The best thing about keeping a boat at Gulf Star Marina is how much of Southwest Florida opens up within an easy run of Matanzas Pass. Some days call for a quick trip out and back. Others are worth turning into a weekend getaway. Here are five easy destinations that work well either way, whether you’re taking the family out for a few hours or planning an overnight stay somewhere like Captiva or Cabbage Key.

Sanibel Island and the Lighthouse Beach Run

Sanibel is one of the most popular runs out of Fort Myers Beach, and for good reason. Head out through Matanzas Pass and run the Gulf side down to San Carlos Bay and the Sanibel Lighthouse area. Anchor off Lighthouse Beach for shelling and swimming, or continue around to the bayside for calmer water on a windy day.

• Best for: shelling, swimming, an easy half-day trip
• Watch for: shallow water and seagrass around the bayside flats, idle down well before you think you need to

Captiva and South Seas Island Resort

Just past Sanibel, Captiva has a different feel, quieter, with great beaches for a longer stay. South Seas Island Resort on the north end of Captiva has a marina and a beachfront you can access by boat, making it a natural lunch stop or full-day or overnight destination. Blind Pass, between Sanibel and Captiva, is a popular anchorage on a calm day, though it can shift with sand and is worth approaching slowly.

• Best for: a full day or overnight stay with a resort-adjacent beach stop
• Watch for: Blind Pass shoaling, run it at idle speed and read the water before committing

Cabbage Key, Useppa, and Cayo Costa: The Island Keys of Pine Island Sound

Head north through Pine Island Sound and you’ll find a string of small islands locally known simply as “the keys,” distinct from the Florida Keys chain down south but every bit as much a destination. Cabbage Key is a classic lunch stop with a dockside restaurant reachable only by boat. Useppa Island offers a historic, walkable village feel. Cayo Costa State Park is the wild card of the group: undeveloped beach, a short walk from the dock to the Gulf side, and about as close to untouched as Southwest Florida gets.

• Best for: a longer day trip with a real change of scenery
• Watch for: current in the passes between islands, and pack water and sun protection since Cayo Costa has limited services

Lovers Key and Estero Bay

For a shorter, calmer day, Estero Bay behind Fort Myers Beach offers protected water that’s easy on first-time passengers or a boat full of kids. Lovers Key State Park has beach access from the water side and calmer conditions than a straight Gulf run, making it a good pick when the forecast is iffy for open water.

• Best for: families, first-time boaters, questionable weather days
• Watch for: posted manatee zones through the bay, idle speed applies through much of this run

A Simple Fort Myers Beach Boat Itinerary for the Day

If you want a single plan instead of picking one destination, this loop works well for most boats and most tanks:

• Depart Gulf Star Marina through Matanzas Pass by mid-morning
• Run the Gulf side to Sanibel’s Lighthouse Beach for a swim and shell break
• Continue to Captiva or South Seas for lunch, or divert to Cabbage Key if you’re up for the longer run
• Head back through calmer bay water in the afternoon as wind typically picks up on the Gulf
• Return through Matanzas Pass with time to spare before the afternoon thunderstorm window

A Few Summer Reminders

• Florida summer afternoons bring reliable thunderstorms; plan to be off the water or headed in by early afternoon
• Fuel up before you leave; the on-site fuel station at Gulf Star makes this a non-issue on the way out
• Check tide before running skinny water routes near Sanibel’s bayside or the flats around Pine Island Sound
• Manatee zones apply through much of Estero Bay and Matanzas Pass; idle down in posted areas

Frequently Asked Questions

How far is Sanibel Island from Fort Myers Beach by boat?

It’s a short, easy run for most boats, typically well under an hour from Matanzas Pass depending on your route and vessel, making it one of the most popular half-day trips out of Gulf Star Marina.

Can I boat to South Seas Resort on Captiva?

Yes. South Seas Island Resort has marina access on the north end of Captiva Island, making it a practical lunch or beach stop on a day trip past Sanibel.

What are ‘the keys’ near Fort Myers Beach?

Locally, boaters use “the keys” to describe the small islands in Pine Island Sound, including Cabbage Key, Useppa Island, and Cayo Costa. These are separate from the Florida Keys chain further south and make for a longer, more secluded day trip.

Is Lovers Key a good trip for beginners?

Yes. Estero Bay and Lovers Key offer more protected water than a Gulf run, which makes this route a good option for new boaters, families, or days with less favorable weather.

Start Your Trip From Gulf Star Marina

Every one of these trips starts the same way: an easy launch through Matanzas Pass. With SpeedyDock scheduling, on-site fuel, and a launch that takes minutes, Gulf Star Marina makes the getting-there part of the day as simple as the destination. Call 239-463-9552 or visit gulfstarmarina.com to plan your next day on the water.