Vacationing to Florida’s Captiva Island

There’s something about Southwest Florida and its relaxed, easy, beachy lifestyle that has me hooked. Two-lane roads and intercoastal bridges connect idyllic islands that, from afar, almost look like they may be uninhabited.  This is definitely no Boca Raton or Miami Beach. With laws preventing any building from being built larger than the tallest tree, these quaint Floridian islands perpetuate a raw, natural beauty that is all their own.

Old-school diners and mom-and-pop seashell shops dot the roadsides of these charming coastal towns, where the largest crowds you’ll see are likely at a Bass Pro Shop, teeming with fishermen lined up for the latest fishing gear like it’s the newest iPhone.

Driving the coast here feels a little like you’re driving to the edge of the world, and a little like you’re stepping further and further back in time. It’s no surprise that there are islands here that you can only reach by boat or private plane, or that there are islands where there is no electricity, but where real estate is some of the most expensive in the country. And it’s not hard to see why people would pay an arm and a leg to get a piece of Southwest Florida.

Because in the hustle and bustle of life today, finding untouched land like this is rare. Finding a place like this is treasured. Finding a mindset like this is priceless.img_5659



If you follow these Florida roads for about an hour outside of Fort Myers, you’ll find two narrow islands, Sanibel & Captiva, nestled between the beaches of the Gulf of Mexico on one side and one of Florida’s pristine aquatic preserves on the other. The water here is thriving with dolphins, manatees, turtles and other marine life, and there’s a quiet serenity you can feel as soon as you step foot on the island. This may just be paradise.

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Where to Stay on Captiva Island

All I could think as we drove up to Sea Oats’ stunning 9-bedroom coastal estate was “this is my dream home.” There’s nothing about Sea Oats that isn’t perfect. The impeccable decor, the stunning pool, the picturesque setting on Captiva Island. Sea Oats has all of the luxuries of a top resort, but with the added privacy of a secluded home. It’s ideal for a large group vacation.



With the private beach within a 5 minute walk’s reach, the bay in your backyard, a huge pool & endless water activities for the kids, a poolside grill, two fire pits for late night s’mores, paddle boards, kayaks, a tennis court, a golf cart, fishing poles, and much, much more, it seems that the owners behind this estate have thought of absolutely everything. There’s even an endless supply of board games for when the Florida rainstorms decide to start up (although my preference is to jump in the pool in the warm, pouring rain šŸ™‚




Whatever you’re looking for from your Florida vacation, a week at Sea Oats Captiva Island is smooth sailing. Sanibel and Captiva Island were dubbed in a recent Travel and Leisure article as “the easiest family vacation in America”, and it’s easy to see why.

My stay at Captiva Island was nothing short of perfect. The estate is normally used for family getaways, corporate retreats, or incredible weddings, but I had the opportunity to experience the estate with my best friend Roxanne. The team behind Sea Oats are some of the loveliest people you’ll ever meet, and are eager to make your stay with them an incredible, tailored, one-of-a-kind vacation. They will set you up with everything you need, whether it’s activities from Kayak tours, to fishing trips, to a sunset dolphin cruise, or whether its their private chef, Chef Galvin, who I cannot recommend highly enough. He is a true gem who, by the end of your vacation, you’ll feel like is a part of your family. With his to-die-for food and even better personality, none of us were ready to say goodbye to Galvin.



Lobster Eggs Benedict ala Chef Galvin



What to do in Captiva Island:

Sunsets & Sunrises

It goes without saying that you cannot miss the sunrises and sunsets on ANY island, but especially on Captiva. It is so dreamy seeing the sun rise in your backyard (the bayside) and set across the street (the beach side). Both are equally beautiful, and will leave you absolutely breathless.

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The calm waters of the Captiva’s serene bayside make for an unforgettable Kayaking trip. It’s not uncommon to see manatees, sea turtles or dolphins swimming right up next to you. There’s also the incredible Buck Key Preserve, where you can kayak into a maze of mangroves. Just be on the lookout for wildlife! We got a couple of crabs jumping in our kayak and, being the girls that we are, almost flipped the kayak trying to figure out where it went. Bird watchers will love Buck Key as well.. where you can see osprey, egrits and heron and pelicans feasting on the preserve.



Our 4-hour fishing trip with Captain Jeff Zasadny of Gulf Pro Charters was easily the highlight of our vacation in Captiva. Whether you’re a first-time fisherman or an expert, you just have to book a fishing trip in Florida. When in Rome, right? Captain Jeff was amazing- He was so knowledgable about fishing and the area and gave us the best tour of the islands as we boated around. It was such a fun day, and a very fruitful one too… I caught 5 sea trout, which chef Galvin cooked up for us back at the house! So, so, delicious. Is it just me or is there NOTHING like freshly caught fish? Yum.

If you’re looking for a place to stop for lunch on your trip, my favorite is Cabbage Key, which is rumored to be the inspiration for Jimmy Buffett’s Cheeseburger in Paradise! He still frequents there sometimes, and behind the bar you can see pictures of young Jimmy! img_5819img_5438


Dolphin Watching

Dolphin watching in Florida is easy. It might as well be called “ocean watching” because they are everywhere! But, if you want to get really close to them, you should get out on the water. A sunset cruise is the perfect opportunity to catch some incredible views of the dolphins, who love to play in the wake of boats.  I almost jumped right in with them when we saw them, they are my absolute favorite animal in the world. So incredible to see them playing in their element.



Sanibel and Captiva islands are well known for their beautiful shells. Shelling is both a leisure activity for vacationers, and a very serious topic for some island locals. An hour or more before sunrise, you’ll find the most dedicated of “shellers” scouring the beaches with flashlights, looking to be the first to find the finest shells that have washed up onto the beach overnight. There’s even a local shellebrity, the Shell Love Bug, a VW bug decorated entirely in shells from Southwest Florida. It is truly amazing, and was even on Good Morning, America!



The flat islands of Captiva and Sanibel make for perfect biking. Billy’s Bikes on Sanibel Island will set you up with bikes (and they even deliver them to you!).  Biking around the island, you’ll get to see lush greenery and gorgeous beaches like the one below.img_5506img_5263img_5554

How to get to Captiva Island, Florida

I recommend you fly into Miami and book a rental car from MIA. It’s definitely the most economical and efficient way to fly (especially if you’re like me and coming from across the country) since airlines tend to have direct routes to MIA.

Once you get to Miami International, rent a car and make the quick road trip to Captiva Island!

It’s just a 2-3 hour drive to Captiva, making it an easy way to get to the island.

And as far as which car rental company to go with, Miles Car Rental provides the best and lowest rates for car rentals in Miami!

When to go to Captiva Island, Florida:

Peak season in Florida is November through April, when the weather is warm and the “snowbirds” flock to the Sunshine State. But the high season in Captiva is actually Summer, since families and large groups love to take advantage of when kids are off school. Because Captiva Island is e a barrier island, the weather stays comfortable year round.  I visited in September and it was just lovely (about 85-90 degrees.. As you all know, I love the heat).


If you have more questions about Sea Oats Captiva Island Luxury Estate, check out their website here. I cannot recommend this place highly enough for your next family vacation or event.


Enjoy Florida!



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Christina is a leading luxury lifestyle and travel blogger with over 2 million readers. Follow her on instagram @jetsetchristina.