For the 50+ Traveler

When I got to be in my 20s (wish I could say not that long ago!) my parents started spending a month each winter in Sanibel Island, Florida, and I would join them every now and then. A couple of times, my sisters and I rented another condo so the cousins could be together. Great memories linger from Sanibel, which is why we took my father, with advancing dementia, there this winter to see if he would enjoy it as he had before.

The multi-generational family travel story (or OG, as we called it, since it was just my parents, my sisters, and I: the originals) is a whole other piece, but you can read about why Sanibel Island is the perfect beach vacation destination here.

That said, Captiva Island is a much smaller piece of land attached to Sanibel Island by a little bridge over an inlet. We had gone there to watch sunsets and to grab a burger at the classic Mucky Duck Restaurant, but I had never really spent time on Captiva Island. That changed recently, and I can honestly say I will be going back -- and dragging the family.

Like Sanibel, you get to Captiva by flying into Southwest Florida International Airport (RSW) and renting a car. Recently, Alaska Airlines started direct flights to RSW from Seattle and Los Angeles which make it a breeze to visit. I upgraded to first-class on my flight back to L.A. and ooh, la, la, I may never be able to go back to coach!

A car is necessary on Captiva Island because although there are taxis and possibly ridesharing, they are not reliable. Having a car allows you to enjoy the beach as well as the restaurants, parks, and museums that do not sit on the beach.

Beach, Captiva Island, Florida.

Things To Do On Captiva Island

Although Captiva is a tiny little island, there are dozens of things to do, and then there is just sitting on the beach reading a good book.

Chasing Sunsets

Explore Captiva by driving around and dreaming about the big waterfront homes and popping out to explore the little beach nooks, especially Blind Beach, which sits at the intersection of Sanibel and Captiva Islands. There is a little bridge from which you will see people exploring the sand bars and doing some surfcasting from shore.

Blind Beach is also one of the best places to watch the area’s vibrant sunsets and perhaps catch a glimpse of the “green flash” (an optical phenomenon you might get to witness during your vacation) as the sun disappears behind the horizon.

Island Cruises And Manatees

Even if not staying at South Seas Resort, organize a cruise from their marina, and with a $5 parking pass, catch a glimpse of the manatees that hang out among the docks. The best place to see these elephants of the sea is the marina area and the lagoon that extends from it. They move slowly and are so gentle, it is hard to imagine these creatures exist in the hectic culture of today.

From the same marina leaves Captiva Cruises. We took the cruise that does daily trips to Cabbage Key, a tiny island famous for its privacy and restaurant accessible only by boat. There are hundreds of dollars of bills hanging from the ceiling here (during the pandemic, they took them down and split almost $5,000 among the staff) and it is a well-known fact that

Jimmy Buffett wrote “Cheeseburger in Paradise” after having one at Cabbage Key. Delicious burgers and the stone crabs are to die for. Drinks are also yummy and the ambiance a mix of laid-back beach and reclusive elegance. Say hi to the manager Scott and ask about the history of this tiny place, which offers a few vacation rentals for those who don’t want to leave.

Dolphins And Remote Islands

While on a Captiva Cruise, the captain and host are on the lookout for dolphins and whales while explaining the history of this magic area. It’s an educational feast, and then here comes the dolphins! And they keep coming. During almost your entire crossing, dolphins play in the surf of the boat and frolic around the bow with jumps, twists, and leaps that amaze even the most seasoned sealife fan. Have your video camera ready.

The boat makes a stop at what looks like another cool island called Useppa Island and the whole experience is just relaxing and made even more fun by the $7 cocktails on board.

Shell Seeking And Beach Walking

Walking the beach and shell-seeking is really the most popular thing to do in Captiva Island. Shells are even more copious than in Sanibel during many times of the year. I was originally intrigued by Captiva when the local tourism agency organized a virtual book club to discuss Anne Morrow Lindbergh’s classic book Gift from the Sea in which she explores life through the shells she finds on the beach. She wrote there and I did, too. Captiva has everything you need, and peace and quiet are readily available for reflection and meditation.

