Destination Tips

Captiva Island Cruising – Sun, Fun and Flawless Beaches

Egret on the beach with swimmers in the background

We were stumped.

The ceiling and walls of Cabbage Key’s breezy back patio were dripping with dollar bills. Where on earth would we leave our “donation” ?

Affixed with gobs of masking tape and mounted with the precision of a leaf blower, I couldn’t see an inch of available space. Thousands of travelers had been here over the years, and it looked as they all left a George Washington behind, scrawled with graffiti in thick black ink: “Tommy 2014!”,  “I used my last dollar”, “Love from Minnesota” and “BH + ER were here!”

Now it was our turn. But where?

We scanned the room for a sliver of prime real estate. Our waitress, having seen this scene a hundred times before, brought us cigar-sized Sharpies and masking tape as soon as she cleared our plates.

One of the homes on North Captiva, which you can only reach by boat.

One of the homes on North Captiva, which you can only reach by boat.

I saw a speck of wood above a window and I went for it, using two pieces of adhesive to keep the dollar secured. I’d written a little promo in block letters “The Insatiable Traveler, ~17.” (Not particularly creative but it got the job done.)

It was a silly game for sure, but one we couldn’t pass up.

When in Rome….

Island Hopping  

An hour and a half earlier, I was at McCarthy’s Marina on Captiva Island, a thin stretch of land north of Sanibel Island connected by a single main road and a barely there bridge, for a half-day of Island hopping as a guest of Captiva Cruises. There were six of us in total.

Captiva has been a favorite of vacationers for decades. It’s relaxed vibe, colorful kitsch, good food, water sports, beaches and western-facing sunsets, much of which is in walking distance of each other, made it a popular place for families to make an annual tradition.

Our cruise would take us north through Pine Island Sound, with a stop at Cabbage Key for lunch, followed by some beach time and shelling on Cayo Costa, then back to Captiva.

People on the front of a boat overlooking Pine Island Sound

The front end of the boat

The Santiva -

The Santiva Photo: Courtesy of Captiva Cruises

We boarded a large powered catamaran called the Santiva. Half open, half enclosed, with simple bench seating. The boat held up to 49 people but since we were only six, we had plenty of room to spread out.

As one might imagine, cruising from island to island was not hard to take. Day after day in the heart of New York City with its concrete and steel, the salt air, vast ocean, and island views were a welcome change of pace.

John, the First Mate and naturalist, narrated the trip with facts and a history lesson about the region. Passing a particularly scraggly portion of North Captiva, he pointed to two juvenile bald eagles in a tree nest the size of a bathtub.  They were far away, but I could still make out the top half of their bodies. As adults, their wingspans can reach as wide as 7.5 feet.

(Fun Fact: Florida has the second largest population of bald eagles in the country after Alaska.)

I kept my eyes peeled for bottlenose dolphins which frequent the area, but no such luck. With wildlife, it’s always a crap shoot.

Back patio of the Cabbage Key Restaurant; dollar bills hanging from ceiling

As we neared Cabbage Key, John pointed to Useppa island to the east.  In the early 1900’s, it was owned by the billionaire Barron Collier, who hosted the likes of Rockefeller, Edison and Ford. They spent their days tarpon fishing and their nights hobnobbing. Today, the entire island is a private club. Captiva Cruises has exclusive touring rights enabling visitors to explore a limited area, visit the History Museum and have lunch at the exclusive Collier Inn.

Cabbage Key

Cabbage Key is 100 acres of “undeveloped paradise” according to the Visit Florida website, with one inn offering a variety of cozy bungalows and a restaurant by the same name. The restaurant greets visitors from its perch on top of an ancient Indian shell mound, raising it 38 feet above sea level. It’s also the home to a rather large gopher tortoise.

In addition to the aforementioned dollar bill decor, Cabbage Key is known for its cheeseburger. Legend has it that Jimmy Buffet was inspired to write “Cheeseburger in Paradise” after dining there. Whether true or not, I can testify that the cheeseburger was, in fact, delicious and the size of my head. I’d also recommend the Caramel Turtle Fudge ice cream pie. I’m a sucker for anything made with caramel and peanuts.

Cayo Costa

After lunch we navigated to nearby Cayo Costa Island, a 2,426 acre Florida State park in the shape of a shark. (At least I think so.) We docked on the east side of its thin southern tip, walking about two minutes to the west side, via a sandy path flanked with palm trees, to find a long strip of pristine beach.

While the others dove into the wake, I chose to take a stab at shelling. Sanibel, Captiva and Cayo Costa are key destinations for avid shellers and its easy to understand why, there seems to be as many shells as there are grains of sand. Many are very tiny, others the size of a dimes or nickels, but I found a few that were larger.

