could join. I was worried about how the trip would be if we were only there for 48 hours and as we got closer, the weather was looking very, very wet. Turns out we had nothing to worry about!! 48 hours felt like a week and the clouds parted for pure sunshine.

This is going to be a little bit of a photo heavy post! I couldn’t narrow it down. It’s impossible to take a bad photo at the hotel and every nook and cranny has something unique to discover.

Gasparilla Inn Room

The three of us had the nicest suite of two rooms. We didn’t spend too much time there, but it was the perfect place to unwind between outings and to get a bit of work done every night. I just love how cheery it’s all decorated. Did I pack my pink and green pajamas to match the hotel? Yes, yes I did.

On our first day there, we went straight out in the drizzling rain to shoot an outfit for a campaign. It was so much fun having the golf cart to zip around town in. This was actually my first time driving one and now I kind of want to live in a neighborhood where you can drive one around instead of a car, ha. After we took photos and grabbed lunch at the Loose Caboose, we went to explore a little bit in the golf cart and got caught in a torrential downpour. We drove right into the rain and could not stop laughing.

Boca Grande

Gasparilla Inn Pink Room

We made it back to the hotel a little wet, changed, and decided to play some Rummikub to see if the rain would pass. Not sure if it’s officially called it or not, but “The Pink Room” is by far my favorite spot in the whole hotel. It’s the coziest, and the pink doesn’t hurt. You have to walk by the pink room to get back to the staircases for the rooms and I always love peeking in to see who’s doing what in there. People will play games, read, do puzzles. They’ll bring in coffees or wine.

I had to include the below photo. My sister and I LOVE Rummikub and we were anxious to teach Carter so we could play the whole trip. We really thought it was going to rain the entire time, so we were prepared with games!

As we were playing though, the dark clouds out of the window started to seem not so bright. I wouldn’t say they cleared completely, but it stopped raining and looked like it would be okay weather for going to the beach. We finished the round (Stacy won 🙄), threw on suits, slathered on sunscreen, and hopped into the golf cart.

Gasparilla Inn Pink Room

Gasparilla Inn Beach Club

Because it had been rainy and then turned cloudy, we pretty much had the entire beach to ourselves. There’s nothing like the Gulf of Mexico in my opinion. So much warmer and calmer than the Atlantic. The Gasparilla Inn has its own beach club, so even though the beach itself (by the water) is public, you have access to chairs, the pool, towel service, and the restaurant. On a sunny day, you can ask them to set up one of the umbrellas for you… they’re YELLOW AND WHITE STRIPED. Could not be cuter. (Or more necessary for a pale girl like me!)

Boca Grande Gasparilla Inn

Seashell Fireplace The Pink Elephant

After a pretty great afternoon down by the water, we headed over to The Pink Elephant for dinner. If you find yourself in Boca Grande, you have to go. It’s actually owned by the inn and has great food. Your drink will come out with these little pink elephants to collect. One of Stacy’s friend’s family has a house in Boca Grande with a giant jar filled with pink elephants from over the years.

Boca Grande Dining Room

We woke up early the next day to 100% sunshine. I had been working in one of the common areas with some to-go coffee for a couple of hours and then met the girls for breakfast. I really wasn’t kidding when I said I dreamed about the pancakes– just look how good they look!!! (The grapefruit, by the way, also divine.)

Boca Grande Breakfast

Gasparilla Inn Beach Club

We spent the entire day out at the beach. For the most part, I stayed under an umbrella (with my laptop, ugh, couldn’t avoid it). We grabbed lunch at The Beach Club and then hopped back on the golf cart to get some ice cream at The Pink Pony. It didn’t last long. In part because it tasted so great and also because the cones didn’t stand a chance in the heat.

The Pink Pony Boca Grande

After ice cream, we went back to the beach where my sister convinced me to come out from under the umbrella. I had sunscreen on and (thankfully!!!) a one-piece and really knew better than to put my fair, still-winter-white skin out in the Florida sun. Of course, I was fried. My skin doesn’t immediately show the burn so I feel like I’m okay and then six hours later, the burn comes to light like a polaroid picture developing. Surprise…. 😰 I still can’t believe how beautiful of a day it turned out to be though. I was picturing a monsoon lasting the duration of our trip. It felt like a Gasparilla Inn miracle!

Gasparilla Inn Activities     Gasparilla Inn

I really wish everyone could get to enjoy The Inn. It’s such a perfect spot for a getaway and easy to get to from Tampa, Naples, or Sarasota airports. You can’t go there and not feel relaxed. It would be perfect for couples, families, or a girls’ trip. Thank you Gasparilla Inn for the accommodations + hospitality! 

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Audrey | Brunch at Audrey's

The inn looks so quaint and charming, and I’m loving all the fresh pops of colour! I love when bad weather forecasts give way to great weather; it really feels like the best gift! This past week, it was forecasted to rain all. frickin. week. But it turned out that it was only a misty sort of rain, and the majority of the time I was out, it wasn’t raining at all! As someone who’s easily affected by weather, I was pleasantly surprised and ever so grateful ^-^ It definitely boosted my mood throughout the week (I mean, besides the fact that I had finished my last week of undergrad finals EVER and was living for Senior Week haha) -Audrey | Brunch at Audrey’s

Jane Davidson | Typically Jane

You are flippin’ gorgeous gal! What a fun trip, I’m so glad that it worked out timing wise because it looks like you all had an amazing time. And can we talk about how dreamy that hotel is?! So cute!

Jordana @WhiteCabana

Florida charm is oozing out of the Gasparilla Inn! I’ve been going to the Tampa area every summer, and I’ve always appreciated your recommendations. Keep ’em coming!


The Inn looks so adorable! Love all of the pink and green. My in-laws recently retired in Longboat Key and I love going down to visit. It’s so peaceful and the Gulf of Mexico really is the best.

Christa | theavidpen

Everything looks absolutely charming and I just love the white and yellow umbrellas on the beach. I’ve only been to Florida once, but I definitely need to make another visit!


I size up so they’re loose and comfy but you can do your regular size too. They shrink a tiny bit

Shannon Mahaney

That place looks like paradise! I grew up on the east coast of Florida and I always felt that the water was nicer on the gulf side. It’s so blue!


I loved seeing all your pictures on Instagram from this trip and this post was lovely. I now know where I want to go whenever I need a quiet, relaxing weekend at a beach!


I agree! The Gasparilla Inn is sooo pretty! Love the pink room too! Never was a guest but visited for the day from Naples where I work at The Ritz-Carlton Beach. Enjoyed your article and your happy experience

Janelle Sisk

May I please ask where your blue seersucker dress is from you were wearing in the photo of you playing a game . Thank you!

On the List

[…] You will get serious inspiration on where to go for your next vacation when you check out Carly the Prepster’s post about her time at The Gasparilla Inn. […]


I am reading this post again because I am trying to plan a trip here, and need some inspo!! I hope my vacay pans out because this place is the absolute cutest!! I agree that every corner is decorated to perfection, and I would also pack clothes to match the decor! Thanks for sharing, Carly!

xx Libby