For water activities like parasailing, paddleboarding, snorkeling, kayaking, and more, Sunny Island Adventures is your place. Located at the entrance to South Seas Island Resort, they also rent bikes and golf carts, an easy way to get around the small island.

Fishing is another option and all types of excursions are available through South Seas or Sunny Island Adventures. On the other end of the spectrum, you’ll find spa and wellness facilities at South Seas and ’Tween Waters Inn.

Signs for restaurants, downtown Captiva Island.

Best Restaurants On Captiva Island

Although Captiva Island is small, the selection of restaurants is pretty significant and varies from fine dining to beach casual. You will not find fast food on Captiva and, as you can imagine, fish and shellfish are prominent on every menu.

I mentioned The Mucky Duck earlier, and this casual beachfront restaurant is wildly popular as a place to see Captiva’s spectacular sunsets, and their t-shirts and hats are as popular as their burgers and fish ‘n’ chips. The Mucky Duck sits at the end of Andy Rosse Lane, and many other restaurants sit on this short street leading to the beach.

RC Otter’s and Sunshine Seafood Cafe sit next to each other and across the street is the Key Lime Bistro. As you may imagine, Key Lime Pie is the highlight at the bistro and it is found on menus and in groceries across the area. At Key Lime Bistro, a crab cake benedict for breakfast or a grouper sandwich for lunch is the way to go.

Family-friendly R.C. Otter’s has a seafood omelet for breakfast and blackened tuna salad and their famous black beans and rice for lunch. They also have an extensive kid’s menu with pancakes, burgers, and more. Next door, Sunshine Seafood Cafe is only open for dinner and is classy yet casual like everywhere. I love the scallops and goat cheese appetizer followed by what the restaurant calls their World Famous Seafood Paella. You can’t go wrong at any of the above.

Two other classics are both themed but could not be more different. “It’s Always Christmas” is the slogan at The Bubble Room on the main Captiva drag. This restaurant is filled with decorations and kitschy decor from everywhere and celebrating everything from holidays to Hollywood. Food seems secondary but they serve hilariously named items like “Smarvelous” She-Crab Soup or the Napoleon Bonaparte prime rib sandwich.

Doc Ford’s in an unpretentious shopping center at the entrance to South Seas Resort is themed as a beach shack and is known for offering a wide array of rums, as a beach bar should. Signature dishes include the seared tuna appetizer and the Yucatan shrimp entree as well as the yummy macadamia nut crusted grouper. There is a reason Doc Ford’s gets named a favorite restaurant on Captiva year after year.

Best Resorts On Captiva Island

Captiva Island has a few options where resorts are concerned and they vary greatly. Many couples and families coming to Captiva opt for vacation rentals, and they can be anything from magnificent mansions to beachfront cottages. Royal Shell and Captiva Island Vacation Rentals are two good choices for the full spectrum of big-to-small rentals, some of which will be on resort properties like South Seas Island Resort.

’Tween Waters Island Resort and Spa is a charming inn at the crux of Sanibel and Captiva. The views are great and there are a spa and restaurant on property as well as several other restaurants nearby. The Captiva Island Inn houses the Key Lime Bistro and is a charming B and B in walking distance to everything.

South Seas Island Resort is the major resort on Captiva and it is stunning. With a range of accommodation from harborside hotel rooms to beach villas to beachfront Homes, there is something for everyone, including those who arrive by boat. A trolley makes the rounds between the activities all over the resort, the restaurants, the kids club, and beach lounging locations.

Eat lunch on the beach at Latitudes Food Shack, have a cocktail at The Crooked Snook Tiki Bar, and then go for a romantic dinner at The Harbourside Bar and Grill. Walk the beach, finding shells along the way, and then watch the sunset from your beachfront condo. That’s what I did and I can’t wait to do it again. As one of my friends who made fond childhood memories at South Seas told me, “South Seas Island Resort is where the palm trees turn to pines. It's unique and it’s magic; truly a place you want to return again and again.”

For more area inspiration, consider the best things to do in Boca Grande and A Return To Old Florida: 6 Fantastic Experiences On Pine Island.