After a long, cold New England winter, the warm Florida sunshine is the type of vacation we needed! Even though we’ve visited Florida a number of times, we’ve never spent time on the Gulf coast. After doing some research my husband and I settled on Pine Island for the first stop of our stay. I came across Pine Island while looking at Airbnb on Sanibel Island and kept seeing homes listed on Pine Island. After doing my research I found that Pine Island was more laid back, not as touristy and less expensive than Sanibel. We were sold!

Where to stay

There are a few hotels when you first arrive on the island in Matlacha. We ended up booking an Airbnb in St. James City which is located on the south part of the island. Our Airbnb was nothing but perfect. It was located in an adorable community, located right on the water.(Use my Airbnb code to get $40 off your home booking and get $15 to use toward an experience worth $50 or more.)As soon as we walked in the door, we immediately felt like we were on a island vacation. The owners have everything you could need; kayaks, bikes, beach towels, fully stocked kitchen and washer and dryer. I could not recommend a better place! We enjoyed taking walks around the island in the morning, there is nothing quite like waking up to a water view.

View from Airbnb
View from Airbnb
Canals in St. James City
Canals in St. James City

What to do

Cayo Costa State Park – The state park is accessible by boat only so if you don’t have your own boat, I highly recommend using Tropic Star Cruises, located in Bokeelia. Bokeelia is located on the north side of the island, about a 20 minute drive from St. James City. You can book either a half-day trip, 9AM-1PM, full-day, 9AM-3PM or you can camp on the island. We chose the full-day. You can bring a cooler, chairs, umbrella etc. The boat ride to Cayo Costa is about an hour, but the views are beautiful and you learn some history about the island which I found very interesting. Once we got of the boat there was a tram waiting for us, which took us to the beach. You can walk but in the heat I wouldn’t recommend it! The beach was beautiful, the water even more so and since the island is only accessible by boat there aren’t many people there. I ended up shelling and found some great shells and sand-dollars. Unfortunately we went to Florida during lovebug season and there were a lot on the island which was a bit annoying. Because of that we ended up changing our trip to the half-day. I would absolutely go back but would pay attention to the time of the year to avoid the lovebug season.

Matlacha – This is the first place you drive by when you get on the island. There are great restaurants, wicked cool shops, art studios and views of the ocean. We spent some time walking around, checking out the shops and getting ice cream. You should definitely check it out if you are on the island.


Caspersen Beach/Venice Beach, Sarasota – Although these beaches are not located on Pine Island, it’s about 1hr 30mins from the island, and is worth the drive. One of the top items on my to-do list for this trip was to find beautiful shells and shark teeth. I did my research and learned that the best time to find shark teeth is at low tide, so we arrived at the beach around 9AM. Since we got there early, there was a ton of parking and barely anyone on the beach. It couldn’t have been better. While there, I found so many beautiful shells (there were shell piles from high tide) and my husband found about 10 shark teeth!

We also saw dolphins and someone on the beach caught a baby hammerhead shark (he released it!)

Venice Beach Pier
Venice Beach Pier

We left once high tide started to come in and made our way over to the Venice Beach Pier to check out the views and man, they don’t disappoint! Even at 11:30AM there was tons of parking and not many people on the beach. Other things to do – Although we didn’t take part in any of the following, other things you can do on the island are; kayaking, paddle boarding, boating, boat tours, fish and bike.

Where to eat

Woody’s Island Rum and Grille – located in St. James City on the island. The restaurant is right on the water with great views, great food and drinks and laid back. You can also dock your boat and grab a bite to eat!

View at Woody's
View at Woody’s

Blue Dog Bar and Grill – located in Matlacha right on the main road as you go enter the island. The restaurant is on the water and has a relaxing atmosphere. Great food (the wings are amazing!) The parking lot is small but if you drive over the bridge – right next to the restaurant there is a larger public parking lot. Great Licks Ice Cream – also located in Matlacha. Amazing, homemade ice cream! We went there twice because it was so good! I highly recommend the key lime flavor! If you are looking for a laid back, island vacation, this is the place to go!


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