When our sons were two and four, my husband and I attempted our first “real” vacation as parents. We planned a few days on Captiva Island, located off Fort Myers on the Gulf Coast of Florida. I was initially nervous about taking such young kids to an unfamiliar area all on our own (previous getaways were huge extended family affairs). But the minute we crossed the causeway to Sanibel Island, I knew we had found something special, a perfect fit for our family. Little did I know just HOW special, and how many memories we would make there for many years to come.

Sanibel and Captiva, which are connected by a small bridge, are unique destinations that feel like a cross between the North Woods of Wisconsin and a quaint Caribbean island. On that first trip, we fell in love with the natural beauty of Sanibel and all it has to offer. But we really connected with with charming, beachy Captiva. Of course, our two-year-old cried in every restaurant and hated the sand. But despite the challenges of traveling with a toddler, we decided Captiva was our perfect place and that this trip would not be our last.

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Today, that adorable but defiant toddler and his big brother are 6-foot, 3-inch tall teenagers, and they have a 9-year-old brother. So life has changed a lot since that first Captiva vacation in 2002. But what has not changed is our love for the Captiva way of life. We returned for our 10th visit this summer. I highly recommend Captiva to families, couples, girlfriends … anyone looking for a truly special tropical place to get away from it all. Here are 10 reasons we just can’t get enough of our island paradise:

Interested in visiting Captiva Island? Book your stay through our trusted partner Trip Beat here!


1. Water at every turn: If you love the ocean – I mean REALLY love the ocean – Captiva is the place for you. It’s a thin strip of land nestled between the Gulf of Mexico and Pine Island Sound. So practically everywhere you look, you have gorgeous water views. And there are endless opportunities for water recreation: take to the bay for stand-up paddle boarding or a dolphin cruise, or hit the Gulf for deep sea fishing or riding wave runners. Also, because Captiva is between two bodies of water, you’re treated to a spectacular sunrise in the morning and unforgettable sunset each evening. Sunsets are major events on Captiva.


2. Heaven on earth, a.k.a. Tween Waters Inn Island Resort: Tween Waters Inn is the main reason Captiva originally captured our hearts and keeps calling us back. This historic resort started almost 90 years ago as a string of simple fishing cottages. Many of those cottages remain today, but they’ve been updated over the years, adding just the right amount of luxury while keeping a rustic feel. The cottages are named after famous past visitors, like Anne Morrow Lindbergh and Theodore Roosevelt. You can also stay in regular hotel rooms and suites (the cottages and suites have kitchens and living rooms and are perfect for our family of five). Tween Waters is not new and shiny, but that’s one of the things we love about it. It’s full of character and history and yet has added modern comforts and updates through the years. And the grounds are covered with tropical flowers and trees and beautiful walkways — you feel transplanted to another world.


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Some of my favorite things about the resort are the beautiful spa, the casual and fine-dining restaurants that are just a few steps from any room, the extensive free continental breakfast buffet that is loaded with fresh fruit and warm homemade pastries that are to die for (I crave them for weeks after we leave!) and the huge pool, which is surrounded by swaying palm trees and always an exciting place to hang out. The deck has tiki huts, tons of chairs, a shaded baby pool, two hot tubs and, in my opinion, the best pool bar in Florida. The Oasis serves casual fare and drinks, including my all-time favorite Piña Colada. Many of the customers are regulars, but you’ll feel just as welcome as they are. The location of Tween Waters also can’t be beat. It’s just a few minutes past the bridge that brings you from Sanibel to Captiva (enjoy looking at the incredible seaside mansions on the way). It’s also close to the wonderful restaurants and shops of “downtown” Captiva, which is a quick drive up the main road or an easy walk up the beach (there’s also a shuttle service). But we spend most of our time at the resort, going back and forth between the pool and beach (more on the beach in No. 3!).

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Another highlight of the resort is the full-service marina, where you can book fishing charters and other boat rides, plus rent kayaks and bikes. My husband, the kids and their aunt had a successful outing with Captain Randy on our last trip. They even accidentally caught a lemon shark, which they thankfully were able to safely release. In the past, we’ve asked our charter captains to clean our fish, then we’ve cooked them for dinner. Kayaking in the bay is another favorite thing to do, and the Tween Waters harbor is a great launching point for exploring the nearby mangrove islands. You’ll likely have to navigate around the manatees that make their home just off shore. We have at times considered trying new accommodations on Captiva. But we’re sentimental about all of our  Tween Waters memories and also just can’t imagine missing out on all this resort has to offer. Also, did I mention it’s a great value compared to some of the island’s other resorts and house rentals? But most importantly, Tween Waters just feels like home – a greatly improved version of home!

