Here’s How To Plan The Excellent Escape To Captiva Island

Historic cottage at Tween Waters on Captiva Island, Florida.

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Even before the pandemic forced many to be wary of crowds and seek refuge in natural, spacious destinations, Captiva Island, with its population of less than 200 residents, has long been a place to get away from it all on the gulf coast of South Florida.

Relatively easy to reach from Tampa Bay (3 hours), Fort Myers (1 hour), and even Miami (3.5 hours), the island provides visitors the chance to relax and recreate at arm’s length.

It’s not difficult to keep to yourself on Captiva, but there’s also plenty to do if you understand the area, are interested in exploring the natural landscape, and know where to go and what to do.

Here are some tips for planning the perfect getaway to Captiva, one that combines rejuvenating downtime, outdoor bliss, nightly sunsets, and fresh seafood:

Know the History

The barrier islands surrounding Fort Myers, including Captiva and nearby Sanibel Island, were once home to the Calusa Indians. You’ll see nods to them, big and small, throughout the region, from the Calusa Heritage Trail at Pineland to the Mound House Museum at Fort Myers Beach (across the water from Sanibel).

On Captiva and Sanibel, look for sign postings in wilderness areas that point out shell mounds and explain how the Calusa once used the resources in this area.

Unfortunately, the Calusa tribe was all but wiped out by the arrival of the Spanish in the late 1700s. Afterward, the coastline became a haven for pirates, who operated in and out of the barrier islands. One notorious pirate named Jose Gaspar arrived in the early 1800s and proceeded to set up a prison on one of the barrier islands. He called it “Isle de los Captivas,” or Captiva Island, and he kept female prisoners there for ransom.

Today, the name brings about better vibes, capturing its calm, quiet atmosphere, abundant waterways, and shell-covered beaches.

Sunset from the west-facing beaches of Captiva Island.

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Understand the Vibe

One thing that’s very important to understand about Captiva before visiting is that it is truly a vacation destination. That is, the tiny island has but a mere handful of residents, with almost all of the available property catering to visitors via hotels, inns, and vacation rentals.

When driving through the island, almost every house (aka mansion) has a sign out front advertising its vacation brand. All this to say, don’t travel to Captiva expecting to stumble upon a bustling local scene. Most people you meet, working in the shops and restaurants, live on Sanibel or Fort Myers.

That said, there is ample chance to connect with the natural world, which is, without question, the main draw of the island. Other than a small downtown, Captiva has avoided mass development and remains largely wild, a combination of coastal mangroves, tall trees, forests, and ocean inlets.

Choose an Appropriate Accommodation

Captiva’s long, narrow shape is good news for visitors. You’d be hard-pressed to find an accommodation on Captiva that doesn’t have a walking path to the beach, and in most cases, accessing both the ocean and the bay are possible on foot from wherever you’re staying.

For a small island, there are numerous accommodation choices. Vacation rentals, many with pools and big backyards, are a popular pick for families. Then there are small inns, like the Captiva Island Inn, that offer a bed-and-breakfast type of stay, and condo/apartment rentals, like Jensen’s. If you’re looking for a proper hotel, there are two on the island: Tween Waters (3-star) and South Seas Resort (4-star).

Because the island is small and the vibe slow, any of these accommodation styles will satisfy your beach-bum desires. The trick is to make life easier in other regards, such as access to downtown, tours, and other services you may want, depending on your specific needs.

The historic Lindberg Cottage at Tween Waters. The cottage has a view of the ocean across the … [+] street.

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For those looking to gain services without losing character, Tween Waters, while not the most modern accommodation on the island (it started as a small fishing lodge in 1931), offers an interesting combination that provides a little bit of everything, including history, convenience, privacy, flexibility, and charm.

Take, for example, its historic cottages. One in particular is dedicated to the Lindberg family, who often vacationed in Captiva (Anne Lindbergh wrote “Gift from the Sea” while visiting Captiva). You can see the beach from the screened-in front porch, and inside, dark wood, old travel memorabilia, and art depicting Florida’s landscapes evoke that “Old Florida” feel. A small kitchen allows you to prepare meals on your own, and the hotel’s pool, spa, restaurant, and bar provide easy, on-site entertainment.

