FORT MYERS SAILING FIELD GUIDE
Pirate Waters, Island Bayous and a Cheeseburger: A 6‑Hour Fishing Run from Fort Myers
A six-hour charter that fishes the bayous and inlets around North Captiva, Cayo Costa and Useppa Islands, with a lunch stop at Cabbage Key’s Cheeseburger in Paradise.
Pirate Waters, Island Bayous and a Cheeseburger: A 6‑Hour Fishing Run from Fort Myers.
Adventure brief
Pirate Waters, Island Bayous and a Cheeseburger: A 6‑Hour Fishing Run from Fort Myers
Set out from Fort Myers into the shallow, maze-like bayous where the legend of pirate José Gaspar still lingers; over six hours you’ll probe inlets and flats around North Captiva, Cayo Costa and Useppa Islands and pause for a shore lunch at Cabbage Key’s Cheeseburger in Paradise—an itinerary built for families and small groups looking to pair fishing with island time.
Fort Myers, Florida, sits at the heart of the Sunshine State’s vibrant Gulf Coast, renowned for its sparkling waters, rich pirate history, and laid-back atmosphere. For those craving a combination of fishing adventure and island flavor, Catch Me If U Can Fishing Charters delivers an experience that blends history, nature, and good eats into a single day. Their signature 6-hour excursion whisks guests through the scenic bayous, inlets, and historic waters where pirate Jose Gaspar once roamed, making it a standout choice in the area’s outdoor offerings.
Setting out from the local marina, guests are greeted with the chance to cast lines in some of Florida’s most productive waters. The route weaves through North Captiva, Cayo Costa, and Useppa Islands—each spot offering a unique glimpse into coastal Florida’s ecology and lore. The crew’s knowledge of these waters is evident as they guide anglers toward prime fishing spots teeming with grouper, snapper, and sea bass. After a fruitful morning on the water, the group pauses for a legendary lunch at Cheeseburger in Paradise—an iconic eatery known for its laid-back vibe and hearty, classic American burgers.
This trip’s appeal extends beyond fishing. Families and friends love the opportunity to connect on the water, spotting dolphins, manatees, and a variety of seabirds along the way. Catch Me If U Can’s focus on authentic, fun-filled outdoor experiences makes it a highlight for visitors seeking a true taste of Fort Myers’ maritime heritage combined with excellent seafood and fresh air.
Whether you’re a seasoned angler or a first-timer, this adventure is engineered to deliver memorable moments. It’s a perfect way to make the most of the warm Florida climate while immersing yourself in the region’s colorful history and waterfront culture.
Route Schematic
Route & Key Stops
Stops follow the saltwater channels and island inlets of the region, with fishing and a designated lunch stop.
North Captiva Bayous
Fish sheltered bayous around North Captiva, working flats and channels favored on this run.
Cayo Costa Inlets
Explore inlets and shoreline structure around Cayo Costa for drifting and sight fishing.
Useppa Island Channels
Probe the inshore channels near Useppa Island as part of the island-hopping route.
Cabbage Key — Cheeseburger in Paradise
Scheduled lunch stop at the iconic Cheeseburger in Paradise Restaurant on Cabbage Key; food costs are not included.
This charter accommodates all ages and is limited to a maximum of six people; confirm personal mobility and sea‑time comfort before booking.
Highlights
Outing Highlights
Fish the pirate waters of José Gaspar
The trip visits the same waters associated with the legend of pirate José Gaspar, threading channels and inlets that make the region memorable beyond its catch.
Bayous and inlets around three barrier islands
Expect a day spent exploring the bayous and inlets that braid around North Captiva, Cayo Costa and Useppa Islands—waterways that define the local saltwater fishing grounds.
Lunch at Cheeseburger in Paradise, Cabbage Key
The itinerary includes a lunch stop at Cabbage Key’s Cheeseburger in Paradise Restaurant; guests should note that food costs at the restaurant are not included in the charter price.
What the day feels like
What the day feels like
Over a six-hour span you move from open water into sheltered bayous and inlets, anchoring for stretches of targeted fishing and breaking for a shore-side meal at Cabbage Key; the pace combines active fishing with time to take in the coastal island scenery.
Suitability
Who it's for
Who this outing suits — and who should think twice.
Practical planner
Details to review before reserving
Total charter time is six hours.
Plan to cover the cost of lunch ashore—food costs at the Cheeseburger in Paradise stop are not included in the charter price.
The charter accommodates up to six people and is open to all ages.
Review cancellation policies before reserving.
Frequently asked questions
Planning Your Outing
How long is the Fishing & Cheeseburger in Paradise trip?
The charter is a six-hour outing.
What does the price cover and how much is it?
Rates are $750 for the first three guests with additional guests at $75 each; food at the lunch stop is not included.
How many people can join a single charter?
The charter accommodates up to six people total.
Is lunch included on the trip?
The itinerary includes a lunch stop at Cabbage Key’s Cheeseburger in Paradise Restaurant, but food costs are not included in the charter price.
Where will we fish during the trip?
The trip explores bayous and inlets around North Captiva, Cayo Costa and Useppa Islands—waters associated with the José Gaspar pirate legend.
Are there age or health restrictions to join?
The charter is open to all ages; confirm any personal health or mobility concerns with the operator before booking.
How this guide was prepared
This field guide is synthesized using verified supplier specifications, route descriptions, and destination data. Some booking links may generate affiliate revenue for ADV Guides.
- Verified: 2026-08-07T13:07:36.330Z
Some booking links may generate revenue for ADV Guides or The Adventure Collective.
Availability, pricing, schedules and operating details can change.
Trip details and contextual sources were reviewed by ADV Guides Editorial.