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3. Beach lover’s paradise: The beaches of Captiva are quite different from many of the beaches in other parts of Florida; meaning there are few people and no high rises – in fact, there’s very little development at all. On many of my morning beach walks, I’m all alone – just me and the sandpipers, sea turtle nests and dolphins (on a lucky day). Sanibel and Captiva also are known as the shelling capital of the world, so you can come away with quite a haul if that’s your thing. You cross the road to get to the Tween Waters beach, which is wide open and features the resort’s famous beach chairs and cabanas available for rental.


4. Dolphins and manatees galore: If you spend a fair amount of time looking at the ocean, you’re pretty much guaranteed some dolphin sightings in the waters surrounding Captiva. And if you go out on a boat cruise, your chances of a close encounter are even better. I love dolphins more than just about anything, so seeing them in their natural surroundings, as they were meant to be seen, is a huge thrill for me. We’ve also seen many manatees in the area, especially at the harbors of Tween Waters and South Seas, the other big resort on the island. These gentle, slow-moving giants are so fun to watch.


5. Island excursions: There are many interesting islands dotting the waters that surround Captiva. We always plan a day to explore these areas by taking an excursion with Captiva Cruises. One of our favorites is the cruise to “Old Florida hideaway” Cabbage Key. There’s not much to do there, and that’s why we like it. You can have lunch in the old inn, where they say Jimmy Buffet was inspired to write “Cheeseburger in Paradise.” I know other Florida restaurants make this claim, but I want to believe it’s true on Cabbage Key, because the burger and views are THAT good! It’s also fun to sign a dollar bill and hang it on the wall, along with the thousands (or millions?) of others. After lunch, we hike around the island and climb to the top of the lookout tower. Then it’s time to make the one-hour trip back to Captiva. Getting there and back is half the fun with Captiva Cruises, because the captains are so knowledgeable about the area’s history and wildlife. They remain true to the “Captiva way,” by being all about conservation and eco-tourism – and they make it fun. The highlight of any cruise is spotting dolphins – and we’ve seen them on every excursion we’ve taken. Watching dolphins out in their ocean home, swimming freely with their families, sure beats Sea World! On our recent visit, three dolphins swam along with us just a few feet off the boat for several minutes (watch the video here). When they were done with us, one of them jumped high out of the water, as if to say goodbye. I won’t soon forget that!

Our other favorite Captiva Cruises destination is Cayo Costa State Park, a secluded island that is a half-hour boat ride from Captiva. Captiva Cruises will drop you at a pier and lead you on a short hike through thick island vegetation. When you emerge, you’re greeted by an expansive, unspoiled beach with crystal clear water. You can almost fool yourself into thinking you’ve been shipwrecked on a deserted island, as you swim, shell, go bird watching and explore. There are no facilities, so you must bring your own food and drinks. You can book a half- or full-day outing. Either way, I think you’ll find this to be one of the most relaxing experiences of your vacation. If you want to get out on the water but don’t want to spend an entire day away from your home base, consider the shorter Dolphin Watch and Wildlife Adventure Cruise or a Sunset Cruise. There’s no better way to learn about the area and take in its beauty – and, of course, the only thing better than seeing dolphins from the shore is cruising along right next to them.

Interested in visiting Captiva Island? Book your stay through our trusted partner Trip Beat here!

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6. Ding Darling: The J.N. Ding Darling National Wildlife Refuge takes up 6,400 acres of Sanibel and is about a 20-minute drive from Captiva. When I first stumbled upon it, I could hardly believe this famous national treasure was so accessible to us. There are many ways to enjoy it, including the interactive visitor and education center and gift shop, where we’ve purchased many souvenirs, books and games; the four-mile wildlife drive (a good option if you have little kids), where we’ve spotted an alligator and tons of species of birds; and many biking and hiking trails. Ding Darling is the perfect place to introduce kids to the ideas of conservation and wildlife protection, but it’s also full of beautiful sights and opportunities for outdoor adventure. I especially love the hiking.


