Disclosure: My trip to Captiva Island was sponsored by the Ft Myers Sanibel Tourism Board.

Is there a place in the world that you return to over and over and over again?

While I absolutely LOVE exploring new places, one place that stole my heart from an early age (think: literally 1 year old) was Captiva Island.

Just off the coast of mainland Florida, this little island just 1.2 miles square is the place where my family would return every year, year after year.

It was the place where my mother, sister, and I would take girls trips to chill by the pool, eat delicious food in fun environments, and escape the cold of the Illinois winter.

It’s the place where my imagination was always running free and the sand was always in between my toes. 

But of course, as we got older and our lives got more complicated, our trips to the island became less and less frequent–until we basically stopped going all together.

And ever since that happened, it’s been a dream of mine to take my mother back to Captiva.

Well, it’s crazy what having a little blog can do, because I got to take my mother back to Captiva Island a lot sooner than I ever thought I would.

So after spending a week scuba diving in Cozumel, Mexico, I flew to Ft Myers International Airport, where I got in after midnight, stayed in an airport hotel, and then met my mom the next morning after she picked up our rental car to drive the 40 minutes across the bridge and larger Sanibel Island to our shared happy place.

Literally the second we got onto the bridge, I felt a weight lift from my chest, and I knew that this would be the exact trip that I needed at that very moment. And, spoiler alert: it was.

Day One

We arrived on Captiva Island and pulled up to the reception of Tween Waters Island Resort (our go-to spot to stay on the island) about an hour before the listed check-in time, but thankfully our room was already ready, so we were able to check in with no trouble at all.

Then, it was a short drive (literally about 10 seconds) over to our building, where we were offered help with our bags but being the #stongindependentwomen we are were able to get them up two short flights of stairs no problem.

Upon tapping our room key and opening up the door, the first thing I noticed was that they had re-decorated since the last time I was there!

white pillows against a white headboard with a blue lamp on a side table

While the rooms used to feature a slightly darker color scheme, they had been completely updated with white-washed furniture and gorgeous sea blue accents. My teal-obsessed self was absolutely head-over-heels with the new look ????

Of course, we also had to check out our balcony, where we had an absolutely perfect palm-tree lined view of the beach and ocean. Dinner while watching the sunset would definitely have to be had out here one evening, we decided.

We also took a peek through the amazing coupon book we were given at reception–full of discounts for both the resort and different activities around the island!

But for our first meal on the island, as per tradition, we gussied up and walked the short ways over to Tween Waters’ fancier on-site restaurant: The Old Captiva House.

The Old Captiva House is located in a gorgeous historic building which was first used as a one-room schoolhouse and is now on the National Registry of Historic Places.

Like the rooms, the Old Captiva House had been redecorated since the last time I was there (I was particularly obsessed with this little nook with a map wallpaper that I want to transplant directly into my home), but the menu was as delicious as ever.

a little nook with a grey couch, white tables and chairs and a blue map of captiva island on the wall

My mom went for a classic steak while I got an amazingly cheesy lobster risotto that had a bunch of hidden, huge chunks of lobster in it. Sooooo good!

As the sun set on our first day on the island, we dug into our food and chatted away excitedly about everything we were going to do in our four days on the island before retiring to our room to pass out in our supremely comfy beds.

Day Two

We woke up without an alarm the next morning, wanting to let ourselves sleep in after exhausting travel days. Then, it was up and dressed to head back to the Old Captiva House for breakfast.

While the Old Captiva House is pretty fancy for dinner, it’s a casual affair for breakfast, with plenty of well-priced breakfast dishes on offer ranging from classic pancakes or eggs & toast to shrimp chorizo omlettes (though I do have to say that I miss the free continental breakfast buffet that was included with your room when we used to visit).

blueberry pancakes

The one thing I didn’t love about breakfast at the Old Captiva House?

The plastic.

And while I hate to call out a place that hosted me so graciously and has had a special spot in my heart for many years, it was really heartbreaking to watch as literally every tables’ drinks that morning were brought out in plastic cups with plastic straws.

I mean… come on. It’s 2020.

a plastic cup with a plastic straw

I let myself believe that first morning that maybe the dishwasher was just broken or something so they were trying to cut down on dishes, but it happened each morning that we were there, so I’m pretty sure it’s just par for the course. This is definitely something that they could work on.

Anyways, plastic problem aside, my pancake breakfast that morning was absolutely heavenly, as was the rest of the day.

After breakfast, we took a quick break in our room (island time already getting to us) before heading off to the Sanibel Community Association Arts Festival, which we saw a sign for on the drive over the day before. It was the last day of the festival, so we knew we wanted to grab the opportunity while we still could!

So we drove on over to Sanibel Island, the slightly larger sister island of Captiva, to take a look around.

And oh my gosh, was this festival right up my alley. After paying a small entrance fee of $3, we were greeted with stands from local artists showing off everything from gorgeous paintings of the Florida landscapes to amazing sea-life inspired jewelry, to fun and sassy hand-embroidered clothes.

I almost left with a giant wooden turtle to hang on my wall and definitely left with a few more swim cover ups than I came in with ????