Though the view of the ocean will tempt you, the Tween Waters marina is just behind you on the bay, with boat rentals and kayak tours available right off property. If you want to head downtown for dinner and drinks, you can ride the hotel’s shuttle, which costs just $5 roundtrip.

To Plan or Not to Plan?

At first glance, it might not seem like there’s much to do on Captiva. The downtown, while charming, shuts down early, and overall, things are quiet.

Many people who visit Captiva have come for this exact vibe – aka, they choose to do nothing at all. Hit the beach, go for a swim, have a cocktail, and relax. Others come to focus on fishing, either from the shore, on a tour, or with a private rental.

You’re never far from the beach on Captiva. Most accommodations have walking paths right from their … [+] door to the beach.

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What most people don’t know is that, from a nature and adventure perspective, there’s more to do on Captiva than one could accomplish in a single trip. Most ventures are perfect for a half-day activity, leaving you the afternoon at leisure.

• The Buck Key Kayak Tour with Captiva Adventures brings you through a mangrove tunnel for an up close and personal look at the area’s natural, dominate ecosystem. Along the way, you’ll have the chance to spot dolphins, manatee, otters, and all kinds of birds, including osprey, egret, and cormorants.
• Captiva Cruises’ offers the usual range of sunset and sailing cruises, but check out the Cayo Costa State Park cruise. Only accessible by boat, Cayo Costa has nine miles of beach and six miles of trails to explore, with a mix of soft white sand and pine forests. It’s a wonderful place to relax, collect shells, and find your own slice of sand. Plus, the cruise takes you past North Captiva, which is mostly undeveloped, as well as Pine Island.
• Shelling in Captiva and nearby Sanibel is a long-standing, traditional activity that continues to delight people who visit. Walking on Captiva’s undeveloped beaches is nice in itself, but you might find it hard to keep your attention on the water and scenery with all the shells you’ll see washed ashore. Whether you are an avid collector or just a simple admirer, beach-combing for shells is simultaneously relaxing and exciting.
• The J.N. “Ding” Darling National Wildlife Refuge, located between Captiva and Sanibel, is a protected mangrove ecosystem that’s a birder’s paradise, with close to 250 species of birds. Each season offers the chance to see something different. Activities include hiking, kayaking, SUPing, bird watching, fishing, nature cruises, and more.

What to Eat and Drink

Captiva is blessed with a bounty from the ocean. Fresh fish, shrimp, and other seafood dominate menus, and many restaurants boast views of the water. There are a variety of options that range from fine dining to casual fare.

Fish tacos at Doc Ford’s on Captiva Island in Florida.

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• If you’re looking for that casual, laid-back beach bar on Captiva, with a view of the water and the sunset, then The Mucky Duck is the place for you. It has rocking chairs lined up along the edge of the beach, as well as picnic tables and a bar outside. The inside is designed as a neighborhood pub. The quality of the food does not fit the price tags – the shrimp cocktail, for example, costs $14 but looks like it was defrosted from Publix. Go for a drink and the sunset, then split somewhere else for dinner.
• If you’re looking for the best bang for buck on island, check out Doc Ford’s. It’s rum bar theme means there are plenty of hot weather, relaxation-inducing cocktails, and if you’re a fan of Bloody Mary’s, don’t miss the one garnished with Yucatan shrimp. The fresh fish, raw bar, and fish tacos are all good options here.
• Looking for lunch on the beach? Stop by Captiva Provision Company to pick up picnic supplies, or order a freshly made sandwich from the deli.
• Downtown, you’ll find a variety of restaurants with live music and fresh fish options. Throw a dart if you’d like, or simply go with whichever has the best music. Keylime Bistro and RC Otter’s are two usual suspects for live music and outdoor seating.
• For fine dining and views of the water, both The Green Flash and The Mad Hatter offer a nice combination of ambiance, selection, and quality.