7. Nature lover’s paradise: Nature lovers flock to Sanibel and Captiva for the unspoiled feel of the islands. Captiva does not have much open space, but it’s developed in a non-commercial way (there is only one business you’ll recognize, and most people don’t complain because it’s a Starbucks, located at the tip). There’s a huge emphasis on protecting the local dolphins, manatees, sea turtle nests, osprey and countless other birds. On Sanibel, you’ll find many protected areas, tree-lined streets and only a few chains. One of them is a vintage walk-up Dairy Queen that frequently has Bald Eagles nesting in the Australian Pines on its property. If you’re looking for main drags lined with bright signs beckoning tourists to mini golf and bumper boats, Sanibel and Captiva might not be for you. But if you want a truly peaceful and natural environment, this is the place.

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8. Biking: Take an easy drive over to Sanibel and rent some bikes from Billy’s, then spend a couple hours or a day exploring 27 miles of trails. Sanibel puts a major emphasis on catering to cyclists. The trails are extensive and offer great variety – go through the middle of town, to the lighthouse, along Gulf Drive or through Ding Darling. The day we bike Sanibel is always one of my favorites; it’s just the best way to see the island. And Billy’s rentals are inexpensive (about $7 for a regular bike for two hours) and cater to all ages and abilities. You’ll find tandems, Weehoos for little ones, baby seats, three-wheeled bikes and more. I also enjoy biking around Captiva (rent one for a couple hours from the Tween Waters marina), but that’s not for kids because you have to ride on thin shoulders next to the road.

bike-group bike-trail


9. Culinary jackpot: My family and I can get a little crazy about our Sanibel/Captiva traditions, so we tend to hit the same favorite restaurants each trip. But we do try to venture to at least one new place each time. We’re never disappointed. Some of our Captiva favorites include Key Lime Bistro and RC Otter’s, located on Andy Rosse Lane, the bustling main drag that runs right into the ocean. We also love Cantina Captiva. The Mucky Duck is one of the more famous restaurants and the island hotspot at sunset. We never miss our tradition of having drinks on the Mucky Duck patio while listening to the live music and watching the sunset. On one lucky occasion, we even saw dolphins jump up just as the sun was sinking into the ocean. That’s also an experience I’ll never forget. Our Mucky Duck outing is also when we try to take some family pictures, because the views there can’t be beat.

family-pics jen-and-paul

On Sanibel, we always hit The Island Cow on the way into town – it’s our favorite, so we simply can’t wait any longer than that. Other recommendations include Gramma Dot’s (at the Sanibel Marina, so it’s fun to get a look at the yachts parked all around the restaurant), Doc Ford’s (which is also now on Captiva and partly owned by one of my favorite authors, Randy Wayne White, whom I finally had a chance to meet on our last visit) and Sanibel Grill (a bar with large booths, a fun atmosphere and, of course, fresh grouper). One of the things we love best about Sanibel/Captiva is that there are very few chains. But one exception that we’re glad about is the old-fashioned, outdoor Dairy Queen on the main drag of Sanibel, where we always make at least one stop.

10. The nostalgia: Okay, this one doesn’t apply to everyone, of course. But I have to include nostalgia because it’s one of the reasons Captiva holds a special place in my heart. On our first trip, my boys were running around the pool area in swim diapers. Now the oldest will be heading to college in year. As our family has evolved, so has the way we enjoy the island. In the early years, we spent most of our time building sand castles and planning the day around naps. old3

Now we’re a little more adventurous, biking Sanibel, hiking Ding Darling, fishing Pine Island Sound and cruising the Gulf on wave runners. We also make the most of the night life. On our last visit, we had a blast with the kids at the Crow’s Nest restaurant and bar at Tween Waters. We all enjoyed the live band and even did a little dancing. Thankfully, my kids have not outgrown “our island.” Some of our family’s best memories have taken place on Captiva. It’s the setting for many firsts and favorite family stories. In fact, when we reminisce, the talk often turns to tales of Captiva. Aunts, uncles, cousins and grandma have traveled with us on many of the trips, and I believe they feel the same Captiva connection.  I hope we’re fortunate enough to keep returning there as a family for many years to come.

In my happy place.
In my happy place.

Check out my flipagram of our June 2016 Captiva vacation, set to what I believe is the perfect theme song for our island paradise: Captiva 2016 flipagram.

A small portion of our Captiva Island experience was hosted by Tween Waters Inn Island Resort. But as is always the case, my opinions are my own. I would never recommend anything that I didn’t truly believe in.

Interested in visiting Captiva Island? Book your stay through our trusted partner Trip Beat here!

Captiva through the years:

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