Then, we took another quick drive to the other side of the island to try out Sanibel Fresh, a casual cafe that the Ft Myers Beaches tourism board had recommended to us. My mom had a simple salad and I indulged my basic Bali self with a smoothie bowl which was so cold it gave me a brain freeze but was still sooo good.

a delicious smoothie bowl with layers of nuts, fruit, and coconut

Finally, it was back to the resort to check out the pool situation. As a kid, the pool was my favorite part of our annual trips to Captiva Island, as I was (and very much still am) a water bum through and through. 

Well, luckily for me, I could now have twice the fun, as a new, adults-only pool had just been built in the last year. And let me tell you, it was pretty much heaven.

a pool with bright blue water, blue lounge chairs, and palm trees
The new oasis pool

My mom and I both alternated swimming around for a few minutes with sun bathing and reading books, and it was truly the perfect end to the afternoon.

For dinner that night, we moved over to the Crow’s Nest Bar and Grill, the more casual on-site restaurant just next to the Old Captiva House, where I indulged in some crack-like mac and cheese salsa dip (yes, it’s as delcious as it sounds) and a southern fried chicken sandwhich that was bigger than my head.

Day Three

The next day took on a similar theme to the one before, just switched around a little bit.

We started off once again with a delicious breakfast at the Old Captiva House (I had eggs, bacon, toast, and breakfast potatoes this time) before sitting by the pool again.

bacon, eggs, toast, and breakfast potatoes on a white plate

This time by the pool, I grabbed a soy milk latte from the new Sanibel Bean coffee bar by the pool (hello my personal paradise) and got a bit of work done while watching kids splash around in the pool.

Then, it was off for an afternoon of exploring! We ditched the car this time to make the short, 20 minute walk into downtown Captiva, admiring all of the huge mansions along the way.

Once it town, we stopped at the Key Lime Bistro-an island favorite for lunch, where I had a delicious chicken sandwich. And, of course, we indulged in some key lime pie to top it all of.

And yes, it was as good as it looks.

a giant slice of key lime pie

On our way back to the resort, we walked along the beach, taking off our shoes and digging our toes into the sand.

I marveled at just how many shells were on the shore and mused aloud that it’s no wonder Captiva and Sanibel are some of the best shelling destinations in the country.

While I personally wouldn’t advise taking seashells home with you, I definitely loved shelling as a kid, and remember picking up bag fulls of shells that my mom would inevitably tell us to put back and pick just a few favorites.

Dinner that night was leftovers on our balcony watching the sunset.

Day Four

For our last full day on the island, we knew we wanted to get in a few more things that were always a part of our traditional visits, including lunch at The Bubble Room and a dolphin watching cruise with Captiva Cruises.

Thankfully, we had just enough time to do both and spend a bit more time by the pool.

First up? Lunch at The Bubble Room (where I also got to meet Sorena, from the Ft Myers tourism board who helped organize this trip, who was so bubbly and nice)!

This quirky little restaurant is a Captiva Island staple, and you absolutely can’t miss it when you go.

From the gorilla cage outside (with no gorilla-he escaped), to the boy-scout uniform-wearing waiters and vintage memorabilia strewn about, to the Christmas room and model train running around the whole restaurant, to the absolutely GIGANTIC pieces of cake for dessert (I highly recommend the orange crunch cake), you honestly can’t get a more fun restaurant experience than this.

addie standing in a gorilla cage with a sign on top saying "do not feed bobo bubble bread he may go ape and escape"

Oh, and the food is delicious too.

After our delicious lunch, it was time for another staple of my mom and I’s Captiva trip: a dolphin-watching cruise with Captiva Cruises!

This fun 1-and-a-half-hour-long cruise is on a boat that goes just the right speed and makes just the right wake that dolphins love to play in, meaning that they actually seek out the boat and you’re basically guaranteed to see some fun-loving dolphins when you go.

In fact, I can’t remember a single time I haven’t seen at least one dolphin when taking this cruise, and it’s so much fun to see them playing in the wake!

This time, we saw one lone dolphin and a pair playing together right at the very beginning, and then another group of three right at the very end.

a dolphin jumping through boat wake
two dolphins playing in boat wake

The cruise is also accompanied with narration from a volunteer guide from the J.N. Ding Darling National Wildlife Refuge, who will tell you all about the different birds and landscapes that you’re seeing.

a JN Ding Darling guide giving commentary on the Captiva dolphin cruise

Finally, the cruise pulled back into the harbour, and we hopped back into our car for one last time by the pool-this time in the hot tub because it was a little more chilling that normal.

And this time, I finally grabbed a strawberry daquiri to go along with it. This was a big moment for me because I used to be absolutely OBSESSED with the virgin strawberry daquiris whenever we came to Tween Waters (so much so that my mom had to impose a 2-a-day limit), so being able to order a NON virgin one was a pretty big deal ???? And while I’m not totally convinced that they’re better than the virgin ones, it was still pretty freaking good.

And that was it… the next morning, I hopped back on a plane to head to Washington DC/my boyfriends house for a few days before going back to Scotland.

Returning to Captiva Island on the tail end of my winter break was the exact refreshing vacation that I needed, and getting to see the look on my mom’s face as she relived memories from when we were small was so rewarding. She was literally always stopping to tell people that I had been coming there since I was one!

I hope our trips to Captiva continue for many years to come.

Stay tuned for a more traditional insider’s guide to Captiva Island (compiled with knowledge from my many years of visits) coming soon!

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Addie Gray is a recent college grad and a passionate solo female traveler. Having traveled to more than 20 countries, she now shares her knowledge on budget travel, solo female travel, and travel photography.

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