Tip: If you’re a sheller, check out Pam Rambo’s (the resident shelling guru) site, iLoveShelling, for tips on where to go, when to go, identifying your shells, and how to clean your finds so that they look fabulous.

Captiva Island, Cabbage Key, Cayo Costa-938520170327

I looked for sea urchins but, alas, there were none to be found. We stayed for an hour before it was time to head back. I was grateful for the brevity, I could feel my lily-white skin, though smothered in sunscreen, beginning to fry.

A family lounging a few hundred yards away, relaxed under a large beach umbrella and I remember thinking it was a smart investment if I ever planned to stay out there for any length of time.

Large shell amongst small shells on Cayo Costa Beach in FloridaOn the way back to Captiva, our beach and food fixes sated, we sat in silence soaking up the view.

From beginning to end the excursion was approximately four hours.  Once docked, we said goodbye to Jorge and John and walked about 5 minutes from where the Marina was located to the opposite end of the road to the The Mucky Duck,  a very popular beachside pub with live music, picnic tables and ice-cold beers.

Granted it didn’t have a dollar bill decor, but we managed to settle for a spectacular view of the sunset.


Here’s how you can go island hopping from Captiva 

Captiva Cruises operates from two locations on Captiva Island: McCarthy’s Marina and South Seas Island Resort.  You’ll be told which dock when you purchase your tickets.

The company offers multiple tours that focus on various activities, dolphin watching, shelling, dining, and sunset cruises. Prices range from $27.50 – $50.00 per adult and from $15.00 – $35.00 per child. You can check out their tours here.

Window reflection of Mucky Duck on Captiva Island, Florida

The Mucky Duck Pub

The combo we did, Cabbage Key and Cayo Costa, is not offered as a single tour unfortunately. You either have to take two separate tours or arrange for a private charter. Rates are $375/hour with a two-hour minimum and a 49 person maximum, so the more the merrier and cheaper per person.

While on a boat you can purchase both alcoholic and nonalcoholic beverages. Meals are not included in the price of your ticket. The Santiva didn’t have any cup holders or trash receptacles for passengers so be prepared to hold your glass until you reach your destination.

Orange sunset over the ocean

Bring everything you think you may need

No matter what cruise you decide to take bring everything you’ll need with you such as sun-screen, hats, towels, beach umbrellas and food, especially if you’re going on a full day tour. There’s nowhere to buy anything once you’ve boarded the boat.


If You’re Not Staying on Captiva

Captiva Cruises is the go-to company for scheduled cruises and private charters for those staying on the island, but if you’re not staying on Captiva and you don’t want to drive all the way there, there are other companies that depart from Sanibel and Fort Myers. Here is a list I found on the Sanibel Island & Captiva Island Chamber of Commerce website. I have not tried any of them except for Captiva Cruises but it’s a good place to start.

I can vouch for a small company called Endless Summer Cruises which is strictly a charter business and leaves from Sanibel. It caters mainly to avid fishermen but my family and I went on a great day-long charter cruise that began with fishing in the morning, then Cabbage Key and Cayo Costa, followed by a long ride around Pine Island Sound where dolphins played in our wake. (There’s some cute video if you click on the link above.)

Bonus video: I was playing around with the Adobe Spark app and it inspired me to put this little ditty of the trip together. Check it out.


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Up Next:  The Best Way to Visit Sanibel Island’s Ding Darling National Wildlife Refuge

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41 replies »

  1. I’ve been to Florida so many times I often forget there are corners of it I may have missed. Need to make it back out I see!

    • I hope you do too, Leah. Just put a little $$ aside month to month for travel, doesn’t have to be a lot. You’ll be amazed how much you’ll accumulate over a little time. 🙂

  2. Sanibel-Captiva is an amazing destination. Your photos captured it beautifully. In 2015, I was disappointed with the number of shells on the beach I hovered around, I expected more . . I just assessed I was at the wrong beach at the wrong time for overflowing shells. The large bird in your photo . . do you know the species . . .I took photos of some birds I was unfamiliar with but never researched them — they were unique.

      • you post prompted me to do a little research on that bird on your photo. I will have to return to my Sanibel Captiva archive, but based on memory I think I may have seen the Ibis. I distinctly recall it had a unique beak and posture. Here’s to the west coast of Florida! A sight to behold.

    • I walked through it but didn’t get to eat there. Are you talking about the orange crunch cake? I’ve heard great things about it. I am going to mention it in a subsequent post. You enjoyed it?

Would love to hear from you!