Everyone who’s ever been to the Midwest in the winter knows, our winters are the worst. And even when it’s not such an awful winter, we all still need a break from the freezing temps to to bust out a bikini by the ocean – it’s the only natural way to deal, right?While I was lucky enough to be between jobs, I took a week off to spend some time with my family in Captiva Island, Florida. And when I say family – I mean the whole gang: my 90 year old grandpa {who’s a real gem!}, my aunt, uncle, cousin and parents – it was a fun few days to soak up some sun and enjoy the island life with my favorite people.

Almost every year, my family and I would make the trek to Captiva Island to spend some time on the beach, fishing off the dock and eating far too much cake by the ocean {and we’re talking actual cake here people – not the Urban Dictionary definition of cake, aye!} It’s a magical island filled with delightful old people {hehe!}, and beautiful, sunny beaches – which is sometimes exactly what you need in the middle of a freezing cold winter.Here’s a little virtual tour of a few of my favorite things to do in Captiva/Sanibel Island if you ever find yourself in southern Florida! Trust me, it’s the perfect little island to explore and relax if you’re looking for an extra warm change of pace 🙂Where to stay: 

As I said before, I’ve been traveling to Captiva for years – and every time we take trip to the island, we always stay at Jensen’s Marina and Cottages. They have the cutest cottages right next to the ocean, and it’s fun to be able to walk out on the dock and fish anytime of day. Plus, the Jensen brothers who still run the place are the sweetest hosts you’ll ever meet – one of them even made us homemade baguettes and brought us honey from his bees! It was pretty darn delicious and made the experience even more fun.  What to do: 

First things first – you have to go to the beautiful beach in Captiva. It’s the perfect, soft sand beach covered in beautiful shells – and best of all, it’s usually not too busy {at least when we’ve been to visit between December and February}. Spend a day soaking up some sun, making sand castles or taking kayaks out for a spin on the ocean.

There’s also a really cute downtown area of Captiva, with tons of delicious restaurants, ice cream shops, stores and more. It’s perfect for spending an hour or two wandering down the streets and stopping in to grab some island eats and sweets.

If you’re looking to be a little more sporty, you can swing by YOLO where they rent out boats, golf carts, bikes and more. On sunny days, we always try to rent bikes to pedal towards Sanibel island, swinging by the beach, stopping for ice cream, or tasty seafood at the Lazy Flamingo.

As for nightlight – I can’t say that Captiva gets too crazy late at night, but I will give them credit for some pretty exceptional hermit crab races {I know, that sounds totally ridiculous, but it’s pretty darn hilarious.} Swing by Tween Waters Inn, a popular hotel on the island and watch the host tell jokes, bet on your favorite crab and watch him or her hopefully win! Don’t worry, there’s always some consultation prizes, and lots of tasty drinks!Where to shop: 

Captiva island is full of adorable clothing shops, art stores, general stores and more – and every time I come to the island I make sure to leave my wallet in my cabin to avoid too many impulse buys – whoops!

I love the iconic Island Store has been open ever since I was a little kid, and I distinctly remember saving up my pennies to buy and Orange Crush and Kit Kats every time I was on vacation. It’s full of products unique to the island {like their amazing key lime pie cookies!} as well as all the essentials you need for your trip. While it’s pricier than back home, it’s perfect for if you’re in a pinch for dinner or need to pick up some last minute souvenirs.

The store aptly named, “Beach Stuff” is also perfect for everything you might need for the beach, your trip or hilarious souvenirs for your besties. I usually go for the alligator egg gum balls {don’t worry, they’re definitely not real} or some shells I “definitely found while walking on the beach” 😉Where to eat:

The food in Captiva is sinfully good – and I always make sure to stuff my face with as many grouper sandwiches and seafood as I can before I head back to the Midwest!

For seafood, I always love The Mucky Duck on the beach for their famous grouper sandwiches and some of the tastiest dishes on the island. It tends to get pretty busy, so be prepared to wait for 30 – 45 minutes for a table. Luckily you’re right by the beach which means waiting by the water with a beer in hand, definitely not too shabby.

I also adore The Lazy Flamingo, which is almost exclusively seafood. We’ve been going to The Lazy Flamingo for years, and my family always orders their oysters and grouper sandwiches {but I hear pretty much anything on the menu is delicious!}  For dessert, The Bubble Room is a must!  Known for their gigantic pieces of homemade pies and cakes {as well as their extra colorful and crazy eclectic decor} I always make sure to swing by The Bubble Room any chance I get to take a slice of cake back to the cabin. While they’re all ridiculously delicious, I personally love the Orange Crunch and White Christmas cake, and I usually make sure to get both of them every time I travel to Captiva. I’m already missing the sun and sand of Florida, but luckily Chicago’s a pretty great place to come back to {minus all the snow and rain!} If you’re looking for the perfect winter getaway, I highly suggest giving Captiva Island a try – it’s the perfect long weekend or week-long trip to get away from it